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Formation of Glucuronic Acid Conjugates of 7,12-Dimethylbenz(a)-anthracene Phenols in 7,12-Dimethylbenz(a)anthracene-treated Hamster Embryo Cell Cultures¹

The Wister Institute of Anatomy and Biology, Philadelphia, Pennsylvania 19104

Secondary cultures of hamster embryo cells exposed to 0.5 nmol [G-³H]7,12-dimethylbenz(a)anthracene (DMBA) per ml medium metabolized more than 90% of the DMBA within 48 hr. Samples of medium were extracted with chloroform, methanol, and water. The chloroform phases contained about one-third of the DMBA metabolites; the major chloroform-extractable metabolite was 8,9-dihydro-8,9-dihydroxy-7,12-dimethylbenz(a)anthracene. ß-Glucuronidase treatment of the aqueous methanol-soluble metabolites converted almost one-half of them to chloroformsoluble metabolites, of which more than 80% were identified as phenolic derivatives of DMBA. Similar metabolite profiles were obtained by treating the medium with ß-glucuronidase before chloroform extraction.

Separation of the methyl group-hydroxylated derivatives of DMBA from the phenolic derivatives was accomplished by high-pressure liquid chromatography. Small amounts of hydroxymethyl derivatives were detected only in the chloroform-extractable material, whereas DMBA phenols were the major component of the ß-glucuronidase-released material. These results indicate that the major pathway of DMBA metabolism in hamster embryo cells is oxidation of the aromatic rings and not oxidation of the methyl groups.

¹ Supported in part by Grants CA 19948, CA 08936, CA 16685, and CA 10815 from the National Cancer Institute. Department of Health, Education and Welfare.

² To whom requests for reprints should be addressed, at the Wistar Institute of Anatomy and Biology, 36th Street at Spruce, Philadelphia, Pa. 19104.

Received 4/10/78. Accepted 7/18/78.