ES2372395T3 - Reactivos de marcado con colorantes de cianina. - Google Patents
Reactivos de marcado con colorantes de cianina. Download PDFInfo
- Publication number
- ES2372395T3 ES2372395T3 ES04791610T ES04791610T ES2372395T3 ES 2372395 T3 ES2372395 T3 ES 2372395T3 ES 04791610 T ES04791610 T ES 04791610T ES 04791610 T ES04791610 T ES 04791610T ES 2372395 T3 ES2372395 T3 ES 2372395T3
- Authority
- ES
- Spain
- Prior art keywords
- groups
- group
- sulfobutyl
- methyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000003153 chemical reaction reagent Substances 0.000 title description 4
- 239000003086 colorant Substances 0.000 title 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- -1 succinimidyl ester Chemical class 0.000 claims abstract description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 13
- 125000004429 atom Chemical group 0.000 claims abstract description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 150000002540 isothiocyanates Chemical class 0.000 claims abstract description 5
- 150000008300 phosphoramidites Chemical class 0.000 claims abstract description 5
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 31
- 102000004169 proteins and genes Human genes 0.000 claims description 31
- 108090000623 proteins and genes Proteins 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
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- 229910006069 SO3H Inorganic materials 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
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- 239000002773 nucleotide Substances 0.000 claims description 6
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- UGIZUKGTKCHOEO-UHFFFAOYSA-N (2e)-2-[(2e,4z)-5-[1-(5-carboxypentyl)-3-methyl-5-sulfo-3-(4-sulfobutyl)indol-1-ium-2-yl]penta-2,4-dienylidene]-3-methyl-1,3-bis(4-sulfobutyl)indole-5-sulfonate Chemical compound OC(=O)CCCCCN1C2=CC=C(S(O)(=O)=O)C=C2C(C)(CCCCS(O)(=O)=O)\C1=C/C=C/C=C/C1=[N+](CCCCS(O)(=O)=O)C2=CC=C(S([O-])(=O)=O)C=C2C1(C)CCCCS(O)(=O)=O UGIZUKGTKCHOEO-UHFFFAOYSA-N 0.000 claims description 2
- QFRWHAVRZLUMIB-UHFFFAOYSA-N 2-[7-[1-(5-carboxypentyl)-3-methyl-5-sulfo-3-(4-sulfobutyl)indol-1-ium-2-yl]hepta-2,4,6-trienylidene]-1-ethyl-3-methyl-3-(4-sulfobutyl)indole-5-sulfonate Chemical compound OS(=O)(=O)CCCCC1(C)C2=CC(S([O-])(=O)=O)=CC=C2[N+](CC)=C1\C=C\C=C\C=C\C=C\1C(CCCCS(O)(=O)=O)(C)C2=CC(S(O)(=O)=O)=CC=C2N/1CCCCCC(O)=O QFRWHAVRZLUMIB-UHFFFAOYSA-N 0.000 claims description 2
- KCLLGUBEMHHCRQ-UHFFFAOYSA-N 2-[7-[5-(carboxymethyl)-3-methyl-1,3-bis(4-sulfobutyl)indol-1-ium-2-yl]hepta-2,4,6-trienylidene]-1-ethyl-3-methyl-3-(4-sulfobutyl)indole-5-sulfonate Chemical compound OS(=O)(=O)CCCCC1(C)C2=CC(S([O-])(=O)=O)=CC=C2[N+](CC)=C1\C=C\C=C\C=C\C=C\1C(CCCCS(O)(=O)=O)(C)C2=CC(CC(O)=O)=CC=C2N/1CCCCS(O)(=O)=O KCLLGUBEMHHCRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
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- 150000002632 lipids Chemical class 0.000 claims description 2
- 230000000813 microbial effect Effects 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000003053 toxin Substances 0.000 claims description 2
- 231100000765 toxin Toxicity 0.000 claims description 2
- 108700012359 toxins Proteins 0.000 claims description 2
- BLTBKTKORYZZSS-UHFFFAOYSA-N 2-[5-[1-(5-carboxypentyl)-3-methyl-5-sulfo-3-(4-sulfobutyl)indol-1-ium-2-yl]penta-2,4-dienylidene]-1-ethyl-3-methyl-3-(4-sulfobutyl)indole-5-sulfonate Chemical compound OS(=O)(=O)CCCCC1(C)C2=CC(S([O-])(=O)=O)=CC=C2[N+](CC)=C1\C=C\C=C\C=C\1C(CCCCS(O)(=O)=O)(C)C2=CC(S(O)(=O)=O)=CC=C2N/1CCCCCC(O)=O BLTBKTKORYZZSS-UHFFFAOYSA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 125
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 44
- 239000000047 product Substances 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 28
- 238000002372 labelling Methods 0.000 description 26
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 239000002299 complementary DNA Substances 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 238000002835 absorbance Methods 0.000 description 20
- 239000003480 eluent Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 238000001514 detection method Methods 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 239000000523 sample Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 11
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- 229940125782 compound 2 Drugs 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 8
- 230000002776 aggregation Effects 0.000 description 8
- 238000004220 aggregation Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 150000003839 salts Chemical group 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 230000008033 biological extinction Effects 0.000 description 7
- 229940125898 compound 5 Drugs 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical group C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 5
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- JYOHYHWVHZATHI-UHFFFAOYSA-N 1-ethyl-2,3-dimethyl-3-(4-sulfobutyl)indol-1-ium-5-sulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C2[N+](CC)=C(C)C(C)(CCCCS(O)(=O)=O)C2=C1 JYOHYHWVHZATHI-UHFFFAOYSA-N 0.000 description 4
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 4
- 241001494479 Pecora Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 3
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- STNNHWPJRRODGI-UHFFFAOYSA-N carbonic acid;n,n-diethylethanamine Chemical compound [O-]C([O-])=O.CC[NH+](CC)CC.CC[NH+](CC)CC STNNHWPJRRODGI-UHFFFAOYSA-N 0.000 description 1
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- NCGWKCHAJOUDHQ-UHFFFAOYSA-N n,n-diethylethanamine;formic acid Chemical class OC=O.OC=O.CCN(CC)CC NCGWKCHAJOUDHQ-UHFFFAOYSA-N 0.000 description 1
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- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
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- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical class [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
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- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Indole Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Laminated Bodies (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
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| US51642803P | 2003-10-31 | 2003-10-31 | |
| US516428P | 2003-10-31 |
Publications (1)
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| ES2372395T3 true ES2372395T3 (es) | 2012-01-19 |
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| ES04791610T Expired - Lifetime ES2372395T3 (es) | 2003-10-31 | 2004-10-29 | Reactivos de marcado con colorantes de cianina. |
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| US (2) | US7750163B2 (https=) |
| EP (2) | EP2360211A1 (https=) |
| JP (1) | JP4943156B2 (https=) |
| CN (1) | CN100577742C (https=) |
| AT (1) | ATE522580T1 (https=) |
| ES (1) | ES2372395T3 (https=) |
| WO (1) | WO2005044923A1 (https=) |
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| ATE488604T1 (de) | 2003-05-20 | 2010-12-15 | Investigen Inc | System zum nachweis von polynukleotiden |
| CN100577742C (zh) * | 2003-10-31 | 2010-01-06 | 阿默森生物科学英国有限公司 | 花青染料标记试剂 |
| JP5214967B2 (ja) | 2004-08-13 | 2013-06-19 | エポック バイオサイエンシズ インコーポレーティッド | ホスホン酸蛍光色素および複合体 |
| US7767834B2 (en) * | 2004-08-13 | 2010-08-03 | Elitech Holding B.V. | Phosphonylated fluorescent dyes and conjugates |
| DE502006007823D1 (de) | 2005-12-05 | 2010-10-21 | Dyomics Gmbh | Hydrophile Marker auf der Basis von diastereomeren Cyaninen |
| DE102006029454A1 (de) * | 2005-12-05 | 2007-06-06 | Dyomics Gmbh | Hydrophile Marker auf Basis von diasteromeren |
| US8021839B2 (en) | 2006-02-24 | 2011-09-20 | Investigen, Inc. | Methods and compositions for detecting polynucleotides |
| US7771947B2 (en) | 2007-02-23 | 2010-08-10 | Investigen, Inc. | Methods and compositions for rapid light-activated isolation and detection of analytes |
| CA2686089A1 (en) * | 2007-05-16 | 2008-11-20 | Ge Healthcare As | Optical imaging agents |
| ATE551073T1 (de) * | 2007-05-16 | 2012-04-15 | Ge Healthcare As | Markierte hgf-bindende peptide für bildgebung |
| US7951959B2 (en) | 2008-09-17 | 2011-05-31 | Thermo Fisher Scientific (Milwaukee) LLC | Hydrophilic labels for biomolecules |
| CN101723874B (zh) * | 2008-10-31 | 2013-09-11 | 深圳迈瑞生物医疗电子股份有限公司 | 花菁类化合物及其在生物样品染色中的用途 |
| US8916137B2 (en) | 2008-11-07 | 2014-12-23 | The General Hospital Corporation | Monofunctional carbocyanine dyes for in vivo and in vitro imaging |
| CN101750476B (zh) * | 2008-12-08 | 2015-06-03 | 深圳迈瑞生物医疗电子股份有限公司 | 血液分析试剂及其使用方法 |
| US8729276B2 (en) * | 2009-04-17 | 2014-05-20 | Korea Institute Of Science And Technology | Cyanine compound for labeling biomolecule and preparation method thereof |
| US20100291706A1 (en) * | 2009-05-15 | 2010-11-18 | Millipore Corporation | Dye conjugates and methods of use |
| GB2478359B (en) * | 2010-03-05 | 2018-09-12 | Innova Biosciences Ltd | Conjugation reactions |
| GB201010878D0 (en) * | 2010-06-29 | 2010-08-11 | Ge Healthcare As | Dye compositiion and dye syntheses |
| CN103052690A (zh) * | 2010-06-29 | 2013-04-17 | 通用电气医疗集团股份有限公司 | 染料组合物和染料合成 |
| US9012242B2 (en) * | 2010-09-20 | 2015-04-21 | Caliper Life Sciences | Multivalent fluorescent probes |
| WO2012048063A2 (en) * | 2010-10-06 | 2012-04-12 | Emd Millipore Corporation | Cyanine compounds, conjugates and method of use |
| EP3029027B1 (en) | 2010-12-21 | 2018-06-27 | Pierce Biotechnology, Inc. | Fluorescent compounds |
| US8877892B2 (en) | 2011-03-15 | 2014-11-04 | Innova Biosciences Limited | Conjugation reactions |
| US8889884B1 (en) | 2011-07-14 | 2014-11-18 | Pierce Biotechnology, Inc. | Phosphine derivatives of fluorescent compounds |
| US9249307B2 (en) | 2011-08-16 | 2016-02-02 | Pierce Biotechnology, Inc. | Benzocyanine compounds |
| EP2758475B1 (en) | 2011-09-23 | 2017-04-26 | Illumina Cambridge Limited | Dyes for labelling molecular ligands |
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| US20160176819A1 (en) * | 2014-12-19 | 2016-06-23 | Washington University | Asymmetrically charged nir fluorophores |
| GB201508858D0 (en) | 2015-05-22 | 2015-07-01 | Illumina Cambridge Ltd | Polymethine compounds with long stokes shifts and their use as fluorescent labels |
| GB201516987D0 (en) | 2015-09-25 | 2015-11-11 | Illumina Cambridge Ltd | Polymethine compounds and their use as fluorescent labels |
| KR20170101360A (ko) * | 2016-02-26 | 2017-09-06 | 에스에프씨 주식회사 | 시아닌계 화합물, 이를 포함하는 생체분자 표지용 염료, 키트 및 조영제 조성물 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5569587A (en) | 1986-04-18 | 1996-10-29 | Carnegie Mellon University | Method for labeling and detecting materials employing luminescent arysulfonate cyanine dyes |
| US6048982A (en) | 1986-04-18 | 2000-04-11 | Carnegie Mellon University | Cyanine dyes as labeling reagents for detection of biological and other materials by luminescence methods |
| US5268486A (en) | 1986-04-18 | 1993-12-07 | Carnegie-Mellon Unversity | Method for labeling and detecting materials employing arylsulfonate cyanine dyes |
| JPH04186342A (ja) * | 1990-11-21 | 1992-07-03 | Fuji Photo Film Co Ltd | 写真感光材料を用いるカラープルーフの作成方法 |
| JPH0531330A (ja) * | 1991-07-31 | 1993-02-09 | Riken Corp | 排ガス浄化方法 |
| JPH05313304A (ja) | 1992-05-11 | 1993-11-26 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
| DE4445065A1 (de) | 1994-12-07 | 1996-06-13 | Diagnostikforschung Inst | Verfahren zur In-vivo-Diagnostik mittels NIR-Strahlung |
| WO2004039894A2 (en) * | 2002-05-10 | 2004-05-13 | Carnegie Mellon University | Chiral indole intermediates and their fluorescent cyanine dyes containing functional groups |
| CA2423806C (en) * | 2000-09-29 | 2009-12-22 | Molecular Probes, Inc. | Modified carbocyanine dyes and their conjugates |
| CN100577742C (zh) * | 2003-10-31 | 2010-01-06 | 阿默森生物科学英国有限公司 | 花青染料标记试剂 |
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- 2004-10-29 JP JP2006537422A patent/JP4943156B2/ja not_active Expired - Fee Related
- 2004-10-29 ES ES04791610T patent/ES2372395T3/es not_active Expired - Lifetime
- 2004-10-29 US US10/576,956 patent/US7750163B2/en not_active Expired - Fee Related
- 2004-10-29 EP EP11156595A patent/EP2360211A1/en not_active Withdrawn
- 2004-10-29 EP EP04791610A patent/EP1678258B1/en not_active Expired - Lifetime
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- 2004-10-29 AT AT04791610T patent/ATE522580T1/de not_active IP Right Cessation
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2010
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| US7750163B2 (en) | 2010-07-06 |
| EP2360211A1 (en) | 2011-08-24 |
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| EP1678258A1 (en) | 2006-07-12 |
| CN1875073A (zh) | 2006-12-06 |
| JP4943156B2 (ja) | 2012-05-30 |
| US8148539B2 (en) | 2012-04-03 |
| ATE522580T1 (de) | 2011-09-15 |
| HK1093520A1 (en) | 2007-03-02 |
| CN100577742C (zh) | 2010-01-06 |
| EP1678258B1 (en) | 2011-08-31 |
| US20070203343A1 (en) | 2007-08-30 |
| WO2005044923A1 (en) | 2005-05-19 |
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