GB2391550A - Quinacridone labelling reagents for fluorescence detection of biological materials - Google Patents
Quinacridone labelling reagents for fluorescence detection of biological materials Download PDFInfo
- Publication number
- GB2391550A GB2391550A GB0326464A GB0326464A GB2391550A GB 2391550 A GB2391550 A GB 2391550A GB 0326464 A GB0326464 A GB 0326464A GB 0326464 A GB0326464 A GB 0326464A GB 2391550 A GB2391550 A GB 2391550A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- quinacridone
- nitro
- mono
- alkyl
- 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.)
- Granted
Links
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
- C09B48/00—Quinacridones
-
- 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
- C09B15/00—Acridine dyes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
-
- 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
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
-
- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
-
- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/536—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase
- G01N33/542—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase with steric inhibition or signal modification, e.g. fluorescent quenching
-
- 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
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/902—Oxidoreductases (1.)
Abstract
Disclosed are new quinacridone dye derivatives having characteristic fluorescence lifetimes. Also disclosed are methods for labelling target biological materials employing the quinacridone dyes and use of the labelled materials in biological assays. The quinacridone derivatives have the structure (I), in which Z<1> and Z<2> independently represent the atoms necessary to complete one ring, two fused ring, or three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R<3>, R<4>, R<5>, R<6>, R<7> and R<8> are independently selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono-or di-nitro-substituted benzyl, amino, mono- or di-C1-C4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C1-6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C1-C20 alkyl, aralkyl, sulphonate, sulphonic acid, quaternary ammonium, the group -E-F and the group -(CH2-)nY; R<1> and R<2> are independently selected from hydrogen, mono- or di-nitro-substituted benzyl, C1-C20 alkyl, aralkyl, the group -E-F and the group -(CH2-)nY; E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl; and n is an integer from 1 to 6. The invention also relates to a set of different fluorescent quinacridone dye derivatives, each dye having a different fluorescence lifetime, the set of dyes being particularly useful for multiparameter analysis.
Description
GB 2391550 A continuation (74) Agent and/or Address for Service: Amersham
PLC Amersham Place, LITTLE CHALFONT, Buckinghamshire, HP7 9NA, United Kingdom
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0113434.5A GB0113434D0 (en) | 2001-06-04 | 2001-06-04 | Quinacridone derivatives as labels for fluorescence detection of biological materials |
PCT/GB2002/002537 WO2002099432A2 (en) | 2001-06-04 | 2002-05-30 | Quinacridone labelling reagents for fluorescence detection of biological materials |
Publications (3)
Publication Number | Publication Date |
---|---|
GB0326464D0 GB0326464D0 (en) | 2003-12-17 |
GB2391550A true GB2391550A (en) | 2004-02-11 |
GB2391550B GB2391550B (en) | 2005-02-02 |
Family
ID=9915774
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GBGB0113434.5A Ceased GB0113434D0 (en) | 2001-06-04 | 2001-06-04 | Quinacridone derivatives as labels for fluorescence detection of biological materials |
GB0326464A Expired - Fee Related GB2391550B (en) | 2001-06-04 | 2002-05-30 | Quinacridone derivatives as labelling reagents for fluorescence detection of biological materials |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GBGB0113434.5A Ceased GB0113434D0 (en) | 2001-06-04 | 2001-06-04 | Quinacridone derivatives as labels for fluorescence detection of biological materials |
Country Status (9)
Country | Link |
---|---|
US (1) | US7335771B2 (en) |
EP (1) | EP1399742B1 (en) |
JP (1) | JP4317444B2 (en) |
AT (1) | ATE502301T1 (en) |
AU (1) | AU2002314302B2 (en) |
CA (1) | CA2449409C (en) |
DE (1) | DE60239458D1 (en) |
GB (2) | GB0113434D0 (en) |
WO (1) | WO2002099432A2 (en) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2398123B (en) * | 2002-04-19 | 2005-03-02 | Amersham Biosciences Uk Ltd | Methods for measuring enzyme activity |
GB0208989D0 (en) | 2002-04-19 | 2002-05-29 | Amersham Biosciences Uk Ltd | Methods for measuring enzyme activity |
GB0217562D0 (en) * | 2002-07-30 | 2002-09-11 | Amersham Biosciences Uk Ltd | Site-specific labelling of proteins using acridone and quinacridone lifetime dyes |
GB0317743D0 (en) * | 2003-07-30 | 2003-09-03 | Amersham Biosciences Uk Ltd | Method for measuring aromatase activity |
US20090057613A1 (en) * | 2004-06-29 | 2009-03-05 | Ciba Specialty Chemicals Holding Inc. | Fluorescent quinacridones |
GB0421693D0 (en) | 2004-09-30 | 2004-11-03 | Amersham Biosciences Uk Ltd | Method for measuring binding of a test compound to a G-protein coupled receptor |
GB0505777D0 (en) * | 2005-03-22 | 2005-04-27 | Amersham Biosciences Uk Ltd | Enzyme detection method and reagent |
ES2322276T3 (en) | 2005-11-28 | 2009-06-18 | Agfa Graphics N.V. | NON-WATERY QUINACRIDONE DISPERSIONS FOR USE IN DISPERSION SYNERGICS. |
CN101448780B (en) | 2006-05-22 | 2014-06-18 | 太阳化学公司 | 2,5-di(methoxyanilino)terephthalic acid polymorphs and quinacridones realized therefrom |
WO2008030120A1 (en) * | 2006-09-07 | 2008-03-13 | Auckland Uniservices Limited | A method for the fluorescent detection of nitroreductase activity using nitro-substituted aromatic compounds |
WO2009112791A1 (en) * | 2008-03-14 | 2009-09-17 | Assaymetrics Limited | Fluorogenic peptides and their method of production |
EP2316890A1 (en) * | 2009-11-03 | 2011-05-04 | Agfa-Gevaert | Preparing and dispersing surface-modified colour pigments |
US8835641B2 (en) * | 2010-07-19 | 2014-09-16 | University Of Ottawa | Fluorescent markers and use thereof for labeling specific protein targets |
JP2014508537A (en) | 2011-03-25 | 2014-04-10 | アルマック・サイエンシーズ・(スコットランド)・リミテッド | Enzyme assay |
CN102276600B (en) * | 2011-04-22 | 2012-11-14 | 华东理工大学 | Quinacridone derivative and application thereof |
GB2511110A (en) * | 2013-02-25 | 2014-08-27 | Sudarshan Chemical Ind Ltd | Pigments |
EP3072975A4 (en) * | 2013-11-21 | 2017-05-03 | The University of Tokyo | Method for detecting fluorescence or absorbance, method for suppressing background, method for measuring adp, method for measuring activity of adp-synthesizing enzyme, and method for measuring activity of glucosyltransferase |
US9701667B2 (en) | 2014-05-05 | 2017-07-11 | University Of Ottawa | Coumarin-based fluorogenic agents and uses thereof for specific protein labelling |
US10591485B2 (en) | 2015-01-23 | 2020-03-17 | University Of Ottawa | Peptide tags for fluorescent labelling of proteins |
JP2017020896A (en) * | 2015-07-10 | 2017-01-26 | 国立大学法人北陸先端科学技術大学院大学 | N-terminal labeling reagent, fluorescence labeled protein using n-terminal labeling reagent, and method for manufacturing fluorescence labeled protein |
US9958452B2 (en) | 2015-12-14 | 2018-05-01 | University Of Ottawa | Highly fluorogenic protein labelling agents |
EP3246969B1 (en) | 2016-05-17 | 2018-12-12 | Samsung SDI Co., Ltd. | Separator for rechargeable battery and rechargeable lithium battery including the same |
US11414387B2 (en) | 2017-11-20 | 2022-08-16 | Stingthera, Inc. | Oxoacridinyl acetic acid derivatives and methods of use |
JP7323539B2 (en) | 2017-11-20 | 2023-08-08 | スティングセラ インコーポレイテッド | Oxoacridinyl acetic acid derivative and method of use |
CN112794813B (en) * | 2020-12-30 | 2022-04-26 | 四川大学华西医院 | Cyclobutene derivative for fluorescent labeling |
CN114605405B (en) * | 2022-03-09 | 2023-09-05 | 吉林大学 | Cell lipid drop fluorescence imaging probe based on quinacridone skeleton and application thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61168666A (en) * | 1985-01-21 | 1986-07-30 | Dainippon Ink & Chem Inc | Pigment composition |
EP0673979B1 (en) * | 1994-03-25 | 2000-08-30 | Ciba SC Holding AG | Fluorescent dyestuffs having cyanimino groups |
US5713999A (en) * | 1996-04-29 | 1998-02-03 | Bayer Corporation | Incorporation of pigment derivatives in quinacridone processes |
GB0208989D0 (en) * | 2002-04-19 | 2002-05-29 | Amersham Biosciences Uk Ltd | Methods for measuring enzyme activity |
-
2001
- 2001-06-04 GB GBGB0113434.5A patent/GB0113434D0/en not_active Ceased
-
2002
- 2002-05-30 EP EP02740872A patent/EP1399742B1/en not_active Expired - Lifetime
- 2002-05-30 US US10/479,659 patent/US7335771B2/en not_active Expired - Fee Related
- 2002-05-30 AT AT02740872T patent/ATE502301T1/en not_active IP Right Cessation
- 2002-05-30 CA CA2449409A patent/CA2449409C/en not_active Expired - Fee Related
- 2002-05-30 AU AU2002314302A patent/AU2002314302B2/en not_active Ceased
- 2002-05-30 JP JP2003502501A patent/JP4317444B2/en not_active Expired - Fee Related
- 2002-05-30 GB GB0326464A patent/GB2391550B/en not_active Expired - Fee Related
- 2002-05-30 WO PCT/GB2002/002537 patent/WO2002099432A2/en active Application Filing
- 2002-05-30 DE DE60239458T patent/DE60239458D1/en not_active Expired - Lifetime
Non-Patent Citations (2)
Title |
---|
Chemical Communications, Vol. 7, no. 6, 21 March 2001 (2001-03-21), pages 561-562 * |
Journal of Photochemistry and Photobiology A: Chemistry, Vol. 137, 4 December 2000 (2000-12-04), pages 99-104 * |
Also Published As
Publication number | Publication date |
---|---|
WO2002099432A3 (en) | 2003-05-01 |
JP2005501228A (en) | 2005-01-13 |
GB0113434D0 (en) | 2001-07-25 |
DE60239458D1 (en) | 2011-04-28 |
EP1399742A2 (en) | 2004-03-24 |
WO2002099432A2 (en) | 2002-12-12 |
AU2002314302B2 (en) | 2006-02-23 |
GB0326464D0 (en) | 2003-12-17 |
US7335771B2 (en) | 2008-02-26 |
JP4317444B2 (en) | 2009-08-19 |
GB2391550B (en) | 2005-02-02 |
CA2449409A1 (en) | 2002-12-12 |
CA2449409C (en) | 2012-07-17 |
EP1399742B1 (en) | 2011-03-16 |
ATE502301T1 (en) | 2011-04-15 |
US20040171014A1 (en) | 2004-09-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20130530 |