Structure-Activity Relationships Among Some Polynuclear Hydrocarbons and Their Hydrogenated Derivatives2

Abstract
Partially hydrogenated derivatives of several polynuclear hydrocarbons were tested for tumorigenic activity by both skin painting and subcutaneous injection in female Swiss mice. Contrary to previous reports, dibenz[a,c]anthracene was weakly carcinogenic, whereas its 10,11,12,13-tetrahydro derivative was inactive. Dibenz[a,j]anthracene was weakly carcinogenic by skin painting, as was 1,2,3,4-tetrahydro-dibenz[a,j]anthracene, whereas 5,6-dihydrodibenz[a,j]anthracene was much more potent than its unsaturated parent; 1,2,3,4,8,9-hexahydro-dibenz[a,j]anthracene was inactive. This pattern of carcinogenic activity contrasted sharply with that of the analogous series of dibenz[a,h]anthracene derivatives. Two benz[a]anthracene derivatives, 8,9,10,11-tetrahydro-7,12-dimethylbenz[a]anthracene and 11,12-dihydro-3-methylcholanthrene, were both carcinogenic by skin painting, though the latter compound does not have a “K-region.” The results of subcutaneous injection of single doses of dibenz[a,h]anthracene and dibenz[a,j]anthracene and of their corresponding dihydro, tetrahydro, and hexahydro derivatives showed significant tumorigenic activity only by dibenz[a,h]anthracene and 1,2,3,4-tetrahydrodibenz[a,h]anthracene, in contrast to skin painting results.