Inhibitory Effects of Pentamethine Trinuclear Cyanine Dyes on ADP/Fe^<2+>-Induced Lipid Peroxidation in Rat Liver Mitochondria : Changes in the Mode of Action with the Hydrophobic Nature of the Dyes

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The effects of various pentamethine trinuclear cyanine dyes, each of which has three alkyl chains, on ADP/Fe^<2+>-induced lipid peroxidation in rat liver mitochondria were examined. Although the dye having the shortest -C_2H_5 chains (tri-S-C_2(5)) did not show any appreciable effect, the dyes having -C_4H_9 (tri-S-C_4(5)), -C_7H_<15> (tri-S-C_7(5)), and -C_<12>H<25> (tri-S-C_<12>(5)) chains significantly inhibited lipid peroxidation, the most potent inhibitory effect being observed with tri-S-C_7(5). The mode of antiperoxidation effect of the dyes was dependent on the length of the alkyl chains. The relatively hydrophilic dye tri-S-C_4(5) was suggested to scavenge radicals more efficiently at or near the membrane surface rather than in the interior of the lipid membrane, whereas the more hydrophobic dye tri-S-C_7(5) was suggested to scavenge radicals efficiently in the membrane rather than at or near the membrane surface. The hydrophilic/hydrophobic balance of the dye was found to regulate the site of action of the dyes.
公益社団法人日本薬学会の論文
1998-02-15