title: Fatty acid conjugates of water-soluble (±)-trans-Selenolane-3,4-diol: effects of alkyl chain length on the antioxidant capacity.
abstract: Fatty acid monoesters of the title compound (DHS(red) ), of variable carbon chain length (propionate, laurate, myristate, palmitate, and stearate), were synthesized, and their antioxidant capacities were evaluated by means of a lipid peroxidation assay with lecithin/cholesterol liposomes. The selenides with long alkyl chains exhibited significant antioxidant activity (IC50 =9-34 μM) against accumulation of lipid hydroperoxide. Incorporation of the myristate into the liposome was ≈50 % by EPMA analysis. Intermediacy of the selenoxide was examined by NMR. In addition, enhancement of interfacial redox catalytic activity was observed for the myristate, but not for PhSeSePh and edaravone, in a PhCl/H2 O biphasic peroxidation assay. These results suggested that a combination of a hydrophilic selenide moiety as a redox center with a long alkyl chain is an effective approach to selenium antioxidants with interfacial glutathione-peroxidase-like (GPx-like) activity. The activity can be controlled by the alkyl chain length.
authors.affiliation: Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292 (Japan). miwaoka@tokai.ac.jp.
authors.forename: Michio
authors.initials: M
authors.lastname: Iwaoka
authors.affiliation: Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292 (Japan).
authors.forename: Nobukazu
authors.initials: N
authors.lastname: Sano
authors.affiliation: Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292 (Japan).
authors.forename: Ying-Yin
authors.initials: YY
authors.lastname: Lin
authors.affiliation: Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292 (Japan).
authors.forename: Arisa
authors.initials: A
authors.lastname: Katakura
authors.affiliation: Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292 (Japan).
authors.forename: Masato
authors.initials: M
authors.lastname: Noguchi
authors.affiliation: Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292 (Japan).
authors.forename: Kohei
authors.initials: K
authors.lastname: Takahashi
authors.affiliation: Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292 (Japan).
authors.forename: Fumio
authors.initials: F
authors.lastname: Kumakura
authors.affiliation: Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292 (Japan).
authors.forename: Kenta
authors.initials: K
authors.lastname: Arai
authors.affiliation: Radiation and Photochemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400 085 (India).
authors.forename: Beena G
authors.initials: BG
authors.lastname: Singh
authors.affiliation: Radiation and Photochemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400 085 (India).
authors.forename: Amit
authors.initials: A
authors.lastname: Kunwar
authors.affiliation: Radiation and Photochemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400 085 (India). kindira@barc.gov.in.
authors.forename: K Indira
authors.initials: KI
authors.lastname: Priyadarsini
mesh_terms: D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D002784:Cholesterol / Q000737:chemistry / Q000378:metabolism; D005227:Fatty Acids / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006018:Glycols / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D054709:Lecithins / Q000737:chemistry / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D008081:Liposomes / Q000737:chemistry / Q000378:metabolism; D016566:Organoselenium Compounds / Q000737:chemistry* / Q000494:pharmacology*; D010084:Oxidation-Reduction; D012995:Solubility; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014867:Water / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D005227:Fatty Acids; D005609:Free Radicals; D006018:Glycols; D054709:Lecithins; D008081:Liposomes; D016566:Organoselenium Compounds; D014867:Water; D002784:Cholesterol
keywords: enzyme models; liposomes; peroxidases; selenoxides; surfactants