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© 1988 Oxford University Press

research-article

Evidence for 4-(3-pyridyl)-4-oxobutylation of DNA in F344 rats treated with the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N'-nitrosonornicotine

Stephen S. Hecht 1, Thomas E. Spratt and Neil Trushin

Division of Chemical Carcinogenesis, American Health Foundation Valhalla, NY 10595, USA

1To whom reprint requests should be sent

DNA was isolated from tissues of K344 rats 24 h after treatment by s.c. injection with [5-3H]4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone ([5-3H]NNK) or [5-3H]N'-nitrosonor-nicotine ([5-3H]NNN) It was hydrolyzed with acid or at pH 7,100°C, and the hydrolysates were analyzed by HPLC. The major product in each case was Identified as 4-hydroxy-1-(3-pyridyl)-1-butanone, formed by hydrolysis of a DNA adduct. It was detected in DNA from the livers of rats treated with [5-3H]NNK or [5-3H]NNN, and in DNA from lungs of rats treated with [5-3H]NNK. These results demonstrate that 4-(3-pyridyl)-4-oxobutylation of DNA occurs in rats treated with NNK or NNN, and are consistent with the hypothesis that these nitrosamines are metabolically activated by {alpha}-hydroxylation.


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