WO2000075237A3 - pH SENSITIVE CYANINE DYES AS REACTIVE FLUORESCENT REAGENTS - Google Patents

pH SENSITIVE CYANINE DYES AS REACTIVE FLUORESCENT REAGENTS Download PDF

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Publication number
WO2000075237A3
WO2000075237A3 PCT/US2000/015682 US0015682W WO0075237A3 WO 2000075237 A3 WO2000075237 A3 WO 2000075237A3 US 0015682 W US0015682 W US 0015682W WO 0075237 A3 WO0075237 A3 WO 0075237A3
Authority
WO
WIPO (PCT)
Prior art keywords
straight
branched alkyl
cyanine dyes
cooh
integer
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.)
Ceased
Application number
PCT/US2000/015682
Other languages
French (fr)
Other versions
WO2000075237A2 (en
WO2000075237A9 (en
Inventor
Ratnakar Mujumdar
John Anthony Smith
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GE Healthcare UK Ltd
Carnegie Mellon University
Original Assignee
Amersham Pharmacia Biotech UK Ltd
Carnegie Mellon University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Amersham Pharmacia Biotech UK Ltd, Carnegie Mellon University filed Critical Amersham Pharmacia Biotech UK Ltd
Priority to JP2001502512A priority Critical patent/JP2003501540A/en
Priority to CA002375740A priority patent/CA2375740A1/en
Priority to EP00942696A priority patent/EP1212375A2/en
Priority to AU57284/00A priority patent/AU5728400A/en
Publication of WO2000075237A2 publication Critical patent/WO2000075237A2/en
Anticipated expiration legal-status Critical
Publication of WO2000075237A3 publication Critical patent/WO2000075237A3/en
Publication of WO2000075237A9 publication Critical patent/WO2000075237A9/en
Ceased legal-status Critical Current

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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
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/84—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving inorganic compounds or pH

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Cell Biology (AREA)
  • Pathology (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention provides pH sensitive cyanine dyes having the structure (I) wherein X and Y are independently selected from >C(C1-C4alkyl)2, sulfur and oxygen; R?1 and R2¿ are independently selected from H, CH¿2?NH2, SO3; phosphate, phosphonate, quaternary ammonium, NO2, (CH2)qCOOH, NCS, CH2NH-COR?7¿ where R7 is C1-C20 straight or branched alkyl and -(CH2) q-COOH where q is an integer from 0-10; R3 is H or -L-P where L is selected from C¿1?-C20 straight or branched alkyl optionally containing 0, 1 or 2 unsaturated groups selected from alkenyl, alkynyl and aryl, and P is selected from a reactive group, H, C1-C20 straight or branched alkyl, SO3?-, NH¿2, quaternary ammonium, CH2NH-COR8 where R8 is C1-C20 straight or branched alkyl, -(CH2)m-COOH, NHR9 where R9 is C1 to C20 straight or branched alkyl or COOH; n is an integer from 0-3; p and r are independently 0, 1, 2, 3 or 4 and where p and/or r is greater than 1, each R1 and each R2 may be different, and m is an integer from 1-10, and salts and protonated derivatives thereof and methods of using same as fluorescent reagents.
PCT/US2000/015682 1999-06-09 2000-06-08 pH SENSITIVE CYANINE DYES AS REACTIVE FLUORESCENT REAGENTS Ceased WO2000075237A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2001502512A JP2003501540A (en) 1999-06-09 2000-06-08 PH-functional cyanine dyes as reactive fluorescent reagents
CA002375740A CA2375740A1 (en) 1999-06-09 2000-06-08 Ph sensitive cyanine dyes as reactive fluorescent reagents
EP00942696A EP1212375A2 (en) 1999-06-09 2000-06-08 Ph sensitive cyanine dyes as reactive fluorescent reagents
AU57284/00A AU5728400A (en) 1999-06-09 2000-06-08 Ph sensitive cyanine dyes as reactive fluorescent reagents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13829799P 1999-06-09 1999-06-09
US60/138,297 1999-06-09

Publications (3)

Publication Number Publication Date
WO2000075237A2 WO2000075237A2 (en) 2000-12-14
WO2000075237A3 true WO2000075237A3 (en) 2002-04-11
WO2000075237A9 WO2000075237A9 (en) 2002-05-10

Family

ID=22481396

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/015682 Ceased WO2000075237A2 (en) 1999-06-09 2000-06-08 pH SENSITIVE CYANINE DYES AS REACTIVE FLUORESCENT REAGENTS

Country Status (5)

Country Link
EP (1) EP1212375A2 (en)
JP (1) JP2003501540A (en)
AU (1) AU5728400A (en)
CA (1) CA2375740A1 (en)
WO (1) WO2000075237A2 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9063127B1 (en) 2013-12-11 2015-06-23 Analiza, Inc. Devices and methods for determining and/or isolating cells such as circulating cancer or fetal cells
US10928405B2 (en) 2013-12-11 2021-02-23 Analiza, Inc. Devices and methods for determining and/or isolating cells such as circulating cancer or fetal cells
US12226543B2 (en) 2019-05-10 2025-02-18 Ecolab Usa Inc. pH sensitive color indicator for sanitizing applications

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6080868A (en) 1998-01-23 2000-06-27 The Perkin-Elmer Corporation Nitro-substituted non-fluorescent asymmetric cyanine dye compounds
WO2004039894A2 (en) * 2002-05-10 2004-05-13 Carnegie Mellon University Chiral indole intermediates and their fluorescent cyanine dyes containing functional groups
EP1322710B2 (en) * 2000-09-29 2015-02-18 Life Technologies Corporation Modified carbocyanine dyes and their conjugates
JP2003048879A (en) 2001-05-31 2003-02-21 Nisshinbo Ind Inc Fluorescent group-containing carbodiimide compound and method for producing the compound
ITPZ20030002A1 (en) 2003-08-12 2005-02-13 Giuseppe Caputo COMPOUNDS OF THE CIANINA TYPE WITH AN ALCHINYLIC ARM
CN100349869C (en) * 2004-12-10 2007-11-21 华东理工大学 Cyanine dye containing end alkynyl radical and its synthesis process
US7972789B2 (en) 2005-11-28 2011-07-05 Dako Denmark A/S Dye compounds
US7279296B2 (en) 2005-12-16 2007-10-09 General Electric Company Compositions and methods for lipoprotein uptake assays
WO2008099914A1 (en) * 2007-02-16 2008-08-21 The University Of Tokyo Fluorescent probe
US8465985B2 (en) 2007-03-01 2013-06-18 The University Of Tokyo Fluorescent probe
JPWO2009107769A1 (en) * 2008-02-29 2011-07-07 国立大学法人 東京大学 Reactive oxygen measurement reagent
FR2934684B1 (en) 2008-07-31 2012-11-16 Cis Bio Int METHOD OF DETECTING INTERNALIZATION OF MEMBRANE PROTEINS.
JP2010184866A (en) * 2009-02-10 2010-08-26 Nagoya Univ Inspection reagent for fluorescent observation of intestinal mucosa
US8051947B2 (en) 2009-03-12 2011-11-08 E.I. Du Pont De Nemours And Company Energy absorbing thermoplastic elastomer
US10053447B2 (en) 2010-12-21 2018-08-21 Pierce Biotechnology, Inc Fluorescent compounds
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
US9751868B2 (en) 2012-02-28 2017-09-05 Pierce Biotechnology, Inc. Benzocyanine compounds
CN104395306B (en) 2012-03-02 2019-04-23 皮尔斯生物科技有限公司 Indole Derivatives as Labeling Dyes for Biomolecules
EP2831587B1 (en) 2012-03-27 2018-05-16 Ventana Medical Systems, Inc. Signaling conjugates and methods of use
CN104540819B (en) 2012-08-28 2019-04-19 皮尔斯生物科技有限公司 Benzopyrylium Compounds
CN103804370A (en) * 2014-02-08 2014-05-21 南京博炫生物科技有限公司 Fluorescent dye compound and preparation method and application thereof
WO2017022559A1 (en) * 2015-08-05 2017-02-09 コニカミノルタ株式会社 Environment-responsive dye-accumulated nano particles, and method for analyzing intracellular environment
JP7423888B2 (en) * 2019-11-22 2024-01-30 株式会社同仁化学研究所 Dye for staining lipid bilayer membranes and method for staining lipid bilayer membranes using the same
CN116601238B (en) 2020-12-17 2025-04-29 伯拉考成像股份公司 pH-responsive cyanine dyes and their conjugates

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4435492A (en) * 1978-10-27 1984-03-06 Hitachi, Ltd. Complex type electrophotographic plate and electrophotographic method using the same
US4524128A (en) * 1983-10-24 1985-06-18 Eastman Kodak Company Spectrally sensitized silver halide photothermographic material
US5268486A (en) * 1986-04-18 1993-12-07 Carnegie-Mellon Unversity Method for labeling and detecting materials employing arylsulfonate cyanine dyes
DE4341618A1 (en) * 1993-12-07 1995-06-08 Univ Schiller Jena Near IR dyes useful as pH indicator for detecting toxins e.g. ammonia
EP0747700A2 (en) * 1995-06-07 1996-12-11 Carnegie-Mellon University Fluorescent labelling complexes with large stokes shifts formed by coupling together cyanine and other fluorochromes capable of resonance energy transfer
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

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4435492A (en) * 1978-10-27 1984-03-06 Hitachi, Ltd. Complex type electrophotographic plate and electrophotographic method using the same
US4524128A (en) * 1983-10-24 1985-06-18 Eastman Kodak Company Spectrally sensitized silver halide photothermographic material
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
DE4341618A1 (en) * 1993-12-07 1995-06-08 Univ Schiller Jena Near IR dyes useful as pH indicator for detecting toxins e.g. ammonia
EP0747700A2 (en) * 1995-06-07 1996-12-11 Carnegie-Mellon University Fluorescent labelling complexes with large stokes shifts formed by coupling together cyanine and other fluorochromes capable of resonance energy transfer

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
MUJUMDAR R B ET AL: "CYANINE DYE LABELING REAGENTS CONTAINING ISOTHIOCYANATE GROUPS", CYTOMETRY,US,ALAN LISS, NEW YORK, vol. 10, no. 1, 1989, pages 11 - 19, XP000034880, ISSN: 0196-4763 *
MUJUMDAR R B ET AL: "CYANINE DYE LABELING REAGENTS: SULFOINDOCYANINE SUCCINIMIDYL ESTERS", BIOCONJUGATE CHEMISTRY,US,AMERICAN CHEMICAL SOCIETY, WASHINGTON, vol. 4, no. 2, 1 March 1993 (1993-03-01), pages 105 - 111, XP000654181, ISSN: 1043-1802 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9063127B1 (en) 2013-12-11 2015-06-23 Analiza, Inc. Devices and methods for determining and/or isolating cells such as circulating cancer or fetal cells
US9709556B2 (en) 2013-12-11 2017-07-18 Analiza, Inc. Devices and methods for determining and/or isolating circulating cancer cells
US10928405B2 (en) 2013-12-11 2021-02-23 Analiza, Inc. Devices and methods for determining and/or isolating cells such as circulating cancer or fetal cells
US12226543B2 (en) 2019-05-10 2025-02-18 Ecolab Usa Inc. pH sensitive color indicator for sanitizing applications

Also Published As

Publication number Publication date
JP2003501540A (en) 2003-01-14
AU5728400A (en) 2000-12-28
WO2000075237A2 (en) 2000-12-14
WO2000075237A9 (en) 2002-05-10
EP1212375A2 (en) 2002-06-12
CA2375740A1 (en) 2000-12-14

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