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Solvolysis of the bay‐region diol‐epoxide of benz[a]anthracene
Author(s) -
Wu Jinn,
Wong Lan K.
Publication year - 1980
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(80)80933-1
Subject(s) - solvolysis , chemistry , library science , stereochemistry , computer science , organic chemistry , hydrolysis
Polynuclear aromatic hydrocarbons (PAH) are a group of potent environmental carcinogens [ 1,2], that require cell-mediated activation before they can react with cellular macromolecules [3-61. Bay-region dial-epoxides have been implicated as the possible intermediates in the carcinogenic or mutagenic process [7-l I]. The accepted hypothesis for this metabolic activation entails metabolic transformation of an angularly fused benzo-ring of a PAH to a transdihydrodiol intermediary metabolite followed by enzymatic epoxidation of the bay-region double bond to form the ultimate bay-region diol-epoxide metabolite. An example of this dial-epoxide is 3,4-dihydroxy1,2-epoxy-1,2,3 ,Ctetrahydrobenz [a] anthracene (I, fig.1). The mutagenicity of this compound is at least IO-times more potent than its corresponding K-region oxide [ 121 (i.e., the 5,6-oxide). The 3,4dihydrodiol of benz [a] anthracene, presumably the precursor metabolite to the bay-region diol-epoxide, was found to be most tumorigenic among all the benz [a] anthracene dihydrodiols tested [ 131. This is consistent with and supportive of the bay-region hypothesis of PAH carcinogenesis.