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Comparison of Metabolism-mediated Binding to DNA of 7-Hydroxymethyl-12-methylbenz(a)anthracene and 7,12-Dimethylbenz(a)anthracene¹

Chemical Carcinogenesis Program, National Cancer Institute Frederick Cancer Research Center, Frederick, Maryland 21701

Comparison of the binding to DNA of 7-hydroxymethyl-12-methylbenz(a)anthracene and 7,12-dimethylbenz(a)anthracene (DMBA) catalyzed by mouse embryo cells in culture or by rat liver microsomes indicates that the products formed are different for the two hydrocarbons. Thus, the hydroxy compound is not an intermediate in the binding of DMBA to DNA in these systems.

Binding of the hydroxy compound to DNA in mouse embryo cells is less efficient than for DMBA and is inhibited by 1,1,1-trichloropropylene 2,3-oxide, an inhibitor of epoxide hydrase. This and the fluorescence spectra of the hydroxy compound-DNA adducts indicate that the hydroxy compound is activated for DNA binding through the formation of a diol-epoxide in the 1,2,3,4-ring. As previously found for DMBA, this is consistent with the activation of this compound through a bay-region diol-epoxide.

¹ This work was sponsored by the National Cancer Institute under Contract N01-CO-75380 with Litton Bionetics, Inc.

² To whom requests for reprints should be addressed, at Molecular Aspects of Chemical Carcinogenesis, Frederick Cancer Research Center, P. O. Box B, Frederick, Md. 21701.

Received 10/ 5/78. Accepted 12/21/78.

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