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

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The reaction of probucol with superoxide(O^<.->_2)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 O^<.->_2 by ESR spectroscopy. The reaction of probucol with O^<.->_2 in acetonitrile was followed by cyclic voltammetry. With the addition of probucol, the oxidation peak current of O^<.->_2 decreased concentration dependently. This suggests that probucol reacts with O^<.->_2, that is, probucol scavenges O^<.->_2 in acetonitrile. 2, 6-Di-tert-butyl-p-benzoquinone was identified as the major product of the reaction of probucol with O^<.->_2 in acetonitrile. Electrochemical oxidation of probucol was also performed. Probucol gives an irreversible oxidation peak at ca. +1.4V vs.the saturated calomel electrode in the cyclic voltammogram. Controlled-potential electrolysis was carried out at +1.2V 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-tert-butylphenol) were identified as the products of anodic oxidation. These redox properties of probucol may correlate with the physiological activities.
社団法人日本薬学会の論文
2001-08-01