Abstract

Enantiomers of 9,10-dihydrobenzo[ a]pyrene 7,8-oxide (DBPO) were stereoselectively conjugated with glutathione (GSH) specifically at benzylic carbon (C 7) in normal Sprague—Dawley (SD) rat liver cytosol: (7 R,8 S)-(+)- > (7 S,8 R)-(−)-DBPOs. In contrast, in liver cytosol of SD rats bearing hepatic hyperplastic nodules induced with chemical carcinogens, (7 S,8 R)-(−)-DBPO was preferentially conjugated with GSH to (7 R,8 S)-(+)-DBPO. GSH S-transferases (GSTs) having sub-unit protein 4 were strongly suggested to play an important role in the preferential conjugation of (7 R,8 S)-(+)-DBPO in the normal rat liver cytosol, while the preferential conjugation of (7 S,8 R)-(−)-DBPO in the liver cytosol of the rat bearing hepatic hyperplastic nodules, was most likely to be attributable to GST 7-7, a characteristically induced protein in the hepatic hyperplastic nodules.

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