ES2548380T3 - 7-Hidroxicumarinas sustituidas con heterociclo reactivas y sus conjugados - Google Patents
7-Hidroxicumarinas sustituidas con heterociclo reactivas y sus conjugados Download PDFInfo
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- ES2548380T3 ES2548380T3 ES10158457.1T ES10158457T ES2548380T3 ES 2548380 T3 ES2548380 T3 ES 2548380T3 ES 10158457 T ES10158457 T ES 10158457T ES 2548380 T3 ES2548380 T3 ES 2548380T3
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- compound
- alkyl
- alkoxy
- amino
- dye
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- 239000003153 chemical reaction reagent Substances 0.000 title claims description 44
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical group C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 title description 32
- 125000000623 heterocyclic group Chemical group 0.000 title description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- -1 azido, amino, hydroxyl Chemical group 0.000 claims abstract description 82
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims abstract description 48
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 47
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 38
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- 150000003573 thiols Chemical class 0.000 claims abstract description 37
- 125000005499 phosphonyl group Chemical group 0.000 claims abstract description 36
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 20
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 18
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 7
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- 150000002463 imidates Chemical class 0.000 claims abstract description 7
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 6
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- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 5
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims abstract description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 4
- DWAOUXYZOSPAOH-UHFFFAOYSA-N 4-[2-(diethylamino)ethoxy]furo[3,2-g]chromen-7-one;hydrochloride Chemical compound [Cl-].O1C(=O)C=CC2=C1C=C1OC=CC1=C2OCC[NH+](CC)CC DWAOUXYZOSPAOH-UHFFFAOYSA-N 0.000 claims abstract description 3
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 125000003636 chemical group Chemical group 0.000 claims description 5
- 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 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
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- CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 description 21
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- 125000000753 cycloalkyl group Chemical group 0.000 description 19
- 125000005647 linker group Chemical group 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- 239000011546 protein dye Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
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- 238000009833 condensation Methods 0.000 description 16
- 230000005494 condensation Effects 0.000 description 16
- 125000000524 functional group Chemical group 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
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- 125000003729 nucleotide group Chemical group 0.000 description 14
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- 239000007787 solid Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
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- 229940125898 compound 5 Drugs 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
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- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 8
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- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- 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
- C07D417/14—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 three 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/13—Tracers or tags
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
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| US9400273B1 (en) | 2009-12-09 | 2016-07-26 | Life Technologies Corporation | 7-hydroxycoumarin-based cell-tracking reagents |
| EP2691383B1 (en) * | 2011-03-30 | 2015-01-21 | 3M Innovative Properties Company | Fluorogenic or fluorophoric compounds and uses thereof |
| KR102022483B1 (ko) * | 2012-03-29 | 2019-09-18 | 스미또모 가가꾸 가부시키가이샤 | 염료용 화합물 |
| ES2628529T3 (es) | 2012-10-24 | 2017-08-03 | Tintes de cianina-azaindolina sustituidos con hidroxamato, y bioconjugados de los mismos | |
| RU2733740C2 (ru) * | 2015-06-29 | 2020-10-06 | Иммуноджен, Инк. | Конъюгаты сконструированных антител с цистеиновыми заменами |
| ITUA20161706A1 (it) * | 2016-03-15 | 2017-09-15 | Cyanagen S R L | Nuovi coloranti cumarinici e relativi coniugati |
| KR102836360B1 (ko) | 2016-04-15 | 2025-07-23 | 베크만 컬터, 인코포레이티드 | 광활성 거대분자 및 그의 용도 |
| JP6821490B2 (ja) * | 2017-04-03 | 2021-01-27 | 日本化薬株式会社 | クマリン化合物又はそれらの塩、並びにこれを含んだ顔料組成物 |
| GB201716931D0 (en) * | 2017-10-16 | 2017-11-29 | Illumina Cambridge Ltd | New fluorescent compounds and their use as biomarkers |
| AU2019425175A1 (en) * | 2019-01-21 | 2021-08-19 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Advanced methods for automated high-performance identification of carbohydrates and carbohydrate mixture composition patterns and systems therefore as well as methods for calibration of multi wavelength fluorescence detection systems therefore, based on new fluorescent dyes |
| CN109721592B (zh) * | 2019-03-04 | 2022-09-30 | 河南理工大学 | 一种含香豆素的氨基吡嗪酰腙衍生物的荧光探针及其制备方法和应用 |
| EP3747957A1 (en) | 2019-06-07 | 2020-12-09 | Universidade de Évora | Fluorescent vinyl tiophene and bitiophene coumarins dyes and method of synthesis thereof |
| WO2021154933A1 (en) * | 2020-01-30 | 2021-08-05 | Aat Bioquest, Inc. | Uv excitable polyfluorene based conjugates and their use in methods of analyte detection |
| US11981964B2 (en) | 2020-07-28 | 2024-05-14 | Illumina Cambridge Limited | Substituted coumarin dyes and uses as fluorescent labels |
| CN112679569B (zh) * | 2020-10-22 | 2022-05-27 | 山西大学 | 一种荧光探针及其制备方法和应用 |
| CN117015711A (zh) | 2021-02-05 | 2023-11-07 | 贝克曼库尔特有限公司 | 用于阻止聚合物染料-抗体缀合物之间的非特异性相互作用的组合物和方法 |
| CN113121513B (zh) * | 2021-04-26 | 2023-05-16 | 安徽大学 | 一种咔唑-香豆素基腙类化合物及其制备方法和用途 |
| JP2024517437A (ja) | 2021-05-04 | 2024-04-22 | ベックマン コールター, インコーポレイテッド | Uv吸収性ポリマー、組成物およびその使用 |
| CN120936679A (zh) | 2023-03-17 | 2025-11-11 | 贝克曼库尔特有限公司 | 苯并噻吩并吡咯花菁染料 |
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| DE3044128A1 (de) | 1980-11-24 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Cumarine, verfahren zu ihrer herstellung und ihre verwendung |
| US4711955A (en) | 1981-04-17 | 1987-12-08 | Yale University | Modified nucleotides and methods of preparing and using same |
| SE8505716D0 (sv) | 1985-12-03 | 1985-12-03 | Biocarb Ab | Novel compounds and conjugates thereof |
| US5047519A (en) | 1986-07-02 | 1991-09-10 | E. I. Du Pont De Nemours And Company | Alkynylamino-nucleotides |
| US5049673A (en) | 1987-10-30 | 1991-09-17 | The Regents Of The University Of California | Fluorescent indicator dyes for calcium working at long wavelengths |
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| NL9001639A (nl) | 1990-07-19 | 1992-02-17 | Amc Amsterdam | Pt-houdende verbinding, werkwijze voor de bereiding ervan, alsmede toepassing van dergelijke verbindingen. |
| US5714327A (en) | 1990-07-19 | 1998-02-03 | Kreatech Diagnostics | Platinum-containing compounds, methods for their preparation and applications thereof |
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| YU187991A (sh) | 1990-12-11 | 1994-09-09 | Hoechst Aktiengesellschaft | 3-(2)-amino-ali tiol-modifikovani, s fluorescentnom bojom vezani nukleozidi, nukleotidi i oligonukleotidi, postupak za njihovo dobijanje i njihova upotreba |
| US5539082A (en) | 1993-04-26 | 1996-07-23 | Nielsen; Peter E. | Peptide nucleic acids |
| US5516911A (en) | 1993-12-30 | 1996-05-14 | The United States Of America As Represented By The Department Of Health And Human Services | Fluorescent intracellular calcium indicators |
| US6150510A (en) | 1995-11-06 | 2000-11-21 | Aventis Pharma Deutschland Gmbh | Modified oligonucleotides, their preparation and their use |
| US5741657A (en) | 1995-03-20 | 1998-04-21 | The Regents Of The University Of California | Fluorogenic substrates for β-lactamase and methods of use |
| US6342379B1 (en) | 1995-06-07 | 2002-01-29 | The Regents Of The University Of California | Detection of transmembrane potentials by optical methods |
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| US5668268A (en) | 1995-11-27 | 1997-09-16 | Hybridon, Inc. | Passivated polymer supports for nucleic acid synthesis |
| US5955604A (en) | 1996-10-15 | 1999-09-21 | The Regents Of The University Of California | Substrates for β-lactamase and uses thereof |
| US5696157A (en) * | 1996-11-15 | 1997-12-09 | Molecular Probes, Inc. | Sulfonated derivatives of 7-aminocoumarin |
| US5830912A (en) * | 1996-11-15 | 1998-11-03 | Molecular Probes, Inc. | Derivatives of 6,8-difluoro-7-hydroxycoumarin |
| US6221612B1 (en) | 1997-08-01 | 2001-04-24 | Aurora Biosciences Corporation | Photon reducing agents for use in fluorescence assays |
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| US6207404B1 (en) | 1999-09-30 | 2001-03-27 | Gentest Corporation | Coumarin-based CYP3A fluorescent assay reagents |
| US7304168B2 (en) | 2003-08-14 | 2007-12-04 | Board Of Regents, University Of Texas System | Photo-caged fluorescent molecules |
| US7674924B2 (en) | 2006-05-22 | 2010-03-09 | Third Wave Technologies, Inc. | Compositions, probes, and conjugates and uses thereof |
| US20100029017A1 (en) | 2008-07-29 | 2010-02-04 | Becton, Dickinson And Company | Mono-chlorinated hydroxycoumarin conjugates |
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- 2010-03-30 ES ES10158457.1T patent/ES2548380T3/es active Active
- 2010-03-31 SG SG201002257-2A patent/SG165300A1/en unknown
- 2010-04-01 JP JP2010085260A patent/JP5697886B2/ja active Active
- 2010-04-01 CN CN201010228953.5A patent/CN101914093B/zh active Active
Also Published As
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| CN101914093A (zh) | 2010-12-15 |
| CN101914093B (zh) | 2015-08-26 |
| JP2010254993A (ja) | 2010-11-11 |
| EP2236508A1 (en) | 2010-10-06 |
| SG165300A1 (en) | 2010-10-28 |
| EP2236508B1 (en) | 2015-08-26 |
| JP5697886B2 (ja) | 2015-04-08 |
| US20100255504A1 (en) | 2010-10-07 |
| US8431416B2 (en) | 2013-04-30 |
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