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.
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 -C12H25 (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.
Kogure
K
K
Faculty of Pharmaceutical Sciences, University of Tokushima, Japan.
Sassa
H
H
Abe
K
K
Kitahara
K
K
Sano
Y
Y
Kawano
H
H
Nakagawa
Y
Y
Terada
H
H
D000244:Adenosine Diphosphate / Q000031:analogs & derivatives* / Q000494:pharmacology; D000818:Animals; D004396:Coloring Agents / Q000494:pharmacology*; D015227:Lipid Peroxidation / Q000187:drug effects*; D008297:Male; D008930:Mitochondria, Liver / Q000187:drug effects* / Q000378:metabolism; D010100:Oxygen / Q000378:metabolism; D051381:Rats; D017208:Rats, Wistar; D017392:Thiobarbituric Acid Reactive Substances / Q000378:metabolism
D004396:Coloring Agents; D017392:Thiobarbituric Acid Reactive Substances; C029936:adenosine diphosphate-ferric chelate; D000244:Adenosine Diphosphate; D010100:Oxygen