JP2003500367A - 生物医学的適用のための新規なシアニンおよびインドシアニン染料バイオコンジュゲート - Google Patents
生物医学的適用のための新規なシアニンおよびインドシアニン染料バイオコンジュゲートInfo
- Publication number
- JP2003500367A JP2003500367A JP2000619463A JP2000619463A JP2003500367A JP 2003500367 A JP2003500367 A JP 2003500367A JP 2000619463 A JP2000619463 A JP 2000619463A JP 2000619463 A JP2000619463 A JP 2000619463A JP 2003500367 A JP2003500367 A JP 2003500367A
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- och
- conh
- nhco
- vary
- peptide
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- Pending
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0028—Disruption, e.g. by heat or ultrasounds, sonophysical or sonochemical activation, e.g. thermosensitive or heat-sensitive liposomes, disruption of calculi with a medicinal preparation and ultrasounds
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13506099P | 1999-05-20 | 1999-05-20 | |
| US60/135,060 | 1999-05-20 | ||
| US09/325,769 | 1999-06-04 | ||
| US09/325,769 US6217848B1 (en) | 1999-05-20 | 1999-06-04 | Cyanine and indocyanine dye bioconjugates for biomedical applications |
| PCT/US2000/011060 WO2000071162A2 (en) | 1999-05-20 | 2000-04-26 | Cyanine and indocyanine dye bioconjugates for biomedical applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003500367A true JP2003500367A (ja) | 2003-01-07 |
| JP2003500367A5 JP2003500367A5 (enExample) | 2010-09-24 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2000619463A Pending JP2003500367A (ja) | 1999-05-20 | 2000-04-26 | 生物医学的適用のための新規なシアニンおよびインドシアニン染料バイオコンジュゲート |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6217848B1 (enExample) |
| EP (2) | EP2058007A3 (enExample) |
| JP (1) | JP2003500367A (enExample) |
| AT (1) | ATE435662T1 (enExample) |
| AU (1) | AU4488800A (enExample) |
| CA (1) | CA2373475C (enExample) |
| DE (1) | DE60042522D1 (enExample) |
| DK (1) | DK1178830T3 (enExample) |
| ES (1) | ES2329542T3 (enExample) |
| PT (1) | PT1178830E (enExample) |
| WO (1) | WO2000071162A2 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005524090A (ja) * | 2002-04-29 | 2005-08-11 | アマシャム・バイオサイエンス・コーポレイション | 生物学的試料のための光線画像分析 |
| WO2011043061A1 (ja) | 2009-10-05 | 2011-04-14 | キヤノン株式会社 | 光音響イメージング用造影剤、及び、それを用いた光音響イメージング方法 |
| WO2013035750A1 (ja) * | 2011-09-05 | 2013-03-14 | Maeda Hiroshi | 高分子型蛍光分子プローブ |
| KR101440109B1 (ko) | 2013-01-29 | 2014-09-12 | 부경대학교 산학협력단 | 위장관암의 림프절 전이 검출용 광음향 단층촬영 시스템 |
| JP2016506420A (ja) * | 2012-10-24 | 2016-03-03 | ベクトン・ディキンソン・アンド・カンパニーＢｅｃｔｏｎ， Ｄｉｃｋｉｎｓｏｎ Ａｎｄ Ｃｏｍｐａｎｙ | ヒドロキサメート置換アザインドリン−シアニン染料およびそのバイオ複合体 |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7175953B2 (en) * | 1999-04-09 | 2007-02-13 | Institute Fuer Diagnostik Forschung | Short-warp peptide-dye conjugate as contrast agent for optical diagnostic |
| US6630570B1 (en) * | 1999-04-09 | 2003-10-07 | Insitut für Diagnostikforschung GmbH | Short-chain peptide-dye conjugates as contrast media for optical diagnosis |
| US20050182434A1 (en) * | 2000-08-11 | 2005-08-18 | National Research Council Of Canada | Method and apparatus for performing intra-operative angiography |
| US6180085B1 (en) * | 2000-01-18 | 2001-01-30 | Mallinckrodt Inc. | Dyes |
| US6190641B1 (en) * | 2000-01-18 | 2001-02-20 | Mallinckrodt Inc. | Indocyanine dyes |
| US7230088B2 (en) * | 2001-07-03 | 2007-06-12 | Mallinckrodt, Inc. | Compounds for dual photodiagnosis and therapy |
| US7790144B2 (en) * | 2000-01-18 | 2010-09-07 | Mallinckrodt Inc. | Receptor-avid exogenous optical contrast and therapeutic agents |
| US7351807B2 (en) * | 2000-01-18 | 2008-04-01 | Mallinckrodt Inc. | Cyanine-sulfenates for dual phototherapy |
| US20030017164A1 (en) * | 2001-07-03 | 2003-01-23 | Mallinckrodt Inc. | Dye-azide compounds for dual phototherapy |
| US6673334B1 (en) * | 2000-10-16 | 2004-01-06 | Mallinkcrodt, Inc. | Light sensitive compounds for instant determination of organ function |
| US7556797B2 (en) * | 2000-10-16 | 2009-07-07 | Mallinckrodt Inc. | Minimally invasive physiological function monitoring agents |
| US6838074B2 (en) | 2001-08-08 | 2005-01-04 | Bristol-Myers Squibb Company | Simultaneous imaging of cardiac perfusion and a vitronectin receptor targeted imaging agent |
| US20030105300A1 (en) * | 2001-10-17 | 2003-06-05 | Mallinckrodt Inc. | Tumor targeted photodiagnostic-phototherapeutic agents |
| IL148921A0 (en) * | 2002-03-26 | 2002-09-12 | Peptor Ltd | Photo active backbone cyclized somatostatin analogs for optical imaging and photodynamic therapy |
| US20040022731A1 (en) * | 2002-04-26 | 2004-02-05 | Alexei Bogdanov | In vivo imaging of apoptosis |
| US7580185B2 (en) | 2002-08-28 | 2009-08-25 | Carl Zeiss Surgical Gmbh | Microscopy system, microscopy method and a method of treating an aneurysm |
| US7303741B2 (en) * | 2002-09-23 | 2007-12-04 | General Electric Company | Systems and methods for high-resolution in vivo imaging of biochemical activity in a living organism |
| US7226577B2 (en) | 2003-01-13 | 2007-06-05 | Bracco Imaging, S. P. A. | Gastrin releasing peptide compounds |
| DE10302787A1 (de) * | 2003-01-24 | 2004-08-12 | Schering Ag | Hydrophile, Thiol-reaktive Cyaninfarbstoffe und deren Konjugate mit Biomolekülen für die Fluoreszenzdiagnostik |
| WO2004080483A1 (en) * | 2003-03-10 | 2004-09-23 | Mpa Technologies, Inc. | Targeted agents for both photodiagnosis and photodynamic therapy |
| WO2005000218A2 (en) * | 2003-05-31 | 2005-01-06 | Washington University | Macrocyclic cyanine and indocyanine bioconjugates provide improved biomedical applications |
| NO20035681D0 (no) * | 2003-12-18 | 2003-12-18 | Amersham Health As | Optisk avbildning av lungekreft |
| NO20035682D0 (no) * | 2003-12-18 | 2003-12-18 | Amersham Health As | Optisk avbildning av ösofagkreft og Barretts ösofag |
| NO20035683D0 (no) * | 2003-12-18 | 2003-12-18 | Amersham Health As | Optisk avbildning av prostatakreft |
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| US20080161744A1 (en) | 2006-09-07 | 2008-07-03 | University Of Rochester Medical Center | Pre-And Intra-Operative Localization of Penile Sentinel Nodes |
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| EP2100621A1 (en) | 2008-03-10 | 2009-09-16 | mivenion GmbH | Polyether polyol dendron conjugates with effector molecules for biological targeting |
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| WO2012054749A1 (en) | 2010-10-20 | 2012-04-26 | Li-Cor, Inc. | Cyanine dyes and their conjugates |
| WO2012123916A2 (en) | 2011-03-15 | 2012-09-20 | Ramot At Tel-Aviv University Ltd. | Activatable fluorogenic compounds and uses thereof as near infrared probes |
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| EP2863801B8 (en) | 2012-06-21 | 2024-06-12 | Stryker Corporation | Quantification and analysis of angiography and perfusion |
| AU2015327665B2 (en) | 2014-09-29 | 2018-09-27 | Stryker European Operations Limited | Imaging a target fluorophore in a biological material in the presence of autofluorescence |
| AU2014408488B2 (en) | 2014-10-09 | 2019-07-18 | Stryker European Operations Limited | Quantification of absolute blood flow in tissue using fluorescence-mediated photoplethysmography |
| US10806804B2 (en) * | 2015-05-06 | 2020-10-20 | Washington University | Compounds having RD targeting motifs and methods of use thereof |
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| WO2023227601A1 (en) | 2022-05-23 | 2023-11-30 | Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Near-infrared fluorescent heptamethine dye conjugates with favorable bleaching properties |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5745457A (en) * | 1980-09-02 | 1982-03-15 | Fuji Photo Film Co Ltd | Microimmunological measuring method |
| JPH05333026A (ja) * | 1992-05-29 | 1993-12-17 | Ibiden Co Ltd | 免疫測定用標識試薬 |
| JPH06118081A (ja) * | 1992-10-06 | 1994-04-28 | Ibiden Co Ltd | 蛍光標識試薬および蛍光免疫測定法 |
| WO1997026920A2 (de) * | 1996-01-23 | 1997-07-31 | Deutsches Krebsforschungszentrum | Konjugat zur unterscheidung von krankhaftem und gesundem gewebe |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE4445065A1 (de) * | 1994-12-07 | 1996-06-13 | Diagnostikforschung Inst | Verfahren zur In-vivo-Diagnostik mittels NIR-Strahlung |
| US5962424A (en) * | 1995-02-21 | 1999-10-05 | Arch Development Corporation | Methods and compositions for targeting selectins |
| WO1997033620A2 (de) * | 1996-03-15 | 1997-09-18 | Pulsion Verw. Gmbh & Co. Medical Systems Kg | Verbindungen zur behandlung von tumoren |
| DE19649971A1 (de) * | 1996-11-19 | 1998-05-28 | Diagnostikforschung Inst | Optische Diagnostika zur Diagnostik neurodegenerativer Krankheiten mittels Nahinfrarot-Strahlung (NIR-Strahlung) |
| WO1998048846A1 (en) | 1997-04-29 | 1998-11-05 | Nycomed Imaging As | Light imaging contrast agents |
| ES2213899T3 (es) | 1997-04-29 | 2004-09-01 | Amersham Health As | Agentes de contraste utilizados en tecnicas de formacion de imagen en base a la luz. |
| WO1999051284A2 (en) * | 1998-04-03 | 1999-10-14 | Mallinckrodt Inc. | Non-covalent bioconjugates useful for diagnosis and therapy |
| EP1131099A2 (en) * | 1999-01-15 | 2001-09-12 | Light Sciences Corporation | Noninvasive vascular therapy |
| US6602274B1 (en) * | 1999-01-15 | 2003-08-05 | Light Sciences Corporation | Targeted transcutaneous cancer therapy |
| WO2000041725A2 (en) * | 1999-01-15 | 2000-07-20 | Light Sciences Corporation | Therapeutic compositions for metabolic bone disorders or bone metastases |
-
1999
- 1999-06-04 US US09/325,769 patent/US6217848B1/en not_active Expired - Fee Related
-
2000
- 2000-04-26 DK DK00926343T patent/DK1178830T3/da active
- 2000-04-26 CA CA2373475A patent/CA2373475C/en not_active Expired - Lifetime
- 2000-04-26 AT AT00926343T patent/ATE435662T1/de not_active IP Right Cessation
- 2000-04-26 PT PT00926343T patent/PT1178830E/pt unknown
- 2000-04-26 WO PCT/US2000/011060 patent/WO2000071162A2/en not_active Ceased
- 2000-04-26 AU AU44888/00A patent/AU4488800A/en not_active Abandoned
- 2000-04-26 ES ES00926343T patent/ES2329542T3/es not_active Expired - Lifetime
- 2000-04-26 JP JP2000619463A patent/JP2003500367A/ja active Pending
- 2000-04-26 EP EP08075854A patent/EP2058007A3/en not_active Withdrawn
- 2000-04-26 EP EP00926343A patent/EP1178830B1/en not_active Expired - Lifetime
- 2000-04-26 DE DE60042522T patent/DE60042522D1/de not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5745457A (en) * | 1980-09-02 | 1982-03-15 | Fuji Photo Film Co Ltd | Microimmunological measuring method |
| JPH05333026A (ja) * | 1992-05-29 | 1993-12-17 | Ibiden Co Ltd | 免疫測定用標識試薬 |
| JPH06118081A (ja) * | 1992-10-06 | 1994-04-28 | Ibiden Co Ltd | 蛍光標識試薬および蛍光免疫測定法 |
| WO1997026920A2 (de) * | 1996-01-23 | 1997-07-31 | Deutsches Krebsforschungszentrum | Konjugat zur unterscheidung von krankhaftem und gesundem gewebe |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005524090A (ja) * | 2002-04-29 | 2005-08-11 | アマシャム・バイオサイエンス・コーポレイション | 生物学的試料のための光線画像分析 |
| WO2011043061A1 (ja) | 2009-10-05 | 2011-04-14 | キヤノン株式会社 | 光音響イメージング用造影剤、及び、それを用いた光音響イメージング方法 |
| WO2013035750A1 (ja) * | 2011-09-05 | 2013-03-14 | Maeda Hiroshi | 高分子型蛍光分子プローブ |
| JPWO2013035750A1 (ja) * | 2011-09-05 | 2015-03-23 | 前田 浩 | 高分子型蛍光分子プローブ |
| JP2016128487A (ja) * | 2011-09-05 | 2016-07-14 | 一般財団法人バイオダイナミックス研究所 | 高分子型蛍光分子プローブ |
| US9636426B2 (en) | 2011-09-05 | 2017-05-02 | Hiroshi Maeda | Polymer-type fluorescent molecule probe |
| US10946109B2 (en) | 2011-09-05 | 2021-03-16 | Hiroshi Maeda | Polymer-type fluorescent molecule probe |
| JP2016506420A (ja) * | 2012-10-24 | 2016-03-03 | ベクトン・ディキンソン・アンド・カンパニーＢｅｃｔｏｎ， Ｄｉｃｋｉｎｓｏｎ Ａｎｄ Ｃｏｍｐａｎｙ | ヒドロキサメート置換アザインドリン−シアニン染料およびそのバイオ複合体 |
| KR101440109B1 (ko) | 2013-01-29 | 2014-09-12 | 부경대학교 산학협력단 | 위장관암의 림프절 전이 검출용 광음향 단층촬영 시스템 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1178830A2 (en) | 2002-02-13 |
| CA2373475A1 (en) | 2000-11-30 |
| DE60042522D1 (de) | 2009-08-20 |
| PT1178830E (pt) | 2009-09-02 |
| AU4488800A (en) | 2000-12-12 |
| ES2329542T3 (es) | 2009-11-27 |
| EP1178830B1 (en) | 2009-07-08 |
| EP2058007A3 (en) | 2009-05-27 |
| US6217848B1 (en) | 2001-04-17 |
| DK1178830T3 (da) | 2009-10-12 |
| WO2000071162A3 (en) | 2001-07-05 |
| CA2373475C (en) | 2012-10-23 |
| EP2058007A2 (en) | 2009-05-13 |
| ATE435662T1 (de) | 2009-07-15 |
| WO2000071162A2 (en) | 2000-11-30 |
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