ES2300106T3 - Conjugados de agente de union al surco menor y oligonucleotidos unidos covalentemente. - Google Patents
Conjugados de agente de union al surco menor y oligonucleotidos unidos covalentemente. Download PDFInfo
- Publication number
- ES2300106T3 ES2300106T3 ES96910723T ES96910723T ES2300106T3 ES 2300106 T3 ES2300106 T3 ES 2300106T3 ES 96910723 T ES96910723 T ES 96910723T ES 96910723 T ES96910723 T ES 96910723T ES 2300106 T3 ES2300106 T3 ES 2300106T3
- Authority
- ES
- Spain
- Prior art keywords
- ring
- group
- minor groove
- carbons
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000027455 binding Effects 0.000 claims abstract description 113
- 108091034117 Oligonucleotide Proteins 0.000 claims abstract description 102
- 230000000295 complement effect Effects 0.000 claims abstract description 34
- 239000011230 binding agent Substances 0.000 claims description 65
- 108020004414 DNA Proteins 0.000 claims description 48
- 125000003729 nucleotide group Chemical group 0.000 claims description 40
- 239000002773 nucleotide Substances 0.000 claims description 39
- 125000004429 atom Chemical group 0.000 claims description 37
- 238000004132 cross linking Methods 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000006413 ring segment Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 125000004122 cyclic group Chemical group 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- 229910052740 iodine Inorganic materials 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims description 18
- 102000053602 DNA Human genes 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000000523 sample Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 238000009396 hybridization Methods 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 150000007523 nucleic acids Chemical class 0.000 claims description 15
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 14
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 14
- 102000039446 nucleic acids Human genes 0.000 claims description 14
- 108020004707 nucleic acids Proteins 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 238000009830 intercalation Methods 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 7
- 125000006853 reporter group Chemical group 0.000 claims description 7
- 102000040650 (ribonucleotides)n+m Human genes 0.000 claims description 6
- LHCPRYRLDOSKHK-UHFFFAOYSA-N 7-deaza-8-aza-adenine Chemical compound NC1=NC=NC2=C1C=NN2 LHCPRYRLDOSKHK-UHFFFAOYSA-N 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- 230000000692 anti-sense effect Effects 0.000 claims description 5
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 claims description 4
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 claims description 4
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 claims description 4
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- ZLAQATDNGLKIEV-UHFFFAOYSA-N 5-methyl-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound CC1=CNC(=S)NC1=O ZLAQATDNGLKIEV-UHFFFAOYSA-N 0.000 claims description 3
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 238000003745 diagnosis Methods 0.000 claims 1
- 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 abstract description 21
- 239000000463 material Substances 0.000 abstract description 3
- 229940046166 oligodeoxynucleotide Drugs 0.000 description 98
- 101500027983 Rattus norvegicus Octadecaneuropeptide Proteins 0.000 description 96
- -1 cromomycin A 3 Chemical compound 0.000 description 64
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 35
- 239000005289 controlled pore glass Substances 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 31
- 239000002585 base Substances 0.000 description 29
- 238000000034 method Methods 0.000 description 29
- 239000000460 chlorine Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 108090000765 processed proteins & peptides Proteins 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000003431 cross linking reagent Substances 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical group OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 10
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 10
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 230000006641 stabilisation Effects 0.000 description 10
- 238000011105 stabilization Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- OJLSSULCTKBVOB-UHFFFAOYSA-N (2,3,5,6-tetrafluorophenyl) 2,2,2-trifluoroacetate Chemical compound FC1=CC(F)=C(F)C(OC(=O)C(F)(F)F)=C1F OJLSSULCTKBVOB-UHFFFAOYSA-N 0.000 description 8
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- SYEVWAVDQJTJMV-UHFFFAOYSA-N 6-carbamoyl-7,8-dihydro-3h-pyrrolo[3,2-e]indole-2-carboxylic acid Chemical group NC(=O)N1CCC2=C1C=CC1=C2C=C(C(O)=O)N1 SYEVWAVDQJTJMV-UHFFFAOYSA-N 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 108010038807 Oligopeptides Proteins 0.000 description 7
- 102000015636 Oligopeptides Human genes 0.000 description 7
- 125000005518 carboxamido group Chemical group 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 238000002515 oligonucleotide synthesis Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000013638 trimer Substances 0.000 description 7
- FSVMNZBNUZWLMV-UHFFFAOYSA-N 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylic acid Chemical compound C1=C2NC(C(=O)O)=CC2=C2CCNC2=C1 FSVMNZBNUZWLMV-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 6
- 229960004630 chlorambucil Drugs 0.000 description 6
- 238000010549 co-Evaporation Methods 0.000 description 6
- 239000002777 nucleoside Substances 0.000 description 6
- 125000003835 nucleoside group Chemical group 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 125000002480 thymidyl group Chemical group 0.000 description 6
- 108700028369 Alleles Proteins 0.000 description 5
- 108010091086 Recombinases Proteins 0.000 description 5
- 102000018120 Recombinases Human genes 0.000 description 5
- 125000004103 aminoalkyl group Chemical group 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 238000005304 joining Methods 0.000 description 5
- ZBQZZJJPSVLHJP-UHFFFAOYSA-N methyl 1,2,3,6-tetrahydropyrrolo[2,3-e]indole-7-carboxylate Chemical compound C1=C2NC(C(=O)OC)=CC2=C2NCCC2=C1 ZBQZZJJPSVLHJP-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000003752 polymerase chain reaction Methods 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 4
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 4
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 description 3
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 3
- CQXXYOLFJXSRMT-UHFFFAOYSA-N 5-diazocyclohexa-1,3-diene Chemical group [N-]=[N+]=C1CC=CC=C1 CQXXYOLFJXSRMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 3
- 229930024421 Adenine Natural products 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 3
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical class NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 3
- 108020004682 Single-Stranded DNA Proteins 0.000 description 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 3
- 229960000643 adenine Drugs 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 229960002684 aminocaproic acid Drugs 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 229940124276 oligodeoxyribonucleotide Drugs 0.000 description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 3
- 150000008300 phosphoramidites Chemical class 0.000 description 3
- 102000040430 polynucleotide Human genes 0.000 description 3
- 108091033319 polynucleotide Proteins 0.000 description 3
- 239000002157 polynucleotide Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000012163 sequencing technique Methods 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- AZPMLJUDKMGFPX-UHFFFAOYSA-N 2-[(4-phenyldiazenylphenyl)methylsulfanyl]ethanol Chemical compound C1=CC(CSCCO)=CC=C1N=NC1=CC=CC=C1 AZPMLJUDKMGFPX-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- XSQLSBQNMAQBSL-IVZWLZJFSA-N 5-(3-aminopropyl)-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(CCCN)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 XSQLSBQNMAQBSL-IVZWLZJFSA-N 0.000 description 2
- MECWCJMWBBVBAG-UHFFFAOYSA-N 6-[methoxy(trityl)amino]hexoxyphosphonamidous acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N(CCCCCCOP(N)O)OC)C1=CC=CC=C1 MECWCJMWBBVBAG-UHFFFAOYSA-N 0.000 description 2
- UFXHUXJLAGKJHQ-UXHICEINSA-N 9H-fluoren-9-ylmethyl N-[(4R,5S)-4-amino-5,6-dihydroxy-3-oxohexyl]carbamate Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)NCCC(=O)[C@@H]([C@@H](CO)O)N UFXHUXJLAGKJHQ-UXHICEINSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 229930010555 Inosine Natural products 0.000 description 2
- 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 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- 229930182816 L-glutamine Natural products 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910003204 NH2 Inorganic materials 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 210000003719 b-lymphocyte Anatomy 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
- 229940000635 beta-alanine Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940104302 cytosine Drugs 0.000 description 2
- SPTYHKZRPFATHJ-HYZXJONISA-N dT6 Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 SPTYHKZRPFATHJ-HYZXJONISA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000001502 gel electrophoresis Methods 0.000 description 2
- 125000005252 haloacyl group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229960003786 inosine Drugs 0.000 description 2
- 230000002687 intercalation Effects 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 2
- 229960004961 mechlorethamine Drugs 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- IDBIFFKSXLYUOT-UHFFFAOYSA-N netropsin Chemical compound C1=C(C(=O)NCCC(N)=N)N(C)C=C1NC(=O)C1=CC(NC(=O)CN=C(N)N)=CN1C IDBIFFKSXLYUOT-UHFFFAOYSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 239000005373 porous glass Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- ZCOSUVZGFDGWFV-UHFFFAOYSA-N pyrrolo[2,3-e]indole Chemical compound C1=CC2=NC=CC2=C2N=CC=C21 ZCOSUVZGFDGWFV-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000012679 serum free medium Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 229940113082 thymine Drugs 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- CAPMCEBUZGWMBU-UHFFFAOYSA-N (2,3,4,5-tetrafluorophenyl) 2,2,2-trifluoroacetate Chemical compound FC1=CC(OC(=O)C(F)(F)F)=C(F)C(F)=C1F CAPMCEBUZGWMBU-UHFFFAOYSA-N 0.000 description 1
- WVWDIQVIUVSDDG-MCBPOFBKSA-N (2S,3R)-2-amino-3-[[bis(2-methoxyphenyl)-phenylmethoxy]methyl]-3-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyloxycarbonyl]pentanoic acid Chemical compound CC[C@](COC(C1=CC=CC=C1)(C2=CC=CC=C2OC)C3=CC=CC=C3OC)([C@@H](C(=O)O)N)C(=O)OC(=O)CCNC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46 WVWDIQVIUVSDDG-MCBPOFBKSA-N 0.000 description 1
- CADQNXRGRFJSQY-WDCZJNDASA-N (2s,3r,4r)-2-fluoro-2,3,4,5-tetrahydroxypentanal Chemical compound OC[C@@H](O)[C@@H](O)[C@](O)(F)C=O CADQNXRGRFJSQY-WDCZJNDASA-N 0.000 description 1
- TWYYFYNJOJGNFP-CUXYNZQBSA-N (2s,4r,5s,6s)-2-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-2-carbamoyl-4-[[(e,4s,6s)-4,6-dimethyloct-2-enoyl]oxymethyl]-5-hydroxy-1,3-dioxane-4,5,6-tricarboxylic acid Chemical compound O1[C@H](C(O)=O)[C@](C(O)=O)(O)[C@](COC(=O)/C=C/[C@@H](C)C[C@@H](C)CC)(C(O)=O)O[C@]1(C(N)=O)CCC(=C)[C@@H](OC(C)=O)[C@H](C)CC1=CC=CC=C1 TWYYFYNJOJGNFP-CUXYNZQBSA-N 0.000 description 1
- ZZKAYQVMXCYGEE-UHFFFAOYSA-N 1,2,3,6-tetrahydropyrrolo[2,3-e]indole-7-carboxylic acid Chemical compound C1=C2NC(C(=O)O)=CC2=C2NCCC2=C1 ZZKAYQVMXCYGEE-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- JBWYRBLDOOOJEU-UHFFFAOYSA-N 1-[chloro-(4-methoxyphenyl)-phenylmethyl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C(Cl)(C=1C=CC(OC)=CC=1)C1=CC=CC=C1 JBWYRBLDOOOJEU-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 description 1
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical class C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 description 1
- MBBMNCNPDPORMT-UPRLRBBYSA-N 2,2,2-trifluoro-N-[3-[1-[(2R,4S,5R)-4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]propyl]acetamide Chemical compound O[C@H]1C[C@@H](O[C@@H]1COC(c1ccccc1)(c1ccccc1)c1ccccc1)n1cc(CCCNC(=O)C(F)(F)F)c(=O)[nH]c1=O MBBMNCNPDPORMT-UPRLRBBYSA-N 0.000 description 1
- QXYLYYZZWZQACI-UHFFFAOYSA-N 2,3,4,5-tetrafluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1F QXYLYYZZWZQACI-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- QLVGHFBUSGYCCG-UHFFFAOYSA-N 2-amino-n-(1-cyano-2-phenylethyl)acetamide Chemical compound NCC(=O)NC(C#N)CC1=CC=CC=C1 QLVGHFBUSGYCCG-UHFFFAOYSA-N 0.000 description 1
- KMEMIMRPZGDOMG-UHFFFAOYSA-N 2-cyanoethoxyphosphonamidous acid Chemical compound NP(O)OCCC#N KMEMIMRPZGDOMG-UHFFFAOYSA-N 0.000 description 1
- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 1
- QUHGSDZVAPFNLV-UHFFFAOYSA-N 4-[(5-acetamidofuran-2-carbonyl)amino]-n-[3-(dimethylamino)propyl]-1-propylpyrrole-2-carboxamide Chemical compound C1=C(C(=O)NCCCN(C)C)N(CCC)C=C1NC(=O)C1=CC=C(NC(C)=O)O1 QUHGSDZVAPFNLV-UHFFFAOYSA-N 0.000 description 1
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
- LPYGXQLRFJTBFA-UHFFFAOYSA-N 6-[(2-methylpropan-2-yl)oxycarbonyl]-7,8-dihydro-3h-pyrrolo[3,2-e]indole-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC2=C1C=CC1=C2C=C(C(O)=O)N1 LPYGXQLRFJTBFA-UHFFFAOYSA-N 0.000 description 1
- BZUZJVLPAKJIBP-UHFFFAOYSA-N 6-amino-1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound O=C1N=C(N)N=C2NNC=C21 BZUZJVLPAKJIBP-UHFFFAOYSA-N 0.000 description 1
- IOJUMJHLFYJDAS-UHFFFAOYSA-N 6-o-tert-butyl 2-o-(2,3,5,6-tetrafluorophenyl) 7,8-dihydro-3h-pyrrolo[3,2-e]indole-2,6-dicarboxylate Chemical class CC(C)(C)OC(=O)N1CCC(C=2C=3)=C1C=CC=2NC=3C(=O)OC1=C(F)C(F)=CC(F)=C1F IOJUMJHLFYJDAS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- TYAHYEQHEIENOO-PJKFIHJXSA-N 9H-fluoren-9-ylmethyl N-[(4R,5S)-4-amino-6-[bis(2-methoxyphenyl)-phenylmethoxy]-5-hydroxy-3-oxohexyl]carbamate Chemical compound C1=CC=CC=2C3=CC=CC=C3C(C1=2)COC(=O)NCCC(=O)[C@@H]([C@H](O)COC(C1=CC=CC=C1)(C1=C(C=CC=C1)OC)C1=C(C=CC=C1)OC)N TYAHYEQHEIENOO-PJKFIHJXSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 108020004635 Complementary DNA Proteins 0.000 description 1
- 108020004394 Complementary RNA Proteins 0.000 description 1
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 1
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 239000003298 DNA probe Substances 0.000 description 1
- 108010067770 Endopeptidase K Proteins 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 108010062347 HLA-DQ Antigens Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 108010042309 Netropsin Proteins 0.000 description 1
- 229930187135 Olivomycin Natural products 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 1
- 241000287433 Turdus Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- VGQOVCHZGQWAOI-YQRHFANHSA-N anthramycin Chemical compound N1[C@H](O)[C@@H]2CC(\C=C\C(N)=O)=CN2C(=O)C2=CC=C(C)C(O)=C12 VGQOVCHZGQWAOI-YQRHFANHSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229950006345 antramycin Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 238000010804 cDNA synthesis Methods 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical group C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 239000003184 complementary RNA Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 229940125796 compound 3d Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000003936 denaturing gel electrophoresis Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000012869 ethanol precipitation Methods 0.000 description 1
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical group [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940029575 guanosine Drugs 0.000 description 1
- 125000005179 haloacetyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000138 intercalating agent Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 108700009084 lexitropsin Proteins 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
- AYYOZKHMSABVRP-UHFFFAOYSA-N methyl 1h-indole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CNC2=C1 AYYOZKHMSABVRP-UHFFFAOYSA-N 0.000 description 1
- FTLOEULOTNVCGF-UHFFFAOYSA-N methyl 1h-indole-7-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1NC=C2 FTLOEULOTNVCGF-UHFFFAOYSA-N 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical class CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- UPBAOYRENQEPJO-UHFFFAOYSA-N n-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide Chemical compound CN1C=C(NC=O)C=C1C(=O)NC1=CN(C)C(C(=O)NC2=CN(C)C(C(=O)NCCC(N)=N)=C2)=C1 UPBAOYRENQEPJO-UHFFFAOYSA-N 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical group 0.000 description 1
- CZDBNBLGZNWKMC-MWQNXGTOSA-N olivomycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1)O[C@H]1O[C@@H](C)[C@H](O)[C@@H](OC2O[C@@H](C)[C@H](O)[C@@H](O)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@H](O)[C@H](OC)[C@H](C)O1 CZDBNBLGZNWKMC-MWQNXGTOSA-N 0.000 description 1
- 229950005848 olivomycin Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229960003171 plicamycin Drugs 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- CQZVSBFXOTZJBC-UHFFFAOYSA-N pyrrolo[2,3-e]indole-2-carboxamide Chemical compound C1=CC2=CC(C(=O)N)=NC2=C2C=CN=C21 CQZVSBFXOTZJBC-UHFFFAOYSA-N 0.000 description 1
- 150000004944 pyrrolopyrimidines Chemical group 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- RAGFPHFDFVNLCG-INYQBOQCSA-N sibiromycin Chemical compound O[C@@H]1[C@@](O)(C)[C@@H](NC)[C@H](C)O[C@H]1OC(C(=C1O)C)=CC(C2=O)=C1N[C@H](O)[C@H]1N2C=C(\C=C\C)C1 RAGFPHFDFVNLCG-INYQBOQCSA-N 0.000 description 1
- RAGFPHFDFVNLCG-UHFFFAOYSA-N sibiromycin Natural products OC1C(O)(C)C(NC)C(C)OC1OC(C(=C1O)C)=CC(C2=O)=C1NC(O)C1N2C=C(C=CC)C1 RAGFPHFDFVNLCG-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 108010042747 stallimycin Proteins 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002699 waste material Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/23—Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
-
- 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
- C07H21/04—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with deoxyribosyl as saccharide radical
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/415,370 US5801155A (en) | 1995-04-03 | 1995-04-03 | Covalently linked oligonucleotide minor grove binder conjugates |
| US415370 | 1995-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2300106T3 true ES2300106T3 (es) | 2008-06-01 |
Family
ID=23645421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES96910723T Expired - Lifetime ES2300106T3 (es) | 1995-04-03 | 1996-04-03 | Conjugados de agente de union al surco menor y oligonucleotidos unidos covalentemente. |
Country Status (12)
| Country | Link |
|---|---|
| US (6) | US5801155A (enExample) |
| EP (1) | EP0819133B1 (enExample) |
| JP (1) | JP4948690B2 (enExample) |
| CN (3) | CN1187363C (enExample) |
| AT (1) | ATE382627T1 (enExample) |
| AU (1) | AU716108B2 (enExample) |
| CA (1) | CA2223678C (enExample) |
| DE (1) | DE69637389T2 (enExample) |
| DK (1) | DK0819133T3 (enExample) |
| ES (1) | ES2300106T3 (enExample) |
| PT (1) | PT819133E (enExample) |
| WO (1) | WO1996032496A2 (enExample) |
Families Citing this family (275)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6339066B1 (en) | 1990-01-11 | 2002-01-15 | Isis Pharmaceuticals, Inc. | Antisense oligonucleotides which have phosphorothioate linkages of high chiral purity and which modulate βI, βII, γ, δ, Ε, ζ and η isoforms of human protein kinase C |
| US6537973B1 (en) | 1992-03-16 | 2003-03-25 | Isis Pharmaceuticals, Inc. | Oligonucleotide inhibition of protein kinase C |
| US5985558A (en) * | 1997-04-14 | 1999-11-16 | Isis Pharmaceuticals Inc. | Antisense oligonucleotide compositions and methods for the inibition of c-Jun and c-Fos |
| US5801155A (en) | 1995-04-03 | 1998-09-01 | Epoch Pharmaceuticals, Inc. | Covalently linked oligonucleotide minor grove binder conjugates |
| US6312894B1 (en) * | 1995-04-03 | 2001-11-06 | Epoch Pharmaceuticals, Inc. | Hybridization and mismatch discrimination using oligonucleotides conjugated to minor groove binders |
| US6090947A (en) | 1996-02-26 | 2000-07-18 | California Institute Of Technology | Method for the synthesis of pyrrole and imidazole carboxamides on a solid support |
| US6506906B1 (en) | 1996-02-26 | 2003-01-14 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
| US6635417B1 (en) * | 1996-07-31 | 2003-10-21 | California Institute Of Technology | Complex formation between DSDNA and oligomer of cyclic heterocycles |
| JP2001513759A (ja) | 1996-02-26 | 2001-09-04 | カリフォルニア・インスティチュート・オブ・テクノロジー | 二本鎖ｄｎａの副溝において結合する改良されたポリアミド |
| US6143901A (en) * | 1996-07-31 | 2000-11-07 | Genesoft, Inc. | Complex formation between dsDNA and pyrrole imidazole polyamides |
| WO1998045284A1 (en) | 1996-02-26 | 1998-10-15 | California Institute Of Technology | Stereochemical control of the dna binding affinity, sequence specificity, and orientation-preference of chiral hairpin polyamides in the minor groove |
| CN1260006A (zh) | 1996-02-26 | 2000-07-12 | 加利福尼亚州技术学院 | 双链dna和杂环低聚物之间复合物的形成 |
| US6555692B1 (en) | 1996-02-26 | 2003-04-29 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
| US9096636B2 (en) | 1996-06-06 | 2015-08-04 | Isis Pharmaceuticals, Inc. | Chimeric oligomeric compounds and their use in gene modulation |
| US5898031A (en) | 1996-06-06 | 1999-04-27 | Isis Pharmaceuticals, Inc. | Oligoribonucleotides for cleaving RNA |
| US7812149B2 (en) | 1996-06-06 | 2010-10-12 | Isis Pharmaceuticals, Inc. | 2′-Fluoro substituted oligomeric compounds and compositions for use in gene modulations |
| US20040266706A1 (en) * | 2002-11-05 | 2004-12-30 | Muthiah Manoharan | Cross-linked oligomeric compounds and their use in gene modulation |
| WO1998035702A1 (en) * | 1996-08-01 | 1998-08-20 | California Institute Of Technology | Inhibition of gene transcription by polyamide dna-binding ligands |
| US6143877A (en) * | 1997-04-30 | 2000-11-07 | Epoch Pharmaceuticals, Inc. | Oligonucleotides including pyrazolo[3,4-D]pyrimidine bases, bound in double stranded nucleic acids |
| US6312925B1 (en) | 1997-05-08 | 2001-11-06 | Epoch Pharmaceuticals, Inc. | Methods and compositions to facilitate D-loop formation by oligonucleotides |
| US6262252B1 (en) * | 1997-05-19 | 2001-07-17 | Mirus, Inc. | Single-step method for labeling nucleic acids with mustard or aziridine labeling reagents |
| JP2002510319A (ja) | 1997-07-01 | 2002-04-02 | アイシス・ファーマシューティカルス・インコーポレーテッド | オリゴヌクレオチドの消化管を介したデリバリーのための組成物及び方法 |
| US5877309A (en) * | 1997-08-13 | 1999-03-02 | Isis Pharmaceuticals, Inc. | Antisense oligonucleotides against JNK |
| US6809193B2 (en) | 1997-08-13 | 2004-10-26 | Isis Pharmaceuticals, Inc. | Antisense oligonucleotide compositions and methods for the modulation of JNK proteins |
| US6133246A (en) * | 1997-08-13 | 2000-10-17 | Isis Pharmaceuticals Inc. | Antisense oligonucleotide compositions and methods for the modulation of JNK proteins |
| US6518017B1 (en) * | 1997-10-02 | 2003-02-11 | Oasis Biosciences Incorporated | Combinatorial antisense library |
| US20030165888A1 (en) * | 2001-07-18 | 2003-09-04 | Brown Bob D. | Oligonucleotide probes and primers comprising universal bases for diagnostic purposes |
| US20060167239A1 (en) * | 1997-12-02 | 2006-07-27 | Slattum Paul M | Compounds and processes for single-pot attachment of a label to siRNA |
| US6683173B2 (en) * | 1998-04-03 | 2004-01-27 | Epoch Biosciences, Inc. | Tm leveling methods |
| US7715989B2 (en) * | 1998-04-03 | 2010-05-11 | Elitech Holding B.V. | Systems and methods for predicting oligonucleotide melting temperature (TmS) |
| US6127121A (en) * | 1998-04-03 | 2000-10-03 | Epoch Pharmaceuticals, Inc. | Oligonucleotides containing pyrazolo[3,4-D]pyrimidines for hybridization and mismatch discrimination |
| US6949367B1 (en) | 1998-04-03 | 2005-09-27 | Epoch Pharmaceuticals, Inc. | Modified oligonucleotides for mismatch discrimination |
| US7045610B2 (en) * | 1998-04-03 | 2006-05-16 | Epoch Biosciences, Inc. | Modified oligonucleotides for mismatch discrimination |
| US6072046A (en) * | 1998-08-26 | 2000-06-06 | Epoch Pharmaceuticals, Inc. | Diaziridinyl-aryl and bis-[di(chloroethyl)amino]-aryl oligonucleotide conjugates and reagents for making the same |
| US6432642B1 (en) * | 1999-01-15 | 2002-08-13 | Pe Corporation (Ny) | Binary probe and clamp composition and methods for a target hybridization detection |
| US6410231B1 (en) * | 1999-02-26 | 2002-06-25 | Incyte Genomics, Inc. | SNP detection |
| WO2000061810A1 (en) * | 1999-04-08 | 2000-10-19 | Oasis Biosciences, Inc. | Antisense oligonucleotides comprising universal and/or degenerate bases |
| US6339147B1 (en) | 1999-07-29 | 2002-01-15 | Epoch Biosciences, Inc. | Attachment of oligonucleotides to solid supports through Schiff base type linkages for capture and detection of nucleic acids |
| 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 |
| US7205105B2 (en) * | 1999-12-08 | 2007-04-17 | Epoch Biosciences, Inc. | Real-time linear detection probes: sensitive 5′-minor groove binder-containing probes for PCR analysis |
| US20040081959A9 (en) * | 1999-12-08 | 2004-04-29 | Epoch Biosciences, Inc. | Fluorescent quenching detection reagents and methods |
| US6727356B1 (en) * | 1999-12-08 | 2004-04-27 | Epoch Pharmaceuticals, Inc. | Fluorescent quenching detection reagents and methods |
| EP1944310A3 (en) | 2000-03-01 | 2008-08-06 | Epoch Biosciences, Inc. | Modified oligonucleotides for mismatch discrimination |
| AU2001243403A1 (en) | 2000-03-01 | 2001-09-12 | Epoch Biosiences, Inc. | Modified oligonucleotides for mismatch discrimination |
| JP2003529609A (ja) * | 2000-03-16 | 2003-10-07 | ジーンソフト インコーポレイティッド | 核酸結合部分を含む荷電した化合物およびその利用法 |
| US7078536B2 (en) * | 2001-03-14 | 2006-07-18 | Genesoft Pharmaceuticals, Inc. | Charged compounds comprising a nucleic acid binding moiety and uses therefor |
| EP1313880A2 (en) * | 2000-05-30 | 2003-05-28 | PE Corporation (NY) | Methods for detecting target nucleic acids using coupled ligation and amplification |
| US6887664B2 (en) | 2000-06-06 | 2005-05-03 | Applera Corporation | Asynchronous primed PCR |
| US7238795B2 (en) * | 2000-08-03 | 2007-07-03 | Roche Molecular Systems, Inc. | Nucleic acid binding compounds containing pyrazolo[3,4-d]pyrimidine analogues of purin-2,6-diamine and their uses |
| US6358679B1 (en) * | 2000-08-24 | 2002-03-19 | Pe Corporation (Ny) | Methods for external controls for nucleic acid amplification |
| JP2004521628A (ja) | 2001-03-08 | 2004-07-22 | アプレラ コーポレイション | オリゴヌクレオチドの切断および脱保護のための試薬 |
| US6774082B2 (en) * | 2001-05-11 | 2004-08-10 | Ibc Advanced Technologies, Inc. | Compositions for separating heterocyclic aromatic amine bases, nucleosides, nucleotides, and nucleotide sequences |
| AU2002339853A1 (en) * | 2001-05-24 | 2002-12-03 | Genospectra, Inc. | Pairs of nucleic acid probes with interactive signaling moieties and nucleic acid probes with enhanced hybridization efficiency and specificity |
| US6825228B2 (en) | 2001-06-13 | 2004-11-30 | Genesoft Pharmaceuticals, Inc. | Benzothiophene compounds having antiinfective activity |
| US8569516B2 (en) | 2001-09-07 | 2013-10-29 | Elitech Holding B.V. | Compounds and methods for fluorescent labeling |
| US6972339B2 (en) | 2001-09-07 | 2005-12-06 | Epoch Biosciences, Inc. | Compounds and methods for fluorescent labeling |
| US6744502B2 (en) * | 2001-09-28 | 2004-06-01 | Pe Corporation (Ny) | Shaped illumination geometry and intensity using a diffractive optical element |
| US6818420B2 (en) * | 2002-02-27 | 2004-11-16 | Biosource International, Inc. | Methods of using FET labeled oligonucleotides that include a 3′-5′ exonuclease resistant quencher domain and compositions for practicing the same |
| WO2003078450A2 (en) * | 2002-03-11 | 2003-09-25 | Epoch Biosciences, Inc. | Negatively charged minor groove binders |
| DE60326735D1 (de) | 2002-08-02 | 2009-04-30 | Genesoft Pharmaceuticals Inc | Biaryl-verbindungen mit antiinfektiver wirkung |
| US7153658B2 (en) * | 2002-09-19 | 2006-12-26 | Applera Corporation | Methods and compositions for detecting targets |
| CA2498320A1 (en) * | 2002-09-20 | 2004-04-01 | Integrated Dna Technologies, Inc. | Anthraquinone quencher dyes, their methods of preparation and use |
| US20040235005A1 (en) * | 2002-10-23 | 2004-11-25 | Ernest Friedlander | Methods and composition for detecting targets |
| AU2003285958A1 (en) * | 2002-10-25 | 2004-05-25 | Genesoft Pharmaceuticals, Inc. | Anti-infective biaryl compounds |
| EP2957568B1 (en) | 2002-11-05 | 2016-12-21 | Ionis Pharmaceuticals, Inc. | Compositions comprising alternating 2'-modified nucleosides for use in gene modulation |
| US20060167271A1 (en) * | 2002-11-14 | 2006-07-27 | Mark Ginsberg | Purified compounds that inhibit intracellular alphax4/paxillin binding |
| AU2003295692A1 (en) * | 2002-11-15 | 2004-06-15 | Sangamo Biosciences, Inc. | Methods and compositions for analysis of regulatory sequences |
| CA2508769A1 (en) * | 2002-12-10 | 2004-06-24 | Oscient Pharmaceuticals Corporation | Antibacterial compounds having a (pyrrole carboxamide)-(benzamide)-(imidazole carboxamide) motif |
| WO2005001129A2 (en) * | 2003-06-06 | 2005-01-06 | Applera Corporation | Mobility cassettes |
| US7348146B2 (en) * | 2003-10-02 | 2008-03-25 | Epoch Biosciences, Inc. | Single nucleotide polymorphism analysis of highly polymorphic target sequences |
| PT1687609E (pt) * | 2003-10-28 | 2015-03-02 | Epoch Biosciences Inc | Sondas fluorescentes para a detecção de adn por hibridação com uma maior sensibilidade e menor ruído de fundo |
| WO2005049849A2 (en) * | 2003-11-14 | 2005-06-02 | Integrated Dna Technologies, Inc. | Fluorescence quenching azo dyes, their methods of preparation and use |
| JP2007534308A (ja) * | 2003-11-19 | 2007-11-29 | アレロジック・バイオサイエンシズ・コーポレーション | 複数のフルオロフォアで標識したオリゴヌクレオチド |
| 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 |
| GB0406015D0 (en) * | 2004-03-17 | 2004-04-21 | Dynal Biotech Asa | Improvements in magnetic polymer particles |
| CA2560945C (en) * | 2004-04-01 | 2013-06-18 | Bio-Rad Laboratories, Inc. | Quantitative amplification with a labeled probe and 3' to 5' exonuclease activity |
| CN101023170B (zh) | 2004-04-26 | 2011-03-02 | 和光纯药工业株式会社 | 结核菌检测用的引物和探针以及使用它们检测人型结核菌的方法 |
| AU2005250432B2 (en) | 2004-05-28 | 2011-09-15 | Asuragen, Inc. | Methods and compositions involving microRNA |
| US8394947B2 (en) | 2004-06-03 | 2013-03-12 | Isis Pharmaceuticals, Inc. | Positionally modified siRNA constructs |
| US20070054276A1 (en) * | 2004-08-12 | 2007-03-08 | Sampson Jeffrey R | Polynucleotide analysis and methods of using nanopores |
| JP2008509675A (ja) | 2004-08-13 | 2008-04-03 | エポック バイオサイエシズ インコーポレーティッド | 増幅方法 |
| US7884086B2 (en) | 2004-09-08 | 2011-02-08 | Isis Pharmaceuticals, Inc. | Conjugates for use in hepatocyte free uptake assays |
| US7642055B2 (en) | 2004-09-21 | 2010-01-05 | Applied Biosystems, Llc | Two-color real-time/end-point quantitation of microRNAs (miRNAs) |
| US20060078894A1 (en) * | 2004-10-12 | 2006-04-13 | Winkler Matthew M | Methods and compositions for analyzing nucleic acids |
| CA2857881A1 (en) | 2004-11-12 | 2006-12-28 | Asuragen, Inc. | Methods and compositions involving mirna and mirna inhibitor molecules |
| WO2006076650A2 (en) * | 2005-01-12 | 2006-07-20 | Applera Corporation | Compositions, methods, and kits for selective amplification of nucleic acids |
| DE602005018840D1 (de) | 2005-04-14 | 2010-02-25 | Applied Biosystems Llc | 3'-modifizierte oligonukleotide mit pseudoisocytosin-nukleobasenderivaten sowie deren anwendungen als primer oder sonden |
| EP2284263B1 (en) | 2005-05-13 | 2013-12-18 | Wako Pure Chemical Industries, Ltd. | Primer and probe for use in detection of mycobacterium kansasii and method for detection of mycobacterium kansasii using the same |
| CA2601554A1 (en) | 2005-05-20 | 2006-11-30 | Integrated Dna Technologies, Inc. | Compounds and methods for labeling oligonucleotides |
| EP1896602A4 (en) * | 2005-06-09 | 2009-08-12 | Epoch Biosciences Inc | IMPROVED AMPLIFICATION PROCESSES ON PRIMER BASIS |
| US20070087360A1 (en) * | 2005-06-20 | 2007-04-19 | Boyd Victoria L | Methods and compositions for detecting nucleotides |
| WO2007041201A2 (en) | 2005-10-03 | 2007-04-12 | Applera Corporation | Compositions, methods, and kits for amplifying nucleic acids |
| JP5239853B2 (ja) | 2006-03-13 | 2013-07-17 | 和光純薬工業株式会社 | 変異遺伝子の検出方法 |
| US20080166712A1 (en) * | 2006-04-10 | 2008-07-10 | Ryusuke Murayama | Gene detection method |
| WO2007129628A1 (ja) | 2006-05-02 | 2007-11-15 | Wako Pure Chemical Industries, Ltd. | マイコバクテリウム・イントラセルラーレ検出用プライマー及びプローブ、並びにこれを用いたマイコバクテリウム・イントラセルラーレの検出方法 |
| WO2007146811A2 (en) * | 2006-06-09 | 2007-12-21 | University Of Miami | Assessment of cellular composition and fractional viability and uses thereof |
| US20090092967A1 (en) * | 2006-06-26 | 2009-04-09 | Epoch Biosciences, Inc. | Method for generating target nucleic acid sequences |
| CA2659632A1 (en) | 2006-08-01 | 2008-02-07 | Applera Corporation | Detection of analytes and nucleic acids |
| EP2057284A4 (en) | 2006-08-04 | 2011-06-29 | Isis Pharmaceuticals Inc | COMPOSITIONS AND METHODS OF MODULATING JNK PROTEINS |
| GB0619325D0 (en) * | 2006-09-30 | 2006-11-08 | Univ Strathclyde | New compounds |
| US8133701B2 (en) * | 2006-12-05 | 2012-03-13 | Sequenom, Inc. | Detection and quantification of biomolecules using mass spectrometry |
| US7902345B2 (en) * | 2006-12-05 | 2011-03-08 | Sequenom, Inc. | Detection and quantification of biomolecules using mass spectrometry |
| US20080131878A1 (en) * | 2006-12-05 | 2008-06-05 | Asuragen, Inc. | Compositions and Methods for the Detection of Small RNA |
| AU2007333106A1 (en) * | 2006-12-08 | 2008-06-19 | Asuragen, Inc. | miR-20 regulated genes and pathways as targets for therapeutic intervention |
| US9938641B2 (en) * | 2006-12-18 | 2018-04-10 | Fluidigm Corporation | Selection of aptamers based on geometry |
| CN101563455B (zh) | 2006-12-18 | 2013-08-21 | 和光纯药工业株式会社 | 鸟分枝杆菌检测用引物和探针、以及使用它们检测鸟分枝杆菌的方法 |
| EP2639316A1 (en) | 2007-05-11 | 2013-09-18 | The Johns Hopkins University | Biomarkers for melanoma |
| US8143006B2 (en) * | 2007-08-03 | 2012-03-27 | Igor Kutyavin | Accelerated cascade amplification (ACA) of nucleic acids comprising strand and sequence specific DNA nicking |
| US8071338B2 (en) * | 2007-08-08 | 2011-12-06 | Roche Molecular Systems, Inc. | Suppression of amplification using an oligonucleotide and a polymerase significantly lacking 5′-3′ nuclease activity |
| ATE549419T1 (de) | 2007-08-29 | 2012-03-15 | Sequenom Inc | Verfahren und zusammensetzungen für die universelle grössenspezifische polymerasekettenreaktion |
| WO2009036332A1 (en) | 2007-09-14 | 2009-03-19 | Asuragen, Inc. | Micrornas differentially expressed in cervical cancer and uses thereof |
| WO2009045536A2 (en) * | 2007-10-05 | 2009-04-09 | The University Of North Carolina At Chapel Hill | Receptor targeted oligonucleotides |
| US20090186015A1 (en) * | 2007-10-18 | 2009-07-23 | Latham Gary J | Micrornas differentially expressed in lung diseases and uses thereof |
| WO2009070805A2 (en) | 2007-12-01 | 2009-06-04 | Asuragen, Inc. | Mir-124 regulated genes and pathways as targets for therapeutic intervention |
| JPWO2009099037A1 (ja) | 2008-02-08 | 2011-05-26 | 和光純薬工業株式会社 | クラミドフィラ・キャビエ検出用プライマー及びプローブ、並びにこれを用いたクラミドフィラ・キャビエの検出方法 |
| US8466266B2 (en) | 2008-04-01 | 2013-06-18 | Biosearch Technologies, Inc. | Stabilized nucleic acid dark quencher-fluorophore probes |
| US20090258928A1 (en) * | 2008-04-08 | 2009-10-15 | Asuragen, Inc. | Methods and compositions for diagnosing and modulating human papillomavirus (hpv) |
| US8575123B2 (en) | 2008-04-11 | 2013-11-05 | Tekmira Pharmaceuticals Corporation | Site-specific delivery of nucleic acids by combining targeting ligands with endosomolytic components |
| EP2990487A1 (en) | 2008-05-08 | 2016-03-02 | Asuragen, INC. | Compositions and methods related to mirna modulation of neovascularization or angiogenesis |
| CN103224932A (zh) | 2008-05-28 | 2013-07-31 | 和光纯药工业株式会社 | 胞内分枝杆菌检测用引物和探针、以及使用该引物和探针检测胞内分枝杆菌的方法 |
| US8097412B2 (en) * | 2008-07-12 | 2012-01-17 | Biodiagnostics, Inc. | DNA-based test for detection of annual and intermediate ryegrass |
| US20110171649A1 (en) * | 2008-09-10 | 2011-07-14 | Igor Kutyavin | Detection of nucleic acids by oligonucleotide probes cleaved in presence of endonuclease v |
| JP2012502660A (ja) * | 2008-09-22 | 2012-02-02 | エフ．ホフマン−ラ ロシュ アーゲー | マイクロアレイ基板上の生体物質の選択的プロセシング |
| US8962580B2 (en) | 2008-09-23 | 2015-02-24 | Alnylam Pharmaceuticals, Inc. | Chemical modifications of monomers and oligonucleotides with cycloaddition |
| WO2010054406A1 (en) | 2008-11-10 | 2010-05-14 | Alnylam Pharmaceuticals, Inc. | Novel lipids and compositions for the delivery of therapeutics |
| US9534255B2 (en) * | 2008-12-17 | 2017-01-03 | Life Technologies Corporation | Methods, compositions, and kits for detecting allelic variants |
| EP3424939A1 (en) | 2009-03-02 | 2019-01-09 | Alnylam Pharmaceuticals Inc. | Nucleic acid chemical modifications |
| CN102428191A (zh) * | 2009-03-18 | 2012-04-25 | 塞昆纳姆股份有限公司 | 热稳定性内切核酸酶在产生报道分子中的应用 |
| CN102428190B (zh) | 2009-03-27 | 2014-02-26 | 生命技术公司 | 用于检测等位基因变体的方法、组合物和试剂盒 |
| KR102066189B1 (ko) | 2009-06-10 | 2020-01-14 | 알닐람 파마슈티칼스 인코포레이티드 | 향상된 지질 조성물 |
| EP2483425B1 (en) | 2009-09-28 | 2016-08-24 | Igor Kutyavin | Methods and compositions for detection of nucleic acids based on stabilized oligonucleotide probe complexes |
| WO2011046972A2 (en) * | 2009-10-12 | 2011-04-21 | Life Technologies Corporation | Compositions and methods for suppressing primer interactions |
| ES2574625T3 (es) | 2009-11-25 | 2016-06-21 | Elitechgroup B.V. | Antagonistas de miARN de oligonucleótido conjugado con aglutinante del surco menor (MGB) |
| EP2509636B1 (en) | 2009-12-07 | 2017-07-19 | Arbutus Biopharma Corporation | Compositions for nucleic acid delivery |
| NZ600725A (en) | 2009-12-18 | 2015-08-28 | Univ British Colombia | Methods and compositions for delivery of nucleic acids |
| WO2011087707A1 (en) | 2009-12-22 | 2011-07-21 | Elitech Holding B.V. | Hypertheromostable endonuclease iv substrate probe |
| US9198972B2 (en) | 2010-01-28 | 2015-12-01 | Alnylam Pharmaceuticals, Inc. | Monomers and oligonucleotides comprising cycloaddition adduct(s) |
| WO2011094580A2 (en) | 2010-01-28 | 2011-08-04 | Alnylam Pharmaceuticals, Inc. | Chelated copper for use in the preparation of conjugated oligonucleotides |
| CN102918155B (zh) | 2010-03-23 | 2015-12-16 | 和光纯药工业株式会社 | 沙眼衣原体检测用引物和探针、以及使用该引物和探针的沙眼衣原体的检测方法 |
| NZ737844A (en) | 2010-03-26 | 2022-09-30 | Dartmouth College | Vista regulatory t cell mediator protein, vista binding agents and use thereof |
| US8916345B2 (en) * | 2010-03-26 | 2014-12-23 | Integrated Dna Technologies, Inc. | Methods for enhancing nucleic acid hybridization |
| US9506057B2 (en) | 2010-03-26 | 2016-11-29 | Integrated Dna Technologies, Inc. | Modifications for antisense compounds |
| US20150231215A1 (en) | 2012-06-22 | 2015-08-20 | Randolph J. Noelle | VISTA Antagonist and Methods of Use |
| US10745467B2 (en) | 2010-03-26 | 2020-08-18 | The Trustees Of Dartmouth College | VISTA-Ig for treatment of autoimmune, allergic and inflammatory disorders |
| US9102938B2 (en) | 2010-04-01 | 2015-08-11 | Alnylam Pharmaceuticals, Inc. | 2′ and 5′ modified monomers and oligonucleotides |
| EP2558596B1 (en) | 2010-04-16 | 2018-03-14 | The Government Of The United States Of America As Reresented By The Secretary Of The Department Of Health & Human Services | Real time pcr assay for detection of bacterial respiratory pathogens |
| WO2011133871A2 (en) | 2010-04-22 | 2011-10-27 | Alnylam Pharmaceuticals, Inc. | 5'-end derivatives |
| WO2011133876A2 (en) | 2010-04-22 | 2011-10-27 | Alnylam Pharmaceuticals, Inc. | Oligonucleotides comprising acyclic and abasic nucleosides and analogs |
| US20130260460A1 (en) | 2010-04-22 | 2013-10-03 | Isis Pharmaceuticals Inc | Conformationally restricted dinucleotide monomers and oligonucleotides |
| GB201007868D0 (en) | 2010-05-11 | 2010-06-23 | Enigma Diagnostics Ltd | Sequence detection assay |
| EP2569452B1 (en) | 2010-05-14 | 2020-03-25 | Life Technologies Corporation | Karyotyping assay |
| EP2576577B1 (en) | 2010-05-28 | 2015-03-18 | Life Technologies Corporation | Synthesis of 2', 3'-dideoxynucleosides for automated dna synthesis and pyrophosphorolysis activated polymerization |
| EP2576599B1 (en) | 2010-06-02 | 2015-03-18 | Merck Patent GmbH | A genetically modified bacterium of the species listeria monocytogenes |
| US20130236968A1 (en) | 2010-06-21 | 2013-09-12 | Alnylam Pharmaceuticals, Inc. | Multifunctional copolymers for nucleic acid delivery |
| US20130189268A1 (en) | 2010-06-22 | 2013-07-25 | Precision Biologics, Inc. | Colon and pancreas cancer specific antigens and antibodies |
| US20130202652A1 (en) | 2010-07-30 | 2013-08-08 | Alnylam Pharmaceuticals, Inc. | Methods and compositions for delivery of active agents |
| WO2012016184A2 (en) | 2010-07-30 | 2012-02-02 | Alnylam Pharmaceuticals, Inc. | Methods and compositions for delivery of active agents |
| EP2896696B1 (en) | 2010-09-07 | 2017-12-27 | Integrated Dna Technologies, Inc. | Modifications for antisense compounds |
| US9068014B2 (en) | 2010-09-23 | 2015-06-30 | Precision Biologics, Inc. | Colon and pancreas cancer peptidomimetics |
| EP2643018B1 (en) | 2010-11-23 | 2020-10-14 | AlderBio Holdings LLC | Anti-il-6 antibodies for the treatment of oral mucositis |
| US9999673B2 (en) | 2011-01-11 | 2018-06-19 | Alnylam Pharmaceuticals, Inc. | PEGylated lipids and their use for drug delivery |
| EP3733870A3 (en) | 2011-01-14 | 2021-01-27 | Life Technologies Corporation | Methods for identification and quantification of mirnas |
| WO2012099896A2 (en) | 2011-01-17 | 2012-07-26 | Life Technologies Corporation | Workflow for detection of ligands using nucleic acids |
| EP2689031B1 (en) | 2011-03-23 | 2016-10-19 | ELITechGroup B.V. | Functionalized 3-alkynyl pyrazolopyrimidine analogues as universal bases and methods of use |
| US8969003B2 (en) | 2011-03-23 | 2015-03-03 | Elitech Holding B.V. | Functionalized 3-alkynyl pyrazolopyrimidine analogues as universal bases and methods of use |
| US20140170653A1 (en) | 2011-04-15 | 2014-06-19 | Life Technologies Corporation | Chemical ligation |
| EP2801626B1 (en) | 2011-05-24 | 2016-04-06 | ELITechGroup B.V. | Detection of methicillin-resistant staphylococcus aureus |
| TWI560200B (en) | 2011-05-25 | 2016-12-01 | Innate Pharma Sa | Anti-kir antibodies for the treatment of inflammatory and autoimmune disorders |
| EP4249603A3 (en) | 2011-06-08 | 2024-01-03 | Life Technologies Corporation | Design and development of novel detergents for use in pcr systems |
| US9567628B2 (en) | 2011-06-08 | 2017-02-14 | Life Technologies Corporation | Polymerization of nucleic acids using proteins having low isoelectric points |
| US9528987B2 (en) | 2011-06-23 | 2016-12-27 | University Of Washington | Reagent patterning in capillarity-based analyzers and associated systems and methods |
| US9056887B2 (en) | 2011-07-26 | 2015-06-16 | Elitech Holding B.V. | Minor groove binder phosphoramidites and methods of use |
| WO2013040251A2 (en) | 2011-09-13 | 2013-03-21 | Asurgen, Inc. | Methods and compositions involving mir-135b for distinguishing pancreatic cancer from benign pancreatic disease |
| WO2013049328A1 (en) | 2011-09-27 | 2013-04-04 | Alnylam Pharmaceuticals, Inc. | Di-aliphatic substituted pegylated lipids |
| GB201119903D0 (en) * | 2011-11-17 | 2011-12-28 | Univ Vilnius | Nucleic acid production and sequence analysis |
| US8981318B1 (en) | 2011-12-30 | 2015-03-17 | Gene Capture, Inc. | Multi-dimensional scanner for nano-second time scale signal detection |
| RU2654484C1 (ru) | 2012-05-11 | 2018-05-21 | Ресет Терапьютикс, Инк. | Карбазолсодержащие сульфонамиды в качестве модуляторов криптохрома |
| US9394574B2 (en) | 2012-06-12 | 2016-07-19 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Methods for detecting Legionella nucleic acids in a sample |
| KR102264617B1 (ko) | 2012-06-14 | 2021-06-14 | 라이프 테크놀로지스 코포레이션 | 폴리머라제 연쇄 반응 (pcr)을 위한 신규 조성물, 방법 및 키트 |
| DK3421486T5 (da) | 2012-06-22 | 2024-09-16 | The Trustees Of Darthmouth College | Nye Vista-IG-konstruktioner og anvendelse af Vista-IG til behandling af autoimmune, allergiske og inflammatoriske lidelser |
| US9890215B2 (en) | 2012-06-22 | 2018-02-13 | King's College London | Vista modulators for diagnosis and treatment of cancer |
| JP6368308B2 (ja) | 2012-09-07 | 2018-08-01 | トラスティーズ・オブ・ダートマス・カレッジ | 癌の診断および治療のためのｖｉｓｔａ調節剤 |
| MX2015004191A (es) | 2012-10-04 | 2016-04-04 | Univ Leland Stanford Junior | Metodos y reactivos para la deteccion, cuantificacion y serotipado de virus del dengue. |
| EP3628746B1 (en) | 2012-11-02 | 2025-08-27 | Life Technologies Corporation | Small rna capture, detection and quantification |
| US9938344B2 (en) | 2012-12-28 | 2018-04-10 | Precision Biologics, Inc. | Humanized monoclonal antibodies and methods of use for the diagnosis and treatment of colon and pancreas cancer |
| CN105050720A (zh) | 2013-01-22 | 2015-11-11 | 华盛顿大学商业化中心 | 顺序递送流体体积和相关的设备、系统和方法 |
| EP2971095B1 (en) | 2013-03-12 | 2019-11-20 | Life Technologies Corporation | Universal reporter-based genotyping methods, reaction mixture and kit |
| WO2014164874A2 (en) | 2013-03-13 | 2014-10-09 | Becton, Dickinson And Company | Methods and compositions for modulation of amplification efficiency |
| WO2014159063A1 (en) | 2013-03-14 | 2014-10-02 | Elitech Holding B.V. | Functionalized 3-alkynyl pyrazolopyrimidine analogues as universal bases and methods of use |
| CN105102635B (zh) | 2013-03-15 | 2020-09-25 | 生命技术公司 | 肺癌的分类和可行性指数 |
| US20150080239A1 (en) | 2013-09-13 | 2015-03-19 | Life Technologies Corporation | Classification and Actionability Indices for Cancer |
| EP2978446B1 (en) | 2013-03-27 | 2020-03-04 | The General Hospital Corporation | Anti-cd33 antibody for use in treating alzheimer's disease |
| WO2014165710A2 (en) | 2013-04-05 | 2014-10-09 | Life Technologies Corporation | Gene fusions |
| WO2014186147A2 (en) | 2013-05-13 | 2014-11-20 | Elitech Holding B.V. | Droplet digital pcr with short minor groove probes |
| EP3399055A1 (en) | 2013-10-22 | 2018-11-07 | The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services | Compositions and methods for detection and discrimination of influenza viruses |
| EP3539944A1 (en) | 2013-10-25 | 2019-09-18 | Life Technologies Corporation | Novel compounds for use in pcr systems and applications thereof |
| WO2015062699A1 (en) | 2013-10-30 | 2015-05-07 | Merck Patent Gmbh | Method for isolating microorganisms from a complex sample |
| US11014987B2 (en) | 2013-12-24 | 2021-05-25 | Janssen Pharmaceutics Nv | Anti-vista antibodies and fragments, uses thereof, and methods of identifying same |
| MY182431A (en) | 2013-12-24 | 2021-01-25 | Janssen Pharmaceutica Nv | Anti-vista antibodies and fragments |
| US20170058366A1 (en) | 2014-02-21 | 2017-03-02 | The United States of America, as represented by th e Secretary, Dept. of Health and Human Services | Hiv-2 nucleic acids and methods of detection |
| WO2015149034A2 (en) | 2014-03-27 | 2015-10-01 | Life Technologies Corporation | Gene fusions and gene variants associated with cancer |
| TWI690521B (zh) | 2014-04-07 | 2020-04-11 | 美商同步製藥公司 | 作為隱花色素調節劑之含有咔唑之醯胺類、胺基甲酸酯類及脲類 |
| US20170044631A1 (en) | 2014-04-14 | 2017-02-16 | The Unite States of America, as represented by the Secretary, Dept. of Health and Human Services | Methods for rapid detection and identification of viral nucleic acids |
| AU2015274504B2 (en) | 2014-06-11 | 2021-02-04 | Kathy A. Green | Use of VISTA agonists and antagonists to suppress or enhance humoral immunity |
| CN106795473A (zh) | 2014-06-11 | 2017-05-31 | 精密公司 | 用于核酸分析的具有集成的测定对照的微流体盒及设备 |
| US9212388B1 (en) | 2014-06-30 | 2015-12-15 | Life Technologies Corporation | Direct quantitative PCR absent minor groove binders |
| WO2016061111A1 (en) | 2014-10-13 | 2016-04-21 | Life Technologies Corporation | Methods, kits & compositions for determining gene copy numbers |
| WO2016090347A1 (en) | 2014-12-05 | 2016-06-09 | Immunext, Inc. | Identification of vsig8 as the putative vista receptor and its use thereof to produce vista/vsig8 modulators |
| US10266903B2 (en) | 2014-12-12 | 2019-04-23 | Elitechgroup, Inc. | Methods and compositions for detecting antibiotic resistant bacteria |
| WO2016094607A2 (en) | 2014-12-12 | 2016-06-16 | Elitechgroup B.V. | Methods and compositions for detecting antibiotic resistant bacteria |
| EP3234141A4 (en) | 2014-12-18 | 2018-06-20 | Alnylam Pharmaceuticals, Inc. | Reversir tm compounds |
| BR112017027870A2 (pt) | 2015-06-24 | 2018-08-28 | Janssen Pharmaceutica Nv | anticorpos e fragmentos anti-vista |
| WO2017015109A1 (en) | 2015-07-17 | 2017-01-26 | Alnylam Pharmaceuticals, Inc. | Multi-targeted single entity conjugates |
| MX2018009800A (es) | 2016-02-12 | 2018-11-09 | Janssen Pharmaceutica Nv | Anticuerpos y fragmentos anti-vista, usos de los mismos y procedimientos de identificacion de los mismos. |
| PH12018502203B1 (en) | 2016-04-15 | 2024-05-15 | Immunext Inc | Anti-human vista antibodies and use thereof |
| US11155885B2 (en) | 2016-05-20 | 2021-10-26 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Real-time reverse transcriptase-polymerase chain reaction assay with modified probe for the diagnosis of rabies viruses and other lyssaviruses |
| US20170362640A1 (en) | 2016-06-16 | 2017-12-21 | Life Technologies Corporation | Novel compositions, methods and kits for microorganism detection |
| WO2018005284A1 (en) | 2016-06-27 | 2018-01-04 | The United State Of America, As Represented By The Secretary, Department Of Health And Human Services | Methods and compositions for influenza a virus subtyping |
| WO2018039599A1 (en) | 2016-08-26 | 2018-03-01 | Life Technologies Corporation | Nucleic acid extraction and amplification controls and methods of use thereof |
| WO2018047148A1 (en) | 2016-09-12 | 2018-03-15 | Novartis Ag | Compounds for the inhibition of mirna |
| EP3592860B1 (en) | 2017-03-08 | 2021-11-03 | Etablissement Français du Sang | Rhd gene allele associated with a weak d phenotype and its uses |
| EP3592757A2 (en) | 2017-03-09 | 2020-01-15 | ELITechGroup, Inc. | Nitrodiarylethenes as fluorescence quenchers for nucleic acid probes |
| ES2909351T3 (es) | 2017-08-17 | 2022-05-06 | Elitechgroup Inc | Quencheres estabilizadores de fluorescencia dúplex para sondas de ácidos nucleicos |
| US20200340041A1 (en) | 2017-11-13 | 2020-10-29 | Life Technologies Corporation | Novel compositions, methods and kits for urinary tract microorganism detection |
| US10689629B1 (en) | 2017-12-06 | 2020-06-23 | Cepheid | Inhibition of nucleic acid polymerases by endonuclease V-cleavable circular oligonucleotide ligands |
| US10724017B1 (en) | 2017-12-06 | 2020-07-28 | Cepheid | Inhibition of DNA polymerases by uracil-DNA glycosylase-cleavable oligonucleotide ligands |
| US10724083B1 (en) | 2017-12-06 | 2020-07-28 | Cepheid | Inhibition of nucleic acid polymerases by endonuclease V-cleavable oligonucleotide ligands |
| AU2019266207B2 (en) | 2018-05-07 | 2025-04-24 | Alnylam Pharmaceuticals, Inc. | Extrahepatic delivery |
| EP3802526A1 (en) | 2018-05-29 | 2021-04-14 | ELITechGroup, Inc. | Carborhodamine compounds and methods of preparation thereof |
| JP2021533769A (ja) | 2018-08-16 | 2021-12-09 | ライフ テクノロジーズ コーポレーション | 核酸の増幅のための試薬、混合物、キット、および方法 |
| TW202028465A (zh) | 2018-09-28 | 2020-08-01 | 美商阿尼拉製藥公司 | 甲狀腺素運載蛋白（ＴＴＲ）ｉＲＮＡ組成物及其治療或預防ＴＴＲ相關眼部疾病之使用方法 |
| WO2020072409A1 (en) | 2018-10-01 | 2020-04-09 | Gen-Probe Incorporated | Compositions and methods for amplifying or detecting varicella-zoster virus |
| JP2022532652A (ja) | 2019-05-17 | 2022-07-15 | アルニラム ファーマスーティカルズ インコーポレイテッド | オリゴヌクレオチドの経口送達 |
| CN114845992A (zh) * | 2019-10-28 | 2022-08-02 | 美国杰龙生物医药公司 | 无定形固体琥珀酰化的3-(脂肪酸酰胺基)-2-羟基-1-(受保护羟基)-丙烷盐及其制备方法 |
| US11987540B2 (en) | 2019-10-28 | 2024-05-21 | Geron Corporation | Crystalline solids of 3-palmitoyl-amido-1,2-propanediol and 3-palmitoyl-amido-2-hydroxy-1-dimethoxytriphenylmethylether-propane and methods of making and using the same |
| WO2021092145A1 (en) | 2019-11-06 | 2021-05-14 | Alnylam Pharmaceuticals, Inc. | Transthyretin (ttr) irna composition and methods of use thereof for treating or preventing ttr-associated ocular diseases |
| AU2020378414A1 (en) | 2019-11-06 | 2022-05-26 | Alnylam Pharmaceuticals, Inc. | Extrahepatic delivery |
| EP3911769B1 (en) | 2020-02-18 | 2022-11-02 | Life Technologies Corporation | Compositions and methods for detection of viral sequences |
| CN115484932B (zh) | 2020-03-04 | 2024-12-10 | 维乎医疗有限公司 | 用于靶向rna递送的组合物和方法 |
| EP3929310A1 (en) | 2020-06-26 | 2021-12-29 | FRAUNHOFER-GESELLSCHAFT zur Förderung der angewandten Forschung e.V. | Methods and means for corona virus nucleic acid detection |
| DE202021100985U1 (de) | 2020-06-26 | 2021-06-18 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Ein diagnostisches Assay-Kit und Mittel zum Nachweis von Coronavirus-Nukleinsäure |
| US20230257745A1 (en) | 2020-07-10 | 2023-08-17 | Alnylam Pharmaceuticals, Inc. | Circular siRNAs |
| US20240060117A1 (en) | 2020-07-23 | 2024-02-22 | Life Technologies Corporation | Energy transfer dye conjugates for use in biological assays |
| KR20230056685A (ko) | 2020-07-23 | 2023-04-27 | 라이프 테크놀로지스 코포레이션 | 염료를 사용한 생물학적 분석을 위한 조성물, 시스템 및 방법 |
| CN116368226A (zh) | 2020-09-04 | 2023-06-30 | 维乎医疗有限公司 | 用于加帽rna的组合物和方法 |
| US20240336914A1 (en) | 2020-12-31 | 2024-10-10 | Alnylam Pharmaceuticals, Inc. | 2'-modified nucleoside based oligonucleotide prodrugs |
| JP2024501857A (ja) | 2020-12-31 | 2024-01-16 | アルナイラム ファーマシューティカルズ， インコーポレイテッド | 環状ジスルフィド修飾リン酸ベースのオリゴヌクレオチドプロドラッグ |
| US20250270619A1 (en) | 2021-01-18 | 2025-08-28 | Life Technologies Corporation | Compositions, kits and methods for direct amplification from crude biological samples |
| WO2022159874A1 (en) | 2021-01-25 | 2022-07-28 | Life Technologies Corporation | Compositions, kits and methods for detection of viral variant sequences |
| US20250333806A1 (en) | 2021-03-23 | 2025-10-30 | Life Technologies Corporation | Compositions, kits, and methods for variant-resistant detection of target viral sequences |
| EP4074839A1 (en) | 2021-04-16 | 2022-10-19 | Biotype GmbH | Optimized oligonucleotide tx probe for a multiplexing analysis of nucleic acids and a multiplexing method |
| US20250270562A1 (en) | 2021-07-09 | 2025-08-28 | Alnylam Pharmaceuticals, Inc. | Bis-rnai compounds for cns delivery |
| KR20240036041A (ko) | 2021-07-21 | 2024-03-19 | 알닐람 파마슈티칼스 인코포레이티드 | 대사 장애-연관 표적 유전자 iRNA 조성물 및 이의 사용 방법 |
| EP4373890A1 (en) | 2021-07-21 | 2024-05-29 | Life Technologies Corporation | Dibenzoxanthene quenchers, uses, and methods of preparation |
| WO2023014729A1 (en) | 2021-08-02 | 2023-02-09 | Life Technologies Corporation | Compositions, kits, and methods for detection of nucleic acid sequence loads |
| CN118369427A (zh) | 2021-10-15 | 2024-07-19 | 阿尔尼拉姆医药品有限公司 | 肝外递送irna组合物及其使用方法 |
| CN118414438A (zh) | 2021-10-20 | 2024-07-30 | 生命科技公司 | 使用内部定量标准物定量核酸序列的组合物、试剂盒和方法 |
| EP4522742A2 (en) | 2022-05-13 | 2025-03-19 | Alnylam Pharmaceuticals, Inc. | Single-stranded loop oligonucleotides |
| CN114672482B (zh) * | 2022-05-31 | 2022-08-30 | 上海百力格生物技术有限公司 | 核酸探针制备方法 |
| AU2023298557A1 (en) | 2022-06-29 | 2025-01-16 | Life Technologies Corporation | Systems and methods for analyte detection from multiplexed assays |
| EP4547758A1 (en) | 2022-06-29 | 2025-05-07 | Life Technologies Corporation | Multiplex dye compounds |
| EP4547683A2 (en) | 2022-06-30 | 2025-05-07 | Alnylam Pharmaceuticals, Inc. | Cyclic-disulfide modified phosphate based oligonucleotide prodrugs |
| WO2024054925A1 (en) | 2022-09-09 | 2024-03-14 | Life Technologies Corporation | Compositions, kits and methods for detection of viral variant sequences |
| EP4594492A1 (en) | 2022-09-30 | 2025-08-06 | Alnylam Pharmaceuticals, Inc. | Modified double-stranded rna agents |
| EP4350002A1 (en) | 2022-10-07 | 2024-04-10 | Biotype GmbH | Nachweis von molekularen analyten auf der grundlage massgeschneiderter sondenkonkurrenz |
| WO2024102839A1 (en) | 2022-11-10 | 2024-05-16 | Life Technologies Corporation | Compositions, kits, and methods for detection of viral sequences |
| EP4646495A1 (en) | 2023-01-02 | 2025-11-12 | Life Technologies Corporation | Compositions, kits and methods for detection of viral sequences |
| US20240254568A1 (en) | 2023-01-27 | 2024-08-01 | Life Technologies Corporation | Compositions, kits, and methods for detecting sti pathogen sequences |
| WO2024168010A2 (en) | 2023-02-09 | 2024-08-15 | Alnylam Pharmaceuticals, Inc. | Reversir molecules and methods of use thereof |
| WO2024216155A1 (en) | 2023-04-12 | 2024-10-17 | Alnylam Pharmaceuticals, Inc. | Extrahepatic delivery of double-stranded rna agents |
| WO2024238460A2 (en) | 2023-05-12 | 2024-11-21 | Life Technologies Corporation | Systems and methods for multiplexed polymerase chain reaction processes and data analysis |
| WO2024238385A2 (en) | 2023-05-12 | 2024-11-21 | Alnylam Pharmaceuticals, Inc. | Single-stranded loop oligonucleotides |
| DE102023124346A1 (de) | 2023-09-09 | 2025-03-13 | Biotype Gmbh | Verfahren zur Detektion des Endometriumkarzinoms Subtyp CN hoch |
| WO2025064660A2 (en) | 2023-09-21 | 2025-03-27 | Alnylam Pharmaceuticals, Inc. | Activin a receptor type 1c (acvr1c) irna compositions and methods of use thereof |
| EP4613876A1 (en) | 2024-03-08 | 2025-09-10 | Pxlence BV | Nucleic acid quantification using universal detection probes |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4169888A (en) | 1977-10-17 | 1979-10-02 | The Upjohn Company | Composition of matter and process |
| US4458066A (en) | 1980-02-29 | 1984-07-03 | University Patents, Inc. | Process for preparing polynucleotides |
| US4358535A (en) | 1980-12-08 | 1982-11-09 | Board Of Regents Of The University Of Washington | Specific DNA probes in diagnostic microbiology |
| US4711955A (en) | 1981-04-17 | 1987-12-08 | Yale University | Modified nucleotides and methods of preparing and using same |
| CA1190838A (en) | 1981-07-17 | 1985-07-23 | Cavit Akin | Homogeneous nucleic acid hybridization diagnostics by non-radiative energy transfer |
| US4942227A (en) * | 1982-01-11 | 1990-07-17 | California Institute Of Technology | Bifunctional molecules having a DNA intercalator or DNA groove binder linked to ethylene diamine tetraacetic acid, their preparation and use to cleave DNA |
| FR2540122B1 (fr) * | 1983-01-27 | 1985-11-29 | Centre Nat Rech Scient | Nouveaux composes comportant une sequence d'oligonucleotide liee a un agent d'intercalation, leur procede de synthese et leur application |
| US4665184A (en) * | 1983-10-12 | 1987-05-12 | California Institute Of Technology | Bifunctional molecules having a DNA intercalator or DNA groove binder linked to ethylene diamine tetraacetic acid |
| US4883750A (en) | 1984-12-13 | 1989-11-28 | Applied Biosystems, Inc. | Detection of specific sequences in nucleic acids |
| US4683202A (en) | 1985-03-28 | 1987-07-28 | Cetus Corporation | Process for amplifying nucleic acid sequences |
| US4683195A (en) | 1986-01-30 | 1987-07-28 | Cetus Corporation | Process for amplifying, detecting, and/or-cloning nucleic acid sequences |
| US4868105A (en) | 1985-12-11 | 1989-09-19 | Chiron Corporation | Solution phase nucleic acid sandwich assay |
| US4800159A (en) | 1986-02-07 | 1989-01-24 | Cetus Corporation | Process for amplifying, detecting, and/or cloning nucleic acid sequences |
| US4868103A (en) | 1986-02-19 | 1989-09-19 | Enzo Biochem, Inc. | Analyte detection by means of energy transfer |
| US5525464A (en) | 1987-04-01 | 1996-06-11 | Hyseq, Inc. | Method of sequencing by hybridization of oligonucleotide probes |
| US5202231A (en) | 1987-04-01 | 1993-04-13 | Drmanac Radoje T | Method of sequencing of genomes by hybridization of oligonucleotide probes |
| US6270961B1 (en) | 1987-04-01 | 2001-08-07 | Hyseq, Inc. | Methods and apparatus for DNA sequencing and DNA identification |
| US5124246A (en) | 1987-10-15 | 1992-06-23 | Chiron Corporation | Nucleic acid multimers and amplified nucleic acid hybridization assays using same |
| CA1323293C (en) | 1987-12-11 | 1993-10-19 | Keith C. Backman | Assay using template-dependent nucleic acid probe reorganization |
| WO1989009221A1 (en) | 1988-03-25 | 1989-10-05 | University Of Virginia Alumni Patents Foundation | Oligonucleotide n-alkylphosphoramidates |
| CA1341584C (en) | 1988-04-06 | 2008-11-18 | Bruce Wallace | Method of amplifying and detecting nucleic acid sequences |
| US4921788A (en) | 1988-04-12 | 1990-05-01 | The Research Foundation Of State University Of New York | Competitive nucleic acid immunoassay for the detection of analytes |
| US5849482A (en) | 1988-09-28 | 1998-12-15 | Epoch Pharmaceuticals, Inc. | Crosslinking oligonucleotides |
| WO1990003370A1 (en) | 1988-09-28 | 1990-04-05 | Microprobe Corporation | DERIVATIVES OF PYRAZOLO[3,4-d]PYRIMIDINE |
| EP0472648A4 (en) | 1989-05-18 | 1992-09-16 | Microprobe Corporation | Crosslinking oligonucleotides |
| CA2024548C (en) * | 1989-09-05 | 2002-05-28 | David Issachar | Analyte specific chemical sensor |
| DE69034150T2 (de) | 1989-10-24 | 2005-08-25 | Isis Pharmaceuticals, Inc., Carlsbad | 2'-Modifizierte Oligonukleotide |
| US5237101A (en) * | 1990-01-26 | 1993-08-17 | The Trustees Of The Univ. Of Penna. | Propargylic and allenic sulfones |
| US5210015A (en) | 1990-08-06 | 1993-05-11 | Hoffman-La Roche Inc. | Homogeneous assay system using the nuclease activity of a nucleic acid polymerase |
| US5512667A (en) | 1990-08-28 | 1996-04-30 | Reed; Michael W. | Trifunctional intermediates for preparing 3'-tailed oligonucleotides |
| US5296350A (en) | 1990-10-31 | 1994-03-22 | The Research Foundation Of State University Of New York | Ion triggered alkylation of biological targets by silyloxy aromatic agents |
| EP0834575B1 (en) | 1990-12-06 | 2001-11-28 | Affymetrix, Inc. (a Delaware Corporation) | Identification of nucleic acids in samples |
| WO1992020698A1 (en) * | 1991-05-17 | 1992-11-26 | Uab Research Foundation | Sequence specific dna binding drugs |
| US5340716A (en) | 1991-06-20 | 1994-08-23 | Snytex (U.S.A.) Inc. | Assay method utilizing photoactivated chemiluminescent label |
| US5419966A (en) * | 1991-06-10 | 1995-05-30 | Microprobe Corporation | Solid support for synthesis of 3'-tailed oligonucleotides |
| JPH06509945A (ja) | 1991-08-19 | 1994-11-10 | マイクロプローブ・コーポレイション | 酵素媒介三本鎖形成のための架橋性オリゴヌクレオチド |
| US5574142A (en) | 1992-12-15 | 1996-11-12 | Microprobe Corporation | Peptide linkers for improved oligonucleotide delivery |
| WO1994017092A1 (en) | 1993-01-26 | 1994-08-04 | Microprobe Corporation | Bifunctional crosslinking oligonucleotides adapted for linking to a desired gene sequence of invading organism or cell |
| US5786138A (en) | 1993-01-29 | 1998-07-28 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Hyperstabilizing antisense nucleic acid binding agents |
| US5395849A (en) * | 1993-10-05 | 1995-03-07 | Bristol-Myers Squibb Company | Hybrid antitumor compounds containing a cyclic enediyne and a DNA-binder |
| US5925517A (en) * | 1993-11-12 | 1999-07-20 | The Public Health Research Institute Of The City Of New York, Inc. | Detectably labeled dual conformation oligonucleotide probes, assays and kits |
| US5538848A (en) * | 1994-11-16 | 1996-07-23 | Applied Biosystems Division, Perkin-Elmer Corp. | Method for detecting nucleic acid amplification using self-quenching fluorescence probe |
| US5446137B1 (en) * | 1993-12-09 | 1998-10-06 | Behringwerke Ag | Oligonucleotides containing 4'-substituted nucleotides |
| US5646126A (en) | 1994-02-28 | 1997-07-08 | Epoch Pharmaceuticals | Sterol modified oligonucleotide duplexes having anticancer activity |
| FR2719048B1 (fr) * | 1994-04-25 | 1996-07-19 | Pasteur Strasbourg I Universit | Bases nucléiques polycationiques et oligonucléotides les contenant. |
| US5968933A (en) * | 1994-08-26 | 1999-10-19 | Auckland Division Cancer Society Of New Zealand Inc. | DNA-targeted alkylating agents |
| US5556752A (en) | 1994-10-24 | 1996-09-17 | Affymetrix, Inc. | Surface-bound, unimolecular, double-stranded DNA |
| US6312894B1 (en) * | 1995-04-03 | 2001-11-06 | Epoch Pharmaceuticals, Inc. | Hybridization and mismatch discrimination using oligonucleotides conjugated to minor groove binders |
| US5801155A (en) * | 1995-04-03 | 1998-09-01 | Epoch Pharmaceuticals, Inc. | Covalently linked oligonucleotide minor grove binder conjugates |
| AU693023B2 (en) * | 1995-05-05 | 1998-06-18 | Applied Biosystems, Llc | Methods and reagents for combined PCR amplification and hybridization probing assay |
| US5912340A (en) | 1995-10-04 | 1999-06-15 | Epoch Pharmaceuticals, Inc. | Selective binding complementary oligonucleotides |
| US5659022A (en) | 1996-01-05 | 1997-08-19 | Epoch Pharmaceuticals, Inc. | Oligonucleotide-cyclopropapyrroloindole conjugates as sequence specific hybridization and crosslinking agents for nucleic acids |
| US5776907A (en) | 1996-05-20 | 1998-07-07 | Texas Biotechnology Corporation | Mitomycin oligonucleotide conjugates |
| US5955590A (en) | 1996-07-15 | 1999-09-21 | Worcester Foundation For Biomedical Research | Conjugates of minor groove DNA binders with antisense oligonucleotides |
| EP0986539A1 (en) | 1997-04-06 | 2000-03-22 | California Institute Of Technology | Dna-binding pyrrole and imidazole polyamide derivatives |
| US6080868A (en) * | 1998-01-23 | 2000-06-27 | The Perkin-Elmer Corporation | Nitro-substituted non-fluorescent asymmetric cyanine dye compounds |
-
1995
- 1995-04-03 US US08/415,370 patent/US5801155A/en not_active Expired - Lifetime
-
1996
- 1996-04-03 ES ES96910723T patent/ES2300106T3/es not_active Expired - Lifetime
- 1996-04-03 CA CA002223678A patent/CA2223678C/en not_active Expired - Lifetime
- 1996-04-03 PT PT96910723T patent/PT819133E/pt unknown
- 1996-04-03 AU AU53842/96A patent/AU716108B2/en not_active Expired
- 1996-04-03 WO PCT/US1996/004559 patent/WO1996032496A2/en not_active Ceased
- 1996-04-03 EP EP96910723A patent/EP0819133B1/en not_active Expired - Lifetime
- 1996-04-03 CN CN96194421.8A patent/CN1187363C/zh not_active Expired - Lifetime
- 1996-04-03 CN CN200410055897.4A patent/CN1644585A/zh active Pending
- 1996-04-03 AT AT96910723T patent/ATE382627T1/de active
- 1996-04-03 DE DE69637389T patent/DE69637389T2/de not_active Expired - Lifetime
- 1996-04-03 DK DK96910723T patent/DK0819133T3/da active
- 1996-04-03 CN CN2009101732576A patent/CN101914099A/zh active Pending
- 1996-04-03 JP JP53105196A patent/JP4948690B2/ja not_active Expired - Lifetime
-
1998
- 1998-08-27 US US09/141,764 patent/US6084102A/en not_active Expired - Lifetime
-
2000
- 2000-02-18 US US09/507,345 patent/US6426408B1/en not_active Expired - Lifetime
- 2000-12-18 US US09/739,928 patent/US6486308B2/en not_active Expired - Lifetime
-
2008
- 2008-07-14 US US12/172,999 patent/US7794945B2/en not_active Expired - Fee Related
-
2010
- 2010-08-31 US US12/847,148 patent/US8465921B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1186496A (zh) | 1998-07-01 |
| JP4948690B2 (ja) | 2012-06-06 |
| US6084102A (en) | 2000-07-04 |
| CA2223678A1 (en) | 1996-10-17 |
| CA2223678C (en) | 2009-09-08 |
| EP0819133A2 (en) | 1998-01-21 |
| AU716108B2 (en) | 2000-02-17 |
| EP0819133B1 (en) | 2008-01-02 |
| US6426408B1 (en) | 2002-07-30 |
| DE69637389D1 (de) | 2008-02-14 |
| US20020052482A1 (en) | 2002-05-02 |
| US8465921B2 (en) | 2013-06-18 |
| PT819133E (pt) | 2008-04-07 |
| CN1644585A (zh) | 2005-07-27 |
| US7794945B2 (en) | 2010-09-14 |
| DE69637389T2 (de) | 2008-12-18 |
| JPH11504626A (ja) | 1999-04-27 |
| US6486308B2 (en) | 2002-11-26 |
| ATE382627T1 (de) | 2008-01-15 |
| CN101914099A (zh) | 2010-12-15 |
| AU5384296A (en) | 1996-10-30 |
| WO1996032496A3 (en) | 1996-11-28 |
| US20110275070A1 (en) | 2011-11-10 |
| US20090048427A1 (en) | 2009-02-19 |
| WO1996032496A2 (en) | 1996-10-17 |
| DK0819133T3 (da) | 2008-05-13 |
| CN1187363C (zh) | 2005-02-02 |
| US5801155A (en) | 1998-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2300106T3 (es) | Conjugados de agente de union al surco menor y oligonucleotidos unidos covalentemente. | |
| US6884584B2 (en) | Hybridization and mismatch discrimination using oligonucleotides conjugated to minor groove binders | |
| ES2204537T3 (es) | Sistesis de oligonucleotidos marcados sobre soportes solidos. | |
| US6593466B1 (en) | Guanidinium functionalized nucleotides and precursors thereof | |
| CN101312941B (zh) | 多核苷酸标记试剂 | |
| US7999098B2 (en) | Triphosphate oligonucleotide modification reagents and uses thereof | |
| Lukhtanov et al. | Oligodeoxynucleotides with conjugated dihydropyrroloindole oligopeptides: Preparation and hybridization properties | |
| ES2269239T3 (es) | Derivados de poliamida-oligonucleotidos, su preparacion y uso. | |
| Wojciechowski et al. | Nucleobase modifications in peptide nucleic acids | |
| De Napoli et al. | A new solid-phase synthesis of oligonucleotides 3′-conjugated with peptides | |
| Iwai et al. | Solid-phase synthesis of protected oligonucleotide blocks: Applications to block condensation on a polymer support and synthesis of a 3'-modified oligonucleotides | |
| Gerrard | Novel nucleotide analogues for forming stable DNA triple helices | |
| US20080207890A1 (en) | Reagents for the Improved Synthesis of Isoguanosine Containing Oligonucleotides | |
| Emanuel | SYNTHESIS, CARBON-13 NMR AND STEREOCHEMISTRY OF A REVERSED AMINOACYL NUCLEOSIDE ANALOG OF PUROMYCIN. | |
| JPWO2001096356A1 (ja) | アンチセンス分子及びそれを用いた遺伝子機能発現の制御方法 |