{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T22:18:02Z","timestamp":1759961882812},"reference-count":50,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2002,5,24]],"date-time":"2002-05-24T00:00:00Z","timestamp":1022198400000},"content-version":"vor","delay-in-days":143,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Environ and Mol Mutagen"],"published-print":{"date-parts":[[2002,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>DNA adducts formed in human uroepithelial cells (HUC) following exposure to <jats:italic>N<\/jats:italic>\u2010hydroxy\u20104\u2010aminobiphenyl (N\u2010OH\u2010ABP), the proximate metabolite of the human bladder carcinogen 4\u2010aminobiphenyl (ABP), were analyzed by the <jats:sup>32<\/jats:sup>P\u2010postlabeling method. Two adducts detected by <jats:sup>32<\/jats:sup>P\u2010postlabeling were previously identified as the 3\u2032,5\u2032\u2010bisphospho derivatives of <jats:italic>N<\/jats:italic>\u2010(deoxyguanosin\u20108\u2010yl)\u20104\u2010aminobiphenyl (dG\u2010C8\u2010ABP) and <jats:italic>N<\/jats:italic>\u2010(deoxyadenosin\u20108\u2010yl)\u20104\u2010aminobiphenyl (dA\u2010C8\u2010ABP) (Frederickson S et al. [1992] Carcinogenesis 13: 955\u2013961; Hatcher and Swaminathan [1995b] Carcinogenesis 16: 295\u2013301). In contrast to the dG\u2010C8\u2010ABP adduct, which was 3\u2032\u2010dephosphorylated by nuclease P1, dA\u2010C8\u2010ABP was resistant to nuclease P1, thus providing an enrichment step before postlabeling. Autoradiography of the two\u2010dimensional thin\u2010layer chromatogram of the postlabeled products obtained following nuclease P1 digestion revealed several minor adducts, one of which has been identified in the present study. Postlabeling analyses following nuclease P1 digestion of the products obtained from the reaction of <jats:italic>N<\/jats:italic>\u2010acetoxy\u20104\u2010aminobiphenyl with deoxyguanosine\u20103\u2032\u2010monophosphate (dGp) demonstrated the presence of this minor adduct. The 3\u2032\u2010monophosphate derivative of the adduct was subsequently chromatographically purified and subjected to spectroscopic analyses. Based on proton NMR and mass spectroscopic analyses of the synthetic product, the chemical structure of the adduct has been identified as <jats:italic>N<\/jats:italic>\u2010(deoxyguanosin\u2010<jats:italic>N<\/jats:italic><jats:sup>2<\/jats:sup>\u2010yl)\u20104\u2010azobiphenyl (dG\u2010N\uf8feN\u2010ABP). <jats:sup>32<\/jats:sup>P\u2010Postlabeling analysis of the nuclease P1\u2013enriched DNA hydrolysate of HUCs treated with N\u2010OH\u2010ABP or <jats:italic>N<\/jats:italic>\u2010hydroxy\u20104\u2010acetylaminobiphenyl (N\u2010OH\u2010AABP) showed the presence of the dG\u2010N\uf8feN\u2010ABP adduct. It was also detected in calf thymus DNA incubated with HUC cytosol and N\u2010OH\u2010ABP in the presence of acetyl\u2010CoA, or incubated with HUC microsomes and N\u2010OH\u2010AABP. These results demonstrate that in the target cells for ABP carcinogenesis in vivo, N\u2010OH\u2010ABP and N\u2010OH\u2010AABP are bioactivated by acyltransferases to reactive arylnitrenium ions that covalently interact at the N2 position of deoxyguanosine in DNA. Environ. Mol. Mutagen. 39:314\u2013322, 2002. \u00a9 2002 Wiley\u2010Liss, Inc.<\/jats:p>","DOI":"10.1002\/em.10079","type":"journal-article","created":{"date-parts":[[2002,10,6]],"date-time":"2002-10-06T12:21:52Z","timestamp":1033906912000},"page":"314-322","source":"Crossref","is-referenced-by-count":14,"title":["Identification of <i>N<\/i>\u2010(deoxyguanosin\u20108\u2010yl)\u20104\u2010azobiphenyl by <sup>32<\/sup>P\u2010postlabeling analyses of DNA in human uroepithelial cells exposed to proximate metabolites of the environmental carcinogen 4\u2010aminobiphenyl"],"prefix":"10.1002","volume":"39","author":[{"given":"James F.","family":"Hatcher","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Santhanam","family":"Swaminathan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2002,5,24]]},"reference":[{"key":"e_1_2_1_2_1","doi-asserted-by":"publisher","DOI":"10.1289\/ehp.8349125"},{"key":"e_1_2_1_3_1","first-page":"81","volume-title":"Mutation and environment","author":"Beland FA","year":"1990"},{"key":"e_1_2_1_4_1","first-page":"1615","article-title":"Induction of thioguanine\u2010resistant mutations in human uroepithelial cells by 4\u2010aminobiphenyl and its N\u2010hydroxy derivatives","volume":"52","author":"Bookland EA","year":"1992","journal-title":"Cancer Res"},{"key":"e_1_2_1_5_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.85.24.9788"},{"key":"e_1_2_1_6_1","first-page":"75","article-title":"Tumors of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. 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