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A molecular orbital study of the metabolism and carcinogenicity of the phenols of benzo(a)pyrene
Author(s) -
Seybold Paul G.,
Gräuslund Astrid
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560180725
Subject(s) - pyrene , carbonium ion , chemistry , phenols , benzo(a)pyrene , epoxide , carcinogen , molecular orbital , phenol , reaction coordinate , stereochemistry , computational chemistry , organic chemistry , molecule , ion , catalysis
Relative tendencies of the twelve isomeric phenol derivatives of benzo(a)pyrene to undergo specific metabolic chemical reactions have been examined using molecular orbital calculations. Considering presumed “activating” reactions alone, the calculations suggest that all the hydroxy derivatives except those substituted on the benzo ring should be capable of forming bay region carbonium ions via epoxide and dihydrodiol intermediates. Oxyradical formation provides a possible competing pathway. The tendency of benzo(a)pyrene phenols to form oxyradicals appears to be strongly influenced by the position of substitution: 6‐hydroxybenzo(a)pyrene is calculated to have the highest tendency to undergo this transformation and 2‐hydroxybenzo(a)pyrene the lowest tendency. It is suggested that the differing carcinogenic activities of the benzo(a)pyrene phenols may be related to their tendencies to form oxyradicals and that this reaction may provide a deactivating reaction pathway for these compounds.