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• W30691936 abstract "Among the mammalian selenoenzymes, glutathione peroxidase (GPx) has attracted much attention due to its enormous importance in the defense against oxidative stress. The chemistry at the active site of GPx has been widely studied with the help of a number of small-molecule organoselenium compounds. Among these, ebselen (2-phenyl-1,2-benzisoselenazole-3(2H)-one) is currently undergoing phase III clinical trial for a number of disease states as it exhibits good antioxidant activity in vivo. However, the catalytic mechanism for the GPx activity of ebselen is not well established. In this article, different catalytic mechanisms proposed in the literature for the GPx-like antioxidant activities of ebselen and related selenenyl amides are described. Recently, it has been observed that ebselen and related compounds show poor catalytic activities in the presence of aryl or benzyl thiols as cofactors. The unusually low catalytic activities of these Sec-amide-substituted compounds have been ascribed to the undesired thiol exchange reactions that take place in the selenenyl sulfide intermediates due to the presence of strong Se...O nonbonded interactions. Furthermore, it has been shown that the extensive thiol exchange reactions can be prevented by using a dithiol as cofactor or by introducing S...N/O nonbonded interactions in selenenyl sulfide intermediates. In addition, it has been observed that the GPx activities of secamide-based compounds can be dramatically enhanced by the substitution at free-NH groups of the amide functionality that prevents the undesired thiol exchange reactions." @default.
• W30691936 created "2016-06-24" @default.
• W30691936 creator A5018401208 @default.
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• W30691936 date "2011-01-01" @default.
• W30691936 modified "2023-09-25" @default.
• W30691936 title "Synthetic Mimics of Selenoproteins" @default.
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• W30691936 doi "https://doi.org/10.1007/978-3-642-22236-8_14" @default.
• W30691936 hasPublicationYear "2011" @default.
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