Amino acid adducts of PAH o-quinones: model studies with naphthalene-1,2-dione

Polycyclic aromatic hydrocarbons (PAHs) are environmental pollutants which may cause cancer and require metabolic activation to exert their carcinogen ic effects. As a step toward identifying the spectrum of PAH o-quinone-amin o acid adducts that may form in biological systems, several naphthalene-1,2 -dione-amino acid adducts were synthesized. Each adduct was formed as a 1,4 -Michael addition product and spectral data corroborate that these adducts were either o-quinones or catechols. PAH o-quinone adducts can be used as s tandards to identify their presence in vitro and in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.