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Fatty Acid Conjugates of Water‐Soluble (±)‐ trans ‐Selenolane‐3,4‐diol: Effects of Alkyl Chain Length on the Antioxidant Capacity
Author(s) -
Iwaoka Michio,
Sano Nobukazu,
Lin YingYin,
Katakura Arisa,
Noguchi Masato,
Takahashi Kohei,
Kumakura Fumio,
Arai Kenta,
Singh Beena G.,
Kunwar Amit,
Priyadarsini K. Indira
Publication year - 2015
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201500047
Subject(s) - chemistry , liposome , lipid peroxidation , antioxidant , alkyl , organic chemistry , moiety , lecithin , fatty acid , chromatography , biochemistry
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 (IC 50 =9–34 μ M ) 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/H 2 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.