Inhibition of Aldose Reductase by 3', 4'-Dihydroxyflavones
A series of 3', 4'-dihydroxyflavones was assayed in vitro for inhibition of lens aldose reductase which has been implicated in the pathogenesis of sugar cataract. All the compounds tested were shown to be potent inhibitors of aldose reductase and 3', 4'-dihydroxy-5, 6, 7, 8-tetra...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1984/02/25, Vol.32(2), pp.767-772 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | OKUDA, JUN MIWA, ICHITOMO INAGAKI, KAZUHIRO HORIE, TOKUNARU NAKAYAMA, MITSURU |
| description | A series of 3', 4'-dihydroxyflavones was assayed in vitro for inhibition of lens aldose reductase which has been implicated in the pathogenesis of sugar cataract. All the compounds tested were shown to be potent inhibitors of aldose reductase and 3', 4'-dihydroxy-5, 6, 7, 8-tetra-methoxyflavone (lens aldose reductase inhibitor 4, LARI 4), the most potent one, inhibited the enzymes from rat and bovine lenses by 50% at 3.2×10-8 and 1.7×10-7M, respectively. Inhibition of the enzyme by 3', 4'-dihydroxyflavones was non-competitive with respect to both DL-glyceraldehyde and reduced form of nicotinamide adenine dinucleotide phosphate. The inhibitory activities of 3', 4'-dihydroxyflavones against lens aldose reductase were pH-dependent, being maximal around pH 7.0. |
| doi_str_mv | 10.1248/cpb.32.767 |
| format | Article |
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All the compounds tested were shown to be potent inhibitors of aldose reductase and 3', 4'-dihydroxy-5, 6, 7, 8-tetra-methoxyflavone (lens aldose reductase inhibitor 4, LARI 4), the most potent one, inhibited the enzymes from rat and bovine lenses by 50% at 3.2×10-8 and 1.7×10-7M, respectively. Inhibition of the enzyme by 3', 4'-dihydroxyflavones was non-competitive with respect to both DL-glyceraldehyde and reduced form of nicotinamide adenine dinucleotide phosphate. The inhibitory activities of 3', 4'-dihydroxyflavones against lens aldose reductase were pH-dependent, being maximal around pH 7.0.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.32.767</identifier><identifier>PMID: 6428761</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>3',4'-dihydroxyflavone ; Aldehyde Reductase - antagonists & inhibitors ; aldose reductase ; Animals ; Biological and medical sciences ; Cattle ; Eye ; eye lens ; Flavonoids - pharmacology ; In Vitro Techniques ; Kinetics ; Lens, Crystalline - enzymology ; Medical sciences ; Pharmacology. Drug treatments ; Rats ; Rats, Inbred Strains ; structure-activity relationship ; Sugar Alcohol Dehydrogenases - antagonists & inhibitors</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1984/02/25, Vol.32(2), pp.767-772</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1985 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c634t-6fdd638bc4ea12da9e825e158d4b95157774eecf5576c92db1419b3c3cb88d363</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9026784$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6428761$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>OKUDA, JUN</creatorcontrib><creatorcontrib>MIWA, ICHITOMO</creatorcontrib><creatorcontrib>INAGAKI, KAZUHIRO</creatorcontrib><creatorcontrib>HORIE, TOKUNARU</creatorcontrib><creatorcontrib>NAKAYAMA, MITSURU</creatorcontrib><title>Inhibition of Aldose Reductase by 3', 4'-Dihydroxyflavones</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A series of 3', 4'-dihydroxyflavones was assayed in vitro for inhibition of lens aldose reductase which has been implicated in the pathogenesis of sugar cataract. All the compounds tested were shown to be potent inhibitors of aldose reductase and 3', 4'-dihydroxy-5, 6, 7, 8-tetra-methoxyflavone (lens aldose reductase inhibitor 4, LARI 4), the most potent one, inhibited the enzymes from rat and bovine lenses by 50% at 3.2×10-8 and 1.7×10-7M, respectively. Inhibition of the enzyme by 3', 4'-dihydroxyflavones was non-competitive with respect to both DL-glyceraldehyde and reduced form of nicotinamide adenine dinucleotide phosphate. The inhibitory activities of 3', 4'-dihydroxyflavones against lens aldose reductase were pH-dependent, being maximal around pH 7.0.</description><subject>3',4'-dihydroxyflavone</subject><subject>Aldehyde Reductase - antagonists & inhibitors</subject><subject>aldose reductase</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cattle</subject><subject>Eye</subject><subject>eye lens</subject><subject>Flavonoids - pharmacology</subject><subject>In Vitro Techniques</subject><subject>Kinetics</subject><subject>Lens, Crystalline - enzymology</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Rats, Inbred Strains</subject><subject>structure-activity relationship</subject><subject>Sugar Alcohol Dehydrogenases - antagonists & inhibitors</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1984</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtrGzEURkVIcN0km-4LswgxlIyjtzTZGSdNAoFAadZCjzv1mPGMK41D_O8rY-Mus7m68B3uJw5C3wieEsr1rV-7KaNTJdUJGhPGVSkoZadojDGuSsok-4K-prTEmAqs2AiNJKdaSTJGd8_donHN0PRd0dfFrA19guIXhI0fbN7ctmCTm4JPyvtmsQ2x_9jWrX3vO0gX6Ky2bYLLw3uO3n4-_J4_lS-vj8_z2UvpJeNDKesQJNPOc7CEBluBpgKI0IG7ShChlOIAvhZCSV_R4AgnlWOeead1yH8_R9f7u-vY_91AGsyqSR7a1nbQb5LRhGQLQn8KEqZFJSXL4I896GOfUoTarGOzsnFrCDY7oyYbNYyabDTD3w9XN24F4YgeFOb86pDb5G1bR9v5Jh2xClOpNM_YfI8t02D_wDG3cWh8C7tGUgm9a6X7kcv_pwsbDXTsH-b9k60</recordid><startdate>19840101</startdate><enddate>19840101</enddate><creator>OKUDA, JUN</creator><creator>MIWA, ICHITOMO</creator><creator>INAGAKI, KAZUHIRO</creator><creator>HORIE, TOKUNARU</creator><creator>NAKAYAMA, MITSURU</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>C1K</scope><scope>7X8</scope></search><sort><creationdate>19840101</creationdate><title>Inhibition of Aldose Reductase by 3', 4'-Dihydroxyflavones</title><author>OKUDA, JUN ; MIWA, ICHITOMO ; INAGAKI, KAZUHIRO ; HORIE, TOKUNARU ; NAKAYAMA, MITSURU</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c634t-6fdd638bc4ea12da9e825e158d4b95157774eecf5576c92db1419b3c3cb88d363</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1984</creationdate><topic>3',4'-dihydroxyflavone</topic><topic>Aldehyde Reductase - antagonists & inhibitors</topic><topic>aldose reductase</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cattle</topic><topic>Eye</topic><topic>eye lens</topic><topic>Flavonoids - pharmacology</topic><topic>In Vitro Techniques</topic><topic>Kinetics</topic><topic>Lens, Crystalline - enzymology</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Rats, Inbred Strains</topic><topic>structure-activity relationship</topic><topic>Sugar Alcohol Dehydrogenases - antagonists & inhibitors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>OKUDA, JUN</creatorcontrib><creatorcontrib>MIWA, ICHITOMO</creatorcontrib><creatorcontrib>INAGAKI, KAZUHIRO</creatorcontrib><creatorcontrib>HORIE, TOKUNARU</creatorcontrib><creatorcontrib>NAKAYAMA, MITSURU</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Environmental Sciences and Pollution Management</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>OKUDA, JUN</au><au>MIWA, ICHITOMO</au><au>INAGAKI, KAZUHIRO</au><au>HORIE, TOKUNARU</au><au>NAKAYAMA, MITSURU</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibition of Aldose Reductase by 3', 4'-Dihydroxyflavones</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1984-01-01</date><risdate>1984</risdate><volume>32</volume><issue>2</issue><spage>767</spage><epage>772</epage><pages>767-772</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>A series of 3', 4'-dihydroxyflavones was assayed in vitro for inhibition of lens aldose reductase which has been implicated in the pathogenesis of sugar cataract. All the compounds tested were shown to be potent inhibitors of aldose reductase and 3', 4'-dihydroxy-5, 6, 7, 8-tetra-methoxyflavone (lens aldose reductase inhibitor 4, LARI 4), the most potent one, inhibited the enzymes from rat and bovine lenses by 50% at 3.2×10-8 and 1.7×10-7M, respectively. Inhibition of the enzyme by 3', 4'-dihydroxyflavones was non-competitive with respect to both DL-glyceraldehyde and reduced form of nicotinamide adenine dinucleotide phosphate. The inhibitory activities of 3', 4'-dihydroxyflavones against lens aldose reductase were pH-dependent, being maximal around pH 7.0.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>6428761</pmid><doi>10.1248/cpb.32.767</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1984/02/25, Vol.32(2), pp.767-772 |
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| language | eng |
| recordid | cdi_proquest_miscellaneous_81112458 |
| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 3',4'-dihydroxyflavone Aldehyde Reductase - antagonists & inhibitors aldose reductase Animals Biological and medical sciences Cattle Eye eye lens Flavonoids - pharmacology In Vitro Techniques Kinetics Lens, Crystalline - enzymology Medical sciences Pharmacology. Drug treatments Rats Rats, Inbred Strains structure-activity relationship Sugar Alcohol Dehydrogenases - antagonists & inhibitors |
| title | Inhibition of Aldose Reductase by 3', 4'-Dihydroxyflavones |
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