SG177676A1 - Novel fluorescent dyes and uses thereof - Google Patents
Novel fluorescent dyes and uses thereof Download PDFInfo
- Publication number
- SG177676A1 SG177676A1 SG2012003125A SG2012003125A SG177676A1 SG 177676 A1 SG177676 A1 SG 177676A1 SG 2012003125 A SG2012003125 A SG 2012003125A SG 2012003125 A SG2012003125 A SG 2012003125A SG 177676 A1 SG177676 A1 SG 177676A1
- Authority
- SG
- Singapore
- Prior art keywords
- dye
- carbon
- bonds
- group
- alkyl
- Prior art date
Links
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 84
- 239000000975 dye Substances 0.000 claims abstract description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- -1 acyl azide Chemical class 0.000 claims description 48
- 239000000460 chlorine Substances 0.000 claims description 47
- 150000002148 esters Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000001188 haloalkyl group Chemical group 0.000 claims description 32
- 125000005647 linker group Chemical group 0.000 claims description 31
- 229910052727 yttrium Inorganic materials 0.000 claims description 31
- 102000004169 proteins and genes Human genes 0.000 claims description 28
- 108090000623 proteins and genes Proteins 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 230000000295 complement effect Effects 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 230000009870 specific binding Effects 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 150000002540 isothiocyanates Chemical class 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 108020004707 nucleic acids Proteins 0.000 claims description 10
- 150000007523 nucleic acids Chemical class 0.000 claims description 10
- 102000039446 nucleic acids Human genes 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000004437 phosphorous atom Chemical group 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 9
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 108091034117 Oligonucleotide Proteins 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 150000002466 imines Chemical class 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 239000002773 nucleotide Substances 0.000 claims description 8
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims description 8
- 230000004044 response Effects 0.000 claims description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 7
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 7
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 150000001266 acyl halides Chemical class 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003729 nucleotide group Chemical group 0.000 claims description 7
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 7
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 150000004676 glycans Chemical class 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- 241000700605 Viruses Species 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 241000894006 Bacteria Species 0.000 claims description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 3
- 229960002317 succinimide Drugs 0.000 claims 3
- 210000004102 animal cell Anatomy 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 239000012491 analyte Substances 0.000 abstract description 26
- 238000002360 preparation method Methods 0.000 abstract description 26
- IGXWBGJHJZYPQS-SSDOTTSWSA-N D-Luciferin Chemical group OC(=O)[C@H]1CSC(C=2SC3=CC=C(O)C=C3N=2)=N1 IGXWBGJHJZYPQS-SSDOTTSWSA-N 0.000 abstract description 24
- 238000001514 detection method Methods 0.000 abstract description 12
- 239000000562 conjugate Substances 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 239000007787 solid Substances 0.000 description 49
- 239000011541 reaction mixture Substances 0.000 description 40
- CYCGRDQQIOGCKX-UHFFFAOYSA-N Dehydro-luciferin Natural products OC(=O)C1=CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 CYCGRDQQIOGCKX-UHFFFAOYSA-N 0.000 description 39
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- BJGNCJDXODQBOB-UHFFFAOYSA-N Fivefly Luciferin Natural products OC(=O)C1CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 BJGNCJDXODQBOB-UHFFFAOYSA-N 0.000 description 35
- DDWFXDSYGUXRAY-UHFFFAOYSA-N Luciferin Natural products CCc1c(C)c(CC2NC(=O)C(=C2C=C)C)[nH]c1Cc3[nH]c4C(=C5/NC(CC(=O)O)C(C)C5CC(=O)O)CC(=O)c4c3C DDWFXDSYGUXRAY-UHFFFAOYSA-N 0.000 description 35
- 239000000523 sample Substances 0.000 description 27
- 235000018102 proteins Nutrition 0.000 description 25
- 239000002253 acid Substances 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229910052786 argon Inorganic materials 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000985 reactive dye Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- NIZMCFUMSHISLW-UHFFFAOYSA-M 4,5-dichlorodithiazol-1-ium;chloride Chemical compound [Cl-].ClC1=NS[S+]=C1Cl NIZMCFUMSHISLW-UHFFFAOYSA-M 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 235000014633 carbohydrates Nutrition 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 230000003993 interaction Effects 0.000 description 10
- 239000003446 ligand Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229940024606 amino acid Drugs 0.000 description 8
- 235000001014 amino acid Nutrition 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 150000001720 carbohydrates Chemical class 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 238000000684 flow cytometry Methods 0.000 description 8
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 7
- 108020004414 DNA Proteins 0.000 description 7
- 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 7
- 230000021615 conjugation Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 108090001008 Avidin Proteins 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 101000738771 Homo sapiens Receptor-type tyrosine-protein phosphatase C Proteins 0.000 description 6
- 102100037422 Receptor-type tyrosine-protein phosphatase C Human genes 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 229940088597 hormone Drugs 0.000 description 6
- 239000002523 lectin Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 108010021625 Immunoglobulin Fragments Proteins 0.000 description 5
- 102000008394 Immunoglobulin Fragments Human genes 0.000 description 5
- 102000004856 Lectins Human genes 0.000 description 5
- 108090001090 Lectins Proteins 0.000 description 5
- 108010090804 Streptavidin Proteins 0.000 description 5
- 238000004458 analytical method Methods 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
- 230000027455 binding Effects 0.000 description 5
- 229960002685 biotin Drugs 0.000 description 5
- 239000011616 biotin Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 125000002228 disulfide group Chemical group 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- 239000005556 hormone Substances 0.000 description 5
- 238000002372 labelling Methods 0.000 description 5
- GASFVSRUEBGMDI-UHFFFAOYSA-N n-aminohydroxylamine Chemical compound NNO GASFVSRUEBGMDI-UHFFFAOYSA-N 0.000 description 5
- VVNCNSJFMMFHPL-UHFFFAOYSA-N penicillamine Chemical compound CC(C)(S)C(N)C(O)=O VVNCNSJFMMFHPL-UHFFFAOYSA-N 0.000 description 5
- 102000004196 processed proteins & peptides Human genes 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- UYHQUNLVWOAJQW-UHFFFAOYSA-N 1,3-benzothiazole-2-carbonitrile Chemical compound C1=CC=C2SC(C#N)=NC2=C1 UYHQUNLVWOAJQW-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- NOMSBEUFLWHSRG-UHFFFAOYSA-N 5,7-dichloro-6-hydroxy-1,3-benzothiazole-2-carbonitrile Chemical compound OC1=C(Cl)C=C2N=C(C#N)SC2=C1Cl NOMSBEUFLWHSRG-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 235000020958 biotin Nutrition 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 238000005206 flow analysis Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002777 nucleoside Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- HUPGZEYAAFYLSC-UHFFFAOYSA-N 4-methoxy-3,5-dimethylaniline Chemical compound COC1=C(C)C=C(N)C=C1C HUPGZEYAAFYLSC-UHFFFAOYSA-N 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003102 growth factor Substances 0.000 description 3
- 238000003018 immunoassay Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 125000003835 nucleoside group Chemical group 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- OUEHOXKSVCSHIG-UHFFFAOYSA-N 5,7-dichloro-6-methoxy-1,3-benzothiazole-2-carbonitrile Chemical compound COC1=C(Cl)C=C2N=C(C#N)SC2=C1Cl OUEHOXKSVCSHIG-UHFFFAOYSA-N 0.000 description 2
- IFPFEXSXBQTQBX-UHFFFAOYSA-N 5,7-difluoro-6-hydroxy-1,3-benzothiazole-2-carbonitrile Chemical compound OC1=C(F)C=C2N=C(C#N)SC2=C1F IFPFEXSXBQTQBX-UHFFFAOYSA-N 0.000 description 2
- CFXRVWIJWIXTHL-UHFFFAOYSA-N 6-chloro-5-hydroxy-1,3-benzothiazole-2-carbonitrile Chemical compound C1=C(Cl)C(O)=CC2=C1SC(C#N)=N2 CFXRVWIJWIXTHL-UHFFFAOYSA-N 0.000 description 2
- HVAVGUOXKZUEBY-UHFFFAOYSA-N 6-chloro-5-methoxy-1,3-benzothiazole-2-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC2=C1SC(C#N)=N2 HVAVGUOXKZUEBY-UHFFFAOYSA-N 0.000 description 2
- NICHCTYGTBQJAO-UHFFFAOYSA-N 6-hydroxy-5,7-dimethyl-1,3-benzothiazole-2-carbonitrile Chemical compound CC1=C(O)C(C)=CC2=C1SC(C#N)=N2 NICHCTYGTBQJAO-UHFFFAOYSA-N 0.000 description 2
- HNRVNBLTJSPHKY-UHFFFAOYSA-N 6-hydroxy-5-(trifluoromethyl)-1,3-benzothiazole-2-carbonitrile Chemical compound C1=C(C(F)(F)F)C(O)=CC2=C1N=C(C#N)S2 HNRVNBLTJSPHKY-UHFFFAOYSA-N 0.000 description 2
- XEBRUDYAKHGZJA-UHFFFAOYSA-N 6-methoxy-5,7-dimethyl-1,3-benzothiazole-2-carbonitrile Chemical compound COC1=C(C)C=C2N=C(C#N)SC2=C1C XEBRUDYAKHGZJA-UHFFFAOYSA-N 0.000 description 2
- ZITXIEKXJSIFIU-UHFFFAOYSA-N 6-methoxy-5-(trifluoromethyl)-1,3-benzothiazole-2-carbonitrile Chemical compound C1=C(C(F)(F)F)C(OC)=CC2=C1N=C(C#N)S2 ZITXIEKXJSIFIU-UHFFFAOYSA-N 0.000 description 2
- HFYYMQJAMHMDGV-UHFFFAOYSA-N 6-methoxy-7-(trifluoromethyl)-1,3-benzothiazole-2-carbonitrile Chemical compound COC1=CC=C2N=C(C#N)SC2=C1C(F)(F)F HFYYMQJAMHMDGV-UHFFFAOYSA-N 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- 102000053602 DNA Human genes 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 108090000288 Glycoproteins Proteins 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
- 108010033040 Histones Proteins 0.000 description 2
- 108060001084 Luciferase Proteins 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- 101710120037 Toxin CcdB Proteins 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 238000006664 bond formation reaction Methods 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000001268 conjugating effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000799 fluorescence microscopy Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000001215 fluorescent labelling Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 229940127121 immunoconjugate Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 102000040430 polynucleotide Human genes 0.000 description 2
- 108091033319 polynucleotide Proteins 0.000 description 2
- 239000002157 polynucleotide Substances 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- AQTUACKQXJNHFQ-LURJTMIESA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCC(O)=O AQTUACKQXJNHFQ-LURJTMIESA-N 0.000 description 1
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical class OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- PXQYVHVDNPLNNM-UHFFFAOYSA-N 1,3-dichloro-2-methoxy-4-nitrobenzene Chemical compound COC1=C(Cl)C=CC([N+]([O-])=O)=C1Cl PXQYVHVDNPLNNM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GGCPQFAYURQNGS-UHFFFAOYSA-N 1,5-dichloro-6-methoxycyclohexa-2,4-dien-1-amine Chemical compound COC1C(Cl)=CC=CC1(N)Cl GGCPQFAYURQNGS-UHFFFAOYSA-N 0.000 description 1
- YNHKVOGCDPODMT-UHFFFAOYSA-N 1-(2-aminoethyl)pyrrole-2,5-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCCN1C(=O)C=CC1=O YNHKVOGCDPODMT-UHFFFAOYSA-N 0.000 description 1
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- VPZJHTWLWKFPQW-UHFFFAOYSA-N 3-chloro-2-methoxyaniline Chemical compound COC1=C(N)C=CC=C1Cl VPZJHTWLWKFPQW-UHFFFAOYSA-N 0.000 description 1
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical class ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
- LNKBDFVSILQKSI-UHFFFAOYSA-N 4-Chloro-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1Cl LNKBDFVSILQKSI-UHFFFAOYSA-N 0.000 description 1
- MCFBUIIRFZBRCU-UHFFFAOYSA-N 4-[1-[5-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]pyridin-2-yl]piperidin-4-yl]oxycyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1OC1CCN(C=2N=CC(=CC=2)C=2NC3=CC(=CC=C3N=2)C(F)(F)F)CC1 MCFBUIIRFZBRCU-UHFFFAOYSA-N 0.000 description 1
- CQJCPOVTPNWVBW-UHFFFAOYSA-N 4-methoxy-3-(trifluoromethyl)aniline Chemical compound COC1=CC=C(N)C=C1C(F)(F)F CQJCPOVTPNWVBW-UHFFFAOYSA-N 0.000 description 1
- VPPVKPAETLKKDE-UHFFFAOYSA-N 5-chloro-4-hydroxy-1,3-benzothiazole-2-carbonitrile Chemical compound OC1=C(Cl)C=CC2=C1N=C(C#N)S2 VPPVKPAETLKKDE-UHFFFAOYSA-N 0.000 description 1
- FKWQESNHGXRZIO-UHFFFAOYSA-N 5-chloro-4-methoxy-1,3-benzothiazole-2-carbonitrile Chemical compound COC1=C(Cl)C=CC2=C1N=C(C#N)S2 FKWQESNHGXRZIO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 102000000844 Cell Surface Receptors Human genes 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 108010065556 Drug Receptors Proteins 0.000 description 1
- 102000013138 Drug Receptors Human genes 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010008488 Glycylglycine Proteins 0.000 description 1
- 102000006947 Histones Human genes 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 239000005089 Luciferase Substances 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 241001274216 Naso Species 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 108020004682 Single-Stranded DNA Proteins 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000011545 carbonate/bicarbonate buffer Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000008045 co-localization Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 150000001944 cysteine derivatives Chemical class 0.000 description 1
- 238000004163 cytometry Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- ULFHSQLFQYTZLS-UHFFFAOYSA-N difluoroamine Chemical compound FNF ULFHSQLFQYTZLS-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 239000000911 dye-antibody conjugate Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LIYGYAHYXQDGEP-UHFFFAOYSA-N firefly oxyluciferin Natural products Oc1csc(n1)-c1nc2ccc(O)cc2s1 LIYGYAHYXQDGEP-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229940043257 glycylglycine Drugs 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 108091008039 hormone receptors Proteins 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000010166 immunofluorescence Methods 0.000 description 1
- 238000007901 in situ hybridization Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229960001913 mecysteine Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- TZJVWRXHKAXSEA-UHFFFAOYSA-N methyl 6-aminohexanoate Chemical compound COC(=O)CCCCCN TZJVWRXHKAXSEA-UHFFFAOYSA-N 0.000 description 1
- MCYHPZGUONZRGO-VKHMYHEASA-N methyl L-cysteinate Chemical compound COC(=O)[C@@H](N)CS MCYHPZGUONZRGO-VKHMYHEASA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 238000007837 multiplex assay Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 150000002482 oligosaccharides Polymers 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- JJVOROULKOMTKG-UHFFFAOYSA-N oxidized Photinus luciferin Chemical compound S1C2=CC(O)=CC=C2N=C1C1=NC(=O)CS1 JJVOROULKOMTKG-UHFFFAOYSA-N 0.000 description 1
- VYNDHICBIRRPFP-UHFFFAOYSA-N pacific blue Chemical compound FC1=C(O)C(F)=C2OC(=O)C(C(=O)O)=CC2=C1 VYNDHICBIRRPFP-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 108010011903 peptide receptors Proteins 0.000 description 1
- 102000014187 peptide receptors Human genes 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000004713 phosphodiesters Chemical class 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
- C09B7/00—Indigoid dyes
-
- 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
- C12Q1/66—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving luciferase
-
- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/535—Production of labelled immunochemicals with enzyme label or co-enzymes, co-factors, enzyme inhibitors or enzyme substrates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Biotechnology (AREA)
- Urology & Nephrology (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biomedical Technology (AREA)
- Physics & Mathematics (AREA)
- Pathology (AREA)
- Genetics & Genomics (AREA)
- Cell Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- General Physics & Mathematics (AREA)
- General Engineering & Computer Science (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22598509P | 2009-07-16 | 2009-07-16 | |
| PCT/US2010/042063 WO2011008912A1 (en) | 2009-07-16 | 2010-07-15 | Novel fluorescent dyes and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG177676A1 true SG177676A1 (en) | 2012-02-28 |
Family
ID=43218117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2012003125A SG177676A1 (en) | 2009-07-16 | 2010-07-15 | Novel fluorescent dyes and uses thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8367842B2 (enExample) |
| EP (1) | EP2454329B1 (enExample) |
| JP (2) | JP5777169B2 (enExample) |
| KR (1) | KR101809758B1 (enExample) |
| CN (1) | CN102498177B (enExample) |
| AU (1) | AU2010273431B2 (enExample) |
| BR (1) | BR112012001043A2 (enExample) |
| CA (1) | CA2768352C (enExample) |
| IN (1) | IN2012DN00454A (enExample) |
| NZ (1) | NZ597512A (enExample) |
| SG (1) | SG177676A1 (enExample) |
| WO (1) | WO2011008912A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5905402B2 (ja) * | 2010-03-11 | 2016-04-20 | プロメガ コーポレイションPromega Corporation | シアノベンゾチアゾール化合物を使用する生物発光アッセイ |
| CN102937576B (zh) * | 2012-06-26 | 2015-10-21 | 广东德美精细化工股份有限公司 | 一种织物除油剂的防沾性能的评价方法 |
| EP2719703A1 (en) * | 2012-10-12 | 2014-04-16 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Precursor molecule for the synthesis of D-luciferin |
| CN102942537B (zh) * | 2012-11-09 | 2014-07-02 | 浙江大学 | 一种用作pH荧光探针的苯并噻唑-苯胺类化合物及其制备方法 |
| US9817929B1 (en) | 2014-06-04 | 2017-11-14 | Calypto Design Systems, Inc. | Formal verification using microtransactions |
| EP4641204A2 (en) | 2016-04-06 | 2025-10-29 | Sony Group Corporation | Ultra bright dimeric or polymeric dyes with spacing linker groups |
| US10400264B2 (en) | 2016-12-01 | 2019-09-03 | Promega Corporation | 5,5-disubstituted luciferins and their use in luciferase-based assays |
| JP7563668B2 (ja) * | 2018-06-05 | 2024-10-08 | プロメガ コーポレイション | 熱安定性ルシフェリンと共に生物発光アッセイに使用するためのルシフェラーゼ酵素 |
| JP7580689B2 (ja) | 2018-06-27 | 2024-11-12 | ソニーグループ株式会社 | デオキシリボースを含むリンカー基を有するポリマー色素 |
| CN112399996A (zh) * | 2018-07-13 | 2021-02-23 | 索尼公司 | 具有包含有机磷酸酯单元的主链的聚合的染料 |
| CN110724114B (zh) * | 2018-07-16 | 2022-10-21 | 北京工商大学 | 一种检测亚硫酸氢根及硫化氢的荧光探针 |
| CN109633151B (zh) * | 2018-12-26 | 2022-03-11 | 西北农林科技大学 | 一种肠炎沙门氏菌检测方法、试纸条及应用 |
| CN110361378B (zh) * | 2019-07-25 | 2021-04-02 | 浙江大学 | 基于荧光素乙酯的orac抗氧化活性评价方法及荧光指示剂 |
| WO2021061057A2 (en) * | 2019-09-26 | 2021-04-01 | Vidyasirimedhi Institute Of Science And Technology | Luciferin derivatives and a method for synthesis thereof |
| EP4256078A1 (en) | 2020-12-07 | 2023-10-11 | Sony Group Corporation | Spacing linker group design for brightness enhancement in dimeric or polymeric dyes |
| EP4310074A4 (en) | 2021-03-19 | 2025-03-26 | Kanto Denka Kogyo Co., Ltd. | D-luciferin, d-luciferin derivative, precursor of these compounds and method for producing these compounds |
| CN116046735B (zh) * | 2022-12-26 | 2025-08-22 | 南京大学 | 一种利用染料组成的传感器阵列检测全氟化合物的方法 |
| CN119462681B (zh) * | 2024-10-16 | 2025-09-30 | 聊城柏莱斯生物科技有限公司 | 一种荧光定量pcr参比染料及其制备方法与应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3537877A1 (de) * | 1985-10-24 | 1987-04-30 | Geiger Reinhard | Luciferin-derivate und immunoassays unter einsatz derartiger luciferin-derivate |
| DE68928412T2 (de) * | 1988-07-08 | 1998-05-20 | Jbl Scient Inc | Herstellung und verwendung von fluoreszierenden benzothiazolderivaten |
| US6140051A (en) * | 1997-07-21 | 2000-10-31 | Promega Biosciences, Inc. | Fluorescent dibenzazole derivatives and methods related thereto |
| US7413536B1 (en) * | 1999-09-14 | 2008-08-19 | Xenoport, Inc. | Substrates and screening methods for transport proteins |
| JP4354280B2 (ja) * | 2002-03-01 | 2009-10-28 | イミューノメディクス、インコーポレイテッド | Rs7抗体 |
| US7541440B2 (en) * | 2002-09-30 | 2009-06-02 | Immunomedics, Inc. | Chimeric, human and humanized anti-granulocyte antibodies and methods of use |
| CN100572555C (zh) * | 2002-10-23 | 2009-12-23 | 犹他大学研究基金会 | 使用饱和染料的扩增子解链分析 |
| DE10302787A1 (de) * | 2003-01-24 | 2004-08-12 | Schering Ag | Hydrophile, Thiol-reaktive Cyaninfarbstoffe und deren Konjugate mit Biomolekülen für die Fluoreszenzdiagnostik |
| JP2006219381A (ja) * | 2005-02-08 | 2006-08-24 | Univ Of Electro-Communications | 複素環化合物及び発光甲虫ルシフェラーゼ発光系用発光基質 |
| EP3312292B1 (en) * | 2005-05-31 | 2019-09-25 | Promega Corporation | Luminogenic and fluorogenic compounds and methods to detect molecules or conditions |
| US20100190180A1 (en) * | 2005-07-06 | 2010-07-29 | Heidi Kay | Materials and Methods for Screening, Diagnosis and Prognosis of Conditions Associated With Stat Protein Expression |
| KR100704007B1 (ko) * | 2006-01-17 | 2007-04-04 | 한국과학기술연구원 | 화학발광 및 형광을 이용한 신속진단키트 및 이의 사용방법 |
| JP5194258B2 (ja) * | 2006-03-27 | 2013-05-08 | 国立大学法人電気通信大学 | 複素環化合物及び発光方法 |
| CN101784897A (zh) * | 2007-05-23 | 2010-07-21 | 应用生物系统有限公司 | 通过从活化的化学发光的基质将能量转移至能量受体染料来检测生物分子的试剂、试剂盒和方法 |
| CN101270105B (zh) * | 2008-04-08 | 2011-09-14 | 杨得锁 | 用于酶活性分析和酶抑制剂筛选的香豆素类化合物及合成方法 |
| US8551721B2 (en) * | 2008-09-09 | 2013-10-08 | Promega Corporation | Bioluminescent detection of cyanohydroxy benzothiazole compounds |
-
2010
- 2010-07-15 IN IN454DEN2012 patent/IN2012DN00454A/en unknown
- 2010-07-15 BR BR112012001043A patent/BR112012001043A2/pt active Search and Examination
- 2010-07-15 JP JP2012520764A patent/JP5777169B2/ja active Active
- 2010-07-15 SG SG2012003125A patent/SG177676A1/en unknown
- 2010-07-15 AU AU2010273431A patent/AU2010273431B2/en active Active
- 2010-07-15 US US12/836,747 patent/US8367842B2/en active Active
- 2010-07-15 CA CA2768352A patent/CA2768352C/en active Active
- 2010-07-15 WO PCT/US2010/042063 patent/WO2011008912A1/en not_active Ceased
- 2010-07-15 CN CN201080040648.1A patent/CN102498177B/zh active Active
- 2010-07-15 EP EP10737419.1A patent/EP2454329B1/en active Active
- 2010-07-15 KR KR1020127003981A patent/KR101809758B1/ko active Active
- 2010-07-15 NZ NZ597512A patent/NZ597512A/en unknown
-
2013
- 2013-01-24 US US13/748,756 patent/US8772501B2/en active Active
-
2015
- 2015-05-27 JP JP2015107038A patent/JP2015165031A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US8772501B2 (en) | 2014-07-08 |
| HK1168122A1 (en) | 2012-12-21 |
| BR112012001043A2 (pt) | 2016-03-15 |
| AU2010273431A2 (en) | 2012-03-01 |
| US20110014599A1 (en) | 2011-01-20 |
| US8367842B2 (en) | 2013-02-05 |
| AU2010273431B2 (en) | 2016-08-25 |
| EP2454329B1 (en) | 2018-04-18 |
| EP2454329A1 (en) | 2012-05-23 |
| KR101809758B1 (ko) | 2017-12-15 |
| CN102498177A (zh) | 2012-06-13 |
| WO2011008912A1 (en) | 2011-01-20 |
| CN102498177B (zh) | 2014-12-24 |
| JP5777169B2 (ja) | 2015-09-09 |
| JP2012533654A (ja) | 2012-12-27 |
| KR20120037486A (ko) | 2012-04-19 |
| NZ597512A (en) | 2014-03-28 |
| CA2768352C (en) | 2016-10-11 |
| IN2012DN00454A (enExample) | 2015-05-15 |
| JP2015165031A (ja) | 2015-09-17 |
| CA2768352A1 (en) | 2011-01-20 |
| US20130131324A1 (en) | 2013-05-23 |
| AU2010273431A1 (en) | 2012-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2010273431B2 (en) | Novel fluorescent dyes and uses thereof | |
| JP4989013B2 (ja) | シアニン色素 | |
| US5877310A (en) | Glycoconjugated fluorescent labeling reagents | |
| JP5697886B2 (ja) | 反応性複素環置換7−ヒドロキシクマリンおよびその複合体 | |
| US6165800A (en) | Chemiluminescent energy transfer conjugates and their uses as labels in binding assays | |
| EP0285179B1 (en) | Fluorescent diagnostic assay, assay elements, and conjugates | |
| JP2003532745A (ja) | エネルギー伝達アッセイ法および試薬 | |
| US20080039630A1 (en) | Cyanine compounds and their application as quenching compounds | |
| EP1928822A1 (en) | Violet laser excitable dyes and their method of use | |
| JPH1088012A (ja) | 発光アリールスルホネートシアニン染料を用いた物質の標識ないし検出方法 | |
| US5981747A (en) | Monomethine cyanines rigidized by a two-carbon chain | |
| EP3341377B1 (en) | Polyfluoreno[4,5-cde]oxepine conjugates and their use in methods of analyte detection | |
| CN1307263C (zh) | 用于饱和标记蛋白质的荧光染料、方法及试剂盒 | |
| EP1163372A1 (en) | Chemically reactive plane-rigidized cyanine dyes and their derivatives | |
| HK1168122B (en) | Novel fluorescent dyes and uses thereof | |
| WO2021154933A1 (en) | Uv excitable polyfluorene based conjugates and their use in methods of analyte detection |