Comparative mutagenicity of 4-(carbethoxynitrosamino)-4-(3-pyridyl)butanal and 4-(carbethoxynitrosamino)-1-(3-pyridy1)-1-butanone, model compounds for α-hydroxylation of n'-nitrosonornicotine

Stephen S. Hecht, Dorothy Lin

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14 Scopus citations

Abstract

4-(Carbethoxynitrosamino)-1-(3-pyridy1)butanal, a stable precursor to the putative diazohydroxide formed by 5'-hyd-roxylation of the tobacco-specific nitrosamine, N'-nitrosonornicotine, was synthesized in six steps from nicotinaldehyde. Its mutagenicity toward S. typhimurium was compared to that of 4-(carbethoxynitrosamino)-1-(3-pyridyl)-1-butanone, a precursor to the diazohydroxide formed by 2'-hydroxylation of N'-nitrosonornicotine. At equimolar doses, 4-(carbethoxy-nitrosamino)-1-(3-pyridy)-1-butanone was a potent mutageon, but 4-(carbethoxynitrosamino)-1-(3-pyridy) butanal was inactive toward strains TA 100 and TA 1535. The results of this study indicate that the putative diazohydroxide formed by 2'-hydroxylation of N'-nitrosonornocotine has higher inherent mutagemicity toward S. typhimurinum than does the corresponding diazohydroxide formed by 5'-hydroxylation.

Original languageEnglish (US)
Pages (from-to)611-614
Number of pages4
JournalCarcinogenesis
Volume7
Issue number4
DOIs
StatePublished - 1986

Bibliographical note

Funding Information:
This study was supported by NCI Grant CA-21393. We thank Mr W.Biles of the In Vitro Facility of The American Health Foundation for carrying out the mutagenicity assays and Ms Gail Thiede for typing the manuscript. This is paper No. 94 in the series 'A Study of Chemical Carcinogenesis'.

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