Chemical Research in Toxicology p. 699 - 702 (1995)
Update date:2022-08-04
Topics:
Sano
Kaya
A new type of 1-nitropyrene-DNA adduct via addition-elimination reaction was synthesized. Treatment of fluorinated 1-nitropyrene with 3'- and 5'-O- protected 2'-deoxyribonucleoside in dimethyl sulfoxide at 140 °C afforded N- (1-nitropyren-6-yl or 8-yl)-2'-deoxyribonucleoside. These DNA adducts resulted from addition of the exocyclic amino group of deoxynucleosides to the fluorinated carbon of the fluoro-1-nitropyrene following elimination of fluoride anion. This is the first report that describes the 1-nitropyrene- DNA adducts in which aromatic ring moiety of 1-nitropyrene is covalently linked to the exocyclic amino group of the deoxyribonucleoside. From our findings, we suggest that the addition-elimination reaction may be responsible for the formation mechanism of the putative 1-nitropyrene-DNA adducts in vivo.
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