JP5416970B2 - ニコチン酸及びピコリン酸誘導近赤外線蛍光団 - Google Patents
ニコチン酸及びピコリン酸誘導近赤外線蛍光団 Download PDFInfo
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
- A61K49/0032—Methine dyes, e.g. cyanine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Pyridine Compounds (AREA)
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| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2003207438A1 (en) | 2002-01-02 | 2003-07-24 | Visen Medical, Inc. | Amine functionalized superparamagnetic nanoparticles for the synthesis of bioconjugates and uses therefor |
| US8227621B2 (en) | 2005-06-30 | 2012-07-24 | Li-Cor, Inc. | Cyanine dyes and methods of use |
| WO2007028118A2 (en) | 2005-09-02 | 2007-03-08 | Visen Medical, Inc. | Nicotinic acid and picolinic acid derived near-infrared fluorophores |
| ES2612738T3 (es) * | 2005-09-02 | 2017-05-18 | Visen Medical, Inc. | Agentes de formación de imágenes fluorescentes biocompatibles |
| DK1934211T3 (en) | 2005-09-02 | 2017-04-10 | Visen Medical Inc | Biocompatible N, N-disubstituted sulfonamide-containing fluorescent color markers |
| US9913917B2 (en) | 2005-12-22 | 2018-03-13 | Visen Medical, Inc. | Biocompatible fluorescent metal oxide nanoparticles |
| JP5643514B2 (ja) | 2007-02-09 | 2014-12-17 | ビセン メディカル, インコーポレイテッド | ポリシクロ染料およびその使用 |
| WO2008109832A2 (en) * | 2007-03-08 | 2008-09-12 | Visen Medical, Inc. | Viable near-infrared fluorochrome labeled cells and methods of making and using same |
| EP2732826B1 (en) * | 2008-01-18 | 2017-11-08 | Visen Medical, Inc. | Fluorescent imaging agents |
| CN102281904A (zh) * | 2008-11-20 | 2011-12-14 | 通用电气医疗集团股份有限公司 | 染料缀合物成像剂 |
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| WO2010121163A2 (en) * | 2009-04-17 | 2010-10-21 | Li-Cor, Inc. | Fluorescent imaging with substituted cyanine dyes |
| JP2011046663A (ja) * | 2009-08-28 | 2011-03-10 | Fujifilm Corp | 近赤外蛍光造影剤 |
| JP2011046662A (ja) * | 2009-08-28 | 2011-03-10 | Fujifilm Corp | 近赤外蛍光造影剤 |
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| US9610367B2 (en) * | 2010-08-24 | 2017-04-04 | Canon Kabushiki Kaisha | Particle and contrast agent having the particle |
| WO2012027623A2 (en) | 2010-08-25 | 2012-03-01 | Pacific Biosciences Of California, Inc. | Cyanine dyes |
| EP2630196B1 (en) | 2010-10-20 | 2017-09-06 | Li-Cor, Inc. | Cyanine dyes and their conjugates |
| EP2707102B1 (en) | 2011-05-09 | 2019-11-13 | Visen Medical, Inc. | Carbonic anhydrase targeting agents and methods of using same |
| CZ304094B6 (cs) * | 2011-12-01 | 2013-10-16 | Vysoká skola chemicko-technologická v Praze | Vyuzití polymethiniových solí jako mitochondriálních sond |
| WO2013148319A1 (en) | 2012-03-30 | 2013-10-03 | Visen Medical, Inc. | Bacterial imaging agents and methods of using same |
| US9315864B2 (en) | 2012-05-18 | 2016-04-19 | Pacific Biosciences Of California, Inc. | Heteroarylcyanine dyes with sulfonic acid substituents |
| US10458915B2 (en) | 2012-05-18 | 2019-10-29 | Pacific Biosciences Of California, Inc. | Heteroarylcyanine dyes |
| CA2882019C (en) | 2012-08-15 | 2021-02-09 | Visen Medical, Inc. | Prostate specific antigen agents and methods of using same for prostate cancer imaging |
| AU2014228504C1 (en) | 2013-03-15 | 2019-10-03 | Visen Medical, Inc. | Substituted silaxanthenium red to near-infrared fluorochromes for in vitro and in vivo imaging and detection |
| CN105339436B (zh) * | 2013-03-15 | 2018-05-25 | 文森医学公司 | 4,4-二取代环己基桥连七甲川花菁染料及其应用 |
| WO2015066296A1 (en) | 2013-10-31 | 2015-05-07 | Beth Israel Deaconess Medical Center | Near-infrared fluorescent nerve contrast agents and methods of use thereof |
| EP4147724A1 (en) * | 2013-10-31 | 2023-03-15 | Beth Israel Deaconess Medical Center | Near-infrared fluorescent contrast bioimaging agents and methods of use thereof |
| CZ306320B6 (cs) * | 2014-04-01 | 2016-11-30 | Vysoká škola chemicko - technologická v Praze | Využití nových typů pentamethiniových solí s expandovanou chinoxalinovou jednotkou v protinádorové terapii |
| GB2567124A (en) * | 2017-05-08 | 2019-04-10 | Vysoka Akola Chemicko Tech V Praze | Imaging agents and methods |
| JP7032969B2 (ja) * | 2018-03-28 | 2022-03-09 | 日本化薬株式会社 | シアニン化合物 |
| US20250082795A1 (en) | 2023-09-12 | 2025-03-13 | Curadel Surgical Innovations, Inc. | Combinations of imaging agent conjugates and application thereof |
Family Cites Families (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3864644A (en) | 1971-03-22 | 1975-02-04 | Eastman Kodak Co | Dye lasers including rigidized carbocyanine dyes |
| DE2121014A1 (de) * | 1971-04-29 | 1972-11-02 | Agfa-Gevaert Ag, 5090 Leverkusen | Sensibilisierte elektrophotographische Schichten |
| US4011086A (en) | 1975-10-14 | 1977-03-08 | Eastman Kodak Company | Photographic emulsions and elements containing rigidized carbocyanine dyes |
| JPS6025781B2 (ja) * | 1977-03-11 | 1985-06-20 | 富士ゼロックス株式会社 | 電子写真用感光材料 |
| US4370401A (en) * | 1979-12-07 | 1983-01-25 | Minnesota Mining And Manufacturing Company | Light sensitive, thermally developable imaging system |
| US6086737A (en) | 1984-03-29 | 2000-07-11 | Li-Cor, Inc. | Sequencing near infrared and infrared fluorescence labeled DNA for detecting using laser diodes and suitable labels therefor |
| US5366603A (en) | 1984-03-29 | 1994-11-22 | Li-Cor, Inc. | Sequencing near infrared and infrared fluorescence labeled DNA for detecting useing laser diodes |
| US5627027A (en) | 1986-04-18 | 1997-05-06 | 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 |
| 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 |
| US5569587A (en) | 1986-04-18 | 1996-10-29 | Carnegie Mellon University | Method for labeling and detecting materials employing luminescent arysulfonate cyanine dyes |
| DE3912046B4 (de) * | 1988-09-02 | 2004-03-25 | Carnegie Mellon University | Verfahren zum Markieren einer Komponente einer wäßrigen Flüssigkeit und lumineszenzphotostabiles Reaktionsprodukt |
| US5073171A (en) | 1989-01-12 | 1991-12-17 | Eaton John W | Biocompatible materials comprising albumin-binding dyes |
| US4981977A (en) | 1989-06-09 | 1991-01-01 | Carnegie-Mellon University | Intermediate for and fluorescent cyanine dyes containing carboxylic acid groups |
| JP2824917B2 (ja) * | 1989-08-30 | 1998-11-18 | 株式会社林原生物化学研究所 | 抗腫瘍剤 |
| US5831098A (en) | 1992-03-16 | 1998-11-03 | Minnesota Mining And Manufacturing Company | 2-methyl-4,4a-dihydro-3H-carbazolium salts and dyes derived therefrom |
| JPH08501097A (ja) | 1992-09-04 | 1996-02-06 | ザ ゼネラル ホスピタル コーポレーション | 臨床診断及び治療用部分を含む生体適合性ポリマー |
| US5808044A (en) | 1993-01-22 | 1998-09-15 | Pharmacia Biotech Inc. | Indocarbocyanine and benzindocarbocyanine phosphoramidites |
| US5453505A (en) | 1994-06-30 | 1995-09-26 | Biometric Imaging, Inc. | N-heteroaromatic ion and iminium ion substituted cyanine dyes for use as fluorescence labels |
| US5605809A (en) | 1994-10-28 | 1997-02-25 | Oncoimmunin, Inc. | Compositions for the detection of proteases in biological samples and methods of use thereof |
| DE4445065A1 (de) | 1994-12-07 | 1996-06-13 | Diagnostikforschung Inst | Verfahren zur In-vivo-Diagnostik mittels NIR-Strahlung |
| US6127134A (en) | 1995-04-20 | 2000-10-03 | Carnegie Mellon University | Difference gel electrophoresis using matched multiple dyes |
| US6008373A (en) | 1995-06-07 | 1999-12-28 | Carnegie Mellon University | Fluorescent labeling complexes with large stokes shift formed by coupling together cyanine and other fluorochromes capable of resonance energy transfer |
| IT1276833B1 (it) | 1995-10-09 | 1997-11-03 | Sorin Biomedica Cardio Spa | Coloranti fluorescenti della famiglia della solfo benz e indocianina |
| US6004536A (en) | 1995-11-14 | 1999-12-21 | Molecular Probes, Inc. | Lipophilic cyanine dyes with enchanced aqueous solubilty |
| DE69706417T2 (de) | 1996-04-19 | 2002-06-27 | Amersham Pharmacia Biotech Uk Ltd., Little Chalfont | Quadratfarbstoffe und deren verwendung in einem fluorescenzsequenzierungsverfahren |
| JPH1071766A (ja) * | 1996-06-25 | 1998-03-17 | Fuji Photo Film Co Ltd | 情報記録媒体及び色素化合物 |
| JP3840301B2 (ja) * | 1996-07-18 | 2006-11-01 | 富士写真フイルム株式会社 | 情報記録媒体 |
| US6027709A (en) | 1997-01-10 | 2000-02-22 | Li-Cor Inc. | Fluorescent cyanine dyes |
| DE19717904A1 (de) | 1997-04-23 | 1998-10-29 | Diagnostikforschung Inst | Säurelabile und enzymatisch spaltbare Farbstoffkonstrukte zur Diagnostik mit Nahinfrarotlicht und zur Therapie |
| US5877310A (en) | 1997-04-25 | 1999-03-02 | Carnegie Mellon University | Glycoconjugated fluorescent labeling reagents |
| WO1999031181A1 (en) | 1997-12-17 | 1999-06-24 | Carnegie Mellon University | Rigidized trimethine cyanine dyes |
| US6133445A (en) | 1997-12-17 | 2000-10-17 | Carnegie Mellon University | Rigidized trimethine cyanine dyes |
| AU3386399A (en) | 1998-04-08 | 1999-10-25 | Ewald A. Terpetschnig | Luminescent compounds |
| US6002003A (en) | 1998-04-14 | 1999-12-14 | Beckman Instruments, Inc. | Cyanine dye activating group with improved coupling selectivity |
| US6083486A (en) | 1998-05-14 | 2000-07-04 | The General Hospital Corporation | Intramolecularly-quenched near infrared fluorescent probes |
| US6592847B1 (en) | 1998-05-14 | 2003-07-15 | The General Hospital Corporation | Intramolecularly-quenched near infrared flourescent probes |
| EP1100520B1 (en) | 1998-07-21 | 2004-09-22 | Cytovia, Inc. | Novel fluorescence dyes and their applications for whole cell fluorescence screening assays for caspases, peptidases, proteases and other enzymes and the use thereof |
| JP2000095758A (ja) | 1998-09-18 | 2000-04-04 | Schering Ag | 近赤外蛍光造影剤および蛍光造影方法 |
| ATE284433T1 (de) | 1999-07-02 | 2004-12-15 | Visen Medical Inc | Fluorescierende cyaninlabels mit einem sulphamidobrückenglied |
| ATE296828T1 (de) | 1999-09-20 | 2005-06-15 | Fuji Photo Film Co Ltd | Verbindungen zur floureszenz-kennzeichnung |
| JP2001323179A (ja) | 1999-10-06 | 2001-11-20 | Hayashibara Biochem Lab Inc | シアニン色素 |
| WO2002038190A2 (en) | 2000-10-27 | 2002-05-16 | Beth Israel Deaconess Medical Center | Non-isotopic detection of osteoblastic activity in vivo using modified bisphosphonates |
| US6615063B1 (en) | 2000-11-27 | 2003-09-02 | The General Hospital Corporation | Fluorescence-mediated molecular tomography |
| EP1209205A1 (en) | 2000-11-28 | 2002-05-29 | Innosense S.r.l. | Improved process and method for the preparation of asymetric monofunctionalised indocyanine labelling reagents and obtained compounds |
| EP1221465A1 (en) | 2001-01-03 | 2002-07-10 | Innosense S.r.l. | Symmetric, monofunctionalised polymethine dyes labelling reagents |
| US20030044353A1 (en) | 2001-01-05 | 2003-03-06 | Ralph Weissleder | Activatable imaging probes |
| AU2003207438A1 (en) | 2002-01-02 | 2003-07-24 | Visen Medical, Inc. | Amine functionalized superparamagnetic nanoparticles for the synthesis of bioconjugates and uses therefor |
| WO2003061711A2 (en) | 2002-01-16 | 2003-07-31 | Visen Medical, Inc. | Chromophore probes for optical imaging |
| AU2003225763A1 (en) | 2002-03-11 | 2003-09-29 | Visen Medical, Inc. | Optical imaging probes |
| EP2410315B1 (en) | 2002-06-04 | 2020-04-01 | Visen Medical, Inc. | Imaging volumes with arbitrary geometries in contact and non-contact tomography |
| EP1593095B1 (en) | 2003-02-05 | 2019-04-17 | The General Hospital Corporation | Method and system for free space optical tomography of diffuse media |
| WO2004108902A2 (en) | 2003-06-04 | 2004-12-16 | Visen Medical, Inc. | Biocompatible fluorescent silicon nanoparticles |
| EP1720945B1 (en) * | 2003-12-05 | 2016-03-16 | Life Technologies Corporation | Methine-substituted cyanine dye compounds |
| US20060099712A1 (en) | 2004-11-08 | 2006-05-11 | Eastman Kodak Company | Correlation of anti-cancer activity of dyes with redox potentials |
| EP1824379B1 (en) | 2004-12-08 | 2017-04-12 | The General Hospital Corporation | System and method for normalized fluorescence or bioluminescence imaging |
| US20060239916A1 (en) | 2005-01-07 | 2006-10-26 | Kai Licha | Use of cyanine dyes for the diagnosis of proliferative diseases |
| ES2612738T3 (es) | 2005-09-02 | 2017-05-18 | Visen Medical, Inc. | Agentes de formación de imágenes fluorescentes biocompatibles |
| DK1934211T3 (en) | 2005-09-02 | 2017-04-10 | Visen Medical Inc | Biocompatible N, N-disubstituted sulfonamide-containing fluorescent color markers |
| WO2007028118A2 (en) | 2005-09-02 | 2007-03-08 | Visen Medical, Inc. | Nicotinic acid and picolinic acid derived near-infrared fluorophores |
| JP6059414B2 (ja) | 2005-09-13 | 2017-01-11 | コーニンクレッカ フィリップス エヌ ヴェKoninklijke Philips N.V. | イメージングに対する多重造影剤注入 |
| US9913917B2 (en) | 2005-12-22 | 2018-03-13 | Visen Medical, Inc. | Biocompatible fluorescent metal oxide nanoparticles |
| WO2007109364A2 (en) | 2006-03-20 | 2007-09-27 | The General Hospital Corporation | Intramolecularly quenched fluorochrome conjugates and methods of use |
| JP5643514B2 (ja) | 2007-02-09 | 2014-12-17 | ビセン メディカル, インコーポレイテッド | ポリシクロ染料およびその使用 |
| WO2008109832A2 (en) | 2007-03-08 | 2008-09-12 | Visen Medical, Inc. | Viable near-infrared fluorochrome labeled cells and methods of making and using same |
| US8314406B2 (en) | 2007-04-06 | 2012-11-20 | The General Hospital Corporation | Systems and methods for optical imaging using early arriving photons |
| EP2732826B1 (en) | 2008-01-18 | 2017-11-08 | Visen Medical, Inc. | Fluorescent imaging agents |
| CA2715034C (en) | 2008-03-14 | 2016-12-06 | Visen Medical, Inc. | Integrin targeting agents and in-vivo and in-vitro imaging methods using the same |
| US8864821B2 (en) | 2008-11-26 | 2014-10-21 | Visen Medical, Inc. | Methods and compositions for identifying subjects at risk of developing stent thrombosis |
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| WO2007028118A2 (en) | 2007-03-08 |
| WO2007028118A3 (en) | 2007-04-26 |
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| US20130272967A1 (en) | 2013-10-17 |
| EP1934202B1 (en) | 2019-01-09 |
| US8455651B2 (en) | 2013-06-04 |
| US20120321562A1 (en) | 2012-12-20 |
| US20080267883A1 (en) | 2008-10-30 |
| JP2009507035A (ja) | 2009-02-19 |
| US8771646B2 (en) | 2014-07-08 |
| JP2013014625A (ja) | 2013-01-24 |
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