Proline interaction with trichloromethyl and trichloromethyl peroxyl free radicals in a model system: studies about the nature of the reaction products formed

Abstract

Trichloromethyl and trichloromethyl peroxyl radicals are known to be produced during CCl4 biotransformation and are considered to be critical for deleterious effects of this haloalkane. In this work we describe our studies on the interaction of both free radicals with a lipid-soluble derivative of the amino acid proline in a model system. The analysis of the reaction products formed by gas chromatography-mass spectrometry of the sylilated derivatives revealed the formation of at least 11 reaction products under anaerobic conditions and 13 under aerobic atmosphere. All of them were tentatively identified and all but 2 were proline analogs. Only 3 incorporated in their structure CCl3 or CCl2 portions of the CCl4 molecule and, consequently, most of the adducts formed would be missed during regular procedures most toxicologists use to determine CCl4. Results were analyzed in relation to the known role of proline in collagen metabolism and of this protein in liver cirrhosis.