Mimicking the Lipid Peroxidation Inhibitory Activity of Phospholipid Hydroperoxide Glutathione Peroxidase GPx4 by Using Fatty Acid Conjugates of a Water-Soluble SelenolaneReportar como inadecuado




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1

Department of Chemistry, School of Science, Tokai University, Kitakaname, Hiratsuka-shi, Kanagawa 259-1292, Japan

2

Radiation and Photochemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, India





*

Author to whom correspondence should be addressed.



Academic Editor: Thomas G. Back

Abstract A series of fatty acid conjugates of trans-3,4-dihydroxy-1-selenolane DHS were synthesized by reacting DHS with appropriate acid chlorides. The obtained monoesters were evaluated for their antioxidant capacities by the lipid peroxidation assay using a lecithin-cholesterol liposome as a model system. The observed antioxidant capacities against accumulation of the lipid hydroperoxide LOOH increased with increasing the alkyl chain length and became saturated for dodecanoic acid C12 or higher fatty acid monoesters, for which the capacities were much greater than those of DHS, its tridecanoic acid C13 diester, and PhSeSePh. On the other hand, the bacteriostatic activity of myristic acid C14 monoester, evaluated through the colony formation assay using Bacillus subtilis, indicated that it has higher affinity to bacterial cell membranes than parent DHS. Since DHS-fatty acid conjugates would inhibit lipid peroxidation through glutathione peroxidase GPx-like 2e− mechanism, higher fatty acid monoesters of DHS can mimic the function of GPx4, which interacts with LOOH to reduce it to harmless alcohol LOH. Importance of the balance between hydrophilicity and lipophilicity for the design of effective GPx4 mimics was suggested. View Full-Text

Keywords: antioxidant; lipid peroxidation; TBARS; colony formation assay antioxidant; lipid peroxidation; TBARS; colony formation assay





Autor: Michio Iwaoka 1,* , Arisa Katakura 1, Jun Mishima 1, Yoshimi Ishihara 1, Amit Kunwar 2 and Kavirayani Indira Priyadarsini 2

Fuente: http://mdpi.com/



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