CA2203494C - Energy transfer dyes with enhanced fluorescence - Google Patents
Energy transfer dyes with enhanced fluorescence Download PDFInfo
- Publication number
- CA2203494C CA2203494C CA002203494A CA2203494A CA2203494C CA 2203494 C CA2203494 C CA 2203494C CA 002203494 A CA002203494 A CA 002203494A CA 2203494 A CA2203494 A CA 2203494A CA 2203494 C CA2203494 C CA 2203494C
- Authority
- CA
- Canada
- Prior art keywords
- dye
- dyes
- energy transfer
- group
- acceptor
- 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 - Fee Related
Links
- 239000000975 dye Substances 0.000 title claims abstract description 585
- 238000012546 transfer Methods 0.000 title claims abstract description 200
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 89
- 125000001424 substituent group Chemical group 0.000 claims abstract description 62
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 47
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 31
- 150000001336 alkenes Chemical class 0.000 claims abstract description 30
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000001301 oxygen Substances 0.000 claims abstract description 28
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011593 sulfur Substances 0.000 claims abstract description 17
- 125000000524 functional group Chemical group 0.000 claims abstract description 15
- 150000001993 dienes Chemical class 0.000 claims abstract description 12
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 108091034117 Oligonucleotide Chemical class 0.000 claims description 98
- 239000001226 triphosphate Substances 0.000 claims description 74
- 235000011178 triphosphate Nutrition 0.000 claims description 74
- -1 isopyrrole Chemical compound 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000003153 chemical reaction reagent Substances 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 47
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 41
- 239000002777 nucleoside Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 150000007523 nucleic acids Chemical group 0.000 claims description 34
- 238000012163 sequencing technique Methods 0.000 claims description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 32
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 claims description 27
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 23
- 230000005284 excitation Effects 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 20
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 125000003368 amide group Chemical group 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 18
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 230000004044 response Effects 0.000 claims description 17
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 claims description 14
- VVZRKVYGKNFTRR-UHFFFAOYSA-N 12h-benzo[a]xanthene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4OC3=CC=C21 VVZRKVYGKNFTRR-UHFFFAOYSA-N 0.000 claims description 14
- IHXWECHPYNPJRR-UHFFFAOYSA-N 3-hydroxycyclobut-2-en-1-one Chemical compound OC1=CC(=O)C1 IHXWECHPYNPJRR-UHFFFAOYSA-N 0.000 claims description 14
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 14
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 13
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 13
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 claims description 13
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 13
- 150000003732 xanthenes Chemical class 0.000 claims description 13
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
- 239000005546 dideoxynucleotide Substances 0.000 claims description 12
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 10
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 10
- 230000000295 complement effect Effects 0.000 claims description 10
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 10
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 10
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 150000003457 sulfones Chemical class 0.000 claims description 6
- XKKCQTLDIPIRQD-JGVFFNPUSA-N 1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)CC1 XKKCQTLDIPIRQD-JGVFFNPUSA-N 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 5
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 5
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 5
- JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 claims description 5
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 5
- 239000001177 diphosphate Substances 0.000 claims description 5
- 235000011180 diphosphates Nutrition 0.000 claims description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 3
- 150000004712 monophosphates Chemical class 0.000 claims description 3
- YKBGVTZYEHREMT-KVQBGUIXSA-N 2'-deoxyguanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 YKBGVTZYEHREMT-KVQBGUIXSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- WKKCYLSCLQVWFD-UHFFFAOYSA-N 1,2-dihydropyrimidin-4-amine Chemical compound N=C1NCNC=C1 WKKCYLSCLQVWFD-UHFFFAOYSA-N 0.000 claims 1
- WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 claims 1
- OCLZPNCLRLDXJC-NTSWFWBYSA-N 2-amino-9-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1CC[C@@H](CO)O1 OCLZPNCLRLDXJC-NTSWFWBYSA-N 0.000 claims 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 abstract description 18
- 239000013615 primer Substances 0.000 description 102
- 125000005647 linker group Chemical group 0.000 description 93
- 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 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 41
- 239000002773 nucleotide Substances 0.000 description 37
- 125000003729 nucleotide group Chemical group 0.000 description 35
- 150000002431 hydrogen Chemical class 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 27
- 239000000243 solution Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000001018 xanthene dye Substances 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- 150000007942 carboxylates Chemical class 0.000 description 16
- 239000012634 fragment Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 108020004414 DNA Proteins 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002835 absorbance Methods 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 238000001712 DNA sequencing Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000002157 polynucleotide Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 102000039446 nucleic acids Human genes 0.000 description 12
- 108020004707 nucleic acids Proteins 0.000 description 12
- 108091033319 polynucleotide Proteins 0.000 description 12
- 102000040430 polynucleotide Human genes 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- 238000005119 centrifugation Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000002372 labelling Methods 0.000 description 10
- 125000003835 nucleoside group Chemical group 0.000 description 10
- 150000008300 phosphoramidites Chemical class 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 10
- 238000001514 detection method Methods 0.000 description 9
- 238000000295 emission spectrum Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000011160 research Methods 0.000 description 9
- 239000001022 rhodamine dye Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- WGTODYJZXSJIAG-UHFFFAOYSA-N tetramethylrhodamine chloride Chemical compound [Cl-].C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C(O)=O WGTODYJZXSJIAG-UHFFFAOYSA-N 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 238000001962 electrophoresis Methods 0.000 description 7
- 230000037230 mobility Effects 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- 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 6
- 239000004202 carbamide Substances 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229940086542 triethylamine Drugs 0.000 description 6
- OAKPWEUQDVLTCN-NKWVEPMBSA-N 2',3'-Dideoxyadenosine-5-triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO[P@@](O)(=O)O[P@](O)(=O)OP(O)(O)=O)O1 OAKPWEUQDVLTCN-NKWVEPMBSA-N 0.000 description 5
- NJYVEMPWNAYQQN-UHFFFAOYSA-N 5-carboxyfluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C21OC(=O)C1=CC(C(=O)O)=CC=C21 NJYVEMPWNAYQQN-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 5
- HDRRAMINWIWTNU-NTSWFWBYSA-N [[(2s,5r)-5-(2-amino-6-oxo-3h-purin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1CC[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 HDRRAMINWIWTNU-NTSWFWBYSA-N 0.000 description 5
- 230000008033 biological extinction Effects 0.000 description 5
- 230000002255 enzymatic effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 4
- 102000053602 DNA Human genes 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229940104302 cytosine Drugs 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000002515 oligonucleotide synthesis Methods 0.000 description 4
- 229920002401 polyacrylamide Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 239000013076 target substance Substances 0.000 description 4
- 229940104230 thymidine Drugs 0.000 description 4
- VKIGAWAEXPTIOL-UHFFFAOYSA-N 2-hydroxyhexanenitrile Chemical compound CCCCC(O)C#N VKIGAWAEXPTIOL-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- BZTDTCNHAFUJOG-UHFFFAOYSA-N 6-carboxyfluorescein Chemical class C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C11OC(=O)C2=CC=C(C(=O)O)C=C21 BZTDTCNHAFUJOG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 3
- 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 3
- 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 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 102000003960 Ligases Human genes 0.000 description 3
- 108090000364 Ligases Proteins 0.000 description 3
- 108091092878 Microsatellite Proteins 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 229960005305 adenosine Drugs 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000011545 carbonate/bicarbonate buffer Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 210000000349 chromosome Anatomy 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 229940029575 guanosine Drugs 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000004713 phosphodiesters Chemical class 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 238000013519 translation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OALHHIHQOFIMEF-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthene]-3-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 OALHHIHQOFIMEF-UHFFFAOYSA-N 0.000 description 2
- UNGMOMJDNDFGJG-UHFFFAOYSA-N 5-carboxy-X-rhodamine Chemical compound [O-]C(=O)C1=CC(C(=O)O)=CC=C1C1=C(C=C2C3=C4CCCN3CCC2)C4=[O+]C2=C1C=C1CCCN3CCCC2=C13 UNGMOMJDNDFGJG-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 2
- 108091081062 Repeated sequence (DNA) Proteins 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 description 2
- 229960003375 aminomethylbenzoic acid Drugs 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- SUYVUBYJARFZHO-RRKCRQDMSA-N dATP Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 SUYVUBYJARFZHO-RRKCRQDMSA-N 0.000 description 2
- HAAZLUGHYHWQIW-KVQBGUIXSA-N dGTP Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 HAAZLUGHYHWQIW-KVQBGUIXSA-N 0.000 description 2
- NHVNXKFIZYSCEB-XLPZGREQSA-N dTTP Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)C1 NHVNXKFIZYSCEB-XLPZGREQSA-N 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000684 flow cytometry Methods 0.000 description 2
- 238000001502 gel electrophoresis Methods 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 125000005179 haloacetyl group Chemical group 0.000 description 2
- 238000009396 hybridization Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003068 molecular probe Substances 0.000 description 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- VFNKZQNIXUFLBC-UHFFFAOYSA-N 2',7'-dichlorofluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=C(O)C=C1OC1=C2C=C(Cl)C(O)=C1 VFNKZQNIXUFLBC-UHFFFAOYSA-N 0.000 description 1
- JNGRENQDBKMCCR-UHFFFAOYSA-N 2-(3-amino-6-iminoxanthen-9-yl)benzoic acid;hydrochloride Chemical compound [Cl-].C=12C=CC(=[NH2+])C=C2OC2=CC(N)=CC=C2C=1C1=CC=CC=C1C(O)=O JNGRENQDBKMCCR-UHFFFAOYSA-N 0.000 description 1
- KDELTXNPUXUBMU-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid boric acid Chemical compound OB(O)O.OB(O)O.OB(O)O.OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KDELTXNPUXUBMU-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- WFLALXNBVTWGKP-UHFFFAOYSA-N 3,6-dichlorobenzene-1,2,4-tricarboxylic acid Chemical compound OC(=O)C1=CC(Cl)=C(C(O)=O)C(C(O)=O)=C1Cl WFLALXNBVTWGKP-UHFFFAOYSA-N 0.000 description 1
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- UHVIHQSYQVURFV-UHFFFAOYSA-N 4,6-dichlorotriazin-5-amine Chemical compound NC1=C(Cl)N=NN=C1Cl UHVIHQSYQVURFV-UHFFFAOYSA-N 0.000 description 1
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 1
- CKTSBUTUHBMZGZ-ULQXZJNLSA-N 4-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-tritiopyrimidin-2-one Chemical compound O=C1N=C(N)C([3H])=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 CKTSBUTUHBMZGZ-ULQXZJNLSA-N 0.000 description 1
- DNWRLMRKDSGSPL-UHFFFAOYSA-N 5-iodopyrimidine Chemical compound IC1=CN=CN=C1 DNWRLMRKDSGSPL-UHFFFAOYSA-N 0.000 description 1
- MVJDUNKELBBNKM-UHFFFAOYSA-N 6-(ethylamino)pyridine-3-carbonitrile Chemical compound CCNC1=CC=C(C#N)C=N1 MVJDUNKELBBNKM-UHFFFAOYSA-N 0.000 description 1
- WQZIDRAQTRIQDX-UHFFFAOYSA-N 6-carboxy-x-rhodamine Chemical compound OC(=O)C1=CC=C(C([O-])=O)C=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 WQZIDRAQTRIQDX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 244000105975 Antidesma platyphyllum Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- PCDQPRRSZKQHHS-XVFCMESISA-N CTP Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 PCDQPRRSZKQHHS-XVFCMESISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- 102000004594 DNA Polymerase I Human genes 0.000 description 1
- 108010017826 DNA Polymerase I Proteins 0.000 description 1
- 108020003215 DNA Probes Proteins 0.000 description 1
- 239000003155 DNA primer Substances 0.000 description 1
- 239000003298 DNA probe Substances 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 102000007260 Deoxyribonuclease I Human genes 0.000 description 1
- 108010008532 Deoxyribonuclease I Proteins 0.000 description 1
- 102100030012 Deoxyribonuclease-1 Human genes 0.000 description 1
- 101710206036 Deoxyribonuclease-1 Proteins 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000026350 Inborn Genetic disease Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 238000012408 PCR amplification Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 108091093037 Peptide nucleic acid Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 108020004682 Single-Stranded DNA Proteins 0.000 description 1
- ARLKCWCREKRROD-POYBYMJQSA-N [[(2s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)CC1 ARLKCWCREKRROD-POYBYMJQSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000006319 alkynyl amino group Chemical group 0.000 description 1
- 238000012801 analytical assay Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- SUYVUBYJARFZHO-UHFFFAOYSA-N dATP Natural products C1=NC=2C(N)=NC=NC=2N1C1CC(O)C(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 SUYVUBYJARFZHO-UHFFFAOYSA-N 0.000 description 1
- RGWHQCVHVJXOKC-SHYZEUOFSA-J dCTP(4-) Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)C1 RGWHQCVHVJXOKC-SHYZEUOFSA-J 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- URGJWIFLBWJRMF-JGVFFNPUSA-N ddTTP Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)CC1 URGJWIFLBWJRMF-JGVFFNPUSA-N 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 239000005549 deoxyribonucleoside Substances 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- PGUYAANYCROBRT-UHFFFAOYSA-N dihydroxy-selanyl-selanylidene-lambda5-phosphane Chemical compound OP(O)([SeH])=[Se] PGUYAANYCROBRT-UHFFFAOYSA-N 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000005021 gait Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000012252 genetic analysis Methods 0.000 description 1
- 208000016361 genetic disease Diseases 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 235000009424 haa Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229920000592 inorganic polymer Polymers 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000001499 laser induced fluorescence spectroscopy Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 125000001805 pentosyl group Chemical group 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000006245 phosphate protecting group Chemical group 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
- 102000054765 polymorphisms of proteins Human genes 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002718 pyrimidine nucleoside Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007894 restriction fragment length polymorphism technique Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000002342 ribonucleoside Substances 0.000 description 1
- JRPHGDYSKGJTKZ-UHFFFAOYSA-K selenophosphate Chemical compound [O-]P([O-])([O-])=[Se] JRPHGDYSKGJTKZ-UHFFFAOYSA-K 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 108010068698 spleen exonuclease Proteins 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
- C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6869—Methods for sequencing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Immunology (AREA)
- Biophysics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Luminescent Compositions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2297589A CA2297589C (en) | 1996-05-03 | 1997-04-23 | Energy transfer dyes with enhanced fluorescence |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/642,330 | 1996-05-03 | ||
| US08/642,330 US5863727A (en) | 1996-05-03 | 1996-05-03 | Energy transfer dyes with enhanced fluorescence |
| US08/726,462 US5800996A (en) | 1996-05-03 | 1996-10-04 | Energy transfer dyes with enchanced fluorescence |
| US08/726,462 | 1996-10-04 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2297589A Division CA2297589C (en) | 1996-05-03 | 1997-04-23 | Energy transfer dyes with enhanced fluorescence |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2203494A1 CA2203494A1 (en) | 1997-11-03 |
| CA2203494C true CA2203494C (en) | 2000-12-26 |
Family
ID=27093992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002203494A Expired - Fee Related CA2203494C (en) | 1996-05-03 | 1997-04-23 | Energy transfer dyes with enhanced fluorescence |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5800996A (enExample) |
| EP (2) | EP0940450B1 (enExample) |
| JP (8) | JP3090626B2 (enExample) |
| AT (2) | ATE335051T1 (enExample) |
| CA (1) | CA2203494C (enExample) |
| DE (2) | DE69736434T2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7825237B2 (en) | 1996-05-03 | 2010-11-02 | Applied Biosystems, Llc | Oligonucleotides and analogs labeled with energy transfer dyes |
Families Citing this family (369)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6723556B1 (en) * | 1982-12-02 | 2004-04-20 | Cornell Research Foundation, Inc. | Nucleic acid encoding a fragment of bovine luteinizing hormone/chorionic gonadotropin receptor |
| US5935522A (en) * | 1990-06-04 | 1999-08-10 | University Of Utah Research Foundation | On-line DNA analysis system with rapid thermal cycling |
| US6787304B1 (en) | 1994-12-28 | 2004-09-07 | Georgetown University | Fluorometric assay for detecting nucleic acid cleavage |
| US20030165908A1 (en) * | 1994-12-30 | 2003-09-04 | Georgetown University | Fluorometric assay for detecting nucleic acid cleavage |
| US5847162A (en) * | 1996-06-27 | 1998-12-08 | The Perkin Elmer Corporation | 4, 7-Dichlororhodamine dyes |
| US5945526A (en) * | 1996-05-03 | 1999-08-31 | Perkin-Elmer Corporation | Energy transfer dyes with enhanced fluorescence |
| US5863727A (en) * | 1996-05-03 | 1999-01-26 | The Perkin-Elmer Corporation | Energy transfer dyes with enhanced fluorescence |
| US5800996A (en) * | 1996-05-03 | 1998-09-01 | The Perkin Elmer Corporation | Energy transfer dyes with enchanced fluorescence |
| US7388092B2 (en) | 1996-05-03 | 2008-06-17 | Applera Corporation | Oligonucleotides and analogs labeled with energy transfer dyes |
| ATE390491T1 (de) * | 1996-06-04 | 2008-04-15 | Univ Utah Res Found | Behälter zum durchführen und beobachten biologischer prozesse |
| AU726501B2 (en) * | 1996-06-04 | 2000-11-09 | University Of Utah Research Foundation | Monitoring hybridization during PCR |
| US5804386A (en) * | 1997-01-15 | 1998-09-08 | Incyte Pharmaceuticals, Inc. | Sets of labeled energy transfer fluorescent primers and their use in multi component analysis |
| ATE273381T1 (de) | 1997-02-12 | 2004-08-15 | Eugene Y Chan | Verfahren zur analyse von polymeren |
| EP2208789B1 (en) * | 1997-03-12 | 2015-07-22 | Applied Biosystems, LLC | DNA polymerases having improved labeled nucleotide incorporation properties |
| CA2265551A1 (en) | 1997-07-11 | 1999-01-21 | Wako Pure Chemical Industries Ltd. | Compounds having energy transfer function and method for dna base sequencing by using the same |
| US7745142B2 (en) | 1997-09-15 | 2010-06-29 | Molecular Devices Corporation | Molecular modification assays |
| US7632651B2 (en) | 1997-09-15 | 2009-12-15 | Mds Analytical Technologies (Us) Inc. | Molecular modification assays |
| US7070921B2 (en) | 2000-04-28 | 2006-07-04 | Molecular Devices Corporation | Molecular modification assays |
| US6130101A (en) * | 1997-09-23 | 2000-10-10 | Molecular Probes, Inc. | Sulfonated xanthene derivatives |
| EP1023463A4 (en) | 1997-10-09 | 2003-01-02 | Transgenomic Inc | MODIFICATION OF DOUBLE-STRANDED DNA TO IMPROVE CHROMATOGRAPHIC SEPARATIONS OF MATCHED ION POLYNUCLEOTIDES |
| US6485901B1 (en) | 1997-10-27 | 2002-11-26 | Boston Probes, Inc. | Methods, kits and compositions pertaining to linear beacons |
| EP1025120B1 (en) * | 1997-10-27 | 2010-08-18 | Boston Probes, Inc. | Methods, kits and compositions pertaining to pna molecular beacons |
| US5936087A (en) | 1997-11-25 | 1999-08-10 | The Perkin-Elmer Corporation | Dibenzorhodamine dyes |
| US6583168B1 (en) * | 1997-11-25 | 2003-06-24 | Applera Corporation | Sulfonated diarylrhodamine dyes |
| CA2319490A1 (en) * | 1998-02-03 | 1999-08-05 | Amersham Pharmacia Biotech Inc. | Energy transfer dyes |
| US6361942B1 (en) | 1998-03-24 | 2002-03-26 | Boston Probes, Inc. | Method, kits and compositions pertaining to detection complexes |
| DE19824535A1 (de) | 1998-06-03 | 1999-12-09 | Roche Diagnostics Gmbh | Neue Rhodamin-Derivate und deren Verwendung |
| GB2341189B (en) * | 1998-08-31 | 2001-06-13 | Amersham Pharm Biotech Inc | Energy transfer dyes |
| US6379957B1 (en) * | 1998-09-21 | 2002-04-30 | Leslie A. Johnston-Dow | Methods for HIV sequencing and genotyping |
| DE19850593A1 (de) * | 1998-11-03 | 2000-05-04 | Biochip Technologies Gmbh | Verfahren zum Nachweis von Hybridisierungsereignissen bei DNA |
| US6232075B1 (en) | 1998-12-14 | 2001-05-15 | Li-Cor, Inc. | Heterogeneous assay for pyrophosphate detection |
| US6635419B1 (en) | 1999-02-16 | 2003-10-21 | Applera Corporation | Polynucleotide sequencing method |
| CA2335359C (en) | 1999-04-23 | 2007-07-17 | Molecular Probes, Inc. | Xanthene dyes and their application as luminescence quenching compounds |
| US6248884B1 (en) | 1999-06-03 | 2001-06-19 | The Perkin-Elmer Corporation | Extended rhodamine compounds useful as fluorescent labels |
| US6358684B1 (en) * | 1999-08-27 | 2002-03-19 | Pe Corporation | UV excitable fluorescent energy transfer dyes |
| US6982146B1 (en) * | 1999-08-30 | 2006-01-03 | The United States Of America As Represented By The Department Of Health And Human Services | High speed parallel molecular nucleic acid sequencing |
| US6191278B1 (en) * | 1999-11-03 | 2001-02-20 | Pe Corporation | Water-soluble rhodamine dyes and conjugates thereof |
| US6372907B1 (en) * | 1999-11-03 | 2002-04-16 | Apptera Corporation | Water-soluble rhodamine dye peptide conjugates |
| US6716994B1 (en) | 2000-01-04 | 2004-04-06 | Applera Corporation | Mobility-Modifying Cyanine Dyes |
| US6221604B1 (en) | 2000-02-07 | 2001-04-24 | Pe Corporation | Electron-deficient nitrogen heterocycle-substituted fluorescein dyes |
| JP4589588B2 (ja) * | 2000-02-28 | 2010-12-01 | 哲雄 長野 | 長寿命励起型蛍光を用いる測定方法 |
| DE10012326A1 (de) * | 2000-03-14 | 2001-09-20 | Philips Corp Intellectual Pty | Flüssigkristall-Farbbildschirm |
| US6346384B1 (en) | 2000-03-27 | 2002-02-12 | Dade Behring Inc. | Real-time monitoring of PCR using LOCI |
| US6465644B1 (en) | 2000-05-02 | 2002-10-15 | Applera Corporation | Sulfonated [8,9] benzophenoxazine dyes and the use of their labelled conjugates |
| US6936702B2 (en) * | 2000-06-07 | 2005-08-30 | Li-Cor, Inc. | Charge-switch nucleotides |
| US6869764B2 (en) | 2000-06-07 | 2005-03-22 | L--Cor, Inc. | Nucleic acid sequencing using charge-switch nucleotides |
| WO2002030944A2 (en) * | 2000-10-11 | 2002-04-18 | Applera Corporation | Fluorescent nucleobase conjugates having anionic linkers |
| US6448407B1 (en) * | 2000-11-01 | 2002-09-10 | Pe Corporation (Ny) | Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis |
| WO2002044425A2 (en) | 2000-12-01 | 2002-06-06 | Visigen Biotechnologies, Inc. | Enzymatic nucleic acid synthesis: compositions and methods for altering monomer incorporation fidelity |
| US7129346B2 (en) * | 2000-12-20 | 2006-10-31 | Molecular Probes, Inc. | Crown ether derivatives |
| US6962992B2 (en) | 2000-12-20 | 2005-11-08 | Molecullar Probes, Inc. | Crown ether derivatives |
| US7579463B2 (en) | 2000-12-20 | 2009-08-25 | Life Technologies Corporation | Crown ether derivatives |
| WO2002079183A1 (en) * | 2001-04-02 | 2002-10-10 | Theratechnologies Inc. | Halogenated rhodamine derivatives and applications thereof |
| JP2005505749A (ja) | 2001-05-21 | 2005-02-24 | アクララ バイオサイエンシーズ, インコーポレイテッド | タンパク質を分析するための方法および組成物 |
| US20020187508A1 (en) * | 2001-06-08 | 2002-12-12 | Wong Gordon G. | Methods and products for analyzing nucleic acids using nick translation |
| US6887690B2 (en) * | 2001-06-22 | 2005-05-03 | Pe Corporation | Dye-labeled ribonucleotide triphosphates |
| US20050042629A1 (en) | 2002-09-13 | 2005-02-24 | Applera Corporation | Thermus scotoductus nucleic acid polymerases |
| JP2005517900A (ja) | 2001-11-21 | 2005-06-16 | アプレラ コーポレイション | デジタルアッセイ |
| AU2002346498A1 (en) | 2001-11-30 | 2003-06-17 | Applera Corporation | Thermus brockianus nucleic acid polymerases |
| US7026166B2 (en) * | 2002-01-22 | 2006-04-11 | Chiron Corporation | Fluorogenic dyes |
| US7166478B2 (en) * | 2002-03-12 | 2007-01-23 | Enzo Life Sciences, Inc., C/O Enzo Biochem, Inc. | Labeling reagents and labeled targets, target labeling processes and other processes for using same in nucleic acid determinations and analyses |
| CA2490961A1 (en) * | 2002-07-01 | 2004-01-08 | Guava Technologies, Inc. | Fluorescent dyes, energy transfer couples and methods |
| WO2004005917A1 (ja) * | 2002-07-08 | 2004-01-15 | Daiichi Pure Chemicals Co., Ltd. | 蛍光プローブ |
| EP1403382A3 (en) * | 2002-08-06 | 2004-05-06 | Roche Diagnostics GmbH | Improved fluorescent resonance energy transfer probes |
| EP1389638A1 (en) * | 2002-08-06 | 2004-02-18 | Roche Diagnostics GmbH | Improved fluorescent resonance energy transfer probes |
| AU2003276974A1 (en) * | 2002-09-25 | 2004-04-19 | Amersham Biosciences Corp | Fluorescent labeling reagents with multiple donors and acceptors |
| EP1405920A3 (en) * | 2002-10-02 | 2004-04-14 | Roche Diagnostics GmbH | Improved FRET process |
| US7407747B2 (en) * | 2002-10-15 | 2008-08-05 | Applera Corporation | Method for drying dye-terminator sequencing reagents |
| JP4206381B2 (ja) * | 2002-10-16 | 2009-01-07 | 哲雄 長野 | パーオキシナイトライト測定用試薬 |
| CA2504443A1 (en) * | 2002-10-30 | 2004-05-13 | Pointilliste, Inc. | Methods for producing polypeptide-tagged collections and capture systems containing the tagged polypeptides |
| US7704756B2 (en) * | 2003-01-21 | 2010-04-27 | Novartis Vaccines And Diagnostics, Inc. | Fluorogenic dyes |
| EP1597577A4 (en) * | 2003-02-10 | 2007-02-21 | Pointilliste Inc | SELF-ARRANGING ARRAYS AND ITS APPLICATION |
| US7696245B2 (en) * | 2003-03-28 | 2010-04-13 | Sekisui Medical Co., Ltd. | Fluorescent probe for zinc |
| US8445702B2 (en) * | 2003-05-05 | 2013-05-21 | Life Technologies Corporation | Zinc binding compounds and their method of use |
| US20050250214A1 (en) * | 2004-05-05 | 2005-11-10 | Gee Kyle R | Zinc binding compounds and their method of use |
| EP1627025B1 (en) * | 2003-05-09 | 2016-10-12 | Applied Biosystems, LLC | Fluorescent polymeric materials containing lipid soluble rhodamine dyes |
| WO2004101709A1 (en) * | 2003-05-09 | 2004-11-25 | Applera Corporation | Phenyl xanthene dyes |
| CA2445420A1 (en) | 2003-07-29 | 2005-01-29 | Invitrogen Corporation | Kinase and phosphatase assays |
| US7619059B2 (en) | 2003-07-29 | 2009-11-17 | Life Technologies Corporation | Bimolecular optical probes |
| US7727752B2 (en) | 2003-07-29 | 2010-06-01 | Life Technologies Corporation | Kinase and phosphatase assays |
| US7271265B2 (en) | 2003-08-11 | 2007-09-18 | Invitrogen Corporation | Cyanine compounds and their application as quenching compounds |
| US7417726B2 (en) * | 2003-09-19 | 2008-08-26 | Applied Biosystems Inc. | Normalization of data using controls |
| US20060029948A1 (en) * | 2003-09-19 | 2006-02-09 | Gary Lim | Sealing cover and dye compatibility selection |
| US7570443B2 (en) | 2003-09-19 | 2009-08-04 | Applied Biosystems, Llc | Optical camera alignment |
| US7667024B2 (en) * | 2003-11-19 | 2010-02-23 | Allelogic Biosciences Corp. | Oligonucleotides labeled with a plurality of fluorophores |
| DK1538154T3 (da) * | 2003-11-20 | 2009-03-02 | Exiqon As | Quencher-sammensætninger, der indeholder anthraquinon-enheder |
| US7776529B2 (en) | 2003-12-05 | 2010-08-17 | Life Technologies Corporation | Methine-substituted cyanine dye compounds |
| EP2607431B1 (en) * | 2003-12-05 | 2016-08-24 | Life Technologies Corporation | Cyanine dye compounds |
| GB0329161D0 (en) | 2003-12-16 | 2004-01-21 | Precisense As | Reagant for detecting an analyte |
| JP4127204B2 (ja) * | 2003-12-17 | 2008-07-30 | セイコーエプソン株式会社 | 液晶表示装置の製造方法 |
| JP2005194244A (ja) * | 2004-01-09 | 2005-07-21 | Shigenobu Yano | 亜鉛イオン蛍光センサー |
| US20050227309A1 (en) | 2004-01-21 | 2005-10-13 | Corry Schuyler B | Optically-detectable enzyme substrates and their method of use |
| WO2005073409A2 (en) * | 2004-01-26 | 2005-08-11 | Applera Corporation | Methods, compositions, and kits for amplifying and sequencing polynucleotides |
| US7344701B2 (en) | 2004-02-03 | 2008-03-18 | Biosearch Technologies, Inc. | Xanthene dyes |
| US20050186606A1 (en) * | 2004-02-11 | 2005-08-25 | Schroeder Benjamin G. | Methods and compositions for detecting nucleic acids |
| EP1725587A2 (en) * | 2004-03-19 | 2006-11-29 | U.S. Genomics, Inc. | Compositions and methods for detection of single molecules |
| PL1740100T3 (pl) * | 2004-04-13 | 2017-09-29 | Biosearch Technologies, Inc. | Barwniki ksantenowe |
| US20050255485A1 (en) * | 2004-05-14 | 2005-11-17 | Livak Kenneth J | Detection of gene duplications |
| US20080103053A1 (en) * | 2005-11-22 | 2008-05-01 | Helicos Biosciences Corporation | Methods and compositions for sequencing a nucleic acid |
| EP2290071B1 (en) | 2004-05-28 | 2014-12-31 | Asuragen, Inc. | Methods and compositions involving microRNA |
| EP1766089A1 (en) * | 2004-06-30 | 2007-03-28 | Applera Corporation | Analog probe complexes |
| WO2006023231A2 (en) | 2004-07-27 | 2006-03-02 | Molecular Probes, Inc. | Fluorescent metal ion indicators with large stokes shift |
| DE602005025782D1 (de) | 2004-09-21 | 2011-02-17 | Life Technologies Corp | Zweifarbige echtzeit/endpunkt-quantifizierung von mikro-rnas (mirnas) |
| EP2314688B1 (en) | 2004-11-12 | 2014-07-16 | Asuragen, Inc. | Methods and compositions involving miRNA and miRNA inhibitor molecules |
| US20060292586A1 (en) * | 2004-12-17 | 2006-12-28 | Schroth Gary P | ID-tag complexes, arrays, and methods of use thereof |
| US20060166238A1 (en) * | 2004-12-22 | 2006-07-27 | Ramsing Niels B | Probes, libraries and kits for analysis of mixtures of nucleic acids and methods for constructing the same |
| WO2006074233A2 (en) | 2005-01-06 | 2006-07-13 | Applera Corporation | Polypeptides having nucleic acid binding activity and compositions and methods for nucleic acid amplification |
| EP1838144B1 (en) | 2005-01-07 | 2016-08-31 | Oregon State University | Method to trigger rna interference |
| JP2008533167A (ja) | 2005-03-15 | 2008-08-21 | アプレラ コーポレイション | 分析物の検出のための、抗体の代替抗原系の使用 |
| EP1886145A2 (en) * | 2005-05-03 | 2008-02-13 | Applera Corporation | Fluorescent detection system and dye set for use therewith |
| JP5306811B2 (ja) | 2005-05-11 | 2013-10-02 | ライフ テクノロジーズ コーポレーション | 2本鎖dnaへの高い選択性を有する蛍光化学物質及びそれらの使用 |
| US7737281B2 (en) * | 2005-05-24 | 2010-06-15 | Enzo Life Sciences, Inc. C/O Enzo Biochem, Inc. | Purine based fluorescent dyes |
| US8357801B2 (en) | 2005-05-24 | 2013-01-22 | Enzo Life Sciences, Inc. | Labeling of target molecules, identification of organelles and other applications, novel compositions, methods and kits |
| US7569695B2 (en) * | 2005-05-24 | 2009-08-04 | Enzo Life Sciences, Inc. | Dyes for the detection or quantification of desirable target molecules |
| US8362250B2 (en) | 2005-05-24 | 2013-01-29 | Enzo Biochem, Inc. | Fluorescent dyes and compounds, methods and kits useful for identifying specific organelles and regions in cells of interest |
| US20090264299A1 (en) | 2006-02-24 | 2009-10-22 | Complete Genomics, Inc. | High throughput genome sequencing on DNA arrays |
| EP1907571B1 (en) | 2005-06-15 | 2017-04-26 | Complete Genomics Inc. | Nucleic acid analysis by random mixtures of non-overlapping fragments |
| US20070087360A1 (en) * | 2005-06-20 | 2007-04-19 | Boyd Victoria L | Methods and compositions for detecting nucleotides |
| US7817273B2 (en) * | 2005-06-30 | 2010-10-19 | Life Technologies Corporation | Two-dimensional spectral imaging system |
| US7663750B2 (en) * | 2005-06-30 | 2010-02-16 | Applied Biosystems, Llc | Two-dimensional spectral imaging system |
| JP4963015B2 (ja) * | 2005-07-28 | 2012-06-27 | 学校法人日本大学 | ヌクレオチド誘導体及びその利用 |
| WO2007024914A2 (en) * | 2005-08-22 | 2007-03-01 | Applera Corporation | Device and method for microfluidic control of a first fluid in contact with a second fluid, wherein the first and second fluids are immiscible |
| US20070134685A1 (en) * | 2005-09-06 | 2007-06-14 | Invitrogen Corporation | Control of chemical modification |
| US20070059713A1 (en) | 2005-09-09 | 2007-03-15 | Lee Jun E | SSB-DNA polymerase fusion proteins |
| US7741467B2 (en) * | 2005-10-05 | 2010-06-22 | Roche Molecular Systems, Inc. | Non-fluorescent energy transfer |
| WO2007044245A2 (en) | 2005-10-07 | 2007-04-19 | Callida Genomics, Inc. | Self-assembled single molecule arrays and uses thereof |
| DE602006016984D1 (de) | 2005-12-12 | 2010-10-28 | Us Gov Health & Human Serv | Sonde zum sequenzieren von nukleinsäure und verwendungsverfahren |
| US8703734B2 (en) | 2005-12-12 | 2014-04-22 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Nanoprobes for detection or modification of molecules |
| US7521577B2 (en) * | 2006-01-12 | 2009-04-21 | Molecular Probes, Inc. | Heavy metal binding compounds and their method of use |
| CN101432439B (zh) | 2006-02-24 | 2013-07-24 | 考利达基因组股份有限公司 | Dna阵列上的高通量基因组测序 |
| EP1994182B1 (en) | 2006-03-15 | 2019-05-29 | Siemens Healthcare Diagnostics Inc. | Degenerate nucleobase analogs |
| CA2653321A1 (en) | 2006-05-26 | 2007-12-06 | Althea Technologies, Inc. | Biochemical analysis of partitioned cells |
| US7910302B2 (en) | 2006-10-27 | 2011-03-22 | Complete Genomics, Inc. | Efficient arrays of amplified polynucleotides |
| US20090111706A1 (en) | 2006-11-09 | 2009-04-30 | Complete Genomics, Inc. | Selection of dna adaptor orientation by amplification |
| 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 |
| US8586743B2 (en) | 2007-01-30 | 2013-11-19 | Life Technologies Corporation | Labeling reagents and methods of their use |
| US11940413B2 (en) | 2007-02-05 | 2024-03-26 | IsoPlexis Corporation | Methods and devices for sequencing nucleic acids in smaller batches |
| US8425861B2 (en) | 2007-04-04 | 2013-04-23 | Netbio, Inc. | Methods for rapid multiplexed amplification of target nucleic acids |
| US20080274458A1 (en) * | 2007-05-01 | 2008-11-06 | Latham Gary J | Nucleic acid quantitation methods |
| WO2008151089A2 (en) * | 2007-05-30 | 2008-12-11 | Invitrogen Corporation | Fluorescent phospholipase a2 indicators |
| US7816135B2 (en) | 2007-07-05 | 2010-10-19 | Becton, Dickinson And Company | Method of analyzing lymphocytes |
| WO2009036332A1 (en) | 2007-09-14 | 2009-03-19 | Asuragen, Inc. | Micrornas differentially expressed in cervical cancer and uses thereof |
| US8017338B2 (en) * | 2007-11-20 | 2011-09-13 | Life Technologies Corporation | Reversible di-nucleotide terminator sequencing |
| US20090171078A1 (en) * | 2007-11-20 | 2009-07-02 | Applied Biosystems Inc. | Method of sequencing nucleic acids using elaborated nucleotide phosphorotiolate compounds |
| WO2009070805A2 (en) | 2007-12-01 | 2009-06-04 | Asuragen, Inc. | Mir-124 regulated genes and pathways as targets for therapeutic intervention |
| WO2009097368A2 (en) | 2008-01-28 | 2009-08-06 | Complete Genomics, Inc. | Methods and compositions for efficient base calling in sequencing reactions |
| US9017973B2 (en) | 2008-03-19 | 2015-04-28 | Intelligent Biosystems, Inc. | Methods and compositions for incorporating nucleotides |
| US20090246762A1 (en) | 2008-03-31 | 2009-10-01 | Applera Corporation, Applied Biosystems Group | Nucleic acid terminators incorporating a cationic moiety and methods for their use |
| EP2285960B1 (en) | 2008-05-08 | 2015-07-08 | Asuragen, INC. | Compositions and methods related to mir-184 modulation of neovascularization or angiogenesis |
| WO2009140541A2 (en) * | 2008-05-16 | 2009-11-19 | Life Technologies Corporation | Dual labeling methods for measuring cellular proliferation |
| US9250249B2 (en) * | 2008-09-08 | 2016-02-02 | Enzo Biochem, Inc. | Autophagy and phospholipidosis pathway assays |
| US9334281B2 (en) * | 2008-09-08 | 2016-05-10 | Enzo Life Sciences, Inc. | Fluorochromes for organelle tracing and multi-color imaging |
| US20100159452A1 (en) * | 2008-12-22 | 2010-06-24 | Roche Molecular Systems, Inc. | Method For Detecting a Target Nucleic Acid in a Sample |
| CA2762986C (en) | 2009-05-22 | 2018-03-06 | Asuragen, Inc. | Mirna biomarkers of prostate disease |
| WO2010147654A2 (en) | 2009-06-15 | 2010-12-23 | Netbio Inc. | Improved methods for forensic dna quantitation |
| US8735074B2 (en) | 2009-08-28 | 2014-05-27 | Asuragen, Inc. | MiRNA biomarkers of lung disease |
| US9133343B2 (en) * | 2009-11-30 | 2015-09-15 | Enzo Biochem, Inc. | Dyes and compositions, and processes for using same in analysis of protein aggregation and other applications |
| JP5838169B2 (ja) | 2009-12-31 | 2016-01-06 | ヴェンタナ メディカル システムズ, インク. | 一意的に特異的核酸プローブを生成するための方法 |
| WO2011106495A1 (en) | 2010-02-26 | 2011-09-01 | Ventana Medical Systems, Inc. | Cytogenic analysis of metaphase chromosomes |
| WO2011106583A1 (en) | 2010-02-26 | 2011-09-01 | Ventana Medical Systems, Inc. | Polytag probes |
| US9190099B2 (en) * | 2010-03-15 | 2015-11-17 | Purdue Research Foundation | Higher order structured dyes with enhanced optical features |
| JP5540867B2 (ja) * | 2010-04-26 | 2014-07-02 | コニカミノルタ株式会社 | 有機蛍光色素内包シリカナノ粒子、その製造方法、それを用いた生体物質標識剤 |
| US20120034603A1 (en) | 2010-08-06 | 2012-02-09 | Tandem Diagnostics, Inc. | Ligation-based detection of genetic variants |
| US20130261003A1 (en) | 2010-08-06 | 2013-10-03 | Ariosa Diagnostics, In. | Ligation-based detection of genetic variants |
| DE102010042634A1 (de) | 2010-10-19 | 2012-04-19 | Atto-Tec Gmbh | Neue Amin-substituierte tricyclische Fluoreszenzfarbstoffe |
| US9777330B2 (en) | 2010-10-29 | 2017-10-03 | Asuragen, Inc. | mPCR methods for analyzing repeat sequences |
| WO2012103031A2 (en) | 2011-01-25 | 2012-08-02 | Ariosa Diagnostics, Inc. | Detection of genetic abnormalities |
| CA2827179C (en) | 2011-01-25 | 2021-04-06 | Minoru S.H. Ko | Zscan4 as a marker for pancreatic stem cells and progenitor cells and use thereof |
| US10131947B2 (en) | 2011-01-25 | 2018-11-20 | Ariosa Diagnostics, Inc. | Noninvasive detection of fetal aneuploidy in egg donor pregnancies |
| WO2012118745A1 (en) | 2011-02-28 | 2012-09-07 | Arnold Oliphant | Assay systems for detection of aneuploidy and sex determination |
| US9562259B2 (en) | 2011-03-14 | 2017-02-07 | Ventana Medical Systems, Inc. | Method of analyzing chromosomal inversions |
| WO2012151111A1 (en) | 2011-05-04 | 2012-11-08 | Htg Molecular Diagnostics, Inc. | Quantitative nuclease protection assay (qnpa) and sequencing (qnps) improvements |
| WO2012155084A1 (en) | 2011-05-12 | 2012-11-15 | Netbio, Inc. | Methods and compositions for rapid multiplex amplification of str loci |
| EP2710146A2 (en) | 2011-05-18 | 2014-03-26 | Life Technologies Corporation | Chromosome conformation analysis |
| CA3113672A1 (en) | 2011-07-01 | 2013-01-10 | Htg Molecular Diagnostics, Inc. | Methods of detecting gene fusions |
| JP5826071B2 (ja) * | 2011-08-30 | 2015-12-02 | 富士フイルム株式会社 | キサンテン誘導体の多量体構造を有する新規化合物、着色組成物、インクジェット記録用インク、インクジェット記録方法、カラーフィルター、及びカラートナー |
| AU2012309824A1 (en) | 2011-09-12 | 2013-04-18 | Abbvie Biotherapeutics Inc. | Artificial NK cells and uses thereof |
| WO2013040251A2 (en) | 2011-09-13 | 2013-03-21 | Asurgen, Inc. | Methods and compositions involving mir-135b for distinguishing pancreatic cancer from benign pancreatic disease |
| US9416153B2 (en) | 2011-10-11 | 2016-08-16 | Enzo Life Sciences, Inc. | Fluorescent dyes |
| JP2014531908A (ja) | 2011-10-14 | 2014-12-04 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 構造アッセンブリによる配列決定 |
| WO2013057586A1 (en) | 2011-10-19 | 2013-04-25 | Oslo Universitetssykehus Hf | Compositions and methods for producing soluble t - cell receptors |
| WO2013108126A2 (en) | 2012-01-16 | 2013-07-25 | University Of Oslo | Methyltransferases and uses thereof |
| CN102618086B (zh) * | 2012-03-07 | 2013-12-11 | 东华大学 | 一种一步法制备梯形宽波段吸收聚炔方酸菁染料的方法 |
| CN102634225B (zh) * | 2012-03-24 | 2013-11-06 | 大连理工大学 | 5(6)取代的罗丹明异构体的拆分合成方法 |
| WO2013167387A1 (en) | 2012-05-10 | 2013-11-14 | Ventana Medical Systems, Inc. | Uniquely specific probes for pten, pik3ca, met, top2a, and mdm2 |
| WO2013177220A1 (en) | 2012-05-21 | 2013-11-28 | The Scripps Research Institute | Methods of sample preparation |
| WO2013184754A2 (en) | 2012-06-05 | 2013-12-12 | President And Fellows Of Harvard College | Spatial sequencing of nucleic acids using dna origami probes |
| US11242564B2 (en) | 2012-07-12 | 2022-02-08 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods for predicting the survival time and treatment responsiveness of a patient suffering from a solid cancer with a signature of at least 7 genes |
| IN2014DN07866A (enExample) | 2012-07-20 | 2015-04-24 | Harvard College | |
| WO2014048942A1 (en) | 2012-09-25 | 2014-04-03 | Ventana Medical Systems, Inc. | Probes for pten, pik3ca, met, and top2a, and method for using the probes |
| US9476089B2 (en) | 2012-10-18 | 2016-10-25 | President And Fellows Of Harvard College | Methods of making oligonucleotide probes |
| WO2014126647A1 (en) * | 2013-02-15 | 2014-08-21 | Empire Technology Development Llc | Photocatalytic degradation of sugar |
| US9540685B2 (en) | 2013-03-15 | 2017-01-10 | President And Fellows Of Harvard College | Methods of identifying homologous genes using FISH |
| WO2015036405A1 (en) | 2013-09-10 | 2015-03-19 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for diagnosing and treating basal cell carcinoma |
| EP3066218B1 (en) | 2013-11-05 | 2018-12-26 | HTG Molecular Diagnostics, Inc. | Methods for detecting nucleic acids |
| BR112016015595A2 (pt) | 2014-01-05 | 2017-10-24 | Biomirna Holdings Ltd | métodos de determinação de câncer de pulmão |
| US10619210B2 (en) | 2014-02-07 | 2020-04-14 | The Johns Hopkins University | Predicting response to epigenetic drug therapy |
| EP3617322A1 (en) | 2014-02-24 | 2020-03-04 | Ventana Medical Systems, Inc. | Automated rna detection using labeled 2 -o-methyl rna oligonucleotide probes and signal amplification systems |
| WO2015169854A1 (en) * | 2014-05-07 | 2015-11-12 | Danmarks Tekniske Universitet | Method for the preparation of intermediates for carboxy-fluoresceins and novel carboxy-fluorescein |
| EP3183054B1 (en) | 2014-08-19 | 2020-09-23 | Roche Diagnostics GmbH | Methods and compositions for nucleic acid detection |
| CA2958292A1 (en) | 2014-08-19 | 2016-02-25 | President And Fellows Of Harvard College | Rna-guided systems for probing and mapping of nucleic acids |
| EP3913066A1 (en) | 2014-09-09 | 2021-11-24 | Igenomx International Genomics Corporation | Compositions for rapid nucleic acid library preparation |
| EP3009147A1 (en) | 2014-10-16 | 2016-04-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for treating resistant glioblastoma |
| CN113403373B (zh) | 2014-11-21 | 2025-04-11 | 布鲁克空间生物学公司 | 无酶且无扩增的测序 |
| WO2016094330A2 (en) | 2014-12-08 | 2016-06-16 | 20/20 Genesystems, Inc | Methods and machine learning systems for predicting the liklihood or risk of having cancer |
| US20180010194A1 (en) | 2015-01-12 | 2018-01-11 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods for the Diagnosis of Pancreatic Cancer |
| US9957393B2 (en) | 2015-03-30 | 2018-05-01 | Enzo Biochem, Inc. | Monoazo dyes with cyclic amine as fluorescence quenchers |
| WO2016177774A1 (en) | 2015-05-04 | 2016-11-10 | Academisch Medisch Centrum | Method of quantifying mirnas using normalization |
| EP3325654B1 (en) | 2015-07-23 | 2020-06-10 | Asuragen, Inc. | Methods, compositions, kits, and uses for analysis of nucleic acids comprising repeating a/t-rich segments |
| WO2017029391A1 (en) | 2015-08-20 | 2017-02-23 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New method for treating cancer |
| WO2017052679A1 (en) | 2015-09-21 | 2017-03-30 | The United States Of America, As Represented By The Secretary, Departmnet Of Health & Human Service | Monoclonal antibodies specific for heartland virus and methods of their use |
| WO2017055327A1 (en) | 2015-09-29 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for quantifying the population of endothelial cells in a tissue sample |
| WO2017055319A1 (en) | 2015-09-29 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for quantifying the population of b cells in a tissue sample |
| WO2017055321A1 (en) | 2015-09-29 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for quantifying the population of fibroblasts in a tissue sample |
| WO2017055322A1 (en) | 2015-09-29 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for quantifying the population of neutrophils in a tissue sample |
| WO2017055326A1 (en) | 2015-09-29 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for quantifying the population of myeloid dendritic cells in a tissue sample |
| WO2017055324A1 (en) | 2015-09-29 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for quantifying the population of cells of monocytic origin in a tissue sample |
| WO2017055325A1 (en) | 2015-09-29 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for quantifying the population of nk cells in a tissue sample |
| WO2017055320A1 (en) | 2015-09-29 | 2017-04-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for quantifying the population of cytotoxic lymphocytes in a tissue sample |
| WO2017060397A1 (en) | 2015-10-09 | 2017-04-13 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting the survival time of subjects suffering from melanoma metastases |
| WO2017067944A1 (en) | 2015-10-19 | 2017-04-27 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting the survival time of subjects suffering from triple negative breast cancer |
| CN108449995B (zh) | 2015-11-06 | 2022-02-01 | 文塔纳医疗系统公司 | 代表性诊断 |
| ES2761266T3 (es) | 2015-11-10 | 2020-05-19 | Inst Nat Sante Rech Med | Métodos para predicción del tiempo de supervivencia de los pacientes con cirrosis alcohólica descompensada |
| US10760135B2 (en) | 2016-01-13 | 2020-09-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods for predicting pancreatic cancer treatment response |
| WO2017182834A1 (en) | 2016-04-19 | 2017-10-26 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New method for treating resistant glioblastoma |
| CN109715825B (zh) | 2016-05-16 | 2023-01-06 | 纳米线科技公司 | 用于检测样品中目标核酸的方法 |
| WO2017200790A1 (en) | 2016-05-20 | 2017-11-23 | 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 |
| WO2017202962A1 (en) | 2016-05-24 | 2017-11-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of non small cell lung cancer (nsclc) that coexists with chronic obstructive pulmonary disease (copd) |
| WO2017218339A1 (en) | 2016-06-13 | 2017-12-21 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Nucleic acids encoding zika virus-like particles and their use in zika virus vaccines and diagnostic assays |
| WO2017216206A1 (en) | 2016-06-14 | 2017-12-21 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting acute severe colitis treatment response |
| JP7021126B2 (ja) * | 2016-06-28 | 2022-02-16 | ヴェンタナ メディカル システムズ, インク. | マルチ色素キノンメチド及びチラミドコンジュゲートによる発色性ihc及びish染色のための新規の色 |
| WO2018011107A1 (en) | 2016-07-11 | 2018-01-18 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of er-alpha 46 in methods and kits for assessing the status of breast cancer |
| WO2018011166A2 (en) | 2016-07-12 | 2018-01-18 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for quantifying the population of myeloid dendritic cells in a tissue sample |
| WO2018045162A1 (en) | 2016-09-01 | 2018-03-08 | Biogen Ma Inc. | Biomarkers predictive of primary progressive multiple sclerosis and uses thereof |
| WO2018046738A1 (en) | 2016-09-12 | 2018-03-15 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting the survival time of patients suffering from cancer |
| WO2018046736A1 (en) | 2016-09-12 | 2018-03-15 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting the survival time of patients suffering from cancer |
| WO2018054960A1 (en) | 2016-09-21 | 2018-03-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting and treating resistance to chemotherapy in npm-alk(+) alcl |
| EP3515453A1 (en) | 2016-09-22 | 2019-07-31 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for reprograming immune environment in a subject in need thereof |
| EP3529205B1 (en) | 2016-10-21 | 2022-06-15 | The United States of America, as represented by the Secretary, Department of Health and Human Services | Molecular nanotags |
| JP6730525B2 (ja) | 2016-11-21 | 2020-07-29 | ナノストリング テクノロジーズ,インコーポレイティド | 化学組成物とそれを利用する方法 |
| WO2018122245A1 (en) | 2016-12-28 | 2018-07-05 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of predicting the survival time of patients suffering from cms3 colorectal cancer |
| WO2018122249A1 (en) | 2016-12-28 | 2018-07-05 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting the survival time of patients suffering from a microsatellite stable colorectal cancer |
| WO2018146239A1 (en) | 2017-02-10 | 2018-08-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Biomarker for outcome in aml patients |
| WO2018162404A1 (en) | 2017-03-06 | 2018-09-13 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Biomarker for outcome in aml patients |
| WO2018172540A1 (en) | 2017-03-24 | 2018-09-27 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method to predict the progression of alzheimer's disease |
| EP3601613B1 (en) | 2017-03-29 | 2021-12-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for assessing pregnancy outcome |
| WO2018189215A1 (en) | 2017-04-12 | 2018-10-18 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for predicting the survival time of a patient suffering from hepatocellular carcinoma |
| WO2018223053A1 (en) | 2017-06-02 | 2018-12-06 | Affymetrix, Inc. | Array-based methods for analysing mixed samples using differently labelled allele-specific probes |
| EP3631008B1 (en) | 2017-06-02 | 2025-12-03 | Affymetrix, Inc. | Array-based methods for analysing mixed samples using differently labelled allele-specific probes |
| WO2019038219A1 (en) | 2017-08-21 | 2019-02-28 | INSERM (Institut National de la Santé et de la Recherche Médicale) | NEW PROGNOSTIC METHOD OF PANCREATIC CANCER |
| WO2019043138A1 (en) | 2017-09-01 | 2019-03-07 | INSERM (Institut National de la Santé et de la Recherche Médicale) | METHOD FOR PREDICTING OUTCOME OF CANCER |
| US11579147B2 (en) | 2017-09-25 | 2023-02-14 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of VNN1 as a biomarker and a therapeutic target in sarcomas |
| WO2019089936A1 (en) | 2017-11-02 | 2019-05-09 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Enhanced chemiluminescent enzyme-linked immunosorbent assay for detection of antibodies against babesia microti |
| JP7038209B2 (ja) | 2017-11-13 | 2022-03-17 | エフ.ホフマン-ラ ロシュ アーゲー | エピタコ電気泳動を使用する試料分析のための装置 |
| WO2019104070A1 (en) | 2017-11-21 | 2019-05-31 | Nanostring Technologies, Inc. | O-nitrobenzyl photocleavable bifunctional linker |
| WO2019133727A1 (en) | 2017-12-29 | 2019-07-04 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Universal influenza virus probe set for enrichment of any influenza virus nucleic acid |
| WO2019207030A1 (en) | 2018-04-26 | 2019-10-31 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for predicting a response with an immune checkpoint inhibitor in a patient suffering from a lung cancer |
| EP3794146B1 (en) | 2018-05-14 | 2025-12-10 | Bruker Spatial Biology, Inc. | Method for identifying a predetermined nucleotide sequence |
| WO2019229489A1 (en) | 2018-05-31 | 2019-12-05 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of mir-146a-5p and mir-186 as biomarkers of osteoarthritis |
| WO2020030954A1 (en) | 2018-08-09 | 2020-02-13 | Integrative Medicine Clinic, Sia | Theranostics-like protein sanps conjugated to integrin and pmsa targeting peptides and therapy of prostate cancer |
| US10513610B1 (en) * | 2018-08-20 | 2019-12-24 | Laiqiang Ying | Sulfonated 4,7-dichlororhodamine dyes and their application |
| WO2020089428A1 (en) | 2018-11-02 | 2020-05-07 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New prognostic method of pancreatic cancer |
| WO2020089432A1 (en) | 2018-11-02 | 2020-05-07 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New prognostic method of pancreatic cancer |
| JP2022514397A (ja) | 2018-12-20 | 2022-02-10 | ライフ テクノロジーズ コーポレーション | 変更されたローダミン染料及びバイオアッセイにおけるそれらの使用 |
| SG11202106121SA (en) | 2018-12-20 | 2021-07-29 | Life Technologies Corp | Asymmetric rhodamine dye and use thereof in biological assays |
| KR20220008253A (ko) | 2019-01-03 | 2022-01-20 | 엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔 (인쎄름) | 암을 앓는 대상에서 cd8+ t 세포 의존성 면역 반응을 향상시키기 위한 방법 및 약학적 조성물 |
| WO2020148349A1 (en) | 2019-01-16 | 2020-07-23 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Variants of erythroferrone and their use |
| EP3918096A1 (en) | 2019-01-31 | 2021-12-08 | The United States of America, as represented by the Secretary, Department of Health and Human Services | Methods and compositions for detecting transfusion-transmitted pathogens |
| EP3924520A1 (en) | 2019-02-13 | 2021-12-22 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and compositions for selecting a cancer treatment in a subject suffering from cancer |
| WO2020182932A1 (en) | 2019-03-13 | 2020-09-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New gene signatures for predicting survival time in patients suffering from renal cell carcinoma |
| WO2020193740A1 (en) | 2019-03-28 | 2020-10-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New strategy for treating pancreatic cancer |
| US20220177978A1 (en) | 2019-04-02 | 2022-06-09 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of predicting and preventing cancer in patients having premalignant lesions |
| EP3719144A1 (en) | 2019-04-05 | 2020-10-07 | Fundación para la Investigación Biomédica del Hospital Universitario de la Paz (FIBHULP) | Mir-151a-3p as an universal endogenous control for exosome cargo normalization |
| KR20210151842A (ko) | 2019-04-15 | 2021-12-14 | 엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔 (인쎄름) | 세포의 집단의 활동적 물질대사를 프로파일링하는 방법 |
| WO2020212586A1 (en) | 2019-04-18 | 2020-10-22 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the treatment and prognosis of cancer |
| JP2022530390A (ja) | 2019-04-24 | 2022-06-29 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 抗精神病剤の応答を予測するための方法 |
| WO2020229521A1 (en) | 2019-05-14 | 2020-11-19 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for inhibiting or reducing bacterial biofilms on a surface |
| WO2020229437A1 (en) | 2019-05-14 | 2020-11-19 | F. Hoffmann-La Roche Ag | Devices and methods for sample analysis |
| WO2021001539A1 (en) | 2019-07-04 | 2021-01-07 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New strategy to detect and treat eosinophilic fasciitis |
| CN114040919A (zh) * | 2019-07-05 | 2022-02-11 | 南京金斯瑞生物科技有限公司 | 一种荧光标记核酸及其合成方法 |
| WO2021013592A1 (en) | 2019-07-19 | 2021-01-28 | Fundación Para La Investigación Biomédica Del Hospital Universitario La Paz (Fibhulp) | Method for determining the response to treatment of a patient affected by non-small cell lung carcinoma (nsclc) |
| WO2021044012A1 (en) | 2019-09-05 | 2021-03-11 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method of treatment and pronostic of acute myeloid leukemia |
| WO2021063968A1 (en) | 2019-09-30 | 2021-04-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method and composition for diagnosing chronic obstructive pulmonary disease |
| CA3157889A1 (en) | 2019-10-17 | 2021-04-22 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods for diagnosing nasal intestinal type adenocarcinomas |
| WO2021076770A1 (en) | 2019-10-18 | 2021-04-22 | The Board Of Trustees Of The Leland Stanford Junior University | Clinical- and industrial-scale intact-tissue sequencing |
| WO2021170777A1 (en) | 2020-02-28 | 2021-09-02 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for diagnosing, prognosing and managing treatment of breast cancer |
| US11359238B2 (en) | 2020-03-06 | 2022-06-14 | Singular Genomics Systems, Inc. | Linked paired strand sequencing |
| US20230086718A1 (en) | 2020-03-20 | 2023-03-23 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for predicting the survival time of a patient suffering from a cancer |
| WO2021250106A1 (en) | 2020-06-10 | 2021-12-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for treating and prognosing cancer like glioblastoma |
| US12209273B2 (en) | 2020-06-12 | 2025-01-28 | 10X Genomics, Inc. | Nucleic acid assays using click chemistry bioconjugation |
| WO2021255204A1 (en) | 2020-06-18 | 2021-12-23 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New strategy for treating pancreatic cancer |
| WO2022015600A2 (en) | 2020-07-13 | 2022-01-20 | Singular Genomics Systems, Inc. | Methods of sequencing complementary polynucleotides |
| WO2022018163A1 (en) | 2020-07-22 | 2022-01-27 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for predicting survival time in patients suffering from cancer |
| WO2022020729A2 (en) | 2020-07-23 | 2022-01-27 | Life Technologies Corporation | Systems and methods for biological analysis |
| CN116323965A (zh) | 2020-07-23 | 2023-06-23 | 生命技术公司 | 使用染料的用于生物分析的组合物、系统和方法 |
| WO2022056078A1 (en) | 2020-09-11 | 2022-03-17 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Rnase h-assisted detection assay for rna (radar) |
| AU2021343471A1 (en) | 2020-09-16 | 2023-05-04 | Bruker Spatial Biology, Inc. | Chemical compositions and methods of using the same |
| WO2022064049A1 (en) | 2020-09-28 | 2022-03-31 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for diagnosing brucella infection |
| US20230383350A1 (en) | 2020-10-20 | 2023-11-30 | Institut National De La Sante Et De La Recherche Medicale | Method for predicting the response to tnf inhibitors |
| EP4208470A4 (en) | 2020-10-22 | 2024-10-30 | Singular Genomics Systems, Inc. | NUCLEIC ACID CIRCULARIZATION AND AMPLIFICATION ON A SURFACE |
| US12071667B2 (en) | 2020-11-04 | 2024-08-27 | 10X Genomics, Inc. | Sequence analysis using meta-stable nucleic acid molecules |
| US20240011094A1 (en) | 2020-11-06 | 2024-01-11 | Institut National de la Santé et de la Recherche Médicale | Methods for diagnosis and treating polycystic ovary syndrome (pcos) |
| WO2022136252A1 (en) | 2020-12-21 | 2022-06-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for prognosis the humoral response of a subject prior to vaccination |
| WO2022135753A1 (en) | 2020-12-21 | 2022-06-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for prognosis the humoral response of a subject prior to vaccination |
| WO2022152698A1 (en) | 2021-01-12 | 2022-07-21 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of npdk-d to evaluate cancer prognosis |
| US12060603B2 (en) | 2021-01-19 | 2024-08-13 | 10X Genomics, Inc. | Methods for internally controlled in situ assays using padlock probes |
| WO2022170212A1 (en) | 2021-02-08 | 2022-08-11 | Singular Genomics Systems, Inc. | Methods and compositions for sequencing complementary polynucleotides |
| US20240044901A1 (en) | 2021-02-09 | 2024-02-08 | Institut National de la Santé et de la Recherche Médicale | New method to pronostic lung cancer |
| US11884977B2 (en) | 2021-03-12 | 2024-01-30 | Singular Genomics Systems, Inc. | Nanoarrays and methods of use thereof |
| WO2022192671A1 (en) | 2021-03-12 | 2022-09-15 | Singular Genomics Systems, Inc. | Nanoarrays and methods of use thereof |
| US20240159760A1 (en) | 2021-03-17 | 2024-05-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for diagnosing pancreatic cancer |
| WO2022207566A1 (en) | 2021-03-29 | 2022-10-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New method to evaluate pancreatic cancer prognosis |
| EP4326903A1 (en) | 2021-04-23 | 2024-02-28 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and compositions for treating cell senescence accumulation related disease |
| US11578320B2 (en) | 2021-04-27 | 2023-02-14 | Singular Genomics Systems, Inc. | High density sequencing and multiplexed priming |
| WO2022235764A1 (en) | 2021-05-05 | 2022-11-10 | Singular Genomics Systems, Inc. | Multiomic analysis device and methods of use thereof |
| CN117396613A (zh) | 2021-06-01 | 2024-01-12 | 10X基因组学有限公司 | 用于分析物检测和探针解析的方法和组合物 |
| EP4347880A1 (en) | 2021-06-02 | 2024-04-10 | 10X Genomics, Inc. | Sample analysis using asymmetric circularizable probes |
| EP4367269A1 (en) | 2021-07-05 | 2024-05-15 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Gene signatures for predicting survival time in patients suffering from renal cell carcinoma |
| CN117651855A (zh) | 2021-07-13 | 2024-03-05 | 10X基因组学有限公司 | 用于制备具有可控厚度的聚合基质的方法 |
| US12139751B2 (en) | 2021-07-30 | 2024-11-12 | 10X Genomics, Inc. | Circularizable probes for in situ analysis |
| WO2023009842A1 (en) | 2021-07-30 | 2023-02-02 | 10X Genomics, Inc. | Methods and compositions for synchronizing reactions in situ |
| US12460251B2 (en) | 2021-08-03 | 2025-11-04 | 10X Genomics, Inc. | Stabilization and/or compaction of nucleic acid molecules |
| CN118043476A (zh) | 2021-08-03 | 2024-05-14 | 10X基因组学有限公司 | 核酸多联体及其稳定和/或压缩方法 |
| US12391984B2 (en) | 2021-08-03 | 2025-08-19 | 10X Genomics, Inc. | Compositions and methods for rolling circle amplification |
| CN117858958A (zh) | 2021-08-16 | 2024-04-09 | 10X基因组学有限公司 | 包含分割条形码区的探针和使用方法 |
| WO2023023638A1 (en) | 2021-08-20 | 2023-02-23 | Singular Genomics Systems, Inc. | Chemical and thermal assisted nucleic acid amplification methods |
| WO2023076832A1 (en) | 2021-10-25 | 2023-05-04 | Singular Genomics Systems, Inc. | Manipulating and detecting biological samples |
| EP4422792A4 (en) | 2021-10-26 | 2025-12-17 | Singular Genomics Systems Inc | TARGETED MULTIPLEX AMPLIFICATION OF POLYNUCLEOTIDS |
| WO2023089159A1 (en) | 2021-11-22 | 2023-05-25 | INSERM (Institut National de la Santé et de la Recherche Médicale) | New strategy targeting stroma/tumor cell crosstalk to treat a cancer |
| EP4423296A2 (en) | 2021-12-27 | 2024-09-04 | 10X Genomics, Inc. | Methods and compositions for rolling circle amplification |
| EP4466376A1 (en) | 2022-01-21 | 2024-11-27 | 10X Genomics, Inc. | Multiple readout signals for analyzing a sample |
| EP4472740A1 (en) | 2022-01-31 | 2024-12-11 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Cd38 as a biomarker and biotarget in t-cell lymphomas |
| WO2023152133A1 (en) | 2022-02-08 | 2023-08-17 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for diagnosing colorectal cancer |
| AU2023223467A1 (en) | 2022-02-23 | 2024-08-08 | Insitro, Inc. | Pooled optical screening and transcriptional measurements of cells comprising barcoded genetic perturbations |
| US20250188521A1 (en) | 2022-03-10 | 2025-06-12 | Singular Genomics Systems, Inc. | Nucleic acid delivery scaffolds |
| EP4505177A1 (en) | 2022-04-01 | 2025-02-12 | 10x Genomics, Inc. | Compositions and methods for targeted masking of autofluorescence |
| EP4519674A1 (en) | 2022-05-06 | 2025-03-12 | 10X Genomics, Inc. | Analysis of antigen and antigen receptor interactions |
| EP4519453A1 (en) | 2022-05-06 | 2025-03-12 | 10X Genomics, Inc. | Methods and compositions for in situ analysis of v(d)j sequences |
| CN119213143A (zh) | 2022-05-11 | 2024-12-27 | 10X基因组学有限公司 | 用于原位测序的组合物和方法 |
| WO2023245190A1 (en) | 2022-06-17 | 2023-12-21 | 10X Genomics, Inc. | Catalytic de-crosslinking of samples for in situ analysis |
| US20240101978A1 (en) | 2022-08-12 | 2024-03-28 | 10X Genomics, Inc. | Puma1 polymerases and uses thereof |
| WO2024040060A1 (en) | 2022-08-16 | 2024-02-22 | 10X Genomics, Inc. | Ap50 polymerases and uses thereof |
| WO2024061930A1 (en) | 2022-09-22 | 2024-03-28 | Institut National de la Santé et de la Recherche Médicale | New method to treat and diagnose peripheral t-cell lymphoma (ptcl) |
| EP4602344A1 (en) | 2022-10-14 | 2025-08-20 | 10X Genomics, Inc. | Methods for analysis of biological samples |
| US20240167081A1 (en) | 2022-11-08 | 2024-05-23 | 10X Genomics,Inc. | Immobilization methods and compositions for in situ detection |
| US20240158852A1 (en) | 2022-11-16 | 2024-05-16 | 10X Genomics, Inc. | Methods and compositions for assessing performance of in situ assays |
| WO2024115935A1 (en) | 2022-11-29 | 2024-06-06 | Inserm | Methods for the treatment of b-cell lymphoma using cd39 inhibitors |
| EP4634404A1 (en) | 2022-12-16 | 2025-10-22 | 10X Genomics, Inc. | Methods and compositions for assessing performance |
| US20240263219A1 (en) | 2023-01-06 | 2024-08-08 | 10X Genomics, Inc. | Methods and compositions for in situ analysis of variant sequences |
| US20240263220A1 (en) | 2023-02-03 | 2024-08-08 | 10X Genomics, Inc. | In situ analysis of variant sequences in biological samples |
| WO2024191684A1 (en) | 2023-03-10 | 2024-09-19 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Detection of hepatitis c virus ribonucleic acid from whole blood using reverse transcription loop-mediated isothermal amplification |
| WO2024196764A2 (en) | 2023-03-17 | 2024-09-26 | Nanostring Technologies, Inc. | Assay for recombinase accessible chromatin and related compositions and methods |
| WO2025090132A2 (en) | 2023-05-12 | 2025-05-01 | Life Technolohgies Corporation | Methods and kits for detecting endotoxin |
| WO2024236131A1 (en) | 2023-05-17 | 2024-11-21 | Institut National de la Santé et de la Recherche Médicale | Stratificate and method to treat a patient suffering from a cancer |
| WO2024245951A1 (en) | 2023-05-26 | 2024-12-05 | Institut National de la Santé et de la Recherche Médicale | Combination of slc8a1 inhibitor and mitochondria-targeted antioxidant for treating melanoma |
| US12319956B2 (en) | 2023-07-31 | 2025-06-03 | 10X Genomics, Inc. | Methods and systems for targeted RNA cleavage and target RNA-primed rolling circle amplification |
| WO2025027127A1 (en) | 2023-08-02 | 2025-02-06 | Institut National de la Santé et de la Recherche Médicale | New prognostic method of kidney failure |
| WO2025045894A1 (en) | 2023-08-28 | 2025-03-06 | Institut National de la Santé et de la Recherche Médicale | Methods and kits for diagnosing cause of nephrotic syndrome and guiding therapy |
| WO2025059422A1 (en) | 2023-09-14 | 2025-03-20 | Bruker Spatial Biology, Inc. | Methods for detecting target nucleic acids in a sample |
| WO2025068340A1 (en) | 2023-09-27 | 2025-04-03 | Institut National de la Santé et de la Recherche Médicale | Method to predict aml outcome |
| WO2025073765A1 (en) | 2023-10-03 | 2025-04-10 | Institut National de la Santé et de la Recherche Médicale | Methods of prognosis and treatment of patients suffering from melanoma |
| WO2025078632A1 (en) | 2023-10-12 | 2025-04-17 | Institut National de la Santé et de la Recherche Médicale | Methods of prognosis and treatment of patients suffering from cancer |
| WO2025101775A1 (en) | 2023-11-07 | 2025-05-15 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Immunogenic compositions comprising full-length influenza virus neuraminidase protein subunits and methods of use |
| WO2025109147A1 (en) | 2023-11-24 | 2025-05-30 | Institut National de la Santé et de la Recherche Médicale | Method to predict the risk of a cardiovascular event in a patient with type 2 diabetes |
| WO2025114473A1 (en) | 2023-11-29 | 2025-06-05 | Institut National de la Santé et de la Recherche Médicale | Method for assessing diseases associated with a loss of p53 function in subjects in need thereof |
| US20250207203A1 (en) | 2023-12-20 | 2025-06-26 | 10X Genomics, Inc. | In situ detection of copy number variations in biological samples |
| WO2025147587A1 (en) | 2024-01-05 | 2025-07-10 | Glyphic Biotechnologies, Inc. | Protein sequencing using super-resolution imaging |
| WO2025240918A1 (en) | 2024-05-17 | 2025-11-20 | 10X Genomics, Inc. | Systems and methods for generating codebooks |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1984001394A1 (fr) * | 1982-09-30 | 1984-04-12 | Iro Ab | Dispositif de stockage, debitage et mesure de fil |
| US4490543A (en) * | 1982-11-12 | 1984-12-25 | University Of Northern Iowa Foundation | Low toxicity radiation sensitizer |
| EP0201751A2 (en) * | 1985-05-08 | 1986-11-20 | Abbott Laboratories | 4'-aminomethyfluorescein derivatives for use in fluorescence polarization immunoassys |
| CA1273552A (en) * | 1985-12-23 | 1990-09-04 | Michael J. Heller | Fluorescent stokes shift probes for polynucleotide hybridization assays |
| US4996143A (en) * | 1985-12-23 | 1991-02-26 | Syngene, Inc. | Fluorescent stokes shift probes for polynucleotide hybridization |
| US4780421A (en) * | 1986-04-03 | 1988-10-25 | Sclavo Inc. | Cleavable labels for use in binding assays |
| US5188934A (en) * | 1989-11-14 | 1993-02-23 | Applied Biosystems, Inc. | 4,7-dichlorofluorescein dyes as molecular probes |
| US5401847A (en) * | 1990-03-14 | 1995-03-28 | Regents Of The University Of California | DNA complexes with dyes designed for energy transfer as fluorescent markers |
| US5453517A (en) * | 1992-02-25 | 1995-09-26 | Molecular Probes, Inc. | Reactive derivatives of bapta used to make ion-selective chelators |
| US5405975A (en) * | 1993-03-29 | 1995-04-11 | Molecular Probes, Inc. | Fluorescent ion-selective diaryldiaza crown ether conjugates |
| JPH04107559A (ja) * | 1990-08-29 | 1992-04-09 | Kao Corp | 感光性組成物及びそれを用いた硬化像の形成方法 |
| US5187085A (en) * | 1990-09-28 | 1993-02-16 | Applied Biosystems, Inc. | Nucleic acid sequence analysis with nucleoside-5'-o-(1-thiotriphosphates) |
| ATE152831T1 (de) * | 1991-09-16 | 1997-05-15 | Molecular Probes Inc | Dimere unsymmetrische cyaninfarbstoffe |
| US5747244A (en) * | 1991-12-23 | 1998-05-05 | Chiron Corporation | Nucleic acid probes immobilized on polystyrene surfaces |
| CA2087413A1 (en) * | 1992-01-17 | 1993-07-18 | Joseph R. Lakowicz | Fluorescent energy transfer immunoassay |
| WO1994005688A1 (en) * | 1992-09-03 | 1994-03-17 | Applied Biosystems, Inc. | 4,7-dichlorofluorescein dyes as molecular probes |
| EP0601889A2 (en) * | 1992-12-10 | 1994-06-15 | Maine Medical Center Research Institute | Nucleic acid probes |
| JP3368011B2 (ja) * | 1993-10-04 | 2003-01-20 | キヤノン株式会社 | 核酸検出法 |
| US5654419A (en) * | 1994-02-01 | 1997-08-05 | The Regents Of The University Of California | Fluorescent labels and their use in separations |
| US5565554A (en) * | 1994-07-29 | 1996-10-15 | The Regents Of The University Of California | Dimeric fluorescent energy transfer dyes comprising asymmetric cyanine azole-indolenine chromophores |
| WO1996004059A1 (en) * | 1994-08-03 | 1996-02-15 | Langley James S | Steam enhancer |
| US5741657A (en) * | 1995-03-20 | 1998-04-21 | The Regents Of The University Of California | Fluorogenic substrates for β-lactamase and methods of use |
| US6008373A (en) * | 1995-06-07 | 1999-12-28 | Carnegie Mellon University | Fluorescent labeling complexes with large stokes shift formed by coupling together cyanine and other fluorochromes capable of resonance energy transfer |
| US5728528A (en) * | 1995-09-20 | 1998-03-17 | The Regents Of The University Of California | Universal spacer/energy transfer dyes |
| US5800996A (en) * | 1996-05-03 | 1998-09-01 | The Perkin Elmer Corporation | Energy transfer dyes with enchanced fluorescence |
-
1996
- 1996-10-04 US US08/726,462 patent/US5800996A/en not_active Expired - Lifetime
-
1997
- 1997-04-23 CA CA002203494A patent/CA2203494C/en not_active Expired - Fee Related
- 1997-05-02 EP EP99201120A patent/EP0940450B1/en not_active Expired - Lifetime
- 1997-05-02 DE DE69736434T patent/DE69736434T2/de not_active Expired - Lifetime
- 1997-05-02 EP EP97303039A patent/EP0805190B1/en not_active Expired - Lifetime
- 1997-05-02 AT AT99201120T patent/ATE335051T1/de not_active IP Right Cessation
- 1997-05-02 DE DE69700935T patent/DE69700935T2/de not_active Expired - Lifetime
- 1997-05-02 AT AT97303039T patent/ATE187752T1/de not_active IP Right Cessation
- 1997-05-06 JP JP09115920A patent/JP3090626B2/ja not_active Expired - Fee Related
-
2000
- 2000-01-19 JP JP2000010933A patent/JP3592173B2/ja not_active Expired - Lifetime
- 2000-01-19 JP JP2000010932A patent/JP2000187036A/ja active Pending
- 2000-01-19 JP JP2000010931A patent/JP2000154381A/ja not_active Withdrawn
-
2003
- 2003-02-05 JP JP2003028821A patent/JP3499238B2/ja not_active Expired - Fee Related
- 2003-08-06 JP JP2003288286A patent/JP2004068023A/ja not_active Withdrawn
- 2003-08-06 JP JP2003288285A patent/JP2004043819A/ja not_active Withdrawn
-
2004
- 2004-04-30 JP JP2004136932A patent/JP2004250713A/ja not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7825237B2 (en) | 1996-05-03 | 2010-11-02 | Applied Biosystems, Llc | Oligonucleotides and analogs labeled with energy transfer dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE335051T1 (de) | 2006-08-15 |
| DE69700935T2 (de) | 2000-04-27 |
| DE69700935D1 (de) | 2000-01-20 |
| JP2000154332A (ja) | 2000-06-06 |
| AU691143B2 (en) | 1998-05-07 |
| JP2000154381A (ja) | 2000-06-06 |
| AU1999597A (en) | 1997-11-20 |
| EP0805190B1 (en) | 1999-12-15 |
| EP0805190A3 (en) | 1998-01-07 |
| JP2004068023A (ja) | 2004-03-04 |
| EP0940450B1 (en) | 2006-08-02 |
| JP2004250713A (ja) | 2004-09-09 |
| DE69736434D1 (de) | 2006-09-14 |
| EP0940450A1 (en) | 1999-09-08 |
| JP2004043819A (ja) | 2004-02-12 |
| JP3499238B2 (ja) | 2004-02-23 |
| JP2003274999A (ja) | 2003-09-30 |
| JPH1088124A (ja) | 1998-04-07 |
| JP2000187036A (ja) | 2000-07-04 |
| ATE187752T1 (de) | 2000-01-15 |
| EP0805190A2 (en) | 1997-11-05 |
| JP3090626B2 (ja) | 2000-09-25 |
| DE69736434T2 (de) | 2007-03-01 |
| CA2203494A1 (en) | 1997-11-03 |
| US5800996A (en) | 1998-09-01 |
| JP3592173B2 (ja) | 2004-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2203494C (en) | Energy transfer dyes with enhanced fluorescence | |
| US6358684B1 (en) | UV excitable fluorescent energy transfer dyes | |
| US5863727A (en) | Energy transfer dyes with enhanced fluorescence | |
| US7169939B2 (en) | Energy transfer dyes with enhanced fluorescence | |
| US20090118485A1 (en) | Oligonucleotides and analogs labeled with energy transfer dyes | |
| US6218124B1 (en) | Method for detecting oligonucleotides using UV light source | |
| CA2297589C (en) | Energy transfer dyes with enhanced fluorescence | |
| US20120172583A1 (en) | Oligonucleotides and Analogs Labeled with Energy Transfer Dyes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130423 |