Synthesis of N-(1-nitropyren-6-yl and 8-yl)-2'-deoxyribonucleosides.
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 degrees 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.
Sano
T
T
Environmental Chemistry Division, National Institute for Environmental Studies, Ibaraki, Japan.
Kaya
K
K
D018736:DNA Adducts / Q000138:chemical synthesis* / Q000737:chemistry; D003853:Deoxyribonucleosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009153:Mutagens / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*; D013057:Spectrum Analysis
D018736:DNA Adducts; D003853:Deoxyribonucleosides; D009153:Mutagens; D011721:Pyrenes; C032668:1-nitropyrene