The Synthesis and Characterization of Some N-Hydroxyaminopyrenes

Abstract

Nitrated polycyclic aromatic hydrocarbons (nitro-PAH) are environmental contaminants that have been identified in extracts of particulates obtained from automobile exhaust, diesel exhaust, and power plant emissions. One of the most abundant nitro-PAH, 1-nitropyrene, has been found to be a powerful bacterial mutagen and a carcinogen in animal tests. In a bacterial strain (Salmonella tvphimurium TA98) 1- nitropyrene undergoes reduction and concomitant covalent binding to DNA, presumably via the N-hydroxy-l-aminopyrene. This labile compound was prepared by the ascorbic acid reduction of 1-nitrosopyrene and was characterized by high performance liquid chromatography (HPLC), combined liquid chromatography-mass spectrometry (LC-MS), ultraviolet-visible (UV-VIS), fluorescence and nuclear magnetic resonance (NMR) spectroscopy (1H and 15N) . In addition the pH stability and some reactions of this compound were studied. The 1,6- and 1,8-hydroxylaminonitropyrenes derived from the very potent mutagens 1,6- and 1,8 dinitropyrene were also synthesized and characterized by high performance liquid chromatography, ultraviolet-visible and nuclear magnetic resonance spectroscopy (1H and 15N) .