ATE522580T1 - Cyaninfarbstoffe als markieragenzien - Google Patents
Cyaninfarbstoffe als markieragenzienInfo
- Publication number
- ATE522580T1 ATE522580T1 AT04791610T AT04791610T ATE522580T1 AT E522580 T1 ATE522580 T1 AT E522580T1 AT 04791610 T AT04791610 T AT 04791610T AT 04791610 T AT04791610 T AT 04791610T AT E522580 T1 ATE522580 T1 AT E522580T1
- Authority
- AT
- Austria
- Prior art keywords
- groups
- dye
- attached
- group
- ring
- Prior art date
Links
- 239000000975 dye Substances 0.000 title abstract 7
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title abstract 2
- 239000003550 marker Substances 0.000 title 1
- 108091034117 Oligonucleotide Proteins 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000001215 fluorescent labelling Methods 0.000 abstract 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical group C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 238000002372 labelling Methods 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 108020004707 nucleic acids Proteins 0.000 abstract 1
- 102000039446 nucleic acids Human genes 0.000 abstract 1
- 150000007523 nucleic acids Chemical class 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 238000010791 quenching Methods 0.000 abstract 1
- 230000000171 quenching effect Effects 0.000 abstract 1
- 125000006850 spacer group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51642803P | 2003-10-31 | 2003-10-31 | |
| PCT/GB2004/004573 WO2005044923A1 (en) | 2003-10-31 | 2004-10-29 | Cyanine dye labelling reagents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE522580T1 true ATE522580T1 (de) | 2011-09-15 |
Family
ID=34572883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT04791610T ATE522580T1 (de) | 2003-10-31 | 2004-10-29 | Cyaninfarbstoffe als markieragenzien |
Country Status (7)
| Country | Link |
|---|---|
| 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=) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US9631096B2 (en) * | 2012-01-20 | 2017-04-25 | Cornell University | Dye compositions, methods of preparation, conjugates thereof, and methods of use |
| CN102608051B (zh) * | 2012-02-21 | 2015-04-08 | 中国科学院化学研究所 | 用于诊断白血病的试剂盒 |
| US9751868B2 (en) | 2012-02-28 | 2017-09-05 | Pierce Biotechnology, Inc. | Benzocyanine compounds |
| WO2013130761A1 (en) | 2012-03-02 | 2013-09-06 | Pierce Biotechnology, Inc. | Indole derivatives as labeling dye for biomolecule |
| US9676787B2 (en) | 2012-08-28 | 2017-06-13 | Pierce Biotechnology, Inc. | Benzopyrylium compounds |
| US8809551B1 (en) | 2013-03-08 | 2014-08-19 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US11813338B2 (en) * | 2013-03-12 | 2023-11-14 | The Trustees Of The University Of Pennsylvania | Diagnosing and treating cancer |
| GB201408077D0 (en) | 2014-05-07 | 2014-06-18 | Illumina Cambridge Ltd | Polymethine compounds and their use as fluorescent labels |
| 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 |
| KR101953819B1 (ko) * | 2017-12-22 | 2019-03-06 | (주)바이오액츠 | 생체 분자 표지를 위한 신규 시아닌 화합물 및 그 제조방법 |
| CN108752406A (zh) * | 2018-05-29 | 2018-11-06 | 苏州百源基因技术有限公司 | 一种荧光标记的核苷酸及其制备方法和用途 |
| JP7359869B2 (ja) * | 2019-12-19 | 2023-10-11 | 富士フイルム株式会社 | 化合物及びこれを用いた蛍光標識生体物質 |
| CA3167456A1 (en) * | 2020-02-10 | 2021-08-19 | C-Biomex Co., Ltd. | Amphoteric fluorescent substance capable of being attached to biomaterials |
| US11964965B2 (en) | 2020-05-08 | 2024-04-23 | On Target Laboratories, LLC | Methods of manufacture and synthesis of fluorescent dye compounds and uses thereof |
| EP4150009A1 (en) * | 2020-05-12 | 2023-03-22 | Université de Strasbourg | Fluorogenic dimer compound, useful as a probe for detection of endogenous receptors |
Family Cites Families (10)
| 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 |
-
2004
- 2004-10-29 CN CN200480032219A patent/CN100577742C/zh not_active Expired - Fee Related
- 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
- 2004-10-29 WO PCT/GB2004/004573 patent/WO2005044923A1/en not_active Ceased
- 2004-10-29 AT AT04791610T patent/ATE522580T1/de not_active IP Right Cessation
-
2010
- 2010-07-01 US US12/828,391 patent/US8148539B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007510031A (ja) | 2007-04-19 |
| US7750163B2 (en) | 2010-07-06 |
| EP2360211A1 (en) | 2011-08-24 |
| ES2372395T3 (es) | 2012-01-19 |
| US20100267937A1 (en) | 2010-10-21 |
| EP1678258A1 (en) | 2006-07-12 |
| CN1875073A (zh) | 2006-12-06 |
| JP4943156B2 (ja) | 2012-05-30 |
| US8148539B2 (en) | 2012-04-03 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |