FI118424B - Nukleiinihappoanalogit ja niiden käyttö diagnostisissa ja analyyttisissä toimenpiteissä - Google Patents
Nukleiinihappoanalogit ja niiden käyttö diagnostisissa ja analyyttisissä toimenpiteissä Download PDFInfo
- Publication number
- FI118424B FI118424B FI935208A FI935208A FI118424B FI 118424 B FI118424 B FI 118424B FI 935208 A FI935208 A FI 935208A FI 935208 A FI935208 A FI 935208A FI 118424 B FI118424 B FI 118424B
- Authority
- FI
- Finland
- Prior art keywords
- nucleic acid
- analogue
- hydrogen
- pna
- acid analogue
- Prior art date
Links
- 150000007523 nucleic acids Chemical class 0.000 title claims description 167
- 102000039446 nucleic acids Human genes 0.000 title claims description 166
- 108020004707 nucleic acids Proteins 0.000 title claims description 166
- 238000002405 diagnostic procedure Methods 0.000 title claims description 5
- 238000004458 analytical method Methods 0.000 title description 40
- 108091093037 Peptide nucleic acid Proteins 0.000 claims abstract description 178
- 108020004414 DNA Proteins 0.000 claims abstract description 121
- 239000003446 ligand Substances 0.000 claims abstract description 51
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 36
- 230000000295 complement effect Effects 0.000 claims abstract description 33
- 102000053602 DNA Human genes 0.000 claims abstract description 26
- -1 hydroxy, methoxy Chemical group 0.000 claims description 92
- 238000000034 method Methods 0.000 claims description 80
- 239000007787 solid Substances 0.000 claims description 55
- 108091034117 Oligonucleotide Proteins 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 45
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 39
- 125000006239 protecting group Chemical group 0.000 claims description 38
- 230000027455 binding Effects 0.000 claims description 35
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 30
- 229940024606 amino acid Drugs 0.000 claims description 28
- 235000001014 amino acid Nutrition 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 27
- 101710163270 Nuclease Proteins 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 150000001413 amino acids Chemical class 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 23
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- 229940113082 thymine Drugs 0.000 claims description 19
- 238000009396 hybridization Methods 0.000 claims description 18
- 125000006850 spacer group Chemical group 0.000 claims description 18
- 238000006073 displacement reaction Methods 0.000 claims description 17
- 238000001514 detection method Methods 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 229940104302 cytosine Drugs 0.000 claims description 15
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 15
- 102000004190 Enzymes Human genes 0.000 claims description 14
- 108090000790 Enzymes Proteins 0.000 claims description 14
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 12
- 229930024421 Adenine Natural products 0.000 claims description 12
- 229960000643 adenine Drugs 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
- 230000002906 microbiologic effect Effects 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- 235000018102 proteins Nutrition 0.000 claims description 7
- 102000004169 proteins and genes Human genes 0.000 claims description 7
- 108090000623 proteins and genes Proteins 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 108010047956 Nucleosomes Proteins 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 150000001371 alpha-amino acids Chemical class 0.000 claims description 6
- 229960002685 biotin Drugs 0.000 claims description 6
- 235000020958 biotin Nutrition 0.000 claims description 6
- 239000011616 biotin Substances 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 210000001623 nucleosome Anatomy 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 238000004925 denaturation Methods 0.000 claims description 5
- 230000036425 denaturation Effects 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 108020004999 messenger RNA Proteins 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229940035893 uracil Drugs 0.000 claims description 5
- 235000014633 carbohydrates Nutrition 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
- 239000000427 antigen Substances 0.000 claims description 3
- 102000036639 antigens Human genes 0.000 claims description 3
- 108091007433 antigens Proteins 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- 239000005547 deoxyribonucleotide Substances 0.000 claims description 3
- 125000002637 deoxyribonucleotide group Chemical group 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 150000003431 steroids Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 24
- 238000000338 in vitro Methods 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 5
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 3
- 229910052711 selenium Inorganic materials 0.000 claims 2
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000002777 nucleoside Substances 0.000 claims 1
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 231
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 124
- 239000000243 solution Substances 0.000 description 114
- 239000011347 resin Substances 0.000 description 104
- 229920005989 resin Polymers 0.000 description 104
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 230000015572 biosynthetic process Effects 0.000 description 90
- 238000003786 synthesis reaction Methods 0.000 description 90
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
- 239000000203 mixture Substances 0.000 description 63
- 238000005859 coupling reaction Methods 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- 230000008878 coupling Effects 0.000 description 49
- 238000010168 coupling process Methods 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- 238000001914 filtration Methods 0.000 description 42
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 42
- 239000000460 chlorine Substances 0.000 description 34
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 31
- 238000003776 cleavage reaction Methods 0.000 description 31
- 239000000178 monomer Substances 0.000 description 31
- 230000007017 scission Effects 0.000 description 31
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- 239000000523 sample Substances 0.000 description 28
- 238000005406 washing Methods 0.000 description 28
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 25
- 239000013612 plasmid Substances 0.000 description 25
- 239000007790 solid phase Substances 0.000 description 25
- 238000003756 stirring Methods 0.000 description 23
- 125000003277 amino group Chemical group 0.000 description 21
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
- 235000019341 magnesium sulphate Nutrition 0.000 description 21
- 239000002244 precipitate Substances 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 20
- 239000003208 petroleum Substances 0.000 description 20
- 238000000746 purification Methods 0.000 description 20
- 229920002684 Sepharose Polymers 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 18
- 239000000872 buffer Substances 0.000 description 18
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 18
- 239000012634 fragment Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 238000003556 assay Methods 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- 239000000499 gel Substances 0.000 description 15
- 238000006386 neutralization reaction Methods 0.000 description 15
- 239000013058 crude material Substances 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
- 238000002835 absorbance Methods 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 13
- 235000017557 sodium bicarbonate Nutrition 0.000 description 13
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
- 238000006467 substitution reaction Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- 125000000524 functional group Chemical class 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 238000010532 solid phase synthesis reaction Methods 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 239000002773 nucleotide Substances 0.000 description 10
- 229920002401 polyacrylamide Polymers 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- DYUUGILMVYJEHY-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-4,4,5,5-tetramethyl-3-oxido-2-phenylimidazol-3-ium Chemical compound CC1(C)C(C)(C)N([O])C(C=2C=CC=CC=2)=[N+]1[O-] DYUUGILMVYJEHY-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000007984 Tris EDTA buffer Substances 0.000 description 9
- 238000000376 autoradiography Methods 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 125000003729 nucleotide group Chemical group 0.000 description 9
- 208000035139 partial with pericentral spikes epilepsy Diseases 0.000 description 9
- 238000010647 peptide synthesis reaction Methods 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- XNPGBDJTEBCMHA-UHFFFAOYSA-N tert-butyl (4-nitrophenyl) carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 XNPGBDJTEBCMHA-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 230000021736 acetylation Effects 0.000 description 8
- 238000006640 acetylation reaction Methods 0.000 description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 239000011324 bead Substances 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000004048 modification Effects 0.000 description 8
- 238000012986 modification Methods 0.000 description 8
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 8
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 241000894007 species Species 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 8
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 7
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 7
- 108091008146 restriction endonucleases Proteins 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- TZDMCKHDYUDRMB-UHFFFAOYSA-N 2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetic acid Chemical compound CC1=CN(CC(O)=O)C(=O)NC1=O TZDMCKHDYUDRMB-UHFFFAOYSA-N 0.000 description 6
- 0 CCC(*)(CC)C(*(CC*=C)C(*(C=C(C)C(*1=C)=*)C1=O)=O)=O Chemical compound CCC(*)(CC)C(*(CC*=C)C(*(C=C(C)C(*1=C)=*)C1=O)=O)=O 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 108020004682 Single-Stranded DNA Proteins 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 6
- 238000000211 autoradiogram Methods 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- 230000029087 digestion Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical group COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 235000011056 potassium acetate Nutrition 0.000 description 6
- 238000003746 solid phase reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000002194 synthesizing effect Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 5
- 230000004568 DNA-binding Effects 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 244000309466 calf Species 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
- 210000001541 thymus gland Anatomy 0.000 description 5
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- OSBLTNPMIGYQGY-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;boric acid Chemical compound OB(O)O.OCC(N)(CO)CO.OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O OSBLTNPMIGYQGY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 239000004471 Glycine Substances 0.000 description 4
- 238000010268 HPLC based assay Methods 0.000 description 4
- 108091028043 Nucleic acid sequence Proteins 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 241000191940 Staphylococcus Species 0.000 description 4
- 239000008051 TBE buffer Substances 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 238000004166 bioassay Methods 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 238000002372 labelling Methods 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 235000015277 pork Nutrition 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000011002 quantification Methods 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 150000003334 secondary amides Chemical class 0.000 description 4
- 108010004034 stable plasma protein solution Proteins 0.000 description 4
- 229910052714 tellurium Inorganic materials 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- ZZKXXDPRBHMOAA-UHFFFAOYSA-N tert-butyl 2-amino-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)C(N)C=O ZZKXXDPRBHMOAA-UHFFFAOYSA-N 0.000 description 4
- 238000013518 transcription Methods 0.000 description 4
- 230000035897 transcription Effects 0.000 description 4
- PIINGYXNCHTJTF-UHFFFAOYSA-N 2-(2-azaniumylethylamino)acetate Chemical compound NCCNCC(O)=O PIINGYXNCHTJTF-UHFFFAOYSA-N 0.000 description 3
- ONHBSJOXWOGKOD-UHFFFAOYSA-N 2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C=CC(NC(=O)OCC=2C=CC=CC=2)=N1 ONHBSJOXWOGKOD-UHFFFAOYSA-N 0.000 description 3
- ZBOVBYTWJJUTEO-UHFFFAOYSA-N 2-[6-(phenylmethoxycarbonylamino)purin-9-yl]acetic acid Chemical compound N1=CN=C2N(CC(=O)O)C=NC2=C1NC(=O)OCC1=CC=CC=C1 ZBOVBYTWJJUTEO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000009881 Aega Species 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 244000269722 Thea sinensis Species 0.000 description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 3
- 239000000853 adhesive Chemical group 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 229960001441 aminoacridine Drugs 0.000 description 3
- 238000004873 anchoring Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- DOABLAGDAOTKAF-UHFFFAOYSA-N benzyl n-(2-oxo-1h-pyrimidin-6-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1=CC=NC(=O)N1 DOABLAGDAOTKAF-UHFFFAOYSA-N 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000004445 quantitative analysis Methods 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000012163 sequencing technique Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
- LRZBBTTUKFVUMZ-UHFFFAOYSA-N 2-(2-amino-6-chloropurin-9-yl)acetic acid Chemical compound NC1=NC(Cl)=C2N=CN(CC(O)=O)C2=N1 LRZBBTTUKFVUMZ-UHFFFAOYSA-N 0.000 description 2
- IZJISFYAFBRVRJ-UHFFFAOYSA-N 2-(2-amino-6-phenylmethoxypurin-9-yl)acetic acid Chemical compound C=12N=CN(CC(O)=O)C2=NC(N)=NC=1OCC1=CC=CC=C1 IZJISFYAFBRVRJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HBKRWYGZVMKRGZ-UHFFFAOYSA-N 3-(5-methyl-2,4-dioxopyrimidin-1-yl)propanoic acid Chemical compound CC1=CN(CCC(O)=O)C(=O)NC1=O HBKRWYGZVMKRGZ-UHFFFAOYSA-N 0.000 description 2
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 2
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 2
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- QTANTQQOYSUMLC-UHFFFAOYSA-O Ethidium cation Chemical compound C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 QTANTQQOYSUMLC-UHFFFAOYSA-O 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 102000003960 Ligases Human genes 0.000 description 2
- 108090000364 Ligases Proteins 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- VIHYIVKEECZGOU-UHFFFAOYSA-N N-acetylimidazole Chemical compound CC(=O)N1C=CN=C1 VIHYIVKEECZGOU-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 108010021757 Polynucleotide 5'-Hydroxyl-Kinase Proteins 0.000 description 2
- 102000008422 Polynucleotide 5'-hydroxyl-kinase Human genes 0.000 description 2
- 108091028664 Ribonucleotide Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 229960003767 alanine Drugs 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 210000004899 c-terminal region Anatomy 0.000 description 2
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 238000010367 cloning Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000012217 deletion Methods 0.000 description 2
- 230000037430 deletion Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
- 238000001962 electrophoresis Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 2
- 229960005542 ethidium bromide Drugs 0.000 description 2
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000001502 gel electrophoresis Methods 0.000 description 2
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- XJEQDMROLAIMRD-UHFFFAOYSA-N methyl 3-(5-methyl-2,4-dioxopyrimidin-1-yl)propanoate Chemical compound COC(=O)CCN1C=C(C)C(=O)NC1=O XJEQDMROLAIMRD-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
- 229910052939 potassium sulfate Inorganic materials 0.000 description 2
- 235000011151 potassium sulphates Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000004451 qualitative analysis Methods 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 239000002336 ribonucleotide Substances 0.000 description 2
- 125000002652 ribonucleotide group Chemical group 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 230000009870 specific binding Effects 0.000 description 2
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 229960001479 tosylchloramide sodium Drugs 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- UHPQFNXOFFPHJW-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanamine Chemical compound C1=CC(C)=CC=C1C(N)C1=CC=CC=C1 UHPQFNXOFFPHJW-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical compound C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 description 1
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 description 1
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 description 1
- PWGLCBCNZAZIIE-UHFFFAOYSA-N 1-methyl-2h-pyrimidine Chemical compound CN1CN=CC=C1 PWGLCBCNZAZIIE-UHFFFAOYSA-N 0.000 description 1
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- LZQSLXNZORCPAR-UHFFFAOYSA-N 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCCNCC(O)=O LZQSLXNZORCPAR-UHFFFAOYSA-N 0.000 description 1
- WCOCCXZFEJGHTC-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(CBr)C=C1 WCOCCXZFEJGHTC-UHFFFAOYSA-N 0.000 description 1
- VUCNQOPCYRJCGQ-UHFFFAOYSA-N 2-[4-(hydroxymethyl)phenoxy]acetic acid Chemical compound OCC1=CC=C(OCC(O)=O)C=C1 VUCNQOPCYRJCGQ-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- HBAHZZVIEFRTEY-UHFFFAOYSA-N 2-heptylcyclohex-2-en-1-one Chemical compound CCCCCCCC1=CCCCC1=O HBAHZZVIEFRTEY-UHFFFAOYSA-N 0.000 description 1
- IKQSNVOJJISMJS-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C+](C)C IKQSNVOJJISMJS-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- SKAYLCIAMUNIHK-UHFFFAOYSA-N 3-hydroxyquinazolin-4-one Chemical compound C1=CC=C2C(=O)N(O)C=NC2=C1 SKAYLCIAMUNIHK-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- QZWFOPZQOWHOOD-UHFFFAOYSA-N 4,9-dichloroacridine-1-carboxylic acid 9-oxo-10H-acridine-4-carboxylic acid Chemical compound C(=O)(O)C1=CC=CC=2C(C3=CC=CC=C3NC12)=O.ClC1=CC=C(C2=C(C3=CC=CC=C3N=C12)Cl)C(=O)O QZWFOPZQOWHOOD-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- CUARLQDWYSRQDF-UHFFFAOYSA-N 5-Nitroacenaphthene Chemical compound C1CC2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] CUARLQDWYSRQDF-UHFFFAOYSA-N 0.000 description 1
- LQLQRFGHAALLLE-UHFFFAOYSA-N 5-bromouracil Chemical compound BrC1=CNC(=O)NC1=O LQLQRFGHAALLLE-UHFFFAOYSA-N 0.000 description 1
- LRSASMSXMSNRBT-UHFFFAOYSA-N 5-methylcytosine Chemical compound CC1=CNC(=O)N=C1N LRSASMSXMSNRBT-UHFFFAOYSA-N 0.000 description 1
- MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 description 1
- XJGFWWJLMVZSIG-UHFFFAOYSA-N 9-aminoacridine Chemical compound C1=CC=C2C(N)=C(C=CC=C3)C3=NC2=C1 XJGFWWJLMVZSIG-UHFFFAOYSA-N 0.000 description 1
- 101150023060 ACR2 gene Proteins 0.000 description 1
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 241001479434 Agfa Species 0.000 description 1
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 1
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- 229910017214 AsGa Inorganic materials 0.000 description 1
- 108090001008 Avidin Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GPVIOOTUCVLUGR-VURMDHGXSA-N C/C(/N)=N\C(\N(C)C=C)=C(/C(N)=S)\N Chemical compound C/C(/N)=N\C(\N(C)C=C)=C(/C(N)=S)\N GPVIOOTUCVLUGR-VURMDHGXSA-N 0.000 description 1
- GKMIDMKPBOUSBQ-UHFFFAOYSA-N CC(C(N1)=O)=CN(C)C1=O Chemical compound CC(C(N1)=O)=CN(C)C1=O GKMIDMKPBOUSBQ-UHFFFAOYSA-N 0.000 description 1
- WGJFZBGSJJRJDL-GDVGLLTNSA-N CN([C@H]1C=C(N)N2)C=CC1C2=O Chemical compound CN([C@H]1C=C(N)N2)C=CC1C2=O WGJFZBGSJJRJDL-GDVGLLTNSA-N 0.000 description 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 108020004635 Complementary DNA Proteins 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 101150022161 Ctsg gene Proteins 0.000 description 1
- 102000004594 DNA Polymerase I Human genes 0.000 description 1
- 108010017826 DNA Polymerase I Proteins 0.000 description 1
- 239000003155 DNA primer Substances 0.000 description 1
- 239000003298 DNA probe Substances 0.000 description 1
- 230000007018 DNA scission Effects 0.000 description 1
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 1
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 206010050789 Hypochromasia Diseases 0.000 description 1
- 235000003332 Ilex aquifolium Nutrition 0.000 description 1
- 241000209027 Ilex aquifolium Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930010555 Inosine Natural products 0.000 description 1
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- HKXLAGBDJVHRQG-YFKPBYRVSA-N L-lysinamide Chemical group NCCCC[C@H](N)C(N)=O HKXLAGBDJVHRQG-YFKPBYRVSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 229920001367 Merrifield resin Polymers 0.000 description 1
- 108010059724 Micrococcal Nuclease Proteins 0.000 description 1
- 241000192041 Micrococcus Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N N-methylaminoacetic acid Natural products C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- DHGYLUFLENKZHH-UHFFFAOYSA-N NCCCNCC(O)=O Chemical compound NCCCNCC(O)=O DHGYLUFLENKZHH-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 244000089486 Phragmites australis subsp australis Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 108010039918 Polylysine Chemical group 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 238000001261 affinity purification Methods 0.000 description 1
- 238000000246 agarose gel electrophoresis Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical group 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000012801 analytical assay Methods 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 210000003423 ankle Anatomy 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- CWBHKBKGKCDGDM-UHFFFAOYSA-N bis[(2,2,2-trifluoroacetyl)oxy]boranyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OB(OC(=O)C(F)(F)F)OC(=O)C(F)(F)F CWBHKBKGKCDGDM-UHFFFAOYSA-N 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- WOBLPDAWNVAVAS-UHFFFAOYSA-N butyl carboxy carbonate Chemical compound CCCCOC(=O)OC(O)=O WOBLPDAWNVAVAS-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000010804 cDNA synthesis Methods 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 238000007813 chromatographic assay Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 238000012631 diagnostic technique Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- JROGBPMEKVAPEH-GXGBFOEMSA-N emetine dihydrochloride Chemical compound Cl.Cl.N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC JROGBPMEKVAPEH-GXGBFOEMSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000005519 fluorenylmethyloxycarbonyl group Chemical group 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000012145 high-salt buffer Substances 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- YSLDOTFAFZJPOC-UHFFFAOYSA-N hydron;methyl 6-aminohexanoate;chloride Chemical compound Cl.COC(=O)CCCCCN YSLDOTFAFZJPOC-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229960003786 inosine Drugs 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- IYUKFAFDFHZKPI-DFWYDOINSA-N methyl (2s)-2-aminopropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@H](C)N IYUKFAFDFHZKPI-DFWYDOINSA-N 0.000 description 1
- CHJAAJCKWCSRDQ-UHFFFAOYSA-N methyl 2-[2-aminoethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate Chemical compound COC(=O)CN(CCN)C(=O)OC(C)(C)C CHJAAJCKWCSRDQ-UHFFFAOYSA-N 0.000 description 1
- HTWDPJYPCXBPFU-UHFFFAOYSA-N methyl 2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]acetate Chemical compound CC(C)(C)OC(=O)NCCCN(CC(=O)OC)C(=O)CN1C=C(C)C(=O)NC1=O HTWDPJYPCXBPFU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006357 methylene carbonyl group Chemical group [H]C([H])([*:1])C([*:2])=O 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical class [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- HRYDKWQESARUIH-UHFFFAOYSA-N n-(6-aminohexyl)-4-nitrobenzamide Chemical compound NCCCCCCNC(=O)C1=CC=C([N+]([O-])=O)C=C1 HRYDKWQESARUIH-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000007899 nucleic acid hybridization Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229940124276 oligodeoxyribonucleotide Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000656 polylysine Chemical group 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UIDUKLCLJMXFEO-UHFFFAOYSA-N propylsilane Chemical compound CCC[SiH3] UIDUKLCLJMXFEO-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 239000012070 reactive reagent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 125000006853 reporter group Chemical group 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003836 solid-state method Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- OWAMQHJPVUGZSB-UHFFFAOYSA-N tert-butyl n-(2,3-dihydroxypropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC(O)CO OWAMQHJPVUGZSB-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
- C07K14/003—Peptide-nucleic acids (PNAs)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6813—Hybridisation assays
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6813—Hybridisation assays
- C12Q1/6832—Enhancement of hybridisation reaction
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6869—Methods for sequencing
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- General Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Peptides Or Proteins (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Polyamides (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK98791 | 1991-05-24 | ||
DK98691 | 1991-05-24 | ||
DK98691A DK98691D0 (da) | 1991-05-24 | 1991-05-24 | Oligonucleotid-analoge betegnet pna, monomere synthoner og fremgangsmaade til fremstilling deraf samt anvendelser deraf |
DK98791A DK98791D0 (da) | 1991-05-24 | 1991-05-24 | Fremgangsmaade til sekvensspecifik genkendelse af et dobbeltstrenget polynucleotid |
DK92510A DK51092D0 (da) | 1991-05-24 | 1992-04-15 | Oligonucleotid-analoge betegnet pna, monomere synthoner og fremgangsmaade til fremstilling deraf samt anvendelser deraf |
DK51092 | 1992-04-15 | ||
PCT/EP1992/001220 WO1992020703A1 (en) | 1991-05-24 | 1992-05-22 | The use of nucleic acid analogues in diagnostics and analytical procedures |
EP9201220 | 1992-05-22 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI935208A0 FI935208A0 (fi) | 1993-11-23 |
FI935208A FI935208A (fi) | 1993-11-23 |
FI118424B true FI118424B (fi) | 2007-11-15 |
Family
ID=27220741
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI935208A FI118424B (fi) | 1991-05-24 | 1993-11-23 | Nukleiinihappoanalogit ja niiden käyttö diagnostisissa ja analyyttisissä toimenpiteissä |
Country Status (16)
Country | Link |
---|---|
US (11) | US6395474B1 (ja) |
EP (5) | EP1162206A3 (ja) |
JP (6) | JP2758988B2 (ja) |
KR (1) | KR0133131B1 (ja) |
AT (3) | ATE205504T1 (ja) |
AU (2) | AU666480B2 (ja) |
BR (1) | BR9206049A (ja) |
CA (2) | CA2109320C (ja) |
DE (2) | DE69220946T2 (ja) |
DK (3) | DK51092D0 (ja) |
ES (2) | ES2164052T3 (ja) |
FI (1) | FI118424B (ja) |
GR (1) | GR3025018T3 (ja) |
HU (1) | HU221003B1 (ja) |
NO (2) | NO312516B1 (ja) |
WO (2) | WO1992020703A1 (ja) |
Families Citing this family (361)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5852182A (en) * | 1990-01-11 | 1998-12-22 | Isis Pharmaceuticals Inc. | Thiol-derivatized oligonucleosides |
WO1993013121A1 (en) * | 1991-12-24 | 1993-07-08 | Isis Pharmaceuticals, Inc. | Gapped 2' modified oligonucleotides |
US5783682A (en) * | 1990-07-27 | 1998-07-21 | Isis Pharmaceuticals, Inc. | Oligonucleotide mimics having nitrogen-containing linkages |
US6228982B1 (en) * | 1992-05-22 | 2001-05-08 | Benget Norden | Double-stranded peptide nucleic acids |
DK51092D0 (da) | 1991-05-24 | 1992-04-15 | Ole Buchardt | Oligonucleotid-analoge betegnet pna, monomere synthoner og fremgangsmaade til fremstilling deraf samt anvendelser deraf |
US5641625A (en) * | 1992-05-22 | 1997-06-24 | Isis Pharmaceuticals, Inc. | Cleaving double-stranded DNA with peptide nucleic acids |
US6713602B1 (en) * | 1991-05-24 | 2004-03-30 | Ole Buchardt | Synthetic procedures for peptide nucleic acids |
US5714331A (en) * | 1991-05-24 | 1998-02-03 | Buchardt, Deceased; Ole | Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility |
US5539082A (en) * | 1993-04-26 | 1996-07-23 | Nielsen; Peter E. | Peptide nucleic acids |
US6441130B1 (en) | 1991-05-24 | 2002-08-27 | Isis Pharmaceuticals, Inc. | Linked peptide nucleic acids |
US6451968B1 (en) * | 1991-05-24 | 2002-09-17 | Isis Pharmaceuticals, Inc. | Peptide nucleic acids |
US5719262A (en) * | 1993-11-22 | 1998-02-17 | Buchardt, Deceased; Ole | Peptide nucleic acids having amino acid side chains |
US7223833B1 (en) * | 1991-05-24 | 2007-05-29 | Isis Pharmaceuticals, Inc. | Peptide nucleic acid conjugates |
US5766855A (en) * | 1991-05-24 | 1998-06-16 | Buchardt, Deceased; Ole | Peptide nucleic acids having enhanced binding affinity and sequence specificity |
US6414112B1 (en) | 1991-05-24 | 2002-07-02 | Ole Buchardt | Peptide nucleic acids having 2,6-diaminopurine nucleobases |
WO1993012135A1 (en) | 1991-12-12 | 1993-06-24 | Gilead Sciences, Inc. | Nuclease stable and binding competent oligomers and methods for their use |
MX9207334A (es) * | 1991-12-18 | 1993-08-01 | Glaxo Inc | Acidos nucleicos peptidicos y formulacion farma- ceutica que los contiene |
US6277603B1 (en) | 1991-12-24 | 2001-08-21 | Isis Pharmaceuticals, Inc. | PNA-DNA-PNA chimeric macromolecules |
US5700922A (en) * | 1991-12-24 | 1997-12-23 | Isis Pharmaceuticals, Inc. | PNA-DNA-PNA chimeric macromolecules |
US6033884A (en) * | 1992-03-20 | 2000-03-07 | Baylor College Of Medicine | Nucleic acid transporter systems and methods of use |
US6770738B1 (en) | 1992-05-22 | 2004-08-03 | Isis Pharmaceuticals, Inc. | Higher order structure and binding of peptide nucleic acids |
GB9211979D0 (en) * | 1992-06-05 | 1992-07-15 | Buchard Ole | Uses of nucleic acid analogues |
US6350853B1 (en) | 1993-04-26 | 2002-02-26 | Peter E. Nielsen | Conjugated peptide nucleic acids having enhanced cellular uptake |
US7825215B1 (en) | 1993-04-26 | 2010-11-02 | Peter E. Nielsen | Substituted nucleic acid mimics |
GB9311386D0 (en) * | 1993-06-02 | 1993-07-21 | Pna Diagnostics As | Nucleic acid analogue assay procedures |
AU7206794A (en) * | 1993-06-11 | 1995-01-03 | Isis Pharmaceuticals, Inc. | Oligomers for modulating ras oncogene |
WO1995004748A1 (en) * | 1993-08-09 | 1995-02-16 | Isis Pharmaceuticals, Inc. | Oligomers for modulating viral processes |
US5527675A (en) * | 1993-08-20 | 1996-06-18 | Millipore Corporation | Method for degradation and sequencing of polymers which sequentially eliminate terminal residues |
DE4331012A1 (de) * | 1993-09-13 | 1995-03-16 | Bayer Ag | Nukleinsäuren-bindende Oligomere mit N-Verzweigung für Therapie und Diagnostik |
DE4331011A1 (de) * | 1993-09-13 | 1995-03-16 | Bayer Ag | Nukleinsäuren-bindende Oligomere mit C-Verzweigung für Therapie und Diagnostik |
EP0720615B1 (en) * | 1993-09-21 | 2000-07-26 | Amersham Pharmacia Biotech UK Limited | Elongation, amplification and sequence determination using a chimeric oligonucleotide |
US6710164B1 (en) | 1993-11-22 | 2004-03-23 | Peter E. Nielsen | Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility |
GB2284209A (en) | 1993-11-25 | 1995-05-31 | Ole Buchardt | Nucleic acid analogue-induced transcription of RNA from a double-stranded DNA template |
GB2284208A (en) * | 1993-11-25 | 1995-05-31 | Pna Diagnostics As | Nucleic acid analogues with a chelating functionality for metal ions |
GB2289677A (en) * | 1993-12-06 | 1995-11-29 | Pna Diagnostics As | Labelling of nucleic acid analogue-peptide chimerae |
GB2285445A (en) * | 1993-12-06 | 1995-07-12 | Pna Diagnostics As | Protecting nucleic acids and methods of analysis |
US6133444A (en) * | 1993-12-22 | 2000-10-17 | Perseptive Biosystems, Inc. | Synthons for the synthesis and deprotection of peptide nucleic acids under mild conditions |
WO1995017403A1 (en) * | 1993-12-22 | 1995-06-29 | Perseptive Biosystems, Inc. | Guanine synthons for peptide nucleic acid synthesis and method for production |
DK145493D0 (da) * | 1993-12-23 | 1993-12-23 | Dako As | Antistof |
US5539083A (en) * | 1994-02-23 | 1996-07-23 | Isis Pharmaceuticals, Inc. | Peptide nucleic acid combinatorial libraries and improved methods of synthesis |
DE4408533A1 (de) * | 1994-03-14 | 1995-09-28 | Hoechst Ag | PNA-Synthese unter Verwendung einer basenlabilen Amino-Schutzgruppe |
US6919441B2 (en) | 1994-03-14 | 2005-07-19 | Aventis Pharma Deutschland Gmbh | Polyamide-oligonucleotide derivatives, their preparation and use |
DE4408534A1 (de) * | 1994-03-14 | 1995-09-28 | Hoechst Ag | Substituierte N-Ethyl-Glycinderivate zur Herstellung von PNA und PNA-/DNA-Hybriden |
DE4408528A1 (de) * | 1994-03-14 | 1995-09-28 | Hoechst Ag | Peptid-Oligonucleotid-Derivate, deren Herstellung und Verwendung |
DE4408531A1 (de) * | 1994-03-14 | 1995-09-28 | Hoechst Ag | PNA-Synthese unter Verwendung einer gegen schwache Säuren labilen Amino-Schutzgruppe |
WO1995029921A1 (en) * | 1994-04-29 | 1995-11-09 | Perseptive Biosystems, Inc. | Activated esters of 1-phenylpyrazolin-5-one for labelling amine-functionalized molecules |
EP0760008A1 (en) | 1994-05-19 | 1997-03-05 | Dako A/S | Pna probes for detection of neisseria gonorrhoeae and chlamydia trachomatis |
US5629152A (en) * | 1994-08-01 | 1997-05-13 | Isis Pharmaceuticals, Inc. | Trisubstituted β-lactams and oligo β-lactamamides |
DE4427980A1 (de) * | 1994-08-08 | 1996-02-15 | Bayer Ag | Nukleinsäuren-bindende Oligomere für Therapie und Diagnostik |
US6558633B1 (en) | 1994-09-21 | 2003-05-06 | Isis Pharmaceuticals, Inc. | Chemical reaction apparatus and methods |
ATE222589T1 (de) * | 1994-10-06 | 2002-09-15 | Isis Pharmaceuticals Inc | Peptid-nukleinsäure-konjugate |
US5629178A (en) * | 1994-10-28 | 1997-05-13 | Genetics & Ivf Institute | Method for enhancing amplification in the polymerase chain reaction employing peptide nucleic acid (PNA) |
UA48150C2 (uk) * | 1994-11-02 | 2002-08-15 | Ай-Сі-Ен Фармасьютикалз | Похідні амінокислот або аміноспиртів, олігонуклеотид |
EP0792283A1 (en) * | 1994-11-14 | 1997-09-03 | Chiron Corporation | SYNTHESIS OF PEPTIDE NUCLEIC ACIDS (PNAs) AND ANALOGUES VIA SUBMONOMER APPROACH |
EP0795032A2 (en) * | 1994-12-22 | 1997-09-17 | Abbott Laboratories | Methods of immobilizing oligonucleotides to solid support materials and methods of using support bound oligonucleotides |
US6475721B2 (en) | 1995-03-04 | 2002-11-05 | Boston Probes, Inc. | Sequence specific detection of nucleic acids using a solid carrier bound with nucleic acid analog probes |
EP0815259B1 (en) * | 1995-03-04 | 2001-05-23 | PNA Diagnostics A/S | Modulation of the binding properties of nucleic acid binding partners |
US6465650B1 (en) | 1995-03-13 | 2002-10-15 | Aventis Pharma Deutschland Gmbh | Substituted N-ethylglycine derivatives for preparing PNA and PNA/DNA hybrids |
EP0840741B1 (en) | 1995-06-07 | 2004-04-28 | Perseptive Biosystems, Inc. | Pna-dna chimeras and pna synthons for their preparation |
JPH11507352A (ja) | 1995-06-07 | 1999-06-29 | ジンタ・インコーポレイテッド | 新規カルバメート基本カチオン性脂質 |
EP0837884A2 (en) * | 1995-06-22 | 1998-04-29 | Dako A/S | Recombinant antibody capable of binding to pna/nucleic acid complexes |
WO1996014341A1 (en) * | 1995-06-22 | 1996-05-17 | Dako A/S | Monoclonal antibody capable of binding to pna/nucleic acid complexes |
GB9519299D0 (en) * | 1995-09-21 | 1995-11-22 | Farrar Gwyneth J | Genetic strategy |
JPH11512617A (ja) * | 1995-10-06 | 1999-11-02 | パーセプテイブ・バイオシステムズ・インコーポレイテツド | ペプチド核酸プローブを用いるハイブリダイゼーション分析のための方法、装置及びキット |
EP1477572A3 (en) * | 1995-10-06 | 2006-02-15 | Perseptive Biosystems, Inc. | Methods and kit for hybridization analysis using peptide nucleic acid probes |
EP0870055B1 (en) | 1995-10-12 | 2007-05-16 | LANSDORP, Peter, M. | Method for detecting multiple copies of a repeat sequence in a nucleic acid molecule |
US6001966A (en) * | 1995-10-19 | 1999-12-14 | Proligo Llc | Method for solution phase synthesis of oligonucleotides and peptides |
US5874532A (en) * | 1997-01-08 | 1999-02-23 | Nexstar Pharmaceuticals, Inc. | Method for solution phase synthesis of oligonucleotides and peptides |
WO1997014793A1 (en) * | 1995-10-20 | 1997-04-24 | Trustees Of Boston University | Nucleic acid clamps |
WO1997018325A1 (en) * | 1995-11-16 | 1997-05-22 | Dako A/S | In situ hybridization to detect specific nucleic acid sequences in eucaryotic samples |
US5888733A (en) * | 1995-11-16 | 1999-03-30 | Dako A/S | In situ hybridization to detect specific nucleic acid sequences in eucaryotic samples |
CA2190430A1 (en) * | 1995-12-12 | 1997-06-13 | Margret Barbara Basinski | Method for measuring genetic messages |
US6180767B1 (en) | 1996-01-11 | 2001-01-30 | Thomas Jefferson University | Peptide nucleic acid conjugates |
US20030069195A1 (en) * | 1996-03-01 | 2003-04-10 | Farrar Gwenyth Jane | Suppression of polymorphic alleles |
US6020126A (en) * | 1996-03-21 | 2000-02-01 | Hsc, Reasearch And Development Limited Partnership | Rapid genetic screening method |
WO1997036005A1 (en) * | 1996-03-26 | 1997-10-02 | Lynx Therapeutics, Inc. | Oligonucleotide treatments and compositions for human melanoma |
US8551970B2 (en) * | 1996-04-02 | 2013-10-08 | Optigen Patents Limited | Genetic suppression and replacement |
US20040234999A1 (en) * | 1996-04-02 | 2004-11-25 | Farrar Gwenyth Jane | Genetic suppression and replacement |
GB9606961D0 (en) | 1996-04-02 | 1996-06-05 | Farrar Gwyneth J | Genetic strategy III |
GB9608803D0 (en) * | 1996-04-27 | 1996-07-03 | Univ Newcastle | Mitochondrial dna defects |
SE506700C2 (sv) * | 1996-05-31 | 1998-02-02 | Mikael Kubista | Sond och förfaranden för analys av nukleinsyra |
US5898031A (en) | 1996-06-06 | 1999-04-27 | Isis Pharmaceuticals, Inc. | Oligoribonucleotides for cleaving RNA |
US20050032068A1 (en) * | 2002-11-05 | 2005-02-10 | Prakash Thazha P. | Sugar and backbone-surrogate-containing oligomeric compounds and compositions for use in gene modulation |
US7812149B2 (en) | 1996-06-06 | 2010-10-12 | Isis Pharmaceuticals, Inc. | 2′-Fluoro substituted oligomeric compounds and compositions for use in gene modulations |
US20050118605A9 (en) * | 1996-06-06 | 2005-06-02 | Baker Brenda F. | Oligomeric compounds having modified bases for binding to adenine and guanine and their use in gene modulation |
US20050042647A1 (en) * | 1996-06-06 | 2005-02-24 | Baker Brenda F. | Phosphorous-linked oligomeric compounds and their use in gene modulation |
US20040171030A1 (en) * | 1996-06-06 | 2004-09-02 | Baker Brenda F. | Oligomeric compounds having modified bases for binding to cytosine and uracil or thymine and their use in gene modulation |
US20040266706A1 (en) * | 2002-11-05 | 2004-12-30 | Muthiah Manoharan | Cross-linked oligomeric compounds and their use in gene modulation |
US9096636B2 (en) * | 1996-06-06 | 2015-08-04 | Isis Pharmaceuticals, Inc. | Chimeric oligomeric compounds and their use in gene modulation |
CA2261566A1 (en) * | 1996-07-24 | 1998-01-29 | Buchardt, Dorte | Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility |
US5858683A (en) * | 1996-08-30 | 1999-01-12 | Matritech, Inc. | Methods and compositions for the detection of cervical cancer |
DE19637339A1 (de) * | 1996-09-13 | 1998-03-19 | Hoechst Ag | Verfahren zur Amplifikation von Nukleinsäuren |
US5919638A (en) * | 1996-10-08 | 1999-07-06 | Abbott Laboratories | Reagents and methods useful for detecting prostate tumors |
US5908845A (en) * | 1996-10-30 | 1999-06-01 | Segev; David | Polyether nucleic acids |
US20050202499A1 (en) | 1996-10-31 | 2005-09-15 | Billing-Medel Patricia A. | Reagents and methods useful for detecting diseases of the breast |
US6444202B1 (en) | 1996-11-25 | 2002-09-03 | Bundesrepublic Deutschland, Vertreten Durch Den Bundesminister Fur Gesundheit | Processed polypeptides with IL-16 activity, processes for their production and their use |
WO1998037232A2 (en) * | 1997-02-24 | 1998-08-27 | Georgia Tech Research Corporation | Method for determining a nucleic acid |
US6117973A (en) * | 1997-02-24 | 2000-09-12 | Georgia Tech Research Corp. | PNA monomers with electron donor or acceptor |
US5932711A (en) * | 1997-03-05 | 1999-08-03 | Mosaic Technologies, Inc. | Nucleic acid-containing polymerizable complex |
US6692912B1 (en) * | 1997-03-05 | 2004-02-17 | Matrix Technologies Corporation | Nucleic acid-containing polymerizable complex |
US6015887A (en) * | 1997-04-11 | 2000-01-18 | Isis Pharmaceuticals, Inc. | Chiral peptide nucleic acids and methods for preparing same |
SE522077C2 (sv) * | 1997-09-05 | 2004-01-13 | Lightup Technologies Ab | Förfarande att välja sekvens hos sond för nukleinsyrahybridisering |
US6617422B1 (en) | 1997-05-23 | 2003-09-09 | Peter Nielsen | Peptide nucleic acid monomers and oligomers |
CA2291839A1 (en) * | 1997-05-28 | 1998-12-03 | Peter E. Nielsen | Conjugated peptide nucleic acids having enhanced cellular uptake |
JPH1149797A (ja) * | 1997-05-30 | 1999-02-23 | Boehringer Mannheim Gmbh | 二次元または三次元幾何学構造体 |
US5962665A (en) | 1997-06-16 | 1999-10-05 | Abbott Laboratories | Nucleic acid primers and probes for detecting HIV-1 and HIV-2 |
WO1998058256A1 (en) * | 1997-06-16 | 1998-12-23 | The University Of North Carolina At Chapel Hill | PEPTIDO OLIGONUCLEOTIDES (PONs) AND THEIR COMBINATORIAL LIBRARIES |
JPH11332595A (ja) * | 1997-07-09 | 1999-12-07 | Masao Karube | プローブpnaによるdnaの検出方法 |
EP0897991B1 (en) * | 1997-08-22 | 2004-12-08 | PNA Diagnostics ApS | Small Triplex Forming PNA Oligos |
US6300318B1 (en) | 1997-09-16 | 2001-10-09 | Peter E. Nielsen | Antibacterial and antibiotic methods using peptide nucleic acids and pharmaceutical compositions therefor |
DE19741739B4 (de) * | 1997-09-22 | 2006-04-27 | Nanogen Recognomics Gmbh | Supramolekulares Paarungssystem, dessen Herstellung und Verwendung |
US6989270B1 (en) | 1997-10-17 | 2006-01-24 | Mayo Foundation For Medical Education And Research | Using polyamide nucleic acid oligomers to engender a biological response |
US6723560B2 (en) | 1998-10-08 | 2004-04-20 | Mayo Foundation For Medical Education And Research | Using polyamide nucleic acid oligomers to engender a biological response |
US6028183A (en) * | 1997-11-07 | 2000-02-22 | Gilead Sciences, Inc. | Pyrimidine derivatives and oligonucleotides containing same |
US6007992A (en) * | 1997-11-10 | 1999-12-28 | Gilead Sciences, Inc. | Pyrimidine derivatives for labeled binding partners |
DE19816550A1 (de) | 1997-12-24 | 1999-06-24 | Roche Diagnostics Gmbh | Universell verwendbarer Aufbau eines Analysenelements und dessen Einsatz zur Analytbestimmung |
US6030997A (en) * | 1998-01-21 | 2000-02-29 | Eilat; Eran | Acid labile prodrugs |
US6326479B1 (en) * | 1998-01-27 | 2001-12-04 | Boston Probes, Inc. | Synthetic polymers and methods, kits or compositions for modulating the solubility of same |
WO1999049293A2 (en) * | 1998-03-24 | 1999-09-30 | Boston Probes, Inc. | Methods, kits and compositions pertaining to detection complexes |
US20040063618A1 (en) * | 2002-09-30 | 2004-04-01 | Muthiah Manoharan | Peptide nucleic acids having improved uptake and tissue distribution |
US20040186071A1 (en) * | 1998-04-13 | 2004-09-23 | Bennett C. Frank | Antisense modulation of CD40 expression |
DE19824900B4 (de) | 1998-06-04 | 2006-05-04 | Roche Diagnostics Gmbh | DNA-Nachweis über einen Strangreassoziationskomplex |
US6664045B1 (en) * | 1998-06-18 | 2003-12-16 | Boston Probes, Inc. | PNA probes, probe sets, methods and kits pertaining to the detection of microorganisms |
EP1095054B1 (en) | 1998-07-09 | 2006-10-25 | Biocept, Inc. | Method of using an improved peptide nucleic acid universal library to optimize dna sequence hybridation |
US6548651B1 (en) | 1998-11-11 | 2003-04-15 | Pantheco A/S | Modified peptide nucleic acid (PNA) molecules |
KR20020007332A (ko) | 1999-03-18 | 2002-01-26 | 추후제출 | 일 단계 샘플 제조 및 복합적인 생물학적 샘플에서 핵산의검출 |
US20020049173A1 (en) * | 1999-03-26 | 2002-04-25 | Bennett C. Frank | Alteration of cellular behavior by antisense modulation of mRNA processing |
US6824866B1 (en) | 1999-04-08 | 2004-11-30 | Affymetrix, Inc. | Porous silica substrates for polymer synthesis and assays |
DE19927783A1 (de) * | 1999-06-18 | 2000-12-21 | Roche Diagnostics Gmbh | Element zur Bestimmung eines Analyts in einer Flüssigkeit, entsprechendes Bestimmungsverfahren unter Verwendung des Elementes sowie Kit zur Bestimmugn eines Analyts |
AU6629200A (en) * | 1999-08-25 | 2001-03-19 | Philip P Garner | Alpha-helical peptide nucleic acid alpha-pna |
CA2384407C (en) | 1999-08-30 | 2009-10-20 | Roche Diagnostics Gmbh | 2-azapurine compounds and their use |
US6348583B1 (en) * | 1999-08-30 | 2002-02-19 | Bio-Rad Laboratories, Inc. | Poly(ether-thioether), poly(ether-sulfoxide) and poly(ether-sulfone) nucleic acids |
US6994964B1 (en) | 1999-09-01 | 2006-02-07 | Affymetrix, Inc. | Macromolecular arrays on polymeric brushes and methods for preparing the same |
US6660845B1 (en) * | 1999-11-23 | 2003-12-09 | Epoch Biosciences, Inc. | Non-aggregating, non-quenching oligomers comprising nucleotide analogues; methods of synthesis and use thereof |
CA2398901C (en) | 2000-02-10 | 2010-11-16 | Massachusetts Eye And Ear Infirmary | Methods and compositions for treating conditions of the eye |
WO2001068673A1 (en) * | 2000-03-14 | 2001-09-20 | Active Motif | Oligonucleotide analogues, methods of synthesis and methods of use |
US6962906B2 (en) | 2000-03-14 | 2005-11-08 | Active Motif | Oligonucleotide analogues, methods of synthesis and methods of use |
US20040014644A1 (en) * | 2000-03-14 | 2004-01-22 | Vladimir Efimov | Oligonucleotide analogues and methods of use for modulating gene expression |
US6936443B2 (en) | 2000-04-03 | 2005-08-30 | Cytyc Corporation | Detection and typing of human papillomavirus using PNA probes |
US20020155427A1 (en) | 2000-04-03 | 2002-10-24 | Cohenford Menashi A. | Detection and typing of human papillomavirus using PNA probes |
US7211381B1 (en) | 2000-04-04 | 2007-05-01 | Abbott Laboratories | β2 andrenergic polymorphism detection |
US6593092B2 (en) | 2000-04-04 | 2003-07-15 | Abbott Laboratories | Beta 2 adrenergic polymorphism detection |
DE10019135A1 (de) | 2000-04-18 | 2001-10-31 | Aventis Pharma Gmbh | Polyamidnukleinsäure-Derivate, Mittel und Verfahren zu ihrer Herstellung |
DE10019136A1 (de) | 2000-04-18 | 2001-10-31 | Aventis Pharma Gmbh | Polyamidnukleinsäure-Derivate, Mittel und Verfahren zu ihrer Herstellung |
US6887664B2 (en) | 2000-06-06 | 2005-05-03 | Applera Corporation | Asynchronous primed PCR |
EP1307469B1 (en) | 2000-08-03 | 2008-01-23 | Boehringer Mannheim Gmbh | Nucleic acid binding compounds containing pyrazolo¬3,4-d pyrimidine analogues of purin-2,6-diamine and their uses |
US20030114410A1 (en) | 2000-08-08 | 2003-06-19 | Technion Research And Development Foundation Ltd. | Pharmaceutical compositions and methods useful for modulating angiogenesis and inhibiting metastasis and tumor fibrosis |
ATE493147T1 (de) | 2000-08-08 | 2011-01-15 | Technion Res & Dev Foundation | Pharmazeutische zusammensetzungen und methoden nützlich zur behandlung von krebs oder leberfibrose |
US7183394B1 (en) * | 2000-08-11 | 2007-02-27 | Garner Philip P | Helical nucleopeptides |
US20050054836A1 (en) * | 2000-11-09 | 2005-03-10 | Cold Spring Harbor Laboratory | Chimeric molecules to modulate gene expression |
JPWO2002051797A1 (ja) * | 2000-12-26 | 2004-09-02 | 池田 壽文 | 新規な機能性ペプチド核酸モノマーとその製法 |
ATE465739T1 (de) | 2001-01-29 | 2010-05-15 | Bio Rad Laboratories | Nukleinsäurederivative |
GB0102388D0 (en) * | 2001-01-31 | 2001-03-14 | Secr Defence | Polymers |
EP1236804A1 (en) | 2001-03-02 | 2002-09-04 | Boehringer Mannheim Gmbh | A method for determination of a nucleic acid using a control |
DK1412517T3 (da) | 2001-03-09 | 2007-03-05 | Boston Probes Inc | Fremgangsmåder, kits og sammensætninger af kombinationsoligomerer |
EP2277897A1 (en) | 2001-04-16 | 2011-01-26 | Wyeth Holdings Corporation | Streptococcus pneumoniae open reading frames encoding polypeptide antigens and uses thereof |
AU2002257284A1 (en) | 2001-05-18 | 2002-12-03 | Boston Probes, Inc. | Pna probes, probe sets, methods and kits pertaining to the detection of candida |
US20030207804A1 (en) * | 2001-05-25 | 2003-11-06 | Muthiah Manoharan | Modified peptide nucleic acids |
US7053195B1 (en) | 2001-06-12 | 2006-05-30 | Syngenta Participatious Ag | Locked nucleic acid containing heteropolymers and related methods |
EP1925672A1 (en) | 2001-06-22 | 2008-05-28 | Syngeta Participations AG | Abiotic stress responsive polynucleotides and polypeptides |
US6921812B1 (en) | 2001-07-03 | 2005-07-26 | Isis Pharmaceuticals, Inc. | Methods of modulating pharmacokinetics of oligonucleotides |
US6852491B2 (en) | 2001-09-04 | 2005-02-08 | Abbott Laboratories | Amplification and detection reagents for HIV-1 |
EP1432826B1 (en) * | 2001-09-24 | 2012-12-12 | Life Technologies Corporation | Methods, kits and compositions pertaining to the suppression of detectable probe binding to randomly distributed repeat sequences in genomic nucleic acid |
EP1442137A4 (en) | 2001-11-07 | 2005-08-31 | Applera Corp | UNIVERSAL NUCLEOTIDES FOR NUCLEIC ACID ANALYSIS |
AU2002362013B2 (en) | 2001-11-21 | 2008-04-24 | Applied Biosystems, Llc. | Digital assay |
KR100464261B1 (ko) | 2002-01-24 | 2005-01-03 | 주식회사 파나진 | Pna 올리고머를 합성하기 위한 신규한 단량체 및 그의제조방법 |
JP2005516300A (ja) | 2002-01-25 | 2005-06-02 | アプレラ コーポレイション | 製品およびサービスに対する注文を発注し、受理し、および充足する方法 |
JP2005520554A (ja) * | 2002-03-21 | 2005-07-14 | ボストン プローブス,インコーポレイテッド | BacillusAnthracisの検出に関するPNAオリゴマー、オリゴマーセット、方法およびキット |
US20030211509A1 (en) * | 2002-03-26 | 2003-11-13 | Wiley Steven R. | TNF-delta ligand and uses thereof |
US7052840B2 (en) | 2002-04-03 | 2006-05-30 | Capitol Genomix, Inc. | Reversible association of nucleic acid with a carboxylated substrate |
US7026120B2 (en) | 2002-04-15 | 2006-04-11 | Abbott Laboratories | Probes for detecting tumor cells |
KR20030084444A (ko) | 2002-04-26 | 2003-11-01 | 주식회사 파나진 | Pna 올리고머를 합성하기 위한 신규한 단량체 및 그의제조방법 |
US7015317B2 (en) | 2002-05-02 | 2006-03-21 | Abbott Laboratories | Polynucleotides for the detection and quantification of hepatitis B virus nucleic acids |
JP2006507798A (ja) * | 2002-05-17 | 2006-03-09 | アプレラ コーポレイション | Listeriaの決定に関するPNAプローブ、プローブセット、方法およびキット |
US20030220844A1 (en) * | 2002-05-24 | 2003-11-27 | Marnellos Georgios E. | Method and system for purchasing genetic data |
JP4588451B2 (ja) * | 2002-09-08 | 2010-12-01 | アプライド バイオシステムズ, エルエルシー | Pnaダイマーおよびpnaオリゴマー合成に関する方法、組成物およびライブラリー |
AU2003304278B2 (en) * | 2002-10-16 | 2009-03-12 | Board Of Regents Of The University Of Texas System | Bead bound combinatorial oligonucleoside phosphorothioate and phosphorodithioate aptamer libraries |
EP1552025A4 (en) * | 2002-10-18 | 2006-12-13 | Cylene Pharmaceuticals Inc | METHODS FOR IDENTIFYING TARGETED ANTIVIRAL MOLECULES TO QUADRUPLEX STRUCTURES |
AU2003291753B2 (en) * | 2002-11-05 | 2010-07-08 | Isis Pharmaceuticals, Inc. | Polycyclic sugar surrogate-containing oligomeric compounds and compositions for use in gene modulation |
US9150605B2 (en) * | 2002-11-05 | 2015-10-06 | Isis Pharmaceuticals, Inc. | Compositions comprising alternating 2′-modified nucleosides for use in gene modulation |
EP1560840B1 (en) | 2002-11-05 | 2015-05-06 | Isis Pharmaceuticals, Inc. | Compositions comprising alternating 2'-modified nucleosides for use in gene modulation |
US9150606B2 (en) * | 2002-11-05 | 2015-10-06 | Isis Pharmaceuticals, Inc. | Compositions comprising alternating 2'-modified nucleosides for use in gene modulation |
US7807802B2 (en) | 2002-11-12 | 2010-10-05 | Abbott Lab | Polynucleotides for the amplification and detection of Chlamydia trachomatis and Neisseria gonorrhoeae |
HUE033832T2 (en) | 2002-11-15 | 2018-01-29 | Idenix Pharmaceuticals Llc | 2'-methyl nucleosides in combination with interferon and Flaviviridae mutation |
AU2003294440A1 (en) * | 2002-11-21 | 2004-06-18 | Epicentre Technologies | Methods for using riboprimers for strand displacement replication of target sequences |
US20040259132A1 (en) * | 2002-11-22 | 2004-12-23 | Henrik Stender | Peptide nucleic acid probes for analysis of pseudomonas (sensu stricto) |
EP2112229A3 (en) | 2002-11-25 | 2009-12-02 | Sequenom, Inc. | Methods for identifying risk of breast cancer and treatments thereof |
US7736909B2 (en) | 2003-01-09 | 2010-06-15 | Board Of Regents, The University Of Texas System | Methods and compositions comprising capture agents |
AU2004209401A1 (en) | 2003-01-30 | 2004-08-19 | Applied Biosystems, Llc. | Methods, mixtures, kits and compositions pertaining to analyte determination |
DK1597366T3 (da) * | 2003-02-11 | 2013-02-25 | Antisense Therapeutics Ltd | Modulering af ekspression af insulin-lignende vækstfaktor receptor I |
AU2003900609A0 (en) * | 2003-02-11 | 2003-02-27 | Antisense Therapeutics Ltd | Modulation of insulin like growth factor i receptor expression |
CN100532550C (zh) | 2003-02-21 | 2009-08-26 | 卫材R&D管理有限公司 | 用于变异基因检测的信号扩增方法 |
CA2528843A1 (en) * | 2003-05-20 | 2005-02-24 | Investigen, Inc. | System for detecting polynucleotides |
WO2005012546A2 (en) * | 2003-07-25 | 2005-02-10 | Andreas Braun | Methods for isolating and identifying novel target-specific structuremers for use in the biological sciences |
JPWO2005010181A1 (ja) * | 2003-07-25 | 2007-09-27 | 株式会社クレディアジャパン | 核酸検出方法 |
WO2005016364A1 (en) * | 2003-08-14 | 2005-02-24 | Guthy-Renker Corporation | Skin care composition including hexapeptide complexes and methods of their manufacture |
US20060198800A1 (en) * | 2003-08-14 | 2006-09-07 | Natalie Dilallo | Skin care compositions including hexapeptide complexes and methods of their manufacture |
WO2005074417A2 (en) * | 2003-09-03 | 2005-08-18 | Salk Institute For Biological Studies | Multiple antigen detection assays and reagents |
US20050148087A1 (en) | 2004-01-05 | 2005-07-07 | Applera Corporation | Isobarically labeled analytes and fragment ions derived therefrom |
DE602005027809D1 (de) | 2004-01-07 | 2011-06-16 | Hitachi Chemical Co Ltd | Primer und sonden zum nachweis von hiv |
US8569474B2 (en) | 2004-03-09 | 2013-10-29 | Isis Pharmaceuticals, Inc. | Double stranded constructs comprising one or more short strands hybridized to a longer strand |
ATE399884T1 (de) | 2004-03-24 | 2008-07-15 | Applera Corp | Codierungs- und decodierungsreaktionen zur bestimmung von target-polynukleotiden |
ATE478158T1 (de) | 2004-04-28 | 2010-09-15 | Eisai R&D Man Co Ltd | Hybridisierungsverfahren |
JP2007535966A (ja) * | 2004-05-04 | 2007-12-13 | ダコ デンマーク アクティーゼルスカブ | 染色体異常を検出するための方法 |
US8394947B2 (en) | 2004-06-03 | 2013-03-12 | Isis Pharmaceuticals, Inc. | Positionally modified siRNA constructs |
WO2005121372A2 (en) * | 2004-06-03 | 2005-12-22 | Isis Pharmaceuticals, Inc. | Double strand compositions comprising differentially modified strands for use in gene modulation |
US20060057611A1 (en) | 2004-06-30 | 2006-03-16 | Applera Corporation | Log-linear amplification |
US7884086B2 (en) | 2004-09-08 | 2011-02-08 | Isis Pharmaceuticals, Inc. | Conjugates for use in hepatocyte free uptake assays |
US7306785B2 (en) * | 2004-09-23 | 2007-12-11 | General Electric Company | Multifunctional cross-bridged tetraaza macrocyclic compounds and methods of making and using |
WO2007044031A2 (en) * | 2004-12-06 | 2007-04-19 | Bioveris Corporation | Methods and compositions for detecting bacillus anthracis |
KR20070093992A (ko) * | 2004-12-11 | 2007-09-19 | 사이토제닉, 인크. | 고품질 핵산의 무세포 생합성 및 그것의 사용 |
EP1836319B1 (en) | 2005-01-06 | 2012-09-19 | Life Technologies Corporation | Polypeptides having nucleic acid binding activity and methods for nucleic acid amplification |
US20090264635A1 (en) | 2005-03-25 | 2009-10-22 | Applera Corporation | Methods and compositions for depleting abundant rna transcripts |
US7229769B2 (en) * | 2005-03-25 | 2007-06-12 | Illumina, Inc. | Compositions and methods for detecting protease activity |
EP1904079A4 (en) | 2005-06-02 | 2009-10-21 | Advandx Inc | PEPTIDE NUCLEIC ACID PROBLEMS FOR THE INVESTIGATION OF MICRO-ORGANISMS |
US8293472B2 (en) | 2005-06-07 | 2012-10-23 | Luminex Corporation | Methods for detection and typing of nucleic acids |
DE602006020577D1 (de) | 2005-07-01 | 2011-04-21 | Dako Denmark As | Monomere und polymere linker zur konjugierung von biologischen molekülen und anderen stoffen |
US20070059713A1 (en) | 2005-09-09 | 2007-03-15 | Lee Jun E | SSB-DNA polymerase fusion proteins |
WO2007056113A2 (en) * | 2005-11-02 | 2007-05-18 | Cylene Pharmaceuticals, Inc. | Methods for targeting quadruplex sequences |
WO2007073149A1 (en) | 2005-12-22 | 2007-06-28 | Keygene N.V. | Alternative nucleotides for improved targeted nucleotide exchange |
US8021839B2 (en) * | 2006-02-24 | 2011-09-20 | Investigen, Inc. | Methods and compositions for detecting polynucleotides |
JPWO2007108378A1 (ja) | 2006-03-15 | 2009-08-06 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | シグナルプローブポリマーの形成方法 |
US10829803B2 (en) | 2006-05-10 | 2020-11-10 | Dxterity Diagnostics Incorporated | Detection of nucleic acid targets using chemically reactive oligonucleotide probes |
US20100196336A1 (en) | 2006-05-23 | 2010-08-05 | Dongsu Park | Modified dendritic cells having enhanced survival and immunogenicity and related compositions and methods |
CN101490551A (zh) | 2006-06-30 | 2009-07-22 | 阿普里拉股份有限公司 | 分析结合相互作用的方法 |
EP2049688B1 (en) | 2006-08-01 | 2018-01-24 | Applied Biosystems, LLC | Detection of analytes and nucleic acids |
US20080096193A1 (en) * | 2006-10-24 | 2008-04-24 | Charles Robert Bupp | Methods and compositions for detecting polynucleotides |
US20080131880A1 (en) * | 2006-11-22 | 2008-06-05 | Bortolin Laura T | PNA-DNA oligomers and methods of use thereof |
EP2099816A1 (en) | 2006-12-04 | 2009-09-16 | Luminex Corporation | Oxocarbonamide peptide nucleic acids and methods of using same |
BRPI0721095B1 (pt) | 2006-12-13 | 2015-09-29 | Luminex Corp | Sistemas e métodos para a análise multíplex de pcr em tempo real |
US9938641B2 (en) * | 2006-12-18 | 2018-04-10 | Fluidigm Corporation | Selection of aptamers based on geometry |
WO2008083261A1 (en) * | 2006-12-29 | 2008-07-10 | Applera Corporation | Systems and methods for detecting nucleic acids |
JP2010514450A (ja) * | 2006-12-29 | 2010-05-06 | アプライド バイオシステムズ インコーポレイテッド | 核酸検出方法及びシステム |
US7803543B2 (en) | 2007-01-19 | 2010-09-28 | Chang Gung University | Methods and kits for the detection of nucleotide mutations using peptide nucleic acid as both PCR clamp and sensor probe |
DK2591795T3 (en) * | 2007-02-23 | 2018-05-07 | Univ New York State Res Found | RNA TARGETING COMPOUNDS AND PROCEDURES FOR PREPARING AND USING THE SAME |
WO2008103702A2 (en) * | 2007-02-23 | 2008-08-28 | Investigen, Inc. | Methods and compositions for rapid light-activated isolation and detection of analytes |
US9260476B2 (en) | 2007-02-23 | 2016-02-16 | The Research Foundation For The State University Of New York | RNA targeting compounds and methods for making and using same |
US9102986B2 (en) | 2007-04-13 | 2015-08-11 | Abbott Molecular Inc. | Primer and probe sequences for detecting Chlamydia trachomatis |
US8097422B2 (en) | 2007-06-20 | 2012-01-17 | Salk Institute For Biological Studies | Kir channel modulators |
EP2167536A1 (en) | 2007-07-03 | 2010-03-31 | Dako Denmark A/S | Mhc multimers, methods for their generation, labeling and use |
IL184627A0 (en) | 2007-07-15 | 2008-12-29 | Technion Res & Dev Foundation | Agents for diagnosing and modulating metastasis and fibrosis as well as inflammation in a mammalian tissue |
ES2402334T3 (es) | 2007-08-02 | 2013-04-30 | Gilead Biologics, Inc | Procedimientos y composiciones para el tratamiento y el diagnóstico de la fibrosis |
SG185315A1 (en) | 2007-10-24 | 2012-11-29 | Eisai R&D Man Co Ltd | Nucleic acid probe, and method of forming probe -polymer |
WO2009057702A1 (ja) | 2007-10-31 | 2009-05-07 | Eisai R & D Management Co., Ltd. | 標的物質検出用ポリマー及び標的物質の検出方法 |
WO2009067628A1 (en) | 2007-11-20 | 2009-05-28 | Applied Biosystems Inc. | Reversible di-nucleotide terminator sequencing |
WO2009067243A2 (en) * | 2007-11-20 | 2009-05-28 | Isis Pharmaceuticals Inc. | Modulation of cd40 expression |
US9605035B2 (en) | 2008-01-10 | 2017-03-28 | Research Development Foundation | Vaccines and diagnostics for the ehrlichioses |
EP4450642A2 (en) | 2008-01-17 | 2024-10-23 | Sequenom, Inc. | Single molecule nucleic acid sequence analysis processes and compositions |
KR101072899B1 (ko) * | 2008-01-21 | 2011-10-17 | 주식회사 파나진 | 아미노산 스페이서가 결합된 펩티드 핵산의 합성 및 그의응용 |
US8709726B2 (en) | 2008-03-11 | 2014-04-29 | Sequenom, Inc. | Nucleic acid-based tests for prenatal gender determination |
KR20090098710A (ko) | 2008-03-14 | 2009-09-17 | 주식회사 씨티아이바이오 | 세포투과성과 핵산 결합력이 좋은 펩타이드 핵산 유도체 |
RU2618868C2 (ru) | 2008-05-27 | 2017-05-11 | Дако Денмарк А/С | Композиции и способы определения хромосомных аберраций с новыми буферами для гибридизации |
US20090312196A1 (en) | 2008-06-13 | 2009-12-17 | Codexis, Inc. | Method of synthesizing polynucleotide variants |
DK3023494T3 (en) | 2008-06-13 | 2019-02-25 | Codexis Inc | PROCEDURE FOR SYNTHESIS OF POLYNUCLEOTIDE VARIETIES |
KR20110059743A (ko) | 2008-09-03 | 2011-06-03 | 난양 테크놀러지컬 유니버시티 | 펩티드 핵산 단량체 및 올리고머 |
US8962247B2 (en) | 2008-09-16 | 2015-02-24 | Sequenom, Inc. | Processes and compositions for methylation-based enrichment of fetal nucleic acid from a maternal sample useful for non invasive prenatal diagnoses |
US8476013B2 (en) | 2008-09-16 | 2013-07-02 | Sequenom, Inc. | Processes and compositions for methylation-based acid enrichment of fetal nucleic acid from a maternal sample useful for non-invasive prenatal diagnoses |
EP3336188B1 (en) | 2008-09-22 | 2020-05-06 | Phio Pharmaceuticals Corp. | Reduced size self-delivering rnai compounds |
EP2342334A4 (en) | 2008-09-29 | 2012-03-14 | Univ Pennsylvania | TARGETED VACCINES ON A TUMOR VASCULAR MARKER |
EP3085794B1 (en) | 2008-10-15 | 2020-03-18 | AXOLABS GmbH | Oligonucleotide detection method |
WO2010054328A2 (en) | 2008-11-07 | 2010-05-14 | Research Development Foundation | Compositions and methods for the inhibition of cripto/grp78 complex formation and signaling |
US8715732B2 (en) * | 2009-01-05 | 2014-05-06 | Cornell University | Nucleic acid hydrogel via rolling circle amplification |
US9107935B2 (en) | 2009-01-06 | 2015-08-18 | Gilead Biologics, Inc. | Chemotherapeutic methods and compositions |
EP2391714B2 (en) | 2009-01-30 | 2019-07-24 | Whitehead Institute for Biomedical Research | Methods for ligation and uses thereof |
US9745574B2 (en) | 2009-02-04 | 2017-08-29 | Rxi Pharmaceuticals Corporation | RNA duplexes with single stranded phosphorothioate nucleotide regions for additional functionality |
US7964355B2 (en) | 2009-02-17 | 2011-06-21 | Investigen, Inc. | Assays based on detection of photobleaching reaction products from dye catalytic complex |
EP2401396B1 (en) | 2009-02-26 | 2016-11-23 | Dako Denmark A/S | Methods for performing a stringent wash step in hybridization applications |
US8063193B2 (en) | 2009-03-27 | 2011-11-22 | Abbott Laboratories | Nucleotide and amino acid sequences encoding an exported protein 1 derived from Plasmodium vivax and uses thereof |
US9976177B2 (en) | 2009-04-01 | 2018-05-22 | Dxterity Diagnostics Incorporated | Chemical ligation dependent probe amplification (CLPA) |
WO2010118243A2 (en) | 2009-04-08 | 2010-10-14 | Genentech, Inc. | Use of il-27 antagonists to treat lupus |
KR20120122869A (ko) | 2009-06-02 | 2012-11-07 | 보드 오브 리전츠, 더 유니버시티 오브 텍사스 시스템 | 신경변성 질환을 갖는 대상에서 항체에 의해 인식되는 소분자의 확인법 |
EP2789689B1 (en) | 2009-06-29 | 2016-04-27 | Luminex Corporation | Chimeric primers with hairpin conformations and methods of using same |
US8614081B2 (en) | 2009-07-23 | 2013-12-24 | Codexis, Inc. | Nitrilase biocatalysts |
DK2462230T3 (en) * | 2009-08-03 | 2015-10-19 | Recombinetics Inc | METHODS AND COMPOSITIONS FOR TARGETED RE-MODIFICATION |
AU2010284036B2 (en) | 2009-08-21 | 2014-12-18 | Gilead Biologics, Inc. | Catalytic domains from lysyl oxidase and LOXL2 |
WO2011047257A1 (en) | 2009-10-16 | 2011-04-21 | The Board Of Regents Of The University Of Texas System | Compositions and methods for producing cyclic peptoid libraries |
CA2781907C (en) | 2009-12-02 | 2019-07-16 | Dako Denmark A/S | Compositions and methods for performing hybridizations with no denaturation |
EP3660165B1 (en) | 2009-12-22 | 2023-01-04 | Sequenom, Inc. | Processes and kits for identifying aneuploidy |
WO2011087789A2 (en) | 2009-12-22 | 2011-07-21 | Becton, Dickinson And Company | Methods for the detection of microorganisms |
RU2615143C2 (ru) | 2010-03-24 | 2017-04-04 | Адвирна | Самодоставляющие PHKi соединения уменьшенного размера |
WO2011133931A1 (en) | 2010-04-22 | 2011-10-27 | Genentech, Inc. | Use of il-27 antagonists for treating inflammatory bowel disease |
MX2017015093A (es) | 2011-01-11 | 2023-03-10 | Seegene Inc | Detección de secuencias de ácido nucleico objetivo mediante ensayo de escisión y extensión del pto. |
KR101569479B1 (ko) | 2011-03-29 | 2015-11-16 | 주식회사 씨젠 | Pto 절단 및 연장-의존적 절단에 의한 타겟 핵산서열의 검출 |
US9193758B2 (en) | 2011-04-08 | 2015-11-24 | Carnegie Mellon University Center For Technology Transfer & Enterprise | Conformationally-preorganized, miniPEG-containing γ-peptide nucleic acids |
CA2834218C (en) | 2011-04-29 | 2021-02-16 | Sequenom, Inc. | Quantification of a minority nucleic acid species using inhibitory oligonucleotides |
MX342067B (es) | 2011-05-04 | 2016-09-09 | Seegene Inc | Detección de secuencias de ácido nucleico objetivo por desdoblamiento e hibridización de oligonucleótido de sonda. |
WO2012158967A1 (en) | 2011-05-17 | 2012-11-22 | Dxterity Diagnostics Incorporated | Methods and compositions for detecting target nucleic acids |
US10662465B2 (en) | 2011-09-30 | 2020-05-26 | Agilent Technologies, Inc. | Hybridization compositions and methods using formamide |
GB201117482D0 (en) | 2011-10-11 | 2011-11-23 | Univ Dundee | Targetiing of miRNA precursors |
US11118226B2 (en) | 2011-10-21 | 2021-09-14 | Agilent Technologies, Inc. | Hybridization compositions and methods |
EP2594942A1 (en) * | 2011-11-16 | 2013-05-22 | Koninklijke Philips Electronics N.V. | Long rigid spacers to enhance binding kinetics in immunoassays |
US20140349879A1 (en) | 2011-12-09 | 2014-11-27 | Eisai R & D Management Co., Ltd. | Method for detecting nucleotide mutation, and detection kit |
ES2930180T3 (es) | 2012-03-02 | 2022-12-07 | Sequenom Inc | Métodos para enriquecer ácido nucleico canceroso a partir de una muestra biológica |
JP5976849B2 (ja) | 2012-03-05 | 2016-08-24 | シージーン アイエヌシー | PTO切断及び伸長アッセイによるターゲット核酸配列でのヌクレオチド変異検出{DetectionofNucleotideVariationonTargetNucleicAcidSequencebyPTOCleavageandExtensionAssay} |
US20150299788A1 (en) | 2012-05-15 | 2015-10-22 | Eisai R&D Management Co., Ltd. | Rna detection method and detection kit |
US9920361B2 (en) | 2012-05-21 | 2018-03-20 | Sequenom, Inc. | Methods and compositions for analyzing nucleic acid |
SG11201407628UA (en) | 2012-05-21 | 2014-12-30 | Scripps Research Inst | Ribosomal polynucleotides and related expression systems |
US10077474B2 (en) | 2012-05-29 | 2018-09-18 | Abbott Molecular, Inc. | Method of designing primers, method of detecting single nucleotide polymorphisms (SNPs), method of distinguishing SNPs, and related primers, detectable oligonucleotides, and kits |
JP2015521862A (ja) | 2012-07-13 | 2015-08-03 | セクエノム, インコーポレイテッド | 非侵襲性の出生前診断に有用な母体サンプル由来の胎児核酸のメチル化に基づく富化のためのプロセスおよび組成物 |
WO2014033314A1 (en) | 2012-09-03 | 2014-03-06 | Uab Bioseka | Antisense oligonucleotide targeting bacterial glucosyltransferases |
US10006909B2 (en) | 2012-09-28 | 2018-06-26 | Vibrant Holdings, Llc | Methods, systems, and arrays for biomolecular analysis |
US10260089B2 (en) | 2012-10-29 | 2019-04-16 | The Research Foundation Of The State University Of New York | Compositions and methods for recognition of RNA using triple helical peptide nucleic acids |
WO2014093291A1 (en) | 2012-12-10 | 2014-06-19 | Advandx, Inc. | Use of probes for mass spectrometric identification of microorganisms or cells and associated conditions of interest |
EP2770065B1 (en) | 2013-02-25 | 2017-12-13 | Seegene, Inc. | Detection of nucleotide variation on target nucleic acid sequence |
US9289502B2 (en) | 2013-03-08 | 2016-03-22 | Emerald Therapeutics, Inc. | Preparation of oligo conjugates |
KR101943623B1 (ko) | 2013-03-13 | 2019-01-30 | 주식회사 씨젠 | 멜팅 피크 분석을 이용한 타겟 핵산서열의 정량 |
EP2971100A1 (en) | 2013-03-13 | 2016-01-20 | Sequenom, Inc. | Primers for dna methylation analysis |
WO2014149356A1 (en) | 2013-03-15 | 2014-09-25 | Abbott Molecular Inc. | Detection of bisulfite converted nucleotide sequences |
WO2014152054A1 (en) | 2013-03-15 | 2014-09-25 | Bio-Rad Laboratories, Inc. | Digital assays for mutation detection |
US10221216B2 (en) | 2013-04-11 | 2019-03-05 | Carnegie Mellon University | Template-directed γPNA synthesis process and γPNA targeting compounds |
US10370415B2 (en) | 2013-04-11 | 2019-08-06 | Carnegie Mellon University | Divalent nucleobase compounds and uses therefor |
CN105339388B (zh) | 2013-07-12 | 2021-06-15 | Emd密理博公司 | 确定利用活性炭从包含靶蛋白的样品去除病毒的方法 |
WO2015008985A1 (en) | 2013-07-15 | 2015-01-22 | Seegene, Inc. | Detection of target nucleic acid sequence by pto cleavage and extension-dependent immobilized oligonucleotide hybridization |
LT6214B (lt) | 2013-10-07 | 2015-08-25 | Uab "Bioseka" | Priešprasminiai oligonukleotidai aterosklerozės ir kardiovaskulinių infekcijų prevencijai |
BR112016007635A2 (pt) | 2013-10-11 | 2017-09-12 | Genentech Inc | inibidores de nsp4 e métodos de uso |
CN105813721B (zh) | 2013-10-16 | 2019-11-05 | 不列颠哥伦比亚大学 | 用于以小体积配制颗粒的装置 |
JP6295322B2 (ja) | 2013-10-18 | 2018-03-14 | シージーン アイエヌシー | hCTOを利用するPTO切断及び延長分析による固相におけるターゲット核酸配列の検出 |
US10028902B2 (en) | 2013-11-08 | 2018-07-24 | Baylor Research Institute | Nuclear localization of GLP-1 stimulates myocardial regeneration and reverses heart failure |
JP6602772B2 (ja) | 2014-01-28 | 2019-11-06 | ダイス モレキュルズ エスヴィー, エルエルシー | 認識化合物付着モノリス、そのアレイ、およびその使用 |
WO2015138774A1 (en) | 2014-03-13 | 2015-09-17 | Sequenom, Inc. | Methods and processes for non-invasive assessment of genetic variations |
WO2015172058A1 (en) | 2014-05-08 | 2015-11-12 | Carnegie Mellon University | Left-handed gamma-peptide nucleic acids, methods of synthesis and uses therefor |
WO2015191777A2 (en) | 2014-06-10 | 2015-12-17 | Dxterity Diagnostics Incorporated | Devices and methods for collecting and stabilizing biological samples |
JP2017522015A (ja) | 2014-06-24 | 2017-08-10 | アボツト・モレキユラー・インコーポレイテツド | ヒトkras中における1塩基多型の検出 |
BR112017001500A2 (pt) | 2014-07-24 | 2018-02-20 | Abbott Molecular Inc | composições e métodos para a detecção e análise de tuberculose por micobactéria |
EP3633047B1 (en) | 2014-08-19 | 2022-12-28 | Pacific Biosciences of California, Inc. | Method of sequencing nucleic acids based on an enrichment of nucleic acids |
WO2016134293A1 (en) | 2015-02-20 | 2016-08-25 | Baylor College Of Medicine | p63 INACTIVATION FOR THE TREATMENT OF HEART FAILURE |
EP3307779A2 (en) | 2015-06-12 | 2018-04-18 | Alector LLC | Anti-cd33 antibodies and methods of use thereof |
KR20180033502A (ko) | 2015-06-12 | 2018-04-03 | 알렉터 엘엘씨 | 항-cd33 항체 및 그의 사용 방법 |
CN108184327A (zh) | 2015-07-14 | 2018-06-19 | 雅培分子公司 | 用于鉴定耐药性结核的组合物和方法 |
KR20180054639A (ko) | 2015-08-28 | 2018-05-24 | 알렉터 엘엘씨 | 항-siglec-7 항체 및 이의 사용 방법 |
US11046999B2 (en) | 2015-09-16 | 2021-06-29 | PetaOmics, Inc. | Methods and compositions for genomic target enrichment and selective DNA sequencing |
WO2017059397A1 (en) | 2015-10-01 | 2017-04-06 | Whitehead Institute For Biomedical Research | Labeling of antibodies |
CN108347916B (zh) | 2015-10-14 | 2022-02-08 | 先时迈纳米生物科技股份有限公司 | 一种减少冰晶形成的组合物及其方法 |
BR112018007611A2 (pt) | 2015-10-14 | 2018-10-23 | Bio Path Holding Inc | ácidos nucleicos p-etóxi para formulação lipossômica |
CN108431041B (zh) | 2015-10-29 | 2022-08-16 | 艾利妥 | 抗siglec-9抗体及其使用方法 |
EP3400097B1 (en) | 2016-01-06 | 2021-01-27 | The University Of British Columbia | Bifurcating mixers and methods of their use and manufacture |
US20190177391A1 (en) | 2016-03-31 | 2019-06-13 | Baylor Research Institute | Angiopoietin-like protein 8 (angptl8) |
US10400274B2 (en) | 2016-06-18 | 2019-09-03 | Jan Biotech, Inc. | Fluorogenic probes and their use in quantitative detection of target RNA sequences |
US10300145B2 (en) | 2016-07-15 | 2019-05-28 | Massachusetts Institute Of Technology | Synthetic nanoparticles for delivery of immunomodulatory compounds |
ES2928654T3 (es) | 2016-09-16 | 2022-11-21 | Bio Path Holdings Inc | Terapia combinada con oligonucleótidos antisentido liposomales |
CN114907272A (zh) | 2016-09-26 | 2022-08-16 | 卡耐基梅隆大学 | 二价核碱基化合物及其用途 |
US11147249B2 (en) | 2016-12-08 | 2021-10-19 | Alector Llc | Siglec transgenic mice and methods of use thereof |
WO2018213316A1 (en) | 2017-05-16 | 2018-11-22 | Alector Llc | Anti-siglec-5 antibodies and methods of use thereof |
US10538808B2 (en) | 2017-05-26 | 2020-01-21 | Vibrant Holdings, Llc | Photoactive compounds and methods for biomolecule detection and sequencing |
CN110662765B (zh) | 2017-08-03 | 2023-09-29 | 艾利妥 | 抗cd33抗体及其使用方法 |
WO2019045532A2 (en) | 2017-08-31 | 2019-03-07 | Seegene, Inc. | EVALUATION OF COMPONENT PERFORMANCE USING A PAIR OF DIMER FORMER PRIMERS |
KR102345601B1 (ko) | 2017-09-29 | 2021-12-30 | 주식회사 씨젠 | Pto 절단 및 연장-의존적 연장 분석에 의한 타겟 핵산 서열의 검출 |
US11470827B2 (en) | 2017-12-12 | 2022-10-18 | Alector Llc | Transgenic mice expressing human TREM proteins and methods of use thereof |
CN111801317A (zh) * | 2017-12-21 | 2020-10-20 | 卡耐基梅隆大学 | 模板导向的核酸靶向型化合物 |
US20210395361A1 (en) | 2018-07-27 | 2021-12-23 | Alector Llc | Anti-siglec-5 antibodies and methods of use thereof |
EP3853378A4 (en) | 2018-09-21 | 2022-05-11 | President and Fellows of Harvard College | METHODS AND COMPOSITIONS FOR THE TREATMENT OF DIABETES, AND METHODS FOR ENCOURAGEMENT OF MRNA ENCODING SECRETED PROTEINS |
EP3997225A1 (en) | 2019-07-10 | 2022-05-18 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the treatment of epilepsy |
US20230016983A1 (en) | 2019-11-19 | 2023-01-19 | lNSERM (INSTITUT NATIONAL DE LA SANTÉ ET DE LA RECHERCHE MÉDICALE) | Antisense oligonucleotides and thier use for the treatment of cancer |
CA3185019A1 (en) | 2020-05-29 | 2021-12-02 | Front Range Biosciences, Inc. | Methods and compositions for pathogen detection in plants |
US20230002779A1 (en) | 2020-06-29 | 2023-01-05 | Front Range Biosciences, Inc. | Characterization of plant cultivars based on terpene synthase gene profiles |
CN116113697A (zh) | 2020-07-10 | 2023-05-12 | 国家健康与医学研究院 | 用于治疗癫痫的方法和组合物 |
WO2022241007A1 (en) * | 2021-05-11 | 2022-11-17 | Mccurdy Russell Lewis | Replaceable floating attractant accessories for fishing line |
WO2023043280A1 (ko) | 2021-09-17 | 2023-03-23 | 주식회사 씨젠 | 합성 비자연 염기를 포함하는 태그 올리고뉴클레오타이드를 이용한 타겟 핵산 서열의 검출 |
CN114409890A (zh) * | 2022-02-28 | 2022-04-29 | 中国科学院长春应用化学研究所 | 一种氨基功能化的聚乙二醇衍生物及其制备方法 |
WO2024017990A1 (en) | 2022-07-21 | 2024-01-25 | Institut National de la Santé et de la Recherche Médicale | Methods and compositions for treating chronic pain disorders |
WO2024146935A1 (en) | 2023-01-06 | 2024-07-11 | Institut National de la Santé et de la Recherche Médicale | Intravenous administration of antisense oligonucleotides for the treatment of pain |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2910130A1 (de) | 1979-03-15 | 1980-09-25 | Franz Rossmoeller | Verbesserte befestigungsvorrichtung zum aufhaengen von paneelen und moebelelementen |
DE2910129C2 (de) | 1979-03-15 | 1986-01-23 | Oskar 4354 Datteln Fleck | Leiste zum Abdichten des Zwischenraums zwischen der Trauflatte eines Daches und den darüberliegenden traufseitigen Dacheindeckungsplatten |
JPS5927900A (ja) | 1982-08-09 | 1984-02-14 | Wakunaga Seiyaku Kk | 固定化オリゴヌクレオチド |
US5166315A (en) * | 1989-12-20 | 1992-11-24 | Anti-Gene Development Group | Sequence-specific binding polymers for duplex nucleic acids |
EP0639582B1 (en) * | 1985-03-15 | 1998-09-16 | Antivirals Inc. | Polynucleotide assay reagent and method |
US5034506A (en) * | 1985-03-15 | 1991-07-23 | Anti-Gene Development Group | Uncharged morpholino-based polymers having achiral intersubunit linkages |
JP2597698B2 (ja) | 1987-10-28 | 1997-04-09 | ハワード・フローレイ・インスティテュト・オブ・イクスペリメンタル・フィジオロジー・アンド・メディシン | オリゴヌクレオチド‐ポリアミド コンジュゲート |
US5216141A (en) | 1988-06-06 | 1993-06-01 | Benner Steven A | Oligonucleotide analogs containing sulfur linkages |
WO1990002749A1 (en) | 1988-09-01 | 1990-03-22 | Forskningscenter Risø | Peptide synthesis method and solid support for use in the method |
JPH02156895A (ja) * | 1988-12-08 | 1990-06-15 | Sumitomo Heavy Ind Ltd | 好塩菌による5’‐ヌクレオチド類の製造法 |
JPH0635469B2 (ja) * | 1989-09-13 | 1994-05-11 | 信 高橋 | ジエチレントリアミン三酢酸化合物及びその製造中間体並びにそれらの製造法 |
US5340716A (en) * | 1991-06-20 | 1994-08-23 | Snytex (U.S.A.) Inc. | Assay method utilizing photoactivated chemiluminescent label |
US6414112B1 (en) * | 1991-05-24 | 2002-07-02 | Ole Buchardt | Peptide nucleic acids having 2,6-diaminopurine nucleobases |
US5719262A (en) * | 1993-11-22 | 1998-02-17 | Buchardt, Deceased; Ole | Peptide nucleic acids having amino acid side chains |
US6451968B1 (en) * | 1991-05-24 | 2002-09-17 | Isis Pharmaceuticals, Inc. | Peptide nucleic acids |
US5539082A (en) * | 1993-04-26 | 1996-07-23 | Nielsen; Peter E. | Peptide nucleic acids |
US6228982B1 (en) * | 1992-05-22 | 2001-05-08 | Benget Norden | Double-stranded peptide nucleic acids |
DK51092D0 (da) * | 1991-05-24 | 1992-04-15 | Ole Buchardt | Oligonucleotid-analoge betegnet pna, monomere synthoner og fremgangsmaade til fremstilling deraf samt anvendelser deraf |
MX9207334A (es) | 1991-12-18 | 1993-08-01 | Glaxo Inc | Acidos nucleicos peptidicos y formulacion farma- ceutica que los contiene |
US6770738B1 (en) * | 1992-05-22 | 2004-08-03 | Isis Pharmaceuticals, Inc. | Higher order structure and binding of peptide nucleic acids |
WO1993024507A1 (en) * | 1992-05-28 | 1993-12-09 | Gilead Sciences, Inc. | Conformationally restrained oligomers containing amide or carbamate linkages for sequence-specific binding |
US5705333A (en) * | 1994-08-05 | 1998-01-06 | The Regents Of The University Of California | Peptide-based nucleic acid mimics(PENAMS) |
US6472209B1 (en) * | 1997-10-17 | 2002-10-29 | Mayo Foundation For Medical Education And Research | Using polyamide nucleic acid oligomers to engender a biological response |
-
1992
- 1992-04-15 DK DK92510A patent/DK51092D0/da not_active Application Discontinuation
- 1992-05-22 DE DE69220946T patent/DE69220946T2/de not_active Expired - Fee Related
- 1992-05-22 EP EP01203303A patent/EP1162206A3/en not_active Withdrawn
- 1992-05-22 AT AT92911165T patent/ATE205504T1/de not_active IP Right Cessation
- 1992-05-22 ES ES92911165T patent/ES2164052T3/es not_active Expired - Lifetime
- 1992-05-22 CA CA002109320A patent/CA2109320C/en not_active Expired - Lifetime
- 1992-05-22 ES ES92923579T patent/ES2107552T3/es not_active Expired - Lifetime
- 1992-05-22 AU AU18806/92A patent/AU666480B2/en not_active Ceased
- 1992-05-22 AU AU18843/92A patent/AU1884392A/en not_active Abandoned
- 1992-05-22 DK DK92923579.4T patent/DK0586618T3/da active
- 1992-05-22 EP EP92911165A patent/EP0586474B1/en not_active Expired - Lifetime
- 1992-05-22 EP EP03077836A patent/EP1411063B1/en not_active Expired - Lifetime
- 1992-05-22 EP EP00203148A patent/EP1074559B1/en not_active Expired - Lifetime
- 1992-05-22 DK DK92911165T patent/DK0586474T3/da active
- 1992-05-22 US US08/108,591 patent/US6395474B1/en not_active Expired - Lifetime
- 1992-05-22 US US08/150,156 patent/US6357163B1/en not_active Expired - Lifetime
- 1992-05-22 AT AT92923579T patent/ATE155483T1/de not_active IP Right Cessation
- 1992-05-22 JP JP4510434A patent/JP2758988B2/ja not_active Expired - Fee Related
- 1992-05-22 EP EP92923579A patent/EP0586618B1/en not_active Expired - Lifetime
- 1992-05-22 AT AT00203148T patent/ATE515569T1/de not_active IP Right Cessation
- 1992-05-22 WO PCT/EP1992/001220 patent/WO1992020703A1/en active IP Right Grant
- 1992-05-22 DE DE69232055T patent/DE69232055T2/de not_active Expired - Lifetime
- 1992-05-22 JP JP51013992A patent/JP3982828B2/ja not_active Expired - Lifetime
- 1992-05-22 WO PCT/EP1992/001219 patent/WO1992020702A1/en active IP Right Grant
- 1992-05-22 HU HU9303023A patent/HU221003B1/hu not_active IP Right Cessation
- 1992-05-22 CA CA002109805A patent/CA2109805A1/en not_active Abandoned
- 1992-05-22 BR BR9206049A patent/BR9206049A/pt not_active Application Discontinuation
-
1993
- 1993-11-15 NO NO19934122A patent/NO312516B1/no not_active IP Right Cessation
- 1993-11-20 KR KR93703558A patent/KR0133131B1/ko not_active IP Right Cessation
- 1993-11-23 NO NO19934235A patent/NO313201B1/no unknown
- 1993-11-23 FI FI935208A patent/FI118424B/fi active IP Right Grant
-
1994
- 1994-12-28 US US08/366,231 patent/US5977296A/en not_active Expired - Lifetime
-
1995
- 1995-06-06 US US08/468,719 patent/US6710163B1/en not_active Expired - Fee Related
-
1997
- 1997-10-14 GR GR970402663T patent/GR3025018T3/el unknown
-
1998
- 1998-12-10 US US09/209,149 patent/US6201103B1/en not_active Expired - Fee Related
-
2001
- 2001-10-23 US US09/983,210 patent/US20020160383A1/en not_active Abandoned
-
2002
- 2002-05-23 US US10/154,890 patent/US7378485B2/en not_active Expired - Fee Related
-
2003
- 2003-01-23 JP JP2003015384A patent/JP2003235590A/ja not_active Withdrawn
- 2003-09-08 US US10/657,600 patent/US20040059087A1/en not_active Abandoned
- 2003-10-22 US US10/691,012 patent/US20060160731A1/en not_active Abandoned
-
2005
- 2005-01-05 US US11/029,005 patent/US20060046255A1/en not_active Abandoned
-
2007
- 2007-06-01 JP JP2007147536A patent/JP2007306926A/ja not_active Withdrawn
-
2008
- 2008-03-10 JP JP2008060342A patent/JP2008253251A/ja not_active Withdrawn
- 2008-10-03 JP JP2008258890A patent/JP2009069158A/ja not_active Withdrawn
-
2011
- 2011-07-25 US US13/190,164 patent/US20120115136A1/en not_active Abandoned
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
FI118424B (fi) | Nukleiinihappoanalogit ja niiden käyttö diagnostisissa ja analyyttisissä toimenpiteissä | |
US6228982B1 (en) | Double-stranded peptide nucleic acids | |
EP0773950B1 (en) | Linked peptide nucleic acids | |
US5786461A (en) | Peptide nucleic acids having amino acid side chains | |
US5539082A (en) | Peptide nucleic acids | |
US5736336A (en) | Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility | |
US6414112B1 (en) | Peptide nucleic acids having 2,6-diaminopurine nucleobases | |
JP3306073B2 (ja) | 増加した結合親和性、配列特異性および溶解性を有するペプチド核酸 | |
US6713602B1 (en) | Synthetic procedures for peptide nucleic acids | |
US6710164B1 (en) | Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility | |
US20030105286A1 (en) | Linked peptide nucleic acids |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FG | Patent granted |
Ref document number: 118424 Country of ref document: FI |