An unusual DNA adduct derived from the powerfully mutagenic environmental contaminant 3-nitrobenzanthrone.
The covalent binding of an N-hydroxy metabolite of the powerfully mutagenic 3-nitrobenzanthrone (NBA) to 2'-deoxyguanosine (dG) and calf thymus DNA has been investigated in vitro. The major adduct obtained from the reaction of the N-acetoxy-N-acetyl derivative (N-Aco-N-Ac-ABA) of 3-aminobenzanthrone (ABA) and dG was identified as N-acetyl-3-amino-2-(2'-deoxyguanosin-8-yl)benzanthrone (dG-N-Ac-ABA) by 1H NMR and mass spectroscopies as well as by the reaction of N-Aco-N-Ac-ABA with the double-stranded calf thymus DNA. The coupling with the dG moiety occurred exclusively at C-2 of benzanthrone (BA), suggesting a significant contribution of a resonance-stabilized arenium ion intermediate derived from BA to the production of this new type of adduct. The preferred conformation of the adduct has been shown to be syn by 1H and 13C NMR.
Enya
T
T
Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan. Community Environmental Science,
Kawanishi
M
M
Suzuki
H
H
Matsui
S
S
Hisamatsu
Y
Y
D000818:Animals; D001551:Benz(a)Anthracenes / Q000737:chemistry*; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry / Q000187:drug effects; D018736:DNA Adducts / Q000737:chemistry*; D003640:Dealkylation; D004785:Environmental Pollutants; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009153:Mutagens / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013950:Thymus Gland / Q000737:chemistry
D001551:Benz(a)Anthracenes; D018736:DNA Adducts; D004785:Environmental Pollutants; D007202:Indicators and Reagents; D009153:Mutagens; D004247:DNA; C117220:3-nitrobenzanthrone