DE69429767T2 - Verbesserte emission bei chemilumineszenzassays - Google Patents

Verbesserte emission bei chemilumineszenzassays

Info

Publication number
DE69429767T2
DE69429767T2 DE69429767T DE69429767T DE69429767T2 DE 69429767 T2 DE69429767 T2 DE 69429767T2 DE 69429767 T DE69429767 T DE 69429767T DE 69429767 T DE69429767 T DE 69429767T DE 69429767 T2 DE69429767 T2 DE 69429767T2
Authority
DE
Germany
Prior art keywords
enzyme
enhancement
dioxetane
analyte
chemiluminescent
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.)
Expired - Lifetime
Application number
DE69429767T
Other languages
English (en)
Other versions
DE69429767D1 (de
Inventor
Irena Y Bronstein
Brooks Edwards
John C Voyta
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.)
Applied Biosystems LLC
Original Assignee
Tropix 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 Tropix Inc filed Critical Tropix Inc
Application granted granted Critical
Publication of DE69429767D1 publication Critical patent/DE69429767D1/de
Publication of DE69429767T2 publication Critical patent/DE69429767T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C07C43/1788—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6551—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring
    • C07F9/65512—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a four-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • 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
    • C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/76—Chemiluminescence; Bioluminescence
    • 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
    • G01N33/581—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with enzyme label (including co-enzymes, co-factors, enzyme inhibitors or substrates)
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes
    • 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
    • Y10S435/81—Packaged device or kit

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Immunology (AREA)
  • Biotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Analytical Chemistry (AREA)
  • Pathology (AREA)
  • Microbiology (AREA)
  • Genetics & Genomics (AREA)
  • General Physics & Mathematics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Zoology (AREA)
  • Cell Biology (AREA)
  • Wood Science & Technology (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plasma & Fusion (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Luminescent Compositions (AREA)
DE69429767T 1993-03-15 1994-03-15 Verbesserte emission bei chemilumineszenzassays Expired - Lifetime DE69429767T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/031,471 US5547836A (en) 1990-08-30 1993-03-15 Enhancement of chemiluminescent assays
PCT/US1994/002549 WO1994021821A1 (en) 1993-03-15 1994-03-15 Improved enhancement of chemiluminescent assays

Publications (2)

Publication Number Publication Date
DE69429767D1 DE69429767D1 (de) 2002-03-14
DE69429767T2 true DE69429767T2 (de) 2002-09-19

Family

ID=21859628

Family Applications (2)

Application Number Title Priority Date Filing Date
DE69434871T Expired - Lifetime DE69434871T2 (de) 1993-03-15 1994-03-15 Erhöhung von Chemilumineszenz in Assays
DE69429767T Expired - Lifetime DE69429767T2 (de) 1993-03-15 1994-03-15 Verbesserte emission bei chemilumineszenzassays

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE69434871T Expired - Lifetime DE69434871T2 (de) 1993-03-15 1994-03-15 Erhöhung von Chemilumineszenz in Assays

Country Status (8)

Country Link
US (2) US5547836A (de)
EP (2) EP1120652B1 (de)
JP (1) JP3632856B2 (de)
AT (2) ATE343135T1 (de)
AU (1) AU6444994A (de)
CA (1) CA2157917C (de)
DE (2) DE69434871T2 (de)
WO (1) WO1994021821A1 (de)

Families Citing this family (46)

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WO1988000695A1 (en) * 1986-07-24 1988-01-28 Quest Systems, Inc. Method of detecting a substance using enzymatically-induced decomposition of dioxetanes
US6022964A (en) 1989-07-17 2000-02-08 Tropix, Inc. Chemiluminescent 1,2-dioxetanes
US5578253A (en) * 1994-11-23 1996-11-26 Lumigen, Inc. Chemiluminescent dialkyl-substituted 1,2-dioxetane compounds, methods of synthesis and use
US5672514A (en) * 1995-02-01 1997-09-30 Fuji Photo Film Co., Ltd. Chemiluminescent detecting method and apparatus
WO1997005209A1 (en) * 1995-07-28 1997-02-13 Kohne David E Method for enhancing chemiluminescence
US5777135A (en) * 1995-07-31 1998-07-07 Lumigen, Inc. Di-substituted 1,2-dioxetane compounds having increased water solubility and assay compositions
US5721370A (en) * 1995-07-31 1998-02-24 Lumigen Inc. Water soluble tri-substituted 1,2-dioxetane compounds and assay compositions having increased storage stability
US5631167A (en) * 1995-07-31 1997-05-20 Bayer Corporation Capsule chemistry analytical methods employing dioxetane chemiluminescence
US5679803A (en) * 1995-10-25 1997-10-21 Tropix, Inc. 1,2 chemiluminescent dioxetanes of improved performance
US5783381A (en) * 1995-10-19 1998-07-21 Tropix, Inc. Chemiluminescent 1,2-dioxetanes
CN1130563C (zh) * 1996-09-19 2003-12-10 第一化学药品株式会社 免疫组织化学染色用组合物及其用途
US6243980B1 (en) 1997-03-07 2001-06-12 Tropix, Inc. Protease inhibitor assay
CA2338883A1 (en) 1998-07-28 2000-02-10 Tropix, Inc. Benzothiazole dioxetanes
US6660529B2 (en) * 1998-07-28 2003-12-09 Pe Corporation Heteroaryl substituted benzothiazole dioxetanes
US6686171B2 (en) 1999-05-10 2004-02-03 Tropix, Inc. Competitive chemiluminescent assay for cyclic nucleotide monophosphates
US6794156B2 (en) * 1999-05-10 2004-09-21 Applera Corporation Cell growth, induction and lysis in an antibody-coated microplate for use in an ELISA
JP2001249079A (ja) * 1999-12-28 2001-09-14 Fujirebio Inc 発光量調節剤を用いた化学発光測定方法及び酵素免疫測定方法
CA2398812A1 (en) * 2000-01-28 2001-08-02 Brij Pal Giri Novel stabilized formulations for chemiluminescent assays
US6767716B2 (en) * 2000-06-17 2004-07-27 Brij P. Giri Chemluminescent systems containing unsaturated 1,2-dioxetanes
US7368296B2 (en) * 2002-01-17 2008-05-06 Applied Biosystems Solid phases optimized for chemiluminescent detection
AU2003239890A1 (en) * 2002-05-23 2003-12-12 Brij Pal Giri POLYMERIC AMMONIUM AND OR PHOSPHONIUM SALTS HAVING ADDED Pi-ELECTRONS AND HIGHER MOLECULAR WEIGHT AS ENHANCERS FOR CHEMILUMINESCENT SYSTEMS
EP1542013B1 (de) * 2002-06-24 2016-04-13 Fujirebio Inc. Chemilumineszenzverbesserer
US7416898B2 (en) * 2002-10-04 2008-08-26 Giri Brij P Chemiluminescent 1,2-dioxetanes
US7390670B2 (en) 2003-02-20 2008-06-24 Lumigen, Inc. Signalling compounds and methods for detecting hydrogen peroxide
US20050019778A1 (en) * 2003-07-17 2005-01-27 Voyta John C. Sequential generation of multiple chemiluminescent signals on solid supports
US20050026151A1 (en) * 2003-07-17 2005-02-03 Voyta John C. Simultaneous generation of multiple chemiluminescent signals on solid supports
JP4259229B2 (ja) 2003-08-28 2009-04-30 東ソー株式会社 １，２−ジオキセタンの化学発光方法および化学発光用組成物
US7879575B2 (en) * 2005-04-27 2011-02-01 The Trustees Of The University Of Pennsylvania Nanostructures that provide a modified nanoenvironment for the enhancement of luminescence
US7919019B2 (en) * 2005-04-27 2011-04-05 The Trustees Of The University Of Pennsylvania Nanostructure enhanced luminescent devices
US20090246888A1 (en) * 2005-04-27 2009-10-01 The Trustees Of The University Of Pennsylvania Nanoassays
CN101784897A (zh) 2007-05-23 2010-07-21 应用生物系统有限公司 通过从活化的化学发光的基质将能量转移至能量受体染料来检测生物分子的试剂、试剂盒和方法
WO2010101839A2 (en) 2009-03-02 2010-09-10 Life Technologies Corporation Chemiluminescent compositions, methods, assays and kits for oxidative enzymes
CN102311730B (zh) 2010-06-30 2014-09-24 深圳迈瑞生物医疗电子股份有限公司 化学发光液,增强化学发光的试剂和方法
CN102311731B (zh) 2010-06-30 2016-08-03 深圳迈瑞生物医疗电子股份有限公司 增强化学发光的试剂、方法和化学发光液
CN102329611B (zh) 2010-07-13 2015-01-07 深圳迈瑞生物医疗电子股份有限公司 化学发光增强试剂及其使用方法和化学发光液
CN103649069B (zh) 2011-05-03 2016-09-14 生命科技公司 闪光和辉光1,2-二氧杂环丁烷类
CN104597233B (zh) 2014-11-05 2016-09-14 深圳市美凯特科技有限公司 用于增强化学发光的增强液及制备化学发光液的方法
US10925281B2 (en) 2014-11-26 2021-02-23 Microban Products Company Surface disinfectant with residual biocidal property
US11026418B2 (en) 2014-11-26 2021-06-08 Microban Products Company Surface disinfectant with residual biocidal property
US10842147B2 (en) 2014-11-26 2020-11-24 Microban Products Company Surface disinfectant with residual biocidal property
US11033023B2 (en) 2014-11-26 2021-06-15 Microban Products Company Surface disinfectant with residual biocidal property
MX2018006391A (es) * 2015-11-23 2019-02-14 Microban Products Desinfectante de superficie con propiedad biocida residual.
EP3379931A4 (de) * 2015-11-23 2019-06-05 Microban Products Company Oberflächendesinfektionsmittel mit verbleibenden bioziden eigenschaften
US11503824B2 (en) 2016-05-23 2022-11-22 Microban Products Company Touch screen cleaning and protectant composition
CN113717714A (zh) * 2021-08-19 2021-11-30 大连博格林生物科技有限公司 一种化学发光增强剂及其制备方法和在化学发光液中的应用
EP4394016A1 (de) 2022-12-30 2024-07-03 Shenzhen Mindray Bio-Medical Electronics Co., Ltd. Chemilumineszente substratlösung, chemilumineszenzverstärker und verwendung davon

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US4962192A (en) * 1986-07-17 1990-10-09 Board Of Governors Of Wayne State University Chemiluminescent 1,2-dioxetane compounds
US5004565A (en) * 1986-07-17 1991-04-02 The Board Of Governors Of Wayne State University Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes
US5112960A (en) * 1989-07-17 1992-05-12 Bronstein Irena Y Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetanes
US4978614A (en) * 1988-10-26 1990-12-18 Tropix, Inc. Method of detecting a substance using enzymatically-induced decomposition of dioxetanes
US4956477A (en) * 1987-12-31 1990-09-11 Tropix, Inc. Synthesis of 1,2-dioxetanes
CA1340590C (en) * 1986-07-24 1999-06-08 John C. Voyta Chemiluminescence enhancement
US5220005A (en) * 1986-07-24 1993-06-15 Tropix, Inc. Substituted adamantyl dioxetanes
US4931223A (en) * 1986-07-24 1990-06-05 Tropix, Inc. Methods of using chemiluminescent 1,2-dioxetanes
US5330900A (en) * 1987-12-31 1994-07-19 Tropix, Inc. Chemiluminescent 3-(substituted adamant-2'-ylidene) 1,2-dioxetanes
US5089630A (en) * 1987-12-31 1992-02-18 Bronstein Irena Y Dioxetanes for use in assays
US4952707A (en) * 1988-06-30 1990-08-28 Tropix, Inc. Enzymatically-cleavable chemiluminescent fused polycyclic ring-containing 1,2-dioxetanes
GB2233451B (en) * 1989-06-27 1993-09-15 Tropix Inc Chemiluminescence enhancement
US5326882A (en) * 1989-07-17 1994-07-05 Tropix, Inc. Chemiluminescent 3-(substituted Adamant-2'-Ylidene) 1,2-dioxetanes
US5336596A (en) * 1991-12-23 1994-08-09 Tropix, Inc. Membrane for chemiluminescent blotting applications

Also Published As

Publication number Publication date
EP0689611B1 (de) 2002-01-30
EP1120652A1 (de) 2001-08-01
AU6444994A (en) 1994-10-11
EP0689611A4 (de) 1998-09-02
ATE343135T1 (de) 2006-11-15
EP1120652B1 (de) 2006-10-18
JP3632856B2 (ja) 2005-03-23
JPH08507694A (ja) 1996-08-20
CA2157917C (en) 2009-11-24
US5654154A (en) 1997-08-05
US5547836A (en) 1996-08-20
WO1994021821A1 (en) 1994-09-29
DE69434871T2 (de) 2007-04-12
DE69429767D1 (de) 2002-03-14
DE69434871D1 (de) 2006-11-30
EP0689611A1 (de) 1996-01-03
ATE212722T1 (de) 2002-02-15
CA2157917A1 (en) 1994-09-29

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