Favism inducing agents: a pulse radiolysis study of isouramil and convicine

Isouramil and covicine, substances implicated in precipitating favic crises in glucose-6-phosphate dehydrogenase deficient individuals, have been studied in N2O-saturated aqueous solutions by pulse radiolysis, and the kinetics of the reactions of both substances with OH radicals were determined. The products of these reactions are addition intermediates absorbing above 330 nm. The decay of the intermediate(s) formed in the isouramil reaction is a biphasic one, while the decay of the corresponding intermediate for the convicine reaction is characterized by a single constant. By analogy to uracil, it is suggested that the OH radical is added to the double bond at either positions 5 or 6 of the pyrimidine ring forming two different intermediates. Each of these intermediates loses a molecule of water indicated by the observed biphasic decay reaction. For convicine on the other hand, position 5 is blocked by the O-gucosidic bond and the addition of the OH radical could take place only at position 6. Thus, a single intermediate is formed and its decay is a single-phase one. It has been shown that although free radicals could not be detected in the course of the reactions between isouramil and oxygen or with cellular components by electron paramagnetic resonance, isouramil can participate in a uni-electron transfer reacton and can form relatively stable intermediates. Thus, it is speculated that in the red blood cells isouramil could give rise to deleterious free radicals