title: Identification of the major adducts formed by reaction of benzo(a)pyrene diol epoxide with DNA in vitro.
abstract: Covalent binding of the benzo[a]pyrene metabolite (+/-)7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene to calf thymus DNA was investigated. Enzymatic hydrolysis of the carcinogen-modified DNA and subsequent separation via reversed-phase high-pressure liquid chromatography resulted in the detection and isolation of seven distinct products. High-resolution mass spectrometry indicates that these products are covalent adducts of deoxyguanosine, deoxyadenosine, and deoxycytidine. The deoxyguanosine and deoxyadenosine adducts involve binding between the activated hydrocarbon (benzo[a]pyrene diol epoxide) and exocyclic amino groups of the respective purines.
mesh_terms: D000225:Adenine; D000818:Animals; D001580:Benzopyrenes; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D003596:Cytosine; D004247:DNA; D004852:Epoxy Compounds; D006147:Guanine; D066298:In Vitro Techniques; D013058:Mass Spectrometry
chemical_list: D001580:Benzopyrenes; D004852:Epoxy Compounds; D006147:Guanine; D003596:Cytosine; D004247:DNA; D000225:Adenine
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