Abstract:
:Structure-uncoupling activity relationship of seven anthraquinone derivatives were investigated using rat liver mitochondria. Three compounds bearing the free hydroxyl group at the beta-position of their anthraquinone nucleus (1,3,6,8-tetrahydroxyanthraquinone, 1-acetyl-2,4,5,7-tetrahydroxy-9,10-anthracenedione and skyrin) exhibited uncoupling effect. Rugulosin, rugulin and physcion (all lacking the hydroxyl at the beta-position) were ineffective. Erythroglaucin, a derivative of physcion with the free hydroxyl group at the gamma-position, exhibited the highest uncoupling activity in the series tested. In addition, erythroglaucin abolished the energy dependent Ca2+ retention in mitochondria and induced Ca2+ leak. It also prevented the energization of mitochondrial membrane by ATP and induced a loss of the ATP induced membrane potential similarly as did carbonylcyanamide-3-chlorophenyl hydrazone (CCCP). The data show that the free hydroxyl group at either the gamma-position or the beta-position of anthraquinone nucleus is a prerequisite of the uncoupling activity of hydroxyanthraquinones.
journal_name
Chem Biol Interactjournal_title
Chemico-biological interactionsauthors
Betina V,Kuzela Sdoi
10.1016/0009-2797(87)90089-5subject
Has Abstractpub_date
1987-01-01 00:00:00pages
179-89issue
2eissn
0009-2797issn
1872-7786pii
0009-2797(87)90089-5journal_volume
62pub_type
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