Abstract
1,2-Diselenolane-3-pentanoic acid, in which the sulfur atoms of alpha-lipoic acid are replaced with selenium, displayed markedly different antioxidant properties when compared to alpha-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 alpha-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 alpha-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.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Antioxidants / chemistry
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Antioxidants / pharmacology*
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Apolipoproteins B / metabolism
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Copper / metabolism*
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Free Radical Scavengers / pharmacology
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Humans
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Lipid Peroxidation / drug effects*
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Lipoproteins, LDL / metabolism*
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Molecular Structure
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Naphthalenes / pharmacology
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Organoselenium Compounds / chemistry
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Organoselenium Compounds / pharmacology*
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Oxidation-Reduction
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Pentanoic Acids / chemistry
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Pentanoic Acids / pharmacology*
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Salicylates / metabolism
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Salicylic Acid
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Serum Albumin / metabolism
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Thiobarbituric Acid Reactive Substances / analysis
Substances
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1,2-diselenolane-3-pentanoic acid
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Antioxidants
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Apolipoproteins B
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Free Radical Scavengers
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Lipoproteins, LDL
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Naphthalenes
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Organoselenium Compounds
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Pentanoic Acids
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Salicylates
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Serum Albumin
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Thiobarbituric Acid Reactive Substances
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N,N'-bis(2-hydroxyperoxy-2-methoxyethyl)-1,4,5,8-naphthalenetetracarboxylic diimide
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Copper
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Salicylic Acid