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The reaction of probucol with superoxide (O2(*-)) was investigated in acetonitrile using both electron spin resonance (ESR) and electrochemical techniques. The formation of phenoxyl radical was observed during the reaction of probucol with O2(*-) by ESR spectroscopy. The reaction of probucol with O2(*-) in acetonitrile was followed by cyclic voltammetry. With the addition of probucol, the oxidation peak current of O2(*-) decreased concentration dependently. This suggests that probucol reacts with O2(*-), that is, probucol scavenges O2(*-) in acetonitrile. 2,6-Di-tert-butyl-p-benzoquinone was identified as the major product of the reaction of probucol with O2(*-) in acetonitrile. Electrochemical oxidation of probucol was also performed. Probucol gives an irreversible oxidation peak at ca. +1.4 V vs. the saturated calomel electrode in the cyclic voltammogram. Controlled-potential electrolysis was carried out at +1.2 V in a divided cell. 2,6-Di-tert-butyl-p-benzoquinone, 4,4'-dithiobis(2,6-di-tert-butylphenol), and 4,4'-trithiobis(2,6-di-tert-butylphenol) were identified as the products of anodic oxidation. These redox properties of probucol may correlate with the physiological activities.

Antioxidative Properties of Probucol Estimated by the Reactivity with Superoxide and by Electrochemical Oxidation.