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  • ENVIRONMENTAL CONTAMINANT 3-NITROBENZANTHRONE  (1)
  • METABOLIC-ACTIVATION  (1)
  • 1
    Keywords: IN-VITRO ; human ; IN-VIVO ; LUNG ; VITRO ; SYSTEM ; DNA adducts ; TISSUE ; MICE ; DNA ; 3-aminobenzanthrone ; 3-nitrobenzanthrone ; CARCINOGENESIS ; DIESEL EXHAUST ; ENVIRONMENTAL CONTAMINANT 3-NITROBENZANTHRONE ; POSTLABELING ANALYSIS ; RAT ; RATS ; TISSUES ; METABOLITES ; IDENTIFICATION ; HUMAN ACETYLTRANSFERASES ; METABOLIC-ACTIVATION ; MUTAGENICITY ; rodent ; PERFORMANCE LIQUID-CHROMATOGRAPHY ; SURFACE SOIL ; V79 CELLS ; RE ; air pollution ; ENZYME ; P-32-postlabeling ; in vivo ; DEOXYGUANOSINE ; LIQUID ; P-32-POSTLABELING ANALYSIS ; xanthine oxidase
    Abstract: 3-Nitrobenzanthrone (3-NBA) is a potent mutagen and potential human carcinogen identified in diesel exhaust and ambient air particulate matter. Previously, we detected the formation of 3-NBA-derived DNA adducts in rodent tissues by P-32-postlabeling, all of which are derived from reductive metabolites of 3-NBA bound to purine bases, but structural identification of these adducts has not yet been reported. We have now prepared 3-NBA-derived DNA adduct standards for P-32-postlabeling by reacting N-acetoxy-3-aminobenzanthrone (N-Aco-ABA) with purine nucleotides. Three deoxyguanosine (dG) adducts have been characterised as N-(2'-deoxy-guanosin-8-yl)-3-aminobenzanthrone-3'-phosphate (dG3'p-C8-N-ABA), 2-(2'-deoxyguanosin-N-2 -yl)-3-aminobenzanthrone-3'-phosphate (dG3'p-N-2-ABA) and 2-2'-(deoxygtianosin-8-yl)-3-aminobenzanthrone-3'-phosphate (dG3'p-C8-C2-ABA), and a deoxyadenosine (dA) adduct was characterised as 2-(2'-deoxyadenosm-N-6-yl)-3-aminobenzanthrone-3'-phosphate (dA3'p-N-6-ABA). 3-NBA-derived DNA adducts formed experimentally in vivo and in vitro were compared with the chemically synthesised adducts. The major 3-NBA-derived DNA adduct formed in rat lung cochromatographed with dG3'p-N-2-ABA in two independent systems (thin layer and high-performance liquid chromatography). This is also the major adduct formed in tissue of rats or mice treated with 3-aminobenzanthrone (3-ABA), the major human metabolite of 3-NBA. Similarly, dG3'p-C8-N-ABA and dA3'p-N-6-ABA cochromatographed with two other adducts formed in various organs of rats or mice treated either with 3-NBA or 3-ABA, whereas dG3'p-C8-C2-ABA did not cochromatograph with my of the adducts found in vivo. Utilizing different enzymatic systems in vitro, including human hepatic microsomes and cytosols, and purified and recombinant enzymes, we found that a variety of enzymes [NAD(P)H:quinone oxidoreductase, xanthine oxidase, NADPH:cytochrome P450 oxidoreductase, cytochrome P450s 1A1 and 1A2, N,O-acetyltransferases 1 and 2, sulfotransferases 1A1 and 1A2, and myeloperoxidase] are able to catalyse the formation of 2-(2-deoxyguanosin-N-2-yl)3-aminobenzanthrone, N-(2'-deoxyguanosin-8-yl)-3-aminobenzanthrone and 2-(2'-deoxyadenosin-N-6-yl)-3-aminobenzanthrone in DNA, after incubation with 3-NBA and/or 3-ABA. (c) 2005Wiley-Liss, Inc
    Type of Publication: Journal article published
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