Journal of medicinal chemistry

Metabolism of 6-substituted benzo [a] pyrene derivatives: O-dealkylation and regiospecificity in aromatic hydroxylation

AJ Alpert, EL Cavalieri

Index: Alpert, Andrew J.; Cavalieri, Ercole L. Journal of Medicinal Chemistry, 1980 , vol. 23, # 8 p. 919 - 927

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Citation Number: 9

Abstract

The carcinogen benzo [a] pyrene (BP) is metabolized by monooxygenase enzymes to phenols, dihydrodiols, and diones. The major product, 3-hydroxy-BP, is measured in the fluorescence assay for aryl hydrocarbon hydroxylase (AHH). In this assay, the BP phenols, which are readily oxidized to nonfluorescent diones, are not detected. Blocking the 6 position with various substituents prevents dione formation and stabilizes the phenolic ...