The identification of 3-methylcholanthrene-9,10-dihydrodiol as an intermediate in the binding of 3-methylcholanthrene to DNA in cells in culture
Two metabolites of 3-methylcholanthrene (3MC), previously shown to be precursors of the DNA-bound form of 3MC observed in embryo cells in culture, were prepared from 3MC by microsomal metabolism and isolated by high pressure liquid chromatography (HPLC). From HPLC analysis of the metabolites of 3MC,...
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| Veröffentlicht in: | Chemico-biological interactions 1978-03, Vol.20 (3), p.367-371 |
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| creator | King, H.W.S. Osborne, M.R. Brookes, P. |
| description | Two metabolites of 3-methylcholanthrene (3MC), previously shown to be precursors of the DNA-bound form of 3MC observed in embryo cells in culture, were prepared from 3MC by microsomal metabolism and isolated by high pressure liquid chromatography (HPLC). From HPLC analysis of the metabolites of 3MC, from mass spectrometric analysis and from comparison with the fluorescence spectra of all 5 possible dihydrodiols of the alkylated benzanthracenes, it was deduced that one of the precursor metabolites was a 9,10-dihydrodiol of 3MC while the other was a 1 or 2-hydroxy derivative thereof. |
| doi_str_mv | 10.1016/0009-2797(78)90114-X |
| format | Article |
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From HPLC analysis of the metabolites of 3MC, from mass spectrometric analysis and from comparison with the fluorescence spectra of all 5 possible dihydrodiols of the alkylated benzanthracenes, it was deduced that one of the precursor metabolites was a 9,10-dihydrodiol of 3MC while the other was a 1 or 2-hydroxy derivative thereof.</description><identifier>ISSN: 0009-2797</identifier><identifier>EISSN: 1872-7786</identifier><identifier>DOI: 10.1016/0009-2797(78)90114-X</identifier><identifier>PMID: 657396</identifier><language>eng</language><publisher>Ireland: Elsevier Ireland Ltd</publisher><subject>Animals ; Cells, Cultured ; Chemical Phenomena ; Chemistry ; DNA - metabolism ; Hydroxylation ; In Vitro Techniques ; Methylcholanthrene - metabolism ; Microsomes - metabolism ; Rats</subject><ispartof>Chemico-biological interactions, 1978-03, Vol.20 (3), p.367-371</ispartof><rights>1978</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-b993873adb40a16acaa70d9435c27de90a04e4fb3be7f3982ff4dabc93e8255e3</citedby><cites>FETCH-LOGICAL-c356t-b993873adb40a16acaa70d9435c27de90a04e4fb3be7f3982ff4dabc93e8255e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/000927977890114X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/657396$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>King, H.W.S.</creatorcontrib><creatorcontrib>Osborne, M.R.</creatorcontrib><creatorcontrib>Brookes, P.</creatorcontrib><title>The identification of 3-methylcholanthrene-9,10-dihydrodiol as an intermediate in the binding of 3-methylcholanthrene to DNA in cells in culture</title><title>Chemico-biological interactions</title><addtitle>Chem Biol Interact</addtitle><description>Two metabolites of 3-methylcholanthrene (3MC), previously shown to be precursors of the DNA-bound form of 3MC observed in embryo cells in culture, were prepared from 3MC by microsomal metabolism and isolated by high pressure liquid chromatography (HPLC). From HPLC analysis of the metabolites of 3MC, from mass spectrometric analysis and from comparison with the fluorescence spectra of all 5 possible dihydrodiols of the alkylated benzanthracenes, it was deduced that one of the precursor metabolites was a 9,10-dihydrodiol of 3MC while the other was a 1 or 2-hydroxy derivative thereof.</description><subject>Animals</subject><subject>Cells, Cultured</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>DNA - metabolism</subject><subject>Hydroxylation</subject><subject>In Vitro Techniques</subject><subject>Methylcholanthrene - metabolism</subject><subject>Microsomes - metabolism</subject><subject>Rats</subject><issn>0009-2797</issn><issn>1872-7786</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1978</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcFuFSEUhomx6m31DbpgZTQpFgZmGDZNmmqtSaObNumOMHDGwcyFCozJfYs-skxv052ugJz_fDl8B6FjRj8xyrpTSqkijVTyg-w_KsqYIHcv0Ib1siFS9t1LtHmOvEGHOf-qT9oI-hq96lrJVbdBDzcTYO8gFD96a4qPAccRc7KFMu1mO8XZhDIlCEDUCaPE-WnnUnQ-zthkbAL2oUDagvOmVFTApRIHH5wPP_-FwiXiz9_P17SFec6Pl2UuS4K36GA0c4Z3T-cRur38cnNxRa5_fP12cX5NLG-7QgaleC-5cYOghnXGGiOpU4K3tpEOFDVUgBgHPoAcueqbcRTODFZx6Ju2BX6E3u-59yn-XiAXvfV5HcYEiEvWUtBWdbyrQbEP2hRzTjDq--S3Ju00o3rdg14l61Wylr1-3IO-q23HT_xlqHKem_bia_lsX4b6xz8eks7WQ7BVYwJbtIv-__y_SDeZmg</recordid><startdate>197803</startdate><enddate>197803</enddate><creator>King, H.W.S.</creator><creator>Osborne, M.R.</creator><creator>Brookes, P.</creator><general>Elsevier Ireland Ltd</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>7X8</scope></search><sort><creationdate>197803</creationdate><title>The identification of 3-methylcholanthrene-9,10-dihydrodiol as an intermediate in the binding of 3-methylcholanthrene to DNA in cells in culture</title><author>King, H.W.S. ; Osborne, M.R. ; Brookes, P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-b993873adb40a16acaa70d9435c27de90a04e4fb3be7f3982ff4dabc93e8255e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1978</creationdate><topic>Animals</topic><topic>Cells, Cultured</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>DNA - metabolism</topic><topic>Hydroxylation</topic><topic>In Vitro Techniques</topic><topic>Methylcholanthrene - metabolism</topic><topic>Microsomes - metabolism</topic><topic>Rats</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>King, H.W.S.</creatorcontrib><creatorcontrib>Osborne, M.R.</creatorcontrib><creatorcontrib>Brookes, P.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chemico-biological interactions</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>King, H.W.S.</au><au>Osborne, M.R.</au><au>Brookes, P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The identification of 3-methylcholanthrene-9,10-dihydrodiol as an intermediate in the binding of 3-methylcholanthrene to DNA in cells in culture</atitle><jtitle>Chemico-biological interactions</jtitle><addtitle>Chem Biol Interact</addtitle><date>1978-03</date><risdate>1978</risdate><volume>20</volume><issue>3</issue><spage>367</spage><epage>371</epage><pages>367-371</pages><issn>0009-2797</issn><eissn>1872-7786</eissn><abstract>Two metabolites of 3-methylcholanthrene (3MC), previously shown to be precursors of the DNA-bound form of 3MC observed in embryo cells in culture, were prepared from 3MC by microsomal metabolism and isolated by high pressure liquid chromatography (HPLC). 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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Animals Cells, Cultured Chemical Phenomena Chemistry DNA - metabolism Hydroxylation In Vitro Techniques Methylcholanthrene - metabolism Microsomes - metabolism Rats |
| title | The identification of 3-methylcholanthrene-9,10-dihydrodiol as an intermediate in the binding of 3-methylcholanthrene to DNA in cells in culture |
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