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

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  • ARAKI Tetsuya
    Drug Metabolism and Physicochemical Property Research Laboratory, Daiichi Pharmaceutical Co., Ltd.
  • KITAOKA Hiroaki
    Drug Metabolism and Physicochemical Property Research Laboratory, Daiichi Pharmaceutical Co., Ltd.

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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.

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