Stereoselective Metabolism of Anthracene, 9-Methylanthracene, 9,10-Dimethylanthracene, 9-Chloroanthracene, and 9-Nitroanthracene by Liver Microsomes of Neonatal Male B6C3F1 Mice

Abstract

Stereoselective metabolism of anthracene, 9-methylanthracene (9-M-A), 9, 10-dimethylanthracene (9, 10-DMA), 9-chloroanthracene (9-Cl-A), and 9-nitroanthracene (9-nitro-A) by liver microsomes of neonatal (15-day old) male B6C3F1 mice in the presence of a NADPH regenerating system was conducted. After incubation, reversed-phase HPLC separation, and spectral analyses the following were identified: anthracene trans-1,2-dihydrodiol, 9-M-A trans-1,2- and -3,4-dihydrodiol, 9,10-DMA trans-1,2-dihydrodiol, 9-Cl-A trans-1,2- and -3,4-dihydrodiol, and 9-nitro-A trans-1,2- and -3,4-dihydrodiol. Circular dichroism (CD) spectral analysis indicated the major enantiomers of the anthracene, 9-M-A, 9,10-DMA, and 9-Cl-A trans-dihydrodiols all had R,R absolute configurations. These results indicate that these compounds are metabolized in a stereoselective manner by liver microsomes of neonatal male B6C3F1 mice.