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WO2004041840A3 - Peptide-bound chromogens used for determining enzymatic activities - Google Patents

Peptide-bound chromogens used for determining enzymatic activities Download PDF

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Publication number
WO2004041840A3
WO2004041840A3 PCT/EP2003/012463 EP0312463W WO2004041840A3 WO 2004041840 A3 WO2004041840 A3 WO 2004041840A3 EP 0312463 W EP0312463 W EP 0312463W WO 2004041840 A3 WO2004041840 A3 WO 2004041840A3
Authority
WO
WIPO (PCT)
Prior art keywords
peptide
atoms
crs
enzymatic activities
amino
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/EP2003/012463
Other languages
German (de)
French (fr)
Other versions
WO2004041840A2 (en
Inventor
Stefan Spichiger
Ursula Spichiger-Keller
Michael Linnhoff
Gleb Zhylyak
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.)
Sigma Aldrich GmbH
Original Assignee
Sigma Aldrich GmbH
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 Sigma Aldrich GmbH filed Critical Sigma Aldrich GmbH
Priority to AU2003286158A priority Critical patent/AU2003286158A1/en
Publication of WO2004041840A2 publication Critical patent/WO2004041840A2/en
Publication of WO2004041840A3 publication Critical patent/WO2004041840A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/13—Labelling of peptides
    • 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
    • C12Q1/37—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase involving peptidase or proteinase
    • 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
    • C12Q2337/00—N-linked chromogens for determinations of peptidases and proteinases
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2400/00—Assays, e.g. immunoassays or enzyme assays, involving carbohydrates
    • G01N2400/10—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • G01N2400/50—Lipopolysaccharides; LPS
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Immunology (AREA)
  • Physics & Mathematics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Peptides Or Proteins (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

The invention relates to a chemical compound of a general formula (I): X-A-B-C-L-CRS, wherein X is hydrogen or a protection group of amino-terminal groups which are routine for peptide chemistry; A and B are a α-, β-, or η-aminoacids containing from 2 to 15 C atoms, up to 4 N atoms, up to 2 S atoms and up to 6 O atoms, A and B can be identical or different, and B eventually being a peptide formed by said amino-acids; C is arginine, lysine, tyrosine, phenylalanine or tryptophan of the homologues respectively ; L is a linker forming a peptide liaison with C ; CRS is a combined cyclic carbon system linked to a L-C-B-A-X radical by means of a nitrogen atom. The inventive compound of said general formula (I) and CRS produce a maximum absorption having a wavelength equal to or higher than 550 nm.
PCT/EP2003/012463 2002-11-07 2003-11-07 Peptide-bound chromogens used for determining enzymatic activities Ceased WO2004041840A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003286158A AU2003286158A1 (en) 2002-11-07 2003-11-07 Peptide-bound chromogens used for determining enzymatic activities

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10251894.7 2002-11-07
DE10251894A DE10251894A1 (en) 2002-11-07 2002-11-07 New peptide-containing benzophenoxazine or napthoquinone derivatives, useful as chromogenic substrates for enzymes, e.g. for diagnosis, monitoring therapy and detecting pyrogens

Publications (2)

Publication Number Publication Date
WO2004041840A2 WO2004041840A2 (en) 2004-05-21
WO2004041840A3 true WO2004041840A3 (en) 2004-07-01

Family

ID=32115349

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/012463 Ceased WO2004041840A2 (en) 2002-11-07 2003-11-07 Peptide-bound chromogens used for determining enzymatic activities

Country Status (3)

Country Link
AU (1) AU2003286158A1 (en)
DE (1) DE10251894A1 (en)
WO (1) WO2004041840A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7671139B1 (en) 2004-06-18 2010-03-02 Bridgestone Corporation Functionalized polymers and tires made therefrom
FR2875242B1 (en) * 2004-09-10 2006-11-17 Biomerieux Sa NOVEL ENZYMATIC SUBSTRATES DERIVED FROM PHENOXAZINONE AND THEIR USE AS DEVELOPER IN THE DETECTION OF MICROORGANISMS WITH PEPTIDASE ACTIVITY
EP1674580A1 (en) * 2004-12-23 2006-06-28 F. Hoffmann-La Roche Ag Method for identifying activators and/or inhibitors of enzyme activity
EP2465941A1 (en) 2010-12-20 2012-06-20 Siemens Healthcare Diagnostics Products GmbH Method for simultaneous determination of multiple coagulation proteases

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0228666A2 (en) * 1986-01-06 1987-07-15 Orion Corporation Ltd Peptide substrates and method for the quantitative assay of endotoxin
US5097014A (en) * 1986-08-28 1992-03-17 Behringwerke Aktiengesellschaft Chromogenic tripeptides
US5175089A (en) * 1988-07-15 1992-12-29 The Trustees Of Columbia University In The City Of New York Method for monitoring periodontal disease by monitoring endotoxins and inflammatory agents
US5334703A (en) * 1989-12-12 1994-08-02 Chromonogenix Ab Chromogenic substrate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0228666A2 (en) * 1986-01-06 1987-07-15 Orion Corporation Ltd Peptide substrates and method for the quantitative assay of endotoxin
US5097014A (en) * 1986-08-28 1992-03-17 Behringwerke Aktiengesellschaft Chromogenic tripeptides
US5175089A (en) * 1988-07-15 1992-12-29 The Trustees Of Columbia University In The City Of New York Method for monitoring periodontal disease by monitoring endotoxins and inflammatory agents
US5334703A (en) * 1989-12-12 1994-08-02 Chromonogenix Ab Chromogenic substrate

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BERGER D ET AL: "QUANTITATIVE ENDOTOXIN DETERMINATION IN BLOOD CHROMOGENIC MODIFICATION OF THE LIMULUS AMOEBOCYTE LYSATE TEST", EUROPEAN SURGICAL RESEARCH, vol. 20, no. 2, 1988, pages 128 - 136, XP009030587, ISSN: 0014-312X *
SEILER K ET AL: "CHARACTERIZATION OF SODIUM-SELECTIVE OPTODE MEMBRANES BASED ON NEUTRAL LONOPHORES AND ASSAY OF SODIUM IN PLASMA", CLINICAL CHEMISTRY, AMERICAN ASSOCIATION FOR CLINICAL CHEMISTRY. WINSTON, US, vol. 37, no. 8, 1 August 1991 (1991-08-01), pages 1350 - 1355, XP000226105, ISSN: 0009-9147 *

Also Published As

Publication number Publication date
DE10251894A1 (en) 2004-05-19
AU2003286158A1 (en) 2004-06-07
AU2003286158A8 (en) 2004-06-07
WO2004041840A2 (en) 2004-05-21

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