CA2067394A1 - Enzyme amplified lanthanide chelate luminescence assay - Google Patents

Enzyme amplified lanthanide chelate luminescence assay

Info

Publication number
CA2067394A1
CA2067394A1 CA002067394A CA2067394A CA2067394A1 CA 2067394 A1 CA2067394 A1 CA 2067394A1 CA 002067394 A CA002067394 A CA 002067394A CA 2067394 A CA2067394 A CA 2067394A CA 2067394 A1 CA2067394 A1 CA 2067394A1
Authority
CA
Canada
Prior art keywords
lanthanide chelate
luminescent lanthanide
enzyme
phosphonooxy
product
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
Application number
CA002067394A
Other languages
French (fr)
Other versions
CA2067394C (en
Inventor
Ramon A. Evangelista
Eva F. Gudgin Templeton
Alfred Pollak
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.)
Kronem Systems Inc
Original Assignee
Ramon A. Evangelista
Eva F. Gudgin Templeton
Alfred Pollak
Kronem Systems Inc.
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 Ramon A. Evangelista, Eva F. Gudgin Templeton, Alfred Pollak, Kronem Systems Inc. filed Critical Ramon A. Evangelista
Publication of CA2067394A1 publication Critical patent/CA2067394A1/en
Application granted granted Critical
Publication of CA2067394C publication Critical patent/CA2067394C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • G01N33/53—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
    • G01N33/58—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
    • G01N2458/00—Labels used in chemical analysis of biological material
    • G01N2458/40—Rare earth chelates
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/968—High energy substrates, e.g. fluorescent, chemiluminescent, radioactive
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S436/00—Chemistry: analytical and immunological testing
    • Y10S436/80—Fluorescent dyes, e.g. rhodamine
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/13—Tracers or tags

Abstract

A method and compounds useful for this method are described for enzyme-amplified signal detection in analytical assays requiring extremely high detection sensitivity which uses a substrate capable of being transformed by an enzyme from a com-pound which does not form a luminescent lanthanide chelate into a product which forms a luminescent lanthanide chelate. The method in which a substrate not capable of forming a highly luminescent lanthanide chelate is enzymatically altered to produce a product which forms a highly luminescent lanthanide chelate and hence is particularly useful in time-resolved luminescence anal-ysis as required in many different heterogeneous or homogeneous assay formats is described herein. Above mentioned com-pounds include benzoic acid, 2-phosphonooxy-derivatives (a), benzophenone, 4-phosphonooxy-derivates (.beta.), as well as (~) and (.delta.).
CA002067394A 1989-12-04 1990-11-13 Enzyme amplified lanthanide chelate luminescence assay Expired - Fee Related CA2067394C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB898927503A GB8927503D0 (en) 1989-12-04 1989-12-04 Enzyme-amplified lanthanide chelate luminescence
GB8927503.6 1989-12-04
PCT/CA1990/000391 WO1991008490A1 (en) 1989-12-04 1990-11-13 Enzyme amplified lanthanid chelate luminescence assay

Publications (2)

Publication Number Publication Date
CA2067394A1 true CA2067394A1 (en) 1991-06-05
CA2067394C CA2067394C (en) 2001-12-18

Family

ID=10667460

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002067394A Expired - Fee Related CA2067394C (en) 1989-12-04 1990-11-13 Enzyme amplified lanthanide chelate luminescence assay

Country Status (8)

Country Link
US (1) US5262299A (en)
EP (1) EP0544662B1 (en)
AT (1) ATE143143T1 (en)
AU (1) AU6715090A (en)
CA (1) CA2067394C (en)
DE (1) DE69028639T2 (en)
GB (1) GB8927503D0 (en)
WO (1) WO1991008490A1 (en)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5367080A (en) * 1990-11-08 1994-11-22 Sterling Winthrop Inc. Complexing agents and targeting radioactive immunoreagents useful in therapeutic and diagnostic imaging compositions and methods
IL102486A (en) * 1991-10-04 1997-11-20 Orgenics Ltd Method and apparatus for detection of nucleic acid sequences with a nucleic acid probe
US5312922A (en) * 1992-04-06 1994-05-17 Nordion International Inc. Europium and terbium chelators for time-resolved fluorometric assays
AT399054B (en) * 1993-05-12 1995-03-27 Thomas Dr Schlederer METHOD FOR DETECTING SUBSTANCES
AU1055997A (en) * 1995-11-30 1997-06-19 Trustees Of Boston University Luminescent probes for protein detection
US5922537A (en) * 1996-11-08 1999-07-13 N.o slashed.AB Immunoassay, Inc. Nanoparticles biosensor
FI970593A (en) * 1997-02-12 1998-08-13 Sakari Mikael Kulmala Use of coated conductors for analytical purposes
FR2792072A1 (en) * 1999-04-08 2000-10-13 Cis Bio Int HOMOGENEOUS METHOD OF DETECTING OR DETERMINING A CHEMICAL OR PHYSICOCHEMICAL INTERACTION
US6838292B1 (en) 1999-04-19 2005-01-04 Alion Science And Technology Corporation Detection of biological warfare agents
US6329205B1 (en) 1999-08-31 2001-12-11 Molecular Probes, Inc. Detection method using luminescent europium-based protein stains
AU2002220082A1 (en) * 2000-10-19 2002-04-29 The General Hospital Corporation Imaging of enzymatic activity
DE10058596A1 (en) * 2000-11-25 2002-06-06 Aventis Pharma Gmbh Method of screening chemical compounds for modulating the interaction of an EVH1 domain or a protein with an EVH1 domain with an EVH1 binding domain or a protein with an EVH1 binding domain, and a method for detecting said interaction
DE10111392A1 (en) * 2001-03-09 2002-09-12 Chromeon Gmbh Bioanalytical measurement method using oxidases
US20030082294A1 (en) * 2001-10-31 2003-05-01 Laurakay Bruhn Surface treatment method for bio-arrays
US8367013B2 (en) 2001-12-24 2013-02-05 Kimberly-Clark Worldwide, Inc. Reading device, method, and system for conducting lateral flow assays
US20030119203A1 (en) 2001-12-24 2003-06-26 Kimberly-Clark Worldwide, Inc. Lateral flow assay devices and methods for conducting assays
US7771922B2 (en) 2002-05-03 2010-08-10 Kimberly-Clark Worldwide, Inc. Biomolecule diagnostic device
US7223534B2 (en) 2002-05-03 2007-05-29 Kimberly-Clark Worldwide, Inc. Diffraction-based diagnostic devices
US7485453B2 (en) 2002-05-03 2009-02-03 Kimberly-Clark Worldwide, Inc. Diffraction-based diagnostic devices
US7214530B2 (en) 2002-05-03 2007-05-08 Kimberly-Clark Worldwide, Inc. Biomolecule diagnostic devices and method for producing biomolecule diagnostic devices
US7223368B2 (en) 2002-05-03 2007-05-29 Kimberly-Clark Worldwide, Inc. Diffraction-based diagnostic devices
US7118855B2 (en) 2002-05-03 2006-10-10 Kimberly-Clark Worldwide, Inc. Diffraction-based diagnostic devices
US7091049B2 (en) 2002-06-26 2006-08-15 Kimberly-Clark Worldwide, Inc. Enhanced diffraction-based biosensor devices
US7285424B2 (en) 2002-08-27 2007-10-23 Kimberly-Clark Worldwide, Inc. Membrane-based assay devices
US7314763B2 (en) 2002-08-27 2008-01-01 Kimberly-Clark Worldwide, Inc. Fluidics-based assay devices
US7169550B2 (en) 2002-09-26 2007-01-30 Kimberly-Clark Worldwide, Inc. Diffraction-based diagnostic devices
US7781172B2 (en) 2003-11-21 2010-08-24 Kimberly-Clark Worldwide, Inc. Method for extending the dynamic detection range of assay devices
US7247500B2 (en) 2002-12-19 2007-07-24 Kimberly-Clark Worldwide, Inc. Reduction of the hook effect in membrane-based assay devices
US7851209B2 (en) 2003-04-03 2010-12-14 Kimberly-Clark Worldwide, Inc. Reduction of the hook effect in assay devices
US20040197819A1 (en) 2003-04-03 2004-10-07 Kimberly-Clark Worldwide, Inc. Assay devices that utilize hollow particles
US20050112703A1 (en) 2003-11-21 2005-05-26 Kimberly-Clark Worldwide, Inc. Membrane-based lateral flow assay devices that utilize phosphorescent detection
US7943395B2 (en) 2003-11-21 2011-05-17 Kimberly-Clark Worldwide, Inc. Extension of the dynamic detection range of assay devices
US7713748B2 (en) 2003-11-21 2010-05-11 Kimberly-Clark Worldwide, Inc. Method of reducing the sensitivity of assay devices
US7943089B2 (en) 2003-12-19 2011-05-17 Kimberly-Clark Worldwide, Inc. Laminated assay devices
US7796266B2 (en) 2004-04-30 2010-09-14 Kimberly-Clark Worldwide, Inc. Optical detection system using electromagnetic radiation to detect presence or quantity of analyte
US7815854B2 (en) 2004-04-30 2010-10-19 Kimberly-Clark Worldwide, Inc. Electroluminescent illumination source for optical detection systems
US7521226B2 (en) 2004-06-30 2009-04-21 Kimberly-Clark Worldwide, Inc. One-step enzymatic and amine detection technique
JP2009292748A (en) * 2008-06-03 2009-12-17 National Institute Of Advanced Industrial & Technology Rare earth metal complex, ink composition using the same and fluorescent labeling agent
US8883857B2 (en) 2012-12-07 2014-11-11 Baylor College Of Medicine Small molecule xanthine oxidase inhibitors and methods of use
EP3136098B1 (en) 2014-04-23 2020-12-09 Konica Minolta, Inc. Medium for resin particles containing fluorescent dye
CN114736255B (en) * 2022-05-11 2023-10-27 湖南超亟检测技术有限责任公司 Fluorescent probe for detecting flavone derivative of beta-galactosidase, preparation method and application thereof, kit and use method thereof

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4058732A (en) * 1975-06-30 1977-11-15 Analytical Radiation Corporation Method and apparatus for improved analytical fluorescent spectroscopy
US4096252A (en) * 1976-06-10 1978-06-20 J. Uriach & Cia S.A. 4-Trifluoromethylbenzoic acid derivatives as thromboembolic agents
US4259313A (en) * 1978-10-18 1981-03-31 Eastman Kodak Company Fluorescent labels
SE428332B (en) * 1979-03-08 1983-06-20 Wallac Oy PROCEDURE FOR FLUORESCENSE SPECTROSCOPIC DETERMINATION OF BIOLOGICALLY ACTIVE SUBSTANCE, LIKE HAPTEN, ANTIBODY OR ANTIGEN
US4637988A (en) * 1981-07-01 1987-01-20 Eastman Kodak Company Fluorescent labels for immunoassay
US4837169A (en) * 1981-07-01 1989-06-06 Eastman Kodak Company Polypyridine Fluorescent labels for immunoassay
CA1205028A (en) * 1981-07-01 1986-05-27 Jerald C. Hinshaw Fluorescent chelates and labeled specific binding reagents prepared therefrom
IL67289A (en) * 1982-03-18 1985-12-31 Miles Lab Homogeneous immunoassay with labeled monoclonal anti-analyte
SE454115B (en) * 1982-09-13 1988-03-28 Wallac Oy HOMOGENIC PHASE ANALYSIS WITH LANTANIDE KELAT AS BRAND SUBSTANCE
SE8301395L (en) * 1983-03-15 1984-09-16 Wallac Oy KELATIZING COMPOUNDS WITH FUNCTIONAL GROUPS WHICH ALLOW COVALENT COUPLING TO BIO-ORGANIC MOLECULES
GB8313217D0 (en) * 1983-05-13 1983-06-22 Glaxo Group Ltd Pharmaceutical compositions
US4687732A (en) * 1983-06-10 1987-08-18 Yale University Visualization polymers and their application to diagnostic medicine
US4737454A (en) * 1983-07-14 1988-04-12 Molecular Diagnostics, Inc. Fast photochemical method of labelling nucleic acids for detection purposes in hybridization assays
US4626501A (en) * 1983-09-02 1986-12-02 Integrated Genetics, Inc. Labeled DNA
IL73577A (en) * 1983-12-12 1989-10-31 Miles Lab Method and reagent system for detecting dna or rna sequences in a test medium containing single stranded dna or rna using antibodies to intercalation complexes with double stranded nucleic acid
EP0146039A3 (en) * 1983-12-12 1986-08-27 Miles Inc. Hybridization assay with immobilization of hybrids by antihybrid binding
GB8420521D0 (en) * 1984-08-13 1984-09-19 Hsc Res Dev Corp Fluorescent label
CA1272443A (en) * 1985-02-22 1990-08-07 Nanibhushan Dattagupta Solution-phase dual hybridization assay for detecting polynucleotide sequences
US4761481A (en) * 1985-03-18 1988-08-02 Baxter Travenol Laboratories, Inc. Substituted pyridine derivatives
SE8502573D0 (en) * 1985-05-23 1985-05-23 Jouko Kanakre FLUORESCENT LANTHANIDE CHELATES USEFUL AS LABELS OF PHYSIOLOGICALLY ACTIVE MATERIALS
US4882269A (en) * 1985-12-13 1989-11-21 Princeton University Amplified hybridization assay
US4810631A (en) * 1986-05-12 1989-03-07 Becton, Dickinson And Company Signal enhancement in immunoassay by modulation of chemical catalysis
SE454781B (en) * 1986-10-17 1988-05-30 Wallac Oy HYBRIDIZATION PROCEDURE FOR THE DETECTION OF POLYNUCLEOTIDE SEQUENCE
IL85596A (en) * 1987-05-18 1992-06-21 Technicon Instr Method for a specific binding enzyme immunoassay
SE8703682L (en) * 1987-09-24 1989-03-25 Wallac Oy HOMOGENIC DETERMINATION METHOD USING AFFINITY REACTIONS
WO1989004375A1 (en) * 1987-10-23 1989-05-18 Siska Diagnostics, Inc. Lanthanide chelate-tagged nucleic acid probes
SE8801702D0 (en) * 1988-05-05 1988-05-05 Pharmacia Ab SET FOR DETERMINATION OF ENZYMATIC ACTIVITY
US5081274A (en) * 1988-09-19 1992-01-14 Nitto Boseki Co., Ltd. 4-acyl-2,6-dihalophenyl-phosphoric acid derivatives useful in the determination of acid phosphatase activity

Also Published As

Publication number Publication date
AU6715090A (en) 1991-06-26
EP0544662A1 (en) 1993-06-09
WO1991008490A1 (en) 1991-06-13
ATE143143T1 (en) 1996-10-15
CA2067394C (en) 2001-12-18
GB8927503D0 (en) 1990-02-07
DE69028639T2 (en) 1997-03-20
US5262299A (en) 1993-11-16
DE69028639D1 (en) 1996-10-24
EP0544662B1 (en) 1996-09-18

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