title: Identification of N5-methyl-N5-formyl-2,5,6-triamino-4-hydroxypyrimidine as a major adduct in rat liver DNA after treatment with the carcinogens, N,N-dimethylnitrosamine or 1,2-dimethylhydrazine.
abstract: A major and previously undetected carcinogen-DNA adduct was found in the livers of rats given N,N-dimethylnitrosamine or 1,2-dimethylhydrazine. This adduct, which accounted for 55% of the total methyl residues in DNA at 72 hours after carcinogen treatment, was chromatographically identical to a synthetic purine ring-opened derivative of 7-methylguanine and could be released from the isolated hepatic DNA by a specific E. coli glycosylase. The synthetic ring-opened adduct was characterized by mass and NMR spectroscopy as N5-methyl-N5-formyl-2,5,6-triamino-4-hydroxypyrimidine and appears to exist in two rotameric forms.
mesh_terms: D019813:1,2-Dimethylhydrazine; D000478:Alkylation; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000302:isolation & purification* / Q000378:metabolism; D004127:Dimethylhydrazines / Q000494:pharmacology*; D004128:Dimethylnitrosamine / Q000494:pharmacology*; D005260:Female; D008099:Liver / Q000378:metabolism*; D008763:Methylhydrazines / Q000494:pharmacology*; D011743:Pyrimidines / Q000302:isolation & purification*; D051381:Rats; D011919:Rats, Inbred Strains
chemical_list: D004127:Dimethylhydrazines; D008763:Methylhydrazines; D011743:Pyrimidines; C037301:N(5)-methyl-N(5)-formyl-2,5,6-triamino-4-hydroxypyrimidine; D004247:DNA; D019813:1,2-Dimethylhydrazine; D004128:Dimethylnitrosamine