JP4927253B2 - 硬化トリメチンシアニン色素 - Google Patents
硬化トリメチンシアニン色素 Download PDFInfo
- Publication number
- JP4927253B2 JP4927253B2 JP2000539092A JP2000539092A JP4927253B2 JP 4927253 B2 JP4927253 B2 JP 4927253B2 JP 2000539092 A JP2000539092 A JP 2000539092A JP 2000539092 A JP2000539092 A JP 2000539092A JP 4927253 B2 JP4927253 B2 JP 4927253B2
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- Prior art keywords
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- compound
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- alkyl
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- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 239000000975 dye Substances 0.000 claims abstract description 70
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 239000013077 target material Substances 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 125000004429 atom Chemical group 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 succinimidyl ester Chemical class 0.000 claims description 89
- 238000000034 method Methods 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 25
- 125000000524 functional group Chemical group 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 108090000623 proteins and genes Proteins 0.000 claims description 23
- 102000004169 proteins and genes Human genes 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 20
- 238000003556 assay Methods 0.000 claims description 19
- 239000007850 fluorescent dye Substances 0.000 claims description 19
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 18
- 108091034117 Oligonucleotide Proteins 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 238000000159 protein binding assay Methods 0.000 claims description 17
- 230000009870 specific binding Effects 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 14
- 239000012491 analyte Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 12
- 238000003776 cleavage reaction Methods 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000007523 nucleic acids Chemical class 0.000 claims description 11
- 102000004190 Enzymes Human genes 0.000 claims description 10
- 108090000790 Enzymes Proteins 0.000 claims description 10
- 230000027455 binding Effects 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
- 230000007017 scission Effects 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 150000001721 carbon Chemical class 0.000 claims description 9
- 150000007942 carboxylates Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 238000002875 fluorescence polarization Methods 0.000 claims description 8
- 108020004707 nucleic acids Proteins 0.000 claims description 8
- 102000039446 nucleic acids Human genes 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
- 150000002632 lipids Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- 238000010791 quenching Methods 0.000 claims description 7
- 230000000171 quenching effect Effects 0.000 claims description 7
- 229910052711 selenium Inorganic materials 0.000 claims description 7
- 239000011669 selenium Chemical class 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 238000005259 measurement Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical class [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical class 0.000 claims description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 3
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical compound NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 claims description 3
- 150000001718 carbodiimides Chemical class 0.000 claims description 3
- 230000000295 complement effect Effects 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000012634 fragment Substances 0.000 claims description 3
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 3
- 238000003018 immunoassay Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002773 nucleotide Substances 0.000 claims description 3
- 125000003729 nucleotide group Chemical group 0.000 claims description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 3
- 150000008300 phosphoramidites Chemical class 0.000 claims description 3
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 102000004882 Lipase Human genes 0.000 claims description 2
- 108090001060 Lipase Proteins 0.000 claims description 2
- 239000004367 Lipase Substances 0.000 claims description 2
- 101710163270 Nuclease Proteins 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 238000001952 enzyme assay Methods 0.000 claims description 2
- 108091008039 hormone receptors Proteins 0.000 claims description 2
- 235000019421 lipase Nutrition 0.000 claims description 2
- 238000007899 nucleic acid hybridization Methods 0.000 claims description 2
- 108091033319 polynucleotide Proteins 0.000 claims description 2
- 102000040430 polynucleotide Human genes 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- 239000003053 toxin Substances 0.000 claims description 2
- 231100000765 toxin Toxicity 0.000 claims description 2
- 238000012163 sequencing technique Methods 0.000 claims 3
- MEZJQXVOMGUAMP-UHFFFAOYSA-N 1-(2-methylnaphthalen-1-yl)pyrrole-2,5-dione Chemical compound CC1=CC=C2C=CC=CC2=C1N1C(=O)C=CC1=O MEZJQXVOMGUAMP-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 108091028043 Nucleic acid sequence Proteins 0.000 claims 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 239000005546 dideoxynucleotide Substances 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 150000002540 isothiocyanates Chemical class 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims 2
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 claims 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 claims 1
- 238000006911 enzymatic reaction Methods 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 238000001525 receptor binding assay Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 230000003595 spectral effect Effects 0.000 abstract description 7
- 230000009257 reactivity Effects 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 126
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 69
- 239000000047 product Substances 0.000 description 67
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 49
- 238000004128 high performance liquid chromatography Methods 0.000 description 34
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 34
- 239000003480 eluent Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 27
- 239000007787 solid Substances 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 235000018102 proteins Nutrition 0.000 description 20
- 239000000523 sample Substances 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 108020004414 DNA Proteins 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- BJDCWCLMFKKGEE-CMDXXVQNSA-N chembl252518 Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-CMDXXVQNSA-N 0.000 description 15
- 238000002372 labelling Methods 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 238000002866 fluorescence resonance energy transfer Methods 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 239000007810 chemical reaction solvent Substances 0.000 description 11
- 238000001514 detection method Methods 0.000 description 11
- 125000004494 ethyl ester group Chemical group 0.000 description 11
- 239000002953 phosphate buffered saline Substances 0.000 description 11
- 108090000765 processed proteins & peptides Proteins 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 108091033380 Coding strand Proteins 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000010287 polarization Effects 0.000 description 7
- 102000003945 NF-kappa B Human genes 0.000 description 6
- 108010057466 NF-kappa B Proteins 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 102100035100 Transcription factor p65 Human genes 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 230000005284 excitation Effects 0.000 description 6
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- MCIPQLOKVXSHTD-UHFFFAOYSA-N 3,3-diethoxyprop-1-ene Chemical compound CCOC(C=C)OCC MCIPQLOKVXSHTD-UHFFFAOYSA-N 0.000 description 5
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 5
- 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 5
- 239000000427 antigen Substances 0.000 description 5
- 102000036639 antigens Human genes 0.000 description 5
- 108091007433 antigens Proteins 0.000 description 5
- 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 description 5
- ZQUVDXMUKIVNOW-UHFFFAOYSA-N n,n'-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1NC=NC1=CC=CC=C1 ZQUVDXMUKIVNOW-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 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 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
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Classifications
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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
- C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
-
- 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
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lasers (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Vehicle Interior And Exterior Ornaments, Soundproofing, And Insulation (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99221297A | 1997-12-17 | 1997-12-17 | |
| US08/992,212 | 1997-12-17 | ||
| PCT/US1998/026665 WO1999031181A1 (en) | 1997-12-17 | 1998-12-16 | Rigidized trimethine cyanine dyes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002508428A JP2002508428A (ja) | 2002-03-19 |
| JP2002508428A5 JP2002508428A5 (https=) | 2012-02-02 |
| JP4927253B2 true JP4927253B2 (ja) | 2012-05-09 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000539092A Expired - Lifetime JP4927253B2 (ja) | 1997-12-17 | 1998-12-16 | 硬化トリメチンシアニン色素 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6686145B1 (https=) |
| EP (1) | EP1042407B1 (https=) |
| JP (1) | JP4927253B2 (https=) |
| AT (1) | ATE205515T1 (https=) |
| AU (1) | AU760598B2 (https=) |
| CA (1) | CA2314188C (https=) |
| DE (1) | DE69801682T2 (https=) |
| DK (1) | DK1042407T3 (https=) |
| ES (1) | ES2165711T3 (https=) |
| WO (1) | WO1999031181A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102777649B1 (ko) * | 2017-11-23 | 2025-03-11 | 에스에프씨 주식회사 | 표지용 염료 및 이를 포함하는 표지용 키트 |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6133445A (en) * | 1997-12-17 | 2000-10-17 | Carnegie Mellon University | Rigidized trimethine cyanine dyes |
| WO2004039894A2 (en) * | 2002-05-10 | 2004-05-13 | Carnegie Mellon University | Chiral indole intermediates and their fluorescent cyanine dyes containing functional groups |
| EP1196398A4 (en) * | 1999-07-06 | 2002-11-06 | Surromed Inc | BRIDGED FLUORESCENT DYES, THEIR PRODUCTION AND USE IN DETECTION METHODS |
| DE19937024A1 (de) * | 1999-08-05 | 2001-02-08 | Bayer Ag | Verwendung von Acylsulfonamido substituierten Polymethin-Farbstoffen als Fluoreszenz-Farbstoffe und/oder Marker |
| EP1223197B1 (en) | 2001-01-03 | 2012-08-08 | Visen Medical, Inc. | Symmetric, monofunctionalised polymethine dyes labelling reagents |
| EP1221465A1 (en) | 2001-01-03 | 2002-07-10 | Innosense S.r.l. | Symmetric, monofunctionalised polymethine dyes labelling reagents |
| EP1781675B1 (en) | 2004-08-13 | 2014-03-26 | Epoch Biosciences, Inc. | Phosphonate fluorescent dyes and conjugates |
| US7419511B2 (en) * | 2004-09-13 | 2008-09-02 | L'oreal, S.A. | Compositions comprising at least one substituted carbocyanin derivative, processes for treating keratin fibers using them, device therefor and uses thereof |
| US7427301B2 (en) | 2004-09-13 | 2008-09-23 | L'ORéAL S.A. | Composition comprising at least one substituted carbocyanin derivative, process for treating keratin fibers using it, device therefor and use thereof |
| US7425221B2 (en) | 2004-09-13 | 2008-09-16 | L'oreal S.A. | Composition comprising at least one substituted derivative of carbocyanine, method for treating keratin fibers using it, device and use |
| FR2875131B1 (fr) * | 2004-09-13 | 2007-09-28 | Oreal | Composition comprenant au moins un derive substitue de carbocyanine, procede de traitement des fibres keratiniques la mettant en oeuvre, dispositif et utilisation |
| EP1794237A2 (en) | 2004-09-30 | 2007-06-13 | GE Healthcare UK Limited | Fluorescent nucleotide analogues |
| US7282373B2 (en) | 2004-12-23 | 2007-10-16 | Rutgers, The State University Of New Jersey | Ultra-high specificity fluorescent labeling |
| US7381572B2 (en) | 2004-12-23 | 2008-06-03 | Rutgers, The State University Of New Jersey | Reagents and procedures for multi-label high-specificity labeling |
| EP1846754A4 (en) * | 2005-02-01 | 2008-10-08 | Sigma Aldrich Co | Detection of polyaminoacids via trimethylphenin staining |
| US7737281B2 (en) * | 2005-05-24 | 2010-06-15 | Enzo Life Sciences, Inc. C/O Enzo Biochem, Inc. | Purine based fluorescent dyes |
| US7569695B2 (en) * | 2005-05-24 | 2009-08-04 | Enzo Life Sciences, Inc. | Dyes for the detection or quantification of desirable target molecules |
| 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 |
| CN101296927A (zh) | 2005-09-02 | 2008-10-29 | Visen医药公司 | 生物相容的含n,n-二取代磺酰胺的荧光染料标记 |
| US7947256B2 (en) | 2005-09-02 | 2011-05-24 | Visen Medical, Inc. | Biocompatible fluorescent imaging agents |
| JP5416970B2 (ja) | 2005-09-02 | 2014-02-12 | ビセン メディカル, インコーポレイテッド | ニコチン酸及びピコリン酸誘導近赤外線蛍光団 |
| US7972789B2 (en) * | 2005-11-28 | 2011-07-05 | Dako Denmark A/S | Dye compounds |
| US9334281B2 (en) * | 2008-09-08 | 2016-05-10 | Enzo Life Sciences, Inc. | Fluorochromes for organelle tracing and multi-color imaging |
| US9250249B2 (en) | 2008-09-08 | 2016-02-02 | Enzo Biochem, Inc. | Autophagy and phospholipidosis pathway assays |
| AU2010219097A1 (en) | 2009-01-13 | 2011-08-04 | Glaxo Group Limited | Pyrimidinecarboxamide derivatives as inhibitors of SYK kinase |
| GB201007203D0 (en) | 2010-04-29 | 2010-06-16 | Glaxo Group Ltd | Novel compounds |
| EP2831587B1 (en) | 2012-03-27 | 2018-05-16 | Ventana Medical Systems, Inc. | Signaling conjugates and methods of use |
| KR102502117B1 (ko) * | 2015-07-16 | 2023-02-22 | 에스에프씨 주식회사 | 염료 화합물 |
| EP3655408B1 (en) | 2017-08-24 | 2021-07-14 | The U.S.A. As Represented By The Secretary, Department Of Health And Human Services | Conformational restriction of cyanine fluorophores in far-red and near-ir range |
| KR102593166B1 (ko) * | 2017-11-23 | 2023-10-25 | 에스에프씨 주식회사 | 표지용 염료 및 이를 포함하는 표지용 키트 |
| AU2019300169A1 (en) | 2018-07-13 | 2021-01-28 | Quantum-Si Incorporated | Biconjugatable labels and methods of use |
| KR102682109B1 (ko) * | 2022-02-10 | 2024-07-05 | 에스에프씨 주식회사 | 신규한 화합물 및 이의 용도 |
| EP4665402A1 (en) | 2023-02-17 | 2025-12-24 | Danmarks Tekniske Universitet | Copolymer-drug conjugate for treatment of tumours |
| WO2025144711A1 (en) * | 2023-12-29 | 2025-07-03 | Illumina, Inc. | Tricyclic polymethine dyes for nucleic acid sequencing |
| CN119285524B (zh) * | 2024-10-11 | 2026-04-10 | 深圳大学 | 一种荧光染料化合物及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3679427A (en) * | 1970-10-30 | 1972-07-25 | Eastman Kodak Co | Rigidized carbocyanine dyes and photographic emulsions |
| US3864644A (en) * | 1971-03-22 | 1975-02-04 | Eastman Kodak Co | Dye lasers including rigidized carbocyanine dyes |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3753721A (en) | 1970-08-13 | 1973-08-21 | Eastman Kodak Co | Photographic materials |
| US3915715A (en) | 1970-08-13 | 1975-10-28 | Eastman Kodak Co | Silver halide photographic materials containing a high weight ratio of gold to sulfur sensitizers and a sensitizing methine dye |
| US3854956A (en) | 1970-10-30 | 1974-12-17 | Eastman Kodak Co | Dyestuffs and spectral sensitizers for silver halide |
| US3821233A (en) | 1970-10-30 | 1974-06-28 | Eastman Kodak Co | Rigidized carbocyanine dyes containing a pyrida-dipyridinium nucleus |
| CA985493A (en) * | 1971-03-22 | 1976-03-16 | Eastman Kodak Company | Dye lasers including rigidized carbocyanine dyes |
| US3904637A (en) | 1972-04-19 | 1975-09-09 | Eastman Kodak Co | 7'a'h,8'a'h-bisbenzothiazolo(3,2-a;-3',2'-a)pyrano (3,2-c;5,6-c'+9 dipyridinium compounds and related derivatives thereof |
| DE69624623T2 (de) | 1995-06-07 | 2003-07-24 | Carnegie Mellon University, Pittsburgh | Versteifte Monomethin-Cyaninfarbstoffe |
| US5658735A (en) | 1995-11-09 | 1997-08-19 | Biometric Imaging, Inc. | Cyclized fluorescent nucleic acid intercalating cyanine dyes and nucleic acid detection methods |
| US6133445A (en) | 1997-12-17 | 2000-10-17 | Carnegie Mellon University | Rigidized trimethine cyanine dyes |
-
1998
- 1998-12-16 ES ES98963218T patent/ES2165711T3/es not_active Expired - Lifetime
- 1998-12-16 EP EP98963218A patent/EP1042407B1/en not_active Expired - Lifetime
- 1998-12-16 DE DE69801682T patent/DE69801682T2/de not_active Expired - Lifetime
- 1998-12-16 AT AT98963218T patent/ATE205515T1/de active
- 1998-12-16 AU AU18288/99A patent/AU760598B2/en not_active Expired
- 1998-12-16 DK DK98963218T patent/DK1042407T3/da active
- 1998-12-16 CA CA002314188A patent/CA2314188C/en not_active Expired - Lifetime
- 1998-12-16 WO PCT/US1998/026665 patent/WO1999031181A1/en not_active Ceased
- 1998-12-16 US US09/581,679 patent/US6686145B1/en not_active Expired - Lifetime
- 1998-12-16 JP JP2000539092A patent/JP4927253B2/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3679427A (en) * | 1970-10-30 | 1972-07-25 | Eastman Kodak Co | Rigidized carbocyanine dyes and photographic emulsions |
| US3864644A (en) * | 1971-03-22 | 1975-02-04 | Eastman Kodak Co | Dye lasers including rigidized carbocyanine dyes |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102777649B1 (ko) * | 2017-11-23 | 2025-03-11 | 에스에프씨 주식회사 | 표지용 염료 및 이를 포함하는 표지용 키트 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU1828899A (en) | 1999-07-05 |
| DE69801682D1 (en) | 2001-10-18 |
| JP2002508428A (ja) | 2002-03-19 |
| WO1999031181A1 (en) | 1999-06-24 |
| EP1042407B1 (en) | 2001-09-12 |
| AU760598B2 (en) | 2003-05-15 |
| CA2314188C (en) | 2009-11-17 |
| ATE205515T1 (de) | 2001-09-15 |
| CA2314188A1 (en) | 1999-06-24 |
| DK1042407T3 (da) | 2001-12-27 |
| EP1042407A1 (en) | 2000-10-11 |
| DE69801682T2 (de) | 2002-06-20 |
| ES2165711T3 (es) | 2002-03-16 |
| US6686145B1 (en) | 2004-02-03 |
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