AU550958B2 - Glycosides of resorufin derivatives - Google Patents

Glycosides of resorufin derivatives

Info

Publication number
AU550958B2
AU550958B2 AU40375/85A AU4037585A AU550958B2 AU 550958 B2 AU550958 B2 AU 550958B2 AU 40375/85 A AU40375/85 A AU 40375/85A AU 4037585 A AU4037585 A AU 4037585A AU 550958 B2 AU550958 B2 AU 550958B2
Authority
AU
Australia
Prior art keywords
glycosides
lower alkyl
group
hydrogen
oligosaccharide
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
AU40375/85A
Other versions
AU4037585A (en
Inventor
Hans-George Batz
Jurgen Hofmann
Christian Klein
Manfred Sernetz
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.)
Roche Diagnostics GmbH
Original Assignee
Boehringer Mannheim 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 Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH
Publication of AU4037585A publication Critical patent/AU4037585A/en
Application granted granted Critical
Publication of AU550958B2 publication Critical patent/AU550958B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/38—[b, e]-condensed with two six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • 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
    • 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
    • C12Q2334/00—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases
    • 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)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Immunology (AREA)
  • Biophysics (AREA)
  • Microbiology (AREA)
  • Analytical Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Saccharide Compounds (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Luminescent Compositions (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The glycosides of resorufin derivatives have the general formulae Ia and Ib <IMAGE> in which R<1> is hydrogen, R<2>, R<3> and R<5>, which can be identical or different, are hydrogen, halogen or a lower alkyl group, R<4> and R<6>, which can be identical or different, are hydrogen, halogen, a cyano, lower alkyl, lower alkoxy, carboxyl, lower alkoxycarbonyl, carboxy-lower alkyl, lower alkoxycarbonyl-lower alkyl or an optionally mono- or disubstituted carboxamide group or the group -COO-(CH2CH2O)n-R<7> in which R<7> is hydrogen or a lower alkyl group and n is an integer from 1 to 4, where R<6> can additionally be a sulphonyl or nitro group, and Y is a nitrogen or the group NO. These compounds are particularly suitable as chromogenic and fluorogenic substrates for determining the activity of corresponding glycosidases or oligosaccharide-cleaving enzymes. The glycosides are obtained by reacting resorufin derivatives with a mono- or oligosaccharide or a 1-halogeno derivative thereof, whose hydroxyl groups are substituted by customary protective groups. This initially results in per-O-substituted glycosides, which can be converted into the claimed compounds by elimination of the protective groups. The glycosides are used as chromogenic and fluorogenic substrates in diagnostic agents for detecting glycosidases or oligosaccharide-cleaving enzymes. The resorufin derivatives employed as starting materials in the preparation of the compounds are also claimed.
AU40375/85A 1984-03-29 1985-03-26 Glycosides of resorufin derivatives Ceased AU550958B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843411574 DE3411574A1 (en) 1984-03-29 1984-03-29 GLYCOSIDES OF RESORUFIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THE USE THEREOF FOR DETERMINING THE ACTIVITY OF GLYCOSIDASES
DE3411574 1984-03-29

Publications (2)

Publication Number Publication Date
AU4037585A AU4037585A (en) 1985-10-03
AU550958B2 true AU550958B2 (en) 1986-04-10

Family

ID=6231957

Family Applications (1)

Application Number Title Priority Date Filing Date
AU40375/85A Ceased AU550958B2 (en) 1984-03-29 1985-03-26 Glycosides of resorufin derivatives

Country Status (15)

Country Link
EP (1) EP0156347B1 (en)
JP (2) JPS60218397A (en)
KR (1) KR870000699B1 (en)
AT (1) ATE66929T1 (en)
AU (1) AU550958B2 (en)
CA (1) CA1257253A (en)
CS (1) CS273162B2 (en)
DD (2) DD235648A5 (en)
DE (2) DE3411574A1 (en)
DK (1) DK140385A (en)
ES (1) ES541589A0 (en)
FI (1) FI81359C (en)
HU (1) HU198734B (en)
SU (2) SU1487824A3 (en)
ZA (1) ZA852333B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU596072B2 (en) * 1984-04-06 1990-04-26 Ahmed Morhaf Fathy Substrates for hydrolases, a method for their preparation and their use

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3534927A1 (en) * 1985-10-01 1987-04-02 Boehringer Mannheim Gmbh PHOSPHATES OF RESORUFIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR DETERMINING THE ACTIVITY OF PHOSPHATASES
DE3629175A1 (en) * 1986-08-28 1988-03-17 Behringwerke Ag CHROMOGENIC COMPOUNDS, METHOD FOR THEIR PRODUCTION AND THEIR USE
US4810636A (en) * 1986-12-09 1989-03-07 Miles Inc. Chromogenic acridinone enzyme substrates
DE3644401A1 (en) * 1986-12-24 1988-07-07 Boehringer Mannheim Gmbh NEW HYDROLASE SUBSTRATES
HUT51677A (en) 1987-04-10 1990-05-28 Univ Southern Australia Process for quantitative determination of ion solutions
DE3732871A1 (en) * 1987-09-30 1989-04-20 Behringwerke Ag CHROMOGENEOUS SUBSTRATES
US4932871A (en) * 1987-11-20 1990-06-12 Miles Inc. Rapid method for preparing chromogenic alpha-amylase substrate compounds at high preparative yields
DE3743908A1 (en) * 1987-12-23 1989-07-06 Boehringer Mannheim Gmbh NEW OLIGOGLUCOSIDE
JPH01211595A (en) * 1988-02-18 1989-08-24 Kikkoman Corp Novel n-acetyl-beta-d-glucosamine derivative, production thereof and utilization thereof to reagent for measuring n-acetyl-beta-d-glucosamidase activity
US5151348A (en) * 1988-12-23 1992-09-29 E. I. Du Pont De Nemours And Company Enzyme-linked immunoassay for measurement of cyclosporin a levels in whole blood samples
US5104980A (en) * 1989-06-12 1992-04-14 Miles Inc. Chromogenic dibenzoxazepinone and dibenzothiazepinone enzyme substrates
KR100710561B1 (en) * 2000-07-12 2007-04-24 에스케이 주식회사 Silent mark for oil product and detection method thereto
WO2002100843A1 (en) * 2001-06-13 2002-12-19 Jianqing Lu Phenoxazine compounds, the compositions containing them and their medicinal uses
FR2854893B1 (en) * 2003-05-13 2006-07-07 Biomerieux Sa NOVEL ENZYMATIC SUBSTRATES DERIVED FROM PHENOXAZINONE AND THEIR USE AS DEVELOPER IN THE DETECTION OF MICROORGANISMS WITH PEPTIDASE ACTIVITY
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
WO2016110378A1 (en) 2015-01-09 2016-07-14 Unilever Plc Laundry treatment composition comprising a dye
EP3932995A1 (en) 2020-07-04 2022-01-05 Emulseo SAS Novel fluorescent substrates and uses thereof in microfluidics

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3378463A (en) * 1965-06-22 1968-04-16 Army Usa Method of measuring enzyme activity
US3391104A (en) * 1966-11-14 1968-07-02 Eastman Kodak Co Light stabilized, poly-alpha-olefin plastic composition
US3950322A (en) * 1973-08-27 1976-04-13 Research Corporation Fluorogenic substrate glycosides
DE2752501A1 (en) * 1977-11-24 1979-05-31 Kurt Prof Dr Wallenfels Alpha-d-malto:dextrin derivs. as indicators - for colorimetric analysis of amylase(s)
US4406832A (en) * 1981-09-03 1983-09-27 Mallinckrodt, Inc. Peptide-type substrates useful in the quantitative determination of endotoxin
NZ206795A (en) * 1983-01-21 1987-08-31 Merck Frosst Canada Inc Phenothiazines, analogues and pharmaceutical compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU596072B2 (en) * 1984-04-06 1990-04-26 Ahmed Morhaf Fathy Substrates for hydrolases, a method for their preparation and their use

Also Published As

Publication number Publication date
DD235648A5 (en) 1986-05-14
EP0156347A2 (en) 1985-10-02
EP0156347B1 (en) 1991-09-04
FI81359C (en) 1990-10-10
CS206485A2 (en) 1990-07-12
ES8603192A1 (en) 1985-12-16
JPH02160771A (en) 1990-06-20
SU1574173A3 (en) 1990-06-23
EP0156347A3 (en) 1988-01-13
DE3411574A1 (en) 1985-10-10
HUT38104A (en) 1986-04-28
DE3583954D1 (en) 1991-10-10
DK140385A (en) 1985-09-30
KR850006427A (en) 1985-10-05
CA1257253A (en) 1989-07-11
DD246120A5 (en) 1987-05-27
FI851248A0 (en) 1985-03-28
HU198734B (en) 1989-11-28
AU4037585A (en) 1985-10-03
FI851248L (en) 1985-09-30
JPS60218397A (en) 1985-11-01
ZA852333B (en) 1985-12-24
DK140385D0 (en) 1985-03-28
ES541589A0 (en) 1985-12-16
SU1487824A3 (en) 1989-06-15
JPH027589B2 (en) 1990-02-19
ATE66929T1 (en) 1991-09-15
CS273162B2 (en) 1991-03-12
FI81359B (en) 1990-06-29
KR870000699B1 (en) 1987-04-07
JPH0579064B2 (en) 1993-11-01

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