Synthesis of 3-nitrobenzo[a]pyrene bay-region trans-7,8-diol anti-9,10-epoxide and the corresponding N[sup 2]-deoxyguanosine adduct
Journal Article
·
· Chemical Research in Toxicology; (United States)
OSTI ID:6848541
- National Center for Toxicological Research, Jefferson, AR (United States)
- Providence Univ., Taichung (Taiwan, Province of China)
3-Nitrobenzo[a]pyrene (3-nitro-BaP) is a potent mutagenic environmental contaminant, and its biological activities have been intensively studied. It is significant to prepare its reactive metabolites and the corresponding modified DNA adducts for biological studies. The synthesis of its oxidized proximate metabolite trans-7,8-dihydroxy-7,8-dihydro-3-nitrobenzo[a]pyrene (3-nitro-BaP-trans-7,8 -dihydrodiol, 1), its oxidized ultimate metabolite trans-7-8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydro-3-nitro-benzo[a]pyrene (3-nitro-BaP-DE, 2), and the corresponding DNA adduct 10-(deoxyguanosin-N[sup 2]-yl)-7,8,9,trihydroxy-7,8,9,10-tetrahydro-3-nitrobenzo[a] pyrene is described. 18 refs., 3 figs., 1 tab.
- OSTI ID:
- 6848541
- Journal Information:
- Chemical Research in Toxicology; (United States), Journal Name: Chemical Research in Toxicology; (United States) Vol. 6:5; ISSN CRTOEC; ISSN 0893-228X
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
550200 -- Biochemistry
560300* -- Chemicals Metabolism & Toxicology
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
AROMATICS
BENZOPYRENE
BIOLOGICAL PATHWAYS
BIOSYNTHESIS
CONDENSED AROMATICS
DNA ADDUCTS
HYDROCARBONS
METABOLITES
MUTAGENESIS
ORGANIC COMPOUNDS
SYNTHESIS
560300* -- Chemicals Metabolism & Toxicology
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
AROMATICS
BENZOPYRENE
BIOLOGICAL PATHWAYS
BIOSYNTHESIS
CONDENSED AROMATICS
DNA ADDUCTS
HYDROCARBONS
METABOLITES
MUTAGENESIS
ORGANIC COMPOUNDS
SYNTHESIS