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Original Article

Antioxidant Activity of Ebselen and Related Selenoorganic Compounds in Microsomal Lipid Peroxidation

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Pages 237-244 | Received 12 Mar 1990, Published online: 07 Jul 2009
 

Abstract

Ebselen, 2-phenyl-1,2-benzisoselenazol-3(2H)one, and its derivatives were compared for their ability to protect microsomal membranes against iron/ADP/ascorbate-induced lipid peroxidation, measured as low-level chemiluminescence and accumulation of thiobarbituric acid-reactive substances (TBARS). The concentrations of the compounds required to double the lag time of the control with no added antioxidants were 0.13μM for ebselen, 0.5μM for the N-pyridyl analog, 0.3-0.7 μM for the selenylsulfides, about 1.0 μM for the selenoxide derivative and 2.0 μM for the sulfur analog of ebselen. The open-chain seleno- and thioether derivatives, on the other hand, exhibited comparatively low abilities to protect the membrane, the lag doubling concentrations for these compounds being 100-1,000 fold higher than that for ebselen.

The rate of loss of α-tocopherol in the microsomal membrane during peroxidation was significantly diminished in the presence of 0.1-0.5μM ebselen, while the glutathione adduct of ebselen was equally effective in protecting the loss of α-tocopherol. The sulphur analogue and, the benzylated and methylated derivatives of ebselen did not afford protection. Ebselen was without effect in microsomes from vitamin E-deficient rats up to 20μM, indicative of the dependence of its protective ability upon α-tocopherol.

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