title: The lipoic acid analogue 1,2-diselenolane-3-pentanoic acid protects human low density lipoprotein against oxidative modification mediated by copper ion.
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.
authors.affiliation: Department of Molecular and Cell Biology, University of California at Berkeley 94720-3200, USA.
authors.forename: S
authors.initials: S
authors.lastname: Matsugo
authors.forename: L J
authors.initials: LJ
authors.lastname: Yan
authors.forename: T
authors.initials: T
authors.lastname: Konishi
authors.forename: H D
authors.initials: HD
authors.lastname: Youn
authors.forename: J K
authors.initials: JK
authors.lastname: Lodge
authors.forename: H
authors.initials: H
authors.lastname: Ulrich
authors.forename: L
authors.initials: L
authors.lastname: Packer
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D001055:Apolipoproteins B / Q000378:metabolism; D003300:Copper / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000494:pharmacology; D006801:Humans; D015227:Lipid Peroxidation / Q000187:drug effects*; D008077:Lipoproteins, LDL / Q000378:metabolism*; D015394:Molecular Structure; D009281:Naphthalenes / Q000494:pharmacology; D016566:Organoselenium Compounds / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010421:Pentanoic Acids / Q000737:chemistry / Q000494:pharmacology*; D012459:Salicylates / Q000378:metabolism; D020156:Salicylic Acid; D012709:Serum Albumin / Q000378:metabolism; D017392:Thiobarbituric Acid Reactive Substances / Q000032:analysis
chemical_list: C109588:1,2-diselenolane-3-pentanoic acid; D000975:Antioxidants; D001055:Apolipoproteins B; D016166:Free Radical Scavengers; D008077:Lipoproteins, LDL; D009281:Naphthalenes; D016566:Organoselenium Compounds; D010421:Pentanoic Acids; D012459:Salicylates; D012709:Serum Albumin; D017392:Thiobarbituric Acid Reactive Substances; C067580:N,N'-bis(2-hydroxyperoxy-2-methoxyethyl)-1,4,5,8-naphthalenetetracarboxylic diimide; D003300:Copper; D020156:Salicylic Acid