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 carcinogenic effects. As a step toward identifying the spectrum of PAH o-quinone-amino 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 standards to identify their presence in vitro and in vivo.