From Arene Oxides to Diol Epoxides and DNA

Abstract

Although the polycyclic aromatic hydrocarbons (PAH) are structurally less complex compared to many other compounds with high biological activity, their metabolism, the chemical reactivity of their metabolites, and the mutagenicity and tumorigenicity of these metabolites have stimulated intensive research into their mechanisms of action. The present report focuses on our contributions to the identification of bay-region and fjord-region diol epoxides as ultimate carcinogens of the PAH and describes some of the remarkable stereochemical control involved in their synthesis, metabolic formation, and expression of tumorigenic activity.

Key Words:

• Polycyclic aromatic hydrocarbons
• carcinogenicity
• NIH Shift
• arene oxides
• diol epoxides
• bay-region theory
• DNA adducts
• conformation and configuration of PAH metabolites