Hydroxyproline reaction with free radicals generated during benzoyl peroxide catalytic decomposition of carbon tetrachloride. Structure of reaction products formed

G.D. CASTRO; J.A. CASTRO

AMINO ACIDS

Springer-Verlag

Año: 1996 vol. 10 p. 283 - 294

0939-4451

Benzoyl peroxide catalytic decomposition of carbon tetrachloride in a model system produces trichloromethyl and trichloromethyl peroxyl free radicals. These radicals are also produced by CCl4 bioactivation in liver and are considered to be responsible for the deleterious effects of this hepatotoxin. In this study, it is attempted to learn about how the CCl3 and CCl3O2 tend to react with hydroxyproline in a model system. Hidroxyproline was selected because of its role in collagen metabolism. During the interaction of both radicals with hydroxyproline a total of 16 reaction products were isolated and identified by gas chromatography-mass spectrometric analysis. All of them were hydroxyproline analogs, no single one contained C from CCl4 and only three contained chlorine. Consequently, most adducts would be missed in experiments where formation of reaction products are studied by formation of 14C or 36Cl labeled adducts (e.g. covalent binding studies used by toxicologists). If similar hydroxyproline analog reaction products were obtained during CCl4 intoxication it might be reasonably expected that they interfered with collagen metabolism and participate in cirrhogenic effects of CCl4 on the liver.