A Model Study of Fecapentaenes: Mutagens of Bacterial Origin with Alkylating Properties
Fecapentaene-14 and -12 are directly acting mutagens that do not require metabolic activation. Their unusual structure suggests a possible mechanism of action. A carbocation that is formed by the addition of an electrophilic species (such as a proton) to the enol ether is most probably the reactive...
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| Veröffentlicht in: | Science (American Association for the Advancement of Science) 1984-08, Vol.225 (4661), p.521-523 |
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| creator | Gupta, Indranil Suzuki, Kunio Bruce, W. Robert Krepinsky, Jiri J. Yates, Peter |
| description | Fecapentaene-14 and -12 are directly acting mutagens that do not require metabolic activation. Their unusual structure suggests a possible mechanism of action. A carbocation that is formed by the addition of an electrophilic species (such as a proton) to the enol ether is most probably the reactive species. A series of model enol ethers with conjugated systems of various lengths was prepared, and a correlation between mutagenicity and increasing reactivity of derived carbocations was found. The glycerol moiety does not play a crucial role in the overall reactivity of the fecapentaenes. |
| doi_str_mv | 10.1126/science.6377497 |
| format | Article |
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The glycerol moiety does not play a crucial role in the overall reactivity of the fecapentaenes.</description><identifier>ISSN: 0036-8075</identifier><identifier>EISSN: 1095-9203</identifier><identifier>DOI: 10.1126/science.6377497</identifier><identifier>PMID: 6377497</identifier><identifier>CODEN: SCIEAS</identifier><language>eng</language><publisher>Washington, DC: The American Association for the Advancement of Science</publisher><subject>Aldehydes ; Alkylating Agents ; Analysis ; Biological and medical sciences ; Cancer ; Cancer research ; Chemical mutagenesis ; Colorectal diseases ; Diet ; Diet in disease ; Ethers ; Feces ; Gastrointestinal diseases ; Genetic research ; Health aspects ; Intestinal diseases ; Medical research ; Medical sciences ; Mutagenicity ; Mutagenicity Tests ; Mutagens ; Mutagens - toxicity ; Mutation ; Oncology, Experimental ; Polyenes - toxicity ; Reactivity ; Salmonella typhimurium - drug effects ; Structure-Activity Relationship ; Toxicology</subject><ispartof>Science (American Association for the Advancement of Science), 1984-08, Vol.225 (4661), p.521-523</ispartof><rights>Copyright 1984 The American Association for the Advancement of Science</rights><rights>1984 INIST-CNRS</rights><rights>COPYRIGHT 1984 American Association for the Advancement of Science</rights><rights>COPYRIGHT 1984 American Association for the Advancement of Science</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c640t-75dc75270f9ef898531ed392c6621d93e1ea55ed99049c313f583d87884d75ec3</citedby><cites>FETCH-LOGICAL-c640t-75dc75270f9ef898531ed392c6621d93e1ea55ed99049c313f583d87884d75ec3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/1694005$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/1694005$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>314,776,780,799,2871,2872,27901,27902,57992,58225</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9705978$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6377497$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gupta, Indranil</creatorcontrib><creatorcontrib>Suzuki, Kunio</creatorcontrib><creatorcontrib>Bruce, W. Robert</creatorcontrib><creatorcontrib>Krepinsky, Jiri J.</creatorcontrib><creatorcontrib>Yates, Peter</creatorcontrib><title>A Model Study of Fecapentaenes: Mutagens of Bacterial Origin with Alkylating Properties</title><title>Science (American Association for the Advancement of Science)</title><addtitle>Science</addtitle><description>Fecapentaene-14 and -12 are directly acting mutagens that do not require metabolic activation. Their unusual structure suggests a possible mechanism of action. A carbocation that is formed by the addition of an electrophilic species (such as a proton) to the enol ether is most probably the reactive species. A series of model enol ethers with conjugated systems of various lengths was prepared, and a correlation between mutagenicity and increasing reactivity of derived carbocations was found. The glycerol moiety does not play a crucial role in the overall reactivity of the fecapentaenes.</description><subject>Aldehydes</subject><subject>Alkylating Agents</subject><subject>Analysis</subject><subject>Biological and medical sciences</subject><subject>Cancer</subject><subject>Cancer research</subject><subject>Chemical mutagenesis</subject><subject>Colorectal diseases</subject><subject>Diet</subject><subject>Diet in disease</subject><subject>Ethers</subject><subject>Feces</subject><subject>Gastrointestinal diseases</subject><subject>Genetic research</subject><subject>Health aspects</subject><subject>Intestinal diseases</subject><subject>Medical research</subject><subject>Medical sciences</subject><subject>Mutagenicity</subject><subject>Mutagenicity Tests</subject><subject>Mutagens</subject><subject>Mutagens - toxicity</subject><subject>Mutation</subject><subject>Oncology, Experimental</subject><subject>Polyenes - toxicity</subject><subject>Reactivity</subject><subject>Salmonella typhimurium - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>Toxicology</subject><issn>0036-8075</issn><issn>1095-9203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1984</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqN0s9v0zAUB_AIgUY3OHMBKQcEh5HNjuM45tZVrEzqKNL4cbSM_RK8uXaxHY3-92RqtA2ph8oHS_5-7CfrvSx7hdEJxmV9GpUBp-CkJoxVnD3JJhhxWvASkafZBCFSFw1i9Hl2GOM1QkPGyUF2MPJJ9nOaX3oNNr9Kvd7kvs3PQck1uCTBQfyYX_ZJduDiXXQmVYJgpM2XwXTG5bcm_c6n9mZjZTKuy78Gv4aQDMQX2bNW2ggvx_0o-37-6dvsc7FYzi9m00Wh6gqlglGtGC0Zajm0DW8owaAJL1Vdl1hzAhgkpaA5RxVXBJOWNkQ3rGkqzSgocpS92767Dv5PDzGJlYkKrJUOfB8FrhBpWI0HeLyFnbQgjGt9ClINP4MgrXfQmuF4SgjjmPFBf9ihh6VhZdQO_v4_PogEf1Mn-xjFxdWXfeXyx77ybL6nbOaLx_J4l1TeWuhADJ2ZLR_r061WwccYoBXrYFYybARG4m76xDh9Yhyn4cabsRv9rxXoe_-Qvx1zGZW0bZBOmXjPOEOUs2Zgr7fsOiYfHqrWvEKIkn-2I-hv</recordid><startdate>19840803</startdate><enddate>19840803</enddate><creator>Gupta, Indranil</creator><creator>Suzuki, Kunio</creator><creator>Bruce, W. Robert</creator><creator>Krepinsky, Jiri J.</creator><creator>Yates, Peter</creator><general>The American Association for the Advancement of Science</general><general>American Association for the Advancement of Science</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>8GL</scope><scope>IBG</scope><scope>IOV</scope><scope>ISN</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>RC3</scope></search><sort><creationdate>19840803</creationdate><title>A Model Study of Fecapentaenes: Mutagens of Bacterial Origin with Alkylating Properties</title><author>Gupta, Indranil ; Suzuki, Kunio ; Bruce, W. Robert ; Krepinsky, Jiri J. ; Yates, Peter</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c640t-75dc75270f9ef898531ed392c6621d93e1ea55ed99049c313f583d87884d75ec3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1984</creationdate><topic>Aldehydes</topic><topic>Alkylating Agents</topic><topic>Analysis</topic><topic>Biological and medical sciences</topic><topic>Cancer</topic><topic>Cancer research</topic><topic>Chemical mutagenesis</topic><topic>Colorectal diseases</topic><topic>Diet</topic><topic>Diet in disease</topic><topic>Ethers</topic><topic>Feces</topic><topic>Gastrointestinal diseases</topic><topic>Genetic research</topic><topic>Health aspects</topic><topic>Intestinal diseases</topic><topic>Medical research</topic><topic>Medical sciences</topic><topic>Mutagenicity</topic><topic>Mutagenicity Tests</topic><topic>Mutagens</topic><topic>Mutagens - toxicity</topic><topic>Mutation</topic><topic>Oncology, Experimental</topic><topic>Polyenes - toxicity</topic><topic>Reactivity</topic><topic>Salmonella typhimurium - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>Toxicology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gupta, Indranil</creatorcontrib><creatorcontrib>Suzuki, Kunio</creatorcontrib><creatorcontrib>Bruce, W. 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Robert</au><au>Krepinsky, Jiri J.</au><au>Yates, Peter</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Model Study of Fecapentaenes: Mutagens of Bacterial Origin with Alkylating Properties</atitle><jtitle>Science (American Association for the Advancement of Science)</jtitle><addtitle>Science</addtitle><date>1984-08-03</date><risdate>1984</risdate><volume>225</volume><issue>4661</issue><spage>521</spage><epage>523</epage><pages>521-523</pages><issn>0036-8075</issn><eissn>1095-9203</eissn><coden>SCIEAS</coden><abstract>Fecapentaene-14 and -12 are directly acting mutagens that do not require metabolic activation. Their unusual structure suggests a possible mechanism of action. A carbocation that is formed by the addition of an electrophilic species (such as a proton) to the enol ether is most probably the reactive species. A series of model enol ethers with conjugated systems of various lengths was prepared, and a correlation between mutagenicity and increasing reactivity of derived carbocations was found. The glycerol moiety does not play a crucial role in the overall reactivity of the fecapentaenes.</abstract><cop>Washington, DC</cop><pub>The American Association for the Advancement of Science</pub><pmid>6377497</pmid><doi>10.1126/science.6377497</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0036-8075 |
| ispartof | Science (American Association for the Advancement of Science), 1984-08, Vol.225 (4661), p.521-523 |
| issn | 0036-8075 1095-9203 |
| language | eng |
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| source | American Association for the Advancement of Science; Jstor Complete Legacy; MEDLINE |
| subjects | Aldehydes Alkylating Agents Analysis Biological and medical sciences Cancer Cancer research Chemical mutagenesis Colorectal diseases Diet Diet in disease Ethers Feces Gastrointestinal diseases Genetic research Health aspects Intestinal diseases Medical research Medical sciences Mutagenicity Mutagenicity Tests Mutagens Mutagens - toxicity Mutation Oncology, Experimental Polyenes - toxicity Reactivity Salmonella typhimurium - drug effects Structure-Activity Relationship Toxicology |
| title | A Model Study of Fecapentaenes: Mutagens of Bacterial Origin with Alkylating Properties |
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