The lipoic acid analogue 1,2-diselenolane-3-pentanoic acid protects human low density lipoprotein against oxidative modification mediated by copper ion

Seiichi Matsugo, Liang Jun Yan, Tetsuya Konishi, Hong Duk Youn, John K. Lodge, Heinz Ulrich, Lester Packer

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

1,2-Diselenolane-3-pentanoic acid, in which the sulfur atoms of α-lipoic acid are replaced with selenium, displayed markedly different antioxidant properties when compared to α-lipoic acid. 1,2-Diselenolane-3-pentanoic acid was unable to inhibit protein oxidative modification of human low density lipoprotein (LDL) and bovine serum albumin induced by copper ion or hydroxyl radical, whereas α-lipoic acid showed significant protection. However, 1,2-diselenolane-3-pentanoic acid was able to inhibit the formation of lipid peroxidation products in LDL after oxidation by copper, while α-lipoic acid did not. Hence the diselenium compound exerts its effects in a lipophilic environment whilst lipoic acid exerts its effects in a hydrophilic environment. These differences in antioxidant activities of the two compounds may be explained, at least in part, by their differing partition coefficients.

Original languageEnglish
Pages (from-to)819-824
Number of pages6
JournalBiochemical and Biophysical Research Communications
Volume240
Issue number3
DOIs
StatePublished - 26 Nov 1997

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