Mutagenicity of thionitrites in the ames test: the biological activity of thiyl free radicals

Thiols, such as glutathione and cysteine, are mutagenic in the Ames test, using Salmonella typhimurium strain TA 100 and rat kidney S-9 preparation [Glatt et al. Science 220, (1983)]. Formation of thiyl free radicals, RS., has been implicated in this effect. We have prepared thionitrite (nitrosylmer...

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Veröffentlicht in:	Biochemical pharmacology 1986-11, Vol.35 (21), p.3847-3851
Hauptverfasser:	CARTER, M. H, JOSEPHY, P. D
Format:	Artikel
Sprache:	eng
Schlagworte:	Biological and medical sciences Chemical mutagenesis Medical sciences Mutagenicity Tests Nitrites - toxicity Salmonella typhimurium - drug effects Sulfhydryl Compounds - toxicity Toxicology
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container_title	Biochemical pharmacology
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creator	CARTER, M. H JOSEPHY, P. D
description	Thiols, such as glutathione and cysteine, are mutagenic in the Ames test, using Salmonella typhimurium strain TA 100 and rat kidney S-9 preparation [Glatt et al. Science 220, (1983)]. Formation of thiyl free radicals, RS., has been implicated in this effect. We have prepared thionitrite (nitrosylmercaptan) derivatives of glutathione and other thiols. These unstable derivatives decompose by homolysis, yielding RS. radicals. Glutathione thionitrite is mutagenic to strains TA 100 and TA 102, in the absence of activation by mammalian S-9 preparations. We suggest that this mutagenicity is evidence for the role of thiyl free radicals as biological reactive intermediates. Since alkyl nitrites readily convert thiols to thionitrites, our findings have implications for the toxicology of nitrosating drugs, such as amyl nitrite.
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Since alkyl nitrites readily convert thiols to thionitrites, our findings have implications for the toxicology of nitrosating drugs, such as amyl nitrite.</description><identifier>ISSN: 0006-2952</identifier><identifier>EISSN: 1873-2968</identifier><identifier>DOI: 10.1016/0006-2952(86)90674-X</identifier><identifier>PMID: 3535804</identifier><identifier>CODEN: BCPCA6</identifier><language>eng</language><publisher>New York, NY: Elsevier Science</publisher><subject>Biological and medical sciences ; Chemical mutagenesis ; Medical sciences ; Mutagenicity Tests ; Nitrites - toxicity ; Salmonella typhimurium - drug effects ; Sulfhydryl Compounds - toxicity ; Toxicology</subject><ispartof>Biochemical pharmacology, 1986-11, Vol.35 (21), p.3847-3851</ispartof><rights>1987 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8254819$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3535804$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>CARTER, M. H</creatorcontrib><creatorcontrib>JOSEPHY, P. D</creatorcontrib><title>Mutagenicity of thionitrites in the ames test: the biological activity of thiyl free radicals</title><title>Biochemical pharmacology</title><addtitle>Biochem Pharmacol</addtitle><description>Thiols, such as glutathione and cysteine, are mutagenic in the Ames test, using Salmonella typhimurium strain TA 100 and rat kidney S-9 preparation [Glatt et al. Science 220, (1983)]. Formation of thiyl free radicals, RS., has been implicated in this effect. We have prepared thionitrite (nitrosylmercaptan) derivatives of glutathione and other thiols. These unstable derivatives decompose by homolysis, yielding RS. radicals. Glutathione thionitrite is mutagenic to strains TA 100 and TA 102, in the absence of activation by mammalian S-9 preparations. We suggest that this mutagenicity is evidence for the role of thiyl free radicals as biological reactive intermediates. Since alkyl nitrites readily convert thiols to thionitrites, our findings have implications for the toxicology of nitrosating drugs, such as amyl nitrite.</description><subject>Biological and medical sciences</subject><subject>Chemical mutagenesis</subject><subject>Medical sciences</subject><subject>Mutagenicity Tests</subject><subject>Nitrites - toxicity</subject><subject>Salmonella typhimurium - drug effects</subject><subject>Sulfhydryl Compounds - toxicity</subject><subject>Toxicology</subject><issn>0006-2952</issn><issn>1873-2968</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1986</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE1LxDAQhoMo67r6DxR6ENFDNWm-vcniF6x4UfAiJW0na6Qfa5MK--_NallPM8-87wwzg9AxwZcEE3GFMRZppnl2rsSFxkKy9G0HTYmSNJaF2kXTrWUfHXj_uUElyARNKKdcYTZF709DMEtoXenCOulsEj5c17rQuwA-cW1kSEwT88jh-hcL19Xd0pWmTkwZ3Pd_57pObA-Q9KbayP4Q7dkY4GiMM_R6d_syf0gXz_eP85tFusqECKnSVAoOzBayAmE0hyrLtKamqkAyVlhOjJQEirLE1HJGMSiaMY0Lia0Shs7Q2d_cVd99DXHRvHG-hLo2LXSDzwkTShLJo_FkNA5FA1W-6l1j-nU-_iPqp6NufDzA9qYtnd_aVMaZIpr-AMNkcFA</recordid><startdate>19861101</startdate><enddate>19861101</enddate><creator>CARTER, M. 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D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p266t-893765e4fb7de6a95ed22993adde744bf51a771ebcc03f5430e832490b70f86a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1986</creationdate><topic>Biological and medical sciences</topic><topic>Chemical mutagenesis</topic><topic>Medical sciences</topic><topic>Mutagenicity Tests</topic><topic>Nitrites - toxicity</topic><topic>Salmonella typhimurium - drug effects</topic><topic>Sulfhydryl Compounds - toxicity</topic><topic>Toxicology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>CARTER, M. H</creatorcontrib><creatorcontrib>JOSEPHY, P. 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Glutathione thionitrite is mutagenic to strains TA 100 and TA 102, in the absence of activation by mammalian S-9 preparations. We suggest that this mutagenicity is evidence for the role of thiyl free radicals as biological reactive intermediates. Since alkyl nitrites readily convert thiols to thionitrites, our findings have implications for the toxicology of nitrosating drugs, such as amyl nitrite.</abstract><cop>New York, NY</cop><pub>Elsevier Science</pub><pmid>3535804</pmid><doi>10.1016/0006-2952(86)90674-X</doi><tpages>5</tpages></addata></record>
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subjects	Biological and medical sciences Chemical mutagenesis Medical sciences Mutagenicity Tests Nitrites - toxicity Salmonella typhimurium - drug effects Sulfhydryl Compounds - toxicity Toxicology
title	Mutagenicity of thionitrites in the ames test: the biological activity of thiyl free radicals
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