JP3090626B2 - 増強された蛍光を有するエネルギー転移色素 - Google Patents
増強された蛍光を有するエネルギー転移色素Info
- Publication number
- JP3090626B2 JP3090626B2 JP09115920A JP11592097A JP3090626B2 JP 3090626 B2 JP3090626 B2 JP 3090626B2 JP 09115920 A JP09115920 A JP 09115920A JP 11592097 A JP11592097 A JP 11592097A JP 3090626 B2 JP3090626 B2 JP 3090626B2
- Authority
- JP
- Japan
- 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 593
- 238000012546 transfer Methods 0.000 title claims abstract description 180
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 77
- 125000001424 substituent group Chemical group 0.000 claims abstract description 40
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 150000001336 alkenes Chemical class 0.000 claims abstract description 23
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000001301 oxygen Substances 0.000 claims abstract description 22
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000011593 sulfur Substances 0.000 claims abstract description 15
- 125000000524 functional group Chemical group 0.000 claims abstract description 14
- 150000001993 dienes Chemical class 0.000 claims abstract description 10
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 108091034117 Oligonucleotide Proteins 0.000 claims description 92
- 239000001226 triphosphate Substances 0.000 claims description 63
- 235000011178 triphosphate Nutrition 0.000 claims description 63
- 239000003153 chemical reaction reagent Substances 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 49
- -1 isopyrole Chemical compound 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 45
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 45
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
- 239000002777 nucleoside Substances 0.000 claims description 35
- 238000012163 sequencing technique Methods 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 150000007523 nucleic acids Chemical group 0.000 claims description 26
- 239000001018 xanthene dye Substances 0.000 claims description 24
- 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 20
- 150000001412 amines Chemical class 0.000 claims description 17
- 150000003732 xanthenes Chemical class 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 16
- 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 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 230000005284 excitation Effects 0.000 claims description 15
- 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
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 14
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 14
- 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 13
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 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
- 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 12
- 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 12
- 150000001408 amides Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000002825 nitriles Chemical class 0.000 claims description 12
- IHXWECHPYNPJRR-UHFFFAOYSA-N 3-hydroxycyclobut-2-en-1-one Chemical compound OC1=CC(=O)C1 IHXWECHPYNPJRR-UHFFFAOYSA-N 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000005546 dideoxynucleotide Substances 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group 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
- 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
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000001022 rhodamine dye Substances 0.000 claims description 10
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 9
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 230000000295 complement effect Effects 0.000 claims description 9
- 125000003835 nucleoside group Chemical group 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 230000004044 response Effects 0.000 claims description 8
- BZTDTCNHAFUJOG-UHFFFAOYSA-N 6-carboxyfluorescein Chemical group C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C11OC(=O)C2=CC=C(C(=O)O)C=C21 BZTDTCNHAFUJOG-UHFFFAOYSA-N 0.000 claims description 7
- 239000001007 phthalocyanine dye Substances 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 5
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- 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
- ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical group C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-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
- 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
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
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- 150000003457 sulfones Chemical class 0.000 claims description 4
- 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 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 3
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Classifications
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- 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
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- 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)
- Biophysics (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Immunology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Luminescent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/642330 | 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 |
| US08/726462 | 1996-10-04 |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
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| JP2000010931A Division JP2000154381A (ja) | 1996-05-03 | 2000-01-19 | 硬質リンカ―を有するエネルギ―転移色素 |
| JP2000010933A Division JP3592173B2 (ja) | 1996-05-03 | 2000-01-19 | シアニンエネルギー転移色素 |
| JP2000010932A Division JP2000187036A (ja) | 1996-05-03 | 2000-01-19 | 長いスト―クスシフトを有するエネルギ―転移色素 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1088124A JPH1088124A (ja) | 1998-04-07 |
| JP3090626B2 true JP3090626B2 (ja) | 2000-09-25 |
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| JP09115920A Expired - Fee Related JP3090626B2 (ja) | 1996-05-03 | 1997-05-06 | 増強された蛍光を有するエネルギー転移色素 |
| JP2000010931A Withdrawn JP2000154381A (ja) | 1996-05-03 | 2000-01-19 | 硬質リンカ―を有するエネルギ―転移色素 |
| JP2000010932A Pending JP2000187036A (ja) | 1996-05-03 | 2000-01-19 | 長いスト―クスシフトを有するエネルギ―転移色素 |
| JP2000010933A Expired - Lifetime JP3592173B2 (ja) | 1996-05-03 | 2000-01-19 | シアニンエネルギー転移色素 |
| JP2003028821A Expired - Fee Related JP3499238B2 (ja) | 1996-05-03 | 2003-02-05 | 核酸配列の配列決定方法 |
| JP2003288285A Withdrawn JP2004043819A (ja) | 1996-05-03 | 2003-08-06 | 硬質リンカ―を有するエネルギ―転移色素 |
| JP2003288286A Withdrawn JP2004068023A (ja) | 1996-05-03 | 2003-08-06 | 硬質リンカ―を有するエネルギ―転移色素 |
| JP2004136932A Withdrawn JP2004250713A (ja) | 1996-05-03 | 2004-04-30 | 硬質リンカ―を有するエネルギ―転移色素 |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000010931A Withdrawn JP2000154381A (ja) | 1996-05-03 | 2000-01-19 | 硬質リンカ―を有するエネルギ―転移色素 |
| JP2000010932A Pending JP2000187036A (ja) | 1996-05-03 | 2000-01-19 | 長いスト―クスシフトを有するエネルギ―転移色素 |
| JP2000010933A Expired - Lifetime JP3592173B2 (ja) | 1996-05-03 | 2000-01-19 | シアニンエネルギー転移色素 |
| JP2003028821A Expired - Fee Related JP3499238B2 (ja) | 1996-05-03 | 2003-02-05 | 核酸配列の配列決定方法 |
| JP2003288285A Withdrawn JP2004043819A (ja) | 1996-05-03 | 2003-08-06 | 硬質リンカ―を有するエネルギ―転移色素 |
| JP2003288286A Withdrawn JP2004068023A (ja) | 1996-05-03 | 2003-08-06 | 硬質リンカ―を有するエネルギ―転移色素 |
| JP2004136932A Withdrawn JP2004250713A (ja) | 1996-05-03 | 2004-04-30 | 硬質リンカ―を有するエネルギ―転移色素 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5800996A (https=) |
| EP (2) | EP0805190B1 (https=) |
| JP (8) | JP3090626B2 (https=) |
| AT (2) | ATE187752T1 (https=) |
| CA (1) | CA2203494C (https=) |
| DE (2) | DE69700935T2 (https=) |
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| 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 |
| US7388092B2 (en) * | 1996-05-03 | 2008-06-17 | Applera Corporation | Oligonucleotides and analogs labeled with energy transfer dyes |
| US5863727A (en) * | 1996-05-03 | 1999-01-26 | The Perkin-Elmer Corporation | Energy transfer dyes with enhanced fluorescence |
| US7825237B2 (en) * | 1996-05-03 | 2010-11-02 | Applied Biosystems, Llc | Oligonucleotides and analogs labeled with energy transfer dyes |
| US5800996A (en) * | 1996-05-03 | 1998-09-01 | The Perkin Elmer Corporation | Energy transfer dyes with enchanced fluorescence |
| US5945526A (en) * | 1996-05-03 | 1999-08-31 | Perkin-Elmer Corporation | Energy transfer dyes with enhanced fluorescence |
| EP1033411B1 (en) * | 1996-06-04 | 2006-02-22 | University of Utah Research Foundation | Fluorescent donor-acceptor pair |
| JP4281877B2 (ja) * | 1996-06-04 | 2009-06-17 | ユニバーシティ オブ ユタ リサーチ ファウンデーション | 生物学的プロセスを実行し且つモニタリングするためのシステムと方法 |
| 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 |
| CN1251609A (zh) | 1997-02-12 | 2000-04-26 | 尤金·Y·查恩 | 分析聚合物的方法和产品 |
| US6265193B1 (en) * | 1997-03-12 | 2001-07-24 | Pe Corporation (Ny) | DNA polymerases having improved labeled nucleotide incorporation properties |
| EP0967219A4 (en) * | 1997-07-11 | 2002-09-11 | Rikagaku Kenkyusho | CONNECTIONS WITH ENERGY TRANSFER FUNCTION AND A METHOD FOR DNA BASE SEQUENCING USING THESE CONNECTIONS |
| US7632651B2 (en) | 1997-09-15 | 2009-12-15 | Mds Analytical Technologies (Us) Inc. | Molecular modification assays |
| US7745142B2 (en) | 1997-09-15 | 2010-06-29 | Molecular Devices Corporation | 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 |
| AU752932B2 (en) * | 1997-10-09 | 2002-10-03 | Transgenomic, Inc. | Modifying double stranded DNA to enhance separations by matched ion polynucleotide chromatography |
| ATE478090T1 (de) | 1997-10-27 | 2010-09-15 | Boston Probes Inc | SICH AUF ßPNA MOLECULAR BEACONSß BEZIEHENDE VERFAHREN, TESTSÄTZE UND ZUSAMMENSETZUNGEN |
| US6485901B1 (en) | 1997-10-27 | 2002-11-26 | Boston Probes, Inc. | Methods, kits and compositions pertaining to linear beacons |
| US6583168B1 (en) * | 1997-11-25 | 2003-06-24 | Applera Corporation | Sulfonated diarylrhodamine dyes |
| US5936087A (en) * | 1997-11-25 | 1999-08-10 | The Perkin-Elmer Corporation | Dibenzorhodamine 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 |
| WO2000036151A1 (en) | 1998-12-14 | 2000-06-22 | Li-Cor, Inc. | A heterogeneous assay for pyrophosphate detection |
| US6635419B1 (en) | 1999-02-16 | 2003-10-21 | Applera Corporation | Polynucleotide sequencing method |
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Also Published As
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|---|---|
| EP0805190B1 (en) | 1999-12-15 |
| DE69700935D1 (de) | 2000-01-20 |
| AU691143B2 (en) | 1998-05-07 |
| EP0805190A2 (en) | 1997-11-05 |
| CA2203494A1 (en) | 1997-11-03 |
| AU1999597A (en) | 1997-11-20 |
| ATE335051T1 (de) | 2006-08-15 |
| JP2004250713A (ja) | 2004-09-09 |
| JPH1088124A (ja) | 1998-04-07 |
| DE69736434D1 (de) | 2006-09-14 |
| JP2004043819A (ja) | 2004-02-12 |
| JP3499238B2 (ja) | 2004-02-23 |
| DE69700935T2 (de) | 2000-04-27 |
| JP2000154332A (ja) | 2000-06-06 |
| JP3592173B2 (ja) | 2004-11-24 |
| EP0805190A3 (en) | 1998-01-07 |
| EP0940450B1 (en) | 2006-08-02 |
| EP0940450A1 (en) | 1999-09-08 |
| ATE187752T1 (de) | 2000-01-15 |
| DE69736434T2 (de) | 2007-03-01 |
| US5800996A (en) | 1998-09-01 |
| JP2004068023A (ja) | 2004-03-04 |
| JP2000187036A (ja) | 2000-07-04 |
| JP2000154381A (ja) | 2000-06-06 |
| JP2003274999A (ja) | 2003-09-30 |
| CA2203494C (en) | 2000-12-26 |
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