Carcinogenicity of benzo[a]pyrene derivatives: the bay region theory

D. M. Jerina, D. R. Thakker, Haruhiko Yagi, Wayne Levin, A. W. Wood, A. H. Conney
1978 Pure and Applied Chemistry  
A substantial body of carcinogenicity data is available for benzo[a)pyrene (BP), benzo[a)anthracene (BA), and numerous known and potential metabolites of these polycyclic hydrocarbons. The tumor data firmly establish that the 7,8dihydrodiol of BP and the 3,4-dihydrodiol of BA are proximate carcinogens and that the 7,8-diol 9,10-epoxides and the 3,4-diol 1,2-epoxides are ultimate carcinogens derived metabolically from the respective hydrocarbons. The data support the "bay region" theory of
more » ... arbon induced carcinogenicity which asserts that diol epoxides an angular benze rings of polycyclic hydrocarbons, in which the epoxide ring forms part of a "bay region" of the hydrocarbon are prime candidates for ultimate carcinogens. Perturbational molecular orbital calculations indicate that electronic properties of the 71-electron system are responsible for the unusually high chemical reactivity of such diol epoxides.
doi:10.1351/pac197850091033 fatcat:6oc66fqhtrd4bffrkftinierim