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Nucleic Acids Research, 1981, Vol. 9, No. 2 375-387
© 1981

MOLECULAR BIOLOGY

Studies on the miscoding properties of 1,N6-ethenoadenine and 3,N4-ethenocytosine, DNA reaction products of vinyl chloride metabolites, during in vitro DNA synthesis

Alain Barbin+, Helmut Bartsch+,*, Philippe Leconte{dagger} and Miroslav Radman{dagger}

+Division of Environmental Carcinogenesis, International Agency for Research on Cancer 150 cours Albert-Thomas, F-69372 Lyon Cédex 2, France {dagger}Department of Molecular Biology, Free University of Brussels 67 rue des Chevaux, B-1640 Rhode-St-Genèse, Belgium

*To whom correspondence should be addressed at the International Agency for Research on Cancer

Received November 3, 1980. 1, N6-Ethenoadenine ({varepsilon}A) and 3,N4-ethenocytosine ({varepsilon}C) are formed when electrophilic vinyl chloride (VC) metabolites, chloroethylene oxide (CEO) or chloroacetaldehyde (CAA) react with adenine and cytosine residues in DNA. They were assayed for their miscoding properties in an in vitro system using Escherichia coli DNA polymerase 1 and synthetic templates prepared by reaction of poly(dA) and poly(dC) with increasing concentrations of CEO or CAA. Following the introduction of etheno groups, an increasing inhibition of DNA synthesis was observed. dGMP was misincorporated on CAA- or CEO-treated poly(dA) templates and dTMP was misincorporated on CAA- or CEO-treated poly(dC) templates, suggesting that {varepsilon}A and {varepsilon}C may miscode. The error rates augmented with the extent of reaction of CEO or CAA with the templates. Base-pairing models are proposed for the {varepsilon}A.G and {varepsilon}C.T pairs. The potentially miscoding properties of {varepsilon}A and {varepsilon}C may explain why metabolically-activated VC and its reactive metabolites specifically induce base-pair substitution mutations in Salmonella typhimurium. Promutagenic lesions may represent one of the initial steps in VC- or CEO-induced carcinogenesis.


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