Tumorigenicity of the diastereomeric benz[a]anthracene 3,4-diol-1,2-epoxides and the (+) - and (-) -enantiomers of benz[a]anthracene 3,4-dihydrodiol in newborn mice
Wislocki, P.G.; Buening, M.K.; Levin, W.; Lehr, R.E.; Thakker, D.R.; Jerina, D.M.; Conney, A.H.
Journal of the National Cancer Institute 63(1): 201-204
1979
ISSN/ISBN: 0027-8874 PMID: 286829 Document Number: 150447
The tumorigenic activity of benz absolute stereochemistry was the second most tumorigenic derivative of BA tested; it produced pulmonary tumors in 71% of the mice with an average of 1.88 tumors per mouse. BA and the (+)-enantiomer of BA 3,4-dihydrodiol had little or no tumorigenic activity at the dose tested. A comparison of the average number of pulmonary tumors per mouse revealed that BA 3,4-diol-1,2-epoxide-2 was about 30-fold more tumorigenic than was BA 3,4-diol-1,2-epoxide-1, 8-fold more tumorigenic than was (-)-BA 3,4-dihydrodiol, and greater than 85-fold more tumorigenic than was BA. These data indicate that in newborn mice BA 3,4-dihydrodiol and a BA 3,4-diol-1,2-epoxide are proximate and ultimate carcinogenic metabolites of BA, respectively.