Peroxidase-Like Catalytic Activity of Anion-Exchange Resins Modified with Metal-Porphyrins in Oxidative Reaction of Hetrocyclic Amines with Hydrogen Peroxide
To elucidate the peroxidase (POD)-like catalytic activity of anion-exchange resins modified with metal-tetrakis(sulfophenyl)porphine (M-TSPPrs), an oxidative reaction of seven mutagenic heterocyclic amines (HCAs) with hydrogen peroxide, which reaction is catalyzed by horse radish POD, was investigat...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2005, Vol.53(8), pp.1006-1010 |
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| creator | Mifune, Masaki Hino, Daiki Sugita, Hikaru Iwado, Akimasa Kitamura, Youji Motohashi, Noriko Tsukamoto, Ikuko Saito, Yutaka |
| description | To elucidate the peroxidase (POD)-like catalytic activity of anion-exchange resins modified with metal-tetrakis(sulfophenyl)porphine (M-TSPPrs), an oxidative reaction of seven mutagenic heterocyclic amines (HCAs) with hydrogen peroxide, which reaction is catalyzed by horse radish POD, was investigated in the presence of M-TSPPrs. Among six M-TSPPrs tested, Mn- and Fe-TSPPrs were found to have a relatively strong POD-like activity for HCAs, in particular for a typical HCA, 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ). The optimal condition for the POD-like activity was selected using Fe- and Mn-TSPPrs. For evaluation of an oxidation product of IQ produced in the presence of Fe-TSPPr, the absorption, NMR and FAB-mass spectra thereof were compared with those of an oxidation product of IQ produced by horse radish POD or a chemical oxidizing agent, sodium hypochlorite. When Fe-TSPPr was present as a catalysts, IQ was converted into the dimmer (hydorazone type) which has no mutagenic activity in umu-test. It was revealed that Fe- and Mn-TSPPrs exhibit a POD-like catalytic activity in oxidative reaction of HCAs with hydrogen peroxide. |
| doi_str_mv | 10.1248/cpb.53.1006 |
| format | Article |
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Among six M-TSPPrs tested, Mn- and Fe-TSPPrs were found to have a relatively strong POD-like activity for HCAs, in particular for a typical HCA, 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ). The optimal condition for the POD-like activity was selected using Fe- and Mn-TSPPrs. For evaluation of an oxidation product of IQ produced in the presence of Fe-TSPPr, the absorption, NMR and FAB-mass spectra thereof were compared with those of an oxidation product of IQ produced by horse radish POD or a chemical oxidizing agent, sodium hypochlorite. When Fe-TSPPr was present as a catalysts, IQ was converted into the dimmer (hydorazone type) which has no mutagenic activity in umu-test. It was revealed that Fe- and Mn-TSPPrs exhibit a POD-like catalytic activity in oxidative reaction of HCAs with hydrogen peroxide.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.53.1006</identifier><identifier>PMID: 16079536</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Amines - chemistry ; Amines - toxicity ; Anion Exchange Resins - chemistry ; Catalysis ; Heterocyclic Compounds - chemistry ; hetrocyclic amine ; Hydrogen Peroxide - chemistry ; metal-porphyrin ; Methanol - chemistry ; Mutagenicity Tests ; Oxidation-Reduction ; oxidative reaction ; peroxidase-like activity ; Porphyrins - chemistry ; Salmonella typhimurium - genetics ; Spectrophotometry, Ultraviolet</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2005, Vol.53(8), pp.1006-1010</ispartof><rights>2005 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2005</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c499t-a651c1de6e5ff31427de425058a8bc127f5419ee26da5b417c9e4ae282a939ed3</citedby><cites>FETCH-LOGICAL-c499t-a651c1de6e5ff31427de425058a8bc127f5419ee26da5b417c9e4ae282a939ed3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16079536$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mifune, Masaki</creatorcontrib><creatorcontrib>Hino, Daiki</creatorcontrib><creatorcontrib>Sugita, Hikaru</creatorcontrib><creatorcontrib>Iwado, Akimasa</creatorcontrib><creatorcontrib>Kitamura, Youji</creatorcontrib><creatorcontrib>Motohashi, Noriko</creatorcontrib><creatorcontrib>Tsukamoto, Ikuko</creatorcontrib><creatorcontrib>Saito, Yutaka</creatorcontrib><title>Peroxidase-Like Catalytic Activity of Anion-Exchange Resins Modified with Metal-Porphyrins in Oxidative Reaction of Hetrocyclic Amines with Hydrogen Peroxide</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>To elucidate the peroxidase (POD)-like catalytic activity of anion-exchange resins modified with metal-tetrakis(sulfophenyl)porphine (M-TSPPrs), an oxidative reaction of seven mutagenic heterocyclic amines (HCAs) with hydrogen peroxide, which reaction is catalyzed by horse radish POD, was investigated in the presence of M-TSPPrs. Among six M-TSPPrs tested, Mn- and Fe-TSPPrs were found to have a relatively strong POD-like activity for HCAs, in particular for a typical HCA, 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ). The optimal condition for the POD-like activity was selected using Fe- and Mn-TSPPrs. For evaluation of an oxidation product of IQ produced in the presence of Fe-TSPPr, the absorption, NMR and FAB-mass spectra thereof were compared with those of an oxidation product of IQ produced by horse radish POD or a chemical oxidizing agent, sodium hypochlorite. When Fe-TSPPr was present as a catalysts, IQ was converted into the dimmer (hydorazone type) which has no mutagenic activity in umu-test. It was revealed that Fe- and Mn-TSPPrs exhibit a POD-like catalytic activity in oxidative reaction of HCAs with hydrogen peroxide.</description><subject>Amines - chemistry</subject><subject>Amines - toxicity</subject><subject>Anion Exchange Resins - chemistry</subject><subject>Catalysis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>hetrocyclic amine</subject><subject>Hydrogen Peroxide - chemistry</subject><subject>metal-porphyrin</subject><subject>Methanol - chemistry</subject><subject>Mutagenicity Tests</subject><subject>Oxidation-Reduction</subject><subject>oxidative reaction</subject><subject>peroxidase-like activity</subject><subject>Porphyrins - chemistry</subject><subject>Salmonella typhimurium - genetics</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkU1vEzEQhi0EoqFw4o4scUQb_LkfN6KoEKRUrRCcLceeTRwSO9hO6f4Y_itebaAX-zDPPGPPi9BbSuaUifajOW3mks8pIfUzNKNcNJVkjD9HM0JIVzFe8yv0KqU9IUyShr9EV7QmTSd5PUN_7iGGR2d1gmrtfgJe6qwPQ3YGL0x2Dy4POPR44V3w1c2j2Wm_BfwNkvMJ3wbregcW_3Z5h2-hdFb3IZ52QxzLzuO7UV00Y4suvuBH2wpyDGYwh3HK0XlIk2E12Bi24PHlUfAavej1IcGby32Nfny--b5cVeu7L1-Xi3VlRNflSteSGmqhBtn3nArWWBDlr7LV7cZQ1vRS0A6A1VbLjaCN6UBoYC3THe_A8mv0fvKeYvh1hpTVPpyjLyMVFTXhbSN4U6gPE2ViSClCr07RHXUcFCVqjEKVKJTkaoyi0O8uzvPmCPaJvey-AJ8mYJ-y3sJ_QMey_QP8k7XTMTqfSjsdFXj-F3XNni0</recordid><startdate>20050801</startdate><enddate>20050801</enddate><creator>Mifune, Masaki</creator><creator>Hino, Daiki</creator><creator>Sugita, Hikaru</creator><creator>Iwado, Akimasa</creator><creator>Kitamura, Youji</creator><creator>Motohashi, Noriko</creator><creator>Tsukamoto, Ikuko</creator><creator>Saito, Yutaka</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>20050801</creationdate><title>Peroxidase-Like Catalytic Activity of Anion-Exchange Resins Modified with Metal-Porphyrins in Oxidative Reaction of Hetrocyclic Amines with Hydrogen Peroxide</title><author>Mifune, Masaki ; Hino, Daiki ; Sugita, Hikaru ; Iwado, Akimasa ; Kitamura, Youji ; Motohashi, Noriko ; Tsukamoto, Ikuko ; Saito, Yutaka</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c499t-a651c1de6e5ff31427de425058a8bc127f5419ee26da5b417c9e4ae282a939ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Amines - chemistry</topic><topic>Amines - toxicity</topic><topic>Anion Exchange Resins - chemistry</topic><topic>Catalysis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>hetrocyclic amine</topic><topic>Hydrogen Peroxide - chemistry</topic><topic>metal-porphyrin</topic><topic>Methanol - chemistry</topic><topic>Mutagenicity Tests</topic><topic>Oxidation-Reduction</topic><topic>oxidative reaction</topic><topic>peroxidase-like activity</topic><topic>Porphyrins - chemistry</topic><topic>Salmonella typhimurium - genetics</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mifune, Masaki</creatorcontrib><creatorcontrib>Hino, Daiki</creatorcontrib><creatorcontrib>Sugita, Hikaru</creatorcontrib><creatorcontrib>Iwado, Akimasa</creatorcontrib><creatorcontrib>Kitamura, Youji</creatorcontrib><creatorcontrib>Motohashi, Noriko</creatorcontrib><creatorcontrib>Tsukamoto, Ikuko</creatorcontrib><creatorcontrib>Saito, Yutaka</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mifune, Masaki</au><au>Hino, Daiki</au><au>Sugita, Hikaru</au><au>Iwado, Akimasa</au><au>Kitamura, Youji</au><au>Motohashi, Noriko</au><au>Tsukamoto, Ikuko</au><au>Saito, Yutaka</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Peroxidase-Like Catalytic Activity of Anion-Exchange Resins Modified with Metal-Porphyrins in Oxidative Reaction of Hetrocyclic Amines with Hydrogen Peroxide</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2005-08-01</date><risdate>2005</risdate><volume>53</volume><issue>8</issue><spage>1006</spage><epage>1010</epage><pages>1006-1010</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>To elucidate the peroxidase (POD)-like catalytic activity of anion-exchange resins modified with metal-tetrakis(sulfophenyl)porphine (M-TSPPrs), an oxidative reaction of seven mutagenic heterocyclic amines (HCAs) with hydrogen peroxide, which reaction is catalyzed by horse radish POD, was investigated in the presence of M-TSPPrs. Among six M-TSPPrs tested, Mn- and Fe-TSPPrs were found to have a relatively strong POD-like activity for HCAs, in particular for a typical HCA, 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ). The optimal condition for the POD-like activity was selected using Fe- and Mn-TSPPrs. For evaluation of an oxidation product of IQ produced in the presence of Fe-TSPPr, the absorption, NMR and FAB-mass spectra thereof were compared with those of an oxidation product of IQ produced by horse radish POD or a chemical oxidizing agent, sodium hypochlorite. When Fe-TSPPr was present as a catalysts, IQ was converted into the dimmer (hydorazone type) which has no mutagenic activity in umu-test. It was revealed that Fe- and Mn-TSPPrs exhibit a POD-like catalytic activity in oxidative reaction of HCAs with hydrogen peroxide.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>16079536</pmid><doi>10.1248/cpb.53.1006</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Amines - chemistry Amines - toxicity Anion Exchange Resins - chemistry Catalysis Heterocyclic Compounds - chemistry hetrocyclic amine Hydrogen Peroxide - chemistry metal-porphyrin Methanol - chemistry Mutagenicity Tests Oxidation-Reduction oxidative reaction peroxidase-like activity Porphyrins - chemistry Salmonella typhimurium - genetics Spectrophotometry, Ultraviolet |
| title | Peroxidase-Like Catalytic Activity of Anion-Exchange Resins Modified with Metal-Porphyrins in Oxidative Reaction of Hetrocyclic Amines with Hydrogen Peroxide |
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