Biological and Pharmaceutical Bulletin
Online ISSN : 1347-5215
Print ISSN : 0918-6158
ISSN-L : 0918-6158
Inhibitory Effects of Pentamethine Trinuclear Cyanine Dyes on ADP/Fe2+-Induced Lipid Peroxidation in Rat Liver Mitochondria : Changes in the Mode of Action with the Hydrophobic Nature of the Dyes
Kentaro KOGURE, Hironori SASSA, Kazutoyo ABE, Katsuyuki KITAHARA, Yuka SANO, Hideto KAWANO, Yoshinori NAKAGAWA, Hiroshi TERADA
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1998 年 21 巻 2 号 p. 180-183

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The effects of various pentamethine trinuclear cyanine dyes, each of which has three alkyl chains, on ADP/Fe2+-induced lipid peroxidation in rat liver mitochondria were examined. Although the dye having the shortest -C2H5 chains (tri-S-C2(5)) did not show any appreciable effect, the dyes having -C4H9 (tri-S-C4(5)), -C7H15 (tri-S-C7(5)), and -C12H<25> (tri-S-C12(5)) chains significantly inhibited lipid peroxidation, the most potent inhibitory effect being observed with tri-S-C7(5). The mode of antiperoxidation effect of the dyes was dependent on the length of the alkyl chains. The relatively hydrophilic dye tri-S-C4(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-C7(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.
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© The Pharmaceutical Society of Japan
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