DK140385A - GLYCOSIDES OF RESORUFIN DERIVATIVES, PROCEDURES FOR PREPARING THEREOF, AND THEIR USE FOR DETERMINING THE ACTIVITY OF GLYCOSIDASES - Google Patents
GLYCOSIDES OF RESORUFIN DERIVATIVES, PROCEDURES FOR PREPARING THEREOF, AND THEIR USE FOR DETERMINING THE ACTIVITY OF GLYCOSIDASES Download PDFInfo
- Publication number
- DK140385A DK140385A DK140385A DK140385A DK140385A DK 140385 A DK140385 A DK 140385A DK 140385 A DK140385 A DK 140385A DK 140385 A DK140385 A DK 140385A DK 140385 A DK140385 A DK 140385A
- Authority
- DK
- Denmark
- Prior art keywords
- glycosides
- lower alkyl
- group
- hydrogen
- glycosidases
- Prior art date
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)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Microbiology (AREA)
- Physics & Mathematics (AREA)
- Saccharide Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Luminescent Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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.
Applications Claiming Priority (1)
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 |
Publications (2)
Publication Number | Publication Date |
---|---|
DK140385D0 DK140385D0 (en) | 1985-03-28 |
DK140385A true DK140385A (en) | 1985-09-30 |
Family
ID=6231957
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK140385A DK140385A (en) | 1984-03-29 | 1985-03-28 | GLYCOSIDES OF RESORUFIN DERIVATIVES, PROCEDURES FOR PREPARING THEREOF, AND THEIR USE FOR DETERMINING THE ACTIVITY OF GLYCOSIDASES |
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) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3412939A1 (en) * | 1984-04-06 | 1985-10-17 | Behringwerke Ag, 3550 Marburg | SUBSTRATES FOR HYDROLASES, METHOD FOR THEIR PRODUCTION AND THEIR USE |
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 |
DE3855790T2 (en) | 1987-04-10 | 1997-06-12 | Univ Southern Australia | Detection of ions in liquids |
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 |
TR201819563T4 (en) | 2015-01-09 | 2019-01-21 | Unilever Nv | Laundry treatment composition containing a dye. |
EP3932995A1 (en) | 2020-07-04 | 2022-01-05 | Emulseo SAS | Novel fluorescent substrates and uses thereof in microfluidics |
Family Cites Families (6)
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 |
-
1984
- 1984-03-29 DE DE19843411574 patent/DE3411574A1/en not_active Withdrawn
-
1985
- 1985-03-22 CS CS206485A patent/CS273162B2/en unknown
- 1985-03-25 AT AT85103496T patent/ATE66929T1/en not_active IP Right Cessation
- 1985-03-25 DE DE8585103496T patent/DE3583954D1/en not_active Expired - Lifetime
- 1985-03-25 EP EP85103496A patent/EP0156347B1/en not_active Expired - Lifetime
- 1985-03-26 AU AU40375/85A patent/AU550958B2/en not_active Ceased
- 1985-03-26 ES ES541589A patent/ES541589A0/en active Granted
- 1985-03-27 DD DD85274494A patent/DD235648A5/en not_active IP Right Cessation
- 1985-03-28 KR KR1019850002139A patent/KR870000699B1/en not_active IP Right Cessation
- 1985-03-28 FI FI851248A patent/FI81359C/en not_active IP Right Cessation
- 1985-03-28 DK DK140385A patent/DK140385A/en not_active Application Discontinuation
- 1985-03-28 ZA ZA852333A patent/ZA852333B/en unknown
- 1985-03-28 CA CA000477854A patent/CA1257253A/en not_active Expired
- 1985-03-28 SU SU853878797A patent/SU1487824A3/en active
- 1985-03-28 HU HU851183A patent/HU198734B/en not_active IP Right Cessation
- 1985-03-29 JP JP60064003A patent/JPS60218397A/en active Granted
-
1986
- 1986-06-17 DD DD86291381A patent/DD246120A5/en not_active IP Right Cessation
- 1986-06-24 SU SU864027681A patent/SU1574173A3/en active
-
1989
- 1989-08-07 JP JP1202971A patent/JPH02160771A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
DD235648A5 (en) | 1986-05-14 |
DE3583954D1 (en) | 1991-10-10 |
CA1257253A (en) | 1989-07-11 |
JPS60218397A (en) | 1985-11-01 |
KR850006427A (en) | 1985-10-05 |
JPH02160771A (en) | 1990-06-20 |
CS206485A2 (en) | 1990-07-12 |
ES8603192A1 (en) | 1985-12-16 |
ZA852333B (en) | 1985-12-24 |
JPH0579064B2 (en) | 1993-11-01 |
EP0156347A2 (en) | 1985-10-02 |
AU550958B2 (en) | 1986-04-10 |
KR870000699B1 (en) | 1987-04-07 |
AU4037585A (en) | 1985-10-03 |
ATE66929T1 (en) | 1991-09-15 |
FI851248L (en) | 1985-09-30 |
HUT38104A (en) | 1986-04-28 |
EP0156347B1 (en) | 1991-09-04 |
CS273162B2 (en) | 1991-03-12 |
DK140385D0 (en) | 1985-03-28 |
ES541589A0 (en) | 1985-12-16 |
FI81359B (en) | 1990-06-29 |
DE3411574A1 (en) | 1985-10-10 |
SU1574173A3 (en) | 1990-06-23 |
DD246120A5 (en) | 1987-05-27 |
FI851248A0 (en) | 1985-03-28 |
HU198734B (en) | 1989-11-28 |
EP0156347A3 (en) | 1988-01-13 |
SU1487824A3 (en) | 1989-06-15 |
JPH027589B2 (en) | 1990-02-19 |
FI81359C (en) | 1990-10-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AHB | Application shelved due to non-payment |