PMID: 4291494Feb 1, 1967Paper

Properties of substituted 2-trifluoromethylbenzimidazoles as uncouplers of oxidative phosphorylation

The Biochemical Journal
O T Jones, W A Watson

Abstract

1. The activity of 25 substituted 2-trifluoromethylbenzimidazoles in uncoupling oxidative phosphorylation by rat-liver mitochondria has been compared. 2. For halogen- or mixed-halogen- and alkyl-substituted analogues, uncoupling activity was proportional to the acidity of the imidazole -NH group. Tetrachloro-2-trifluoromethylbenzimidazole was the most active (50% uncoupling of oxidative phosphorylation at 7.9x10(-8)m, pK5.04). Nitro-substituted analogues were less active than predicted from pK considerations or from partition-coefficient measurements. 3. Introduction of an -NH(2) or -CO(2)H substitutent caused a loss of uncoupling activity, as did alkylation at position 1 of the imidazole ring. 4. Benzimidazoles active as uncouplers stimulated mitochondrial adenosine triphosphatase but not all stimulated the oxidation of succinate in the absence of a phosphate acceptor. 5. 4,5-Dichloro-2-trifluoromethylbenzimidazole inhibited the succinate-oxidase system at about the same concentration required for uncoupling (0.52mum for 50% inhibition of both activities) and the site of this inhibition appears to lie between succinate dehydrogenase and cytochrome b.

Citations

Jan 1, 1968·Histochemie. Histochemistry. Histochimie·M Kalina, J M Palmer
Jun 3, 2000·Annual Review of Pharmacology and Toxicology·K B Wallace, A A Starkov
Sep 1, 1990·Journal of Veterinary Pharmacology and Therapeutics·Q A McKellar, E W Scott
Jan 1, 1988·Teratogenesis, Carcinogenesis, and Mutagenesis·T TsuchiyaM Ishidate
May 29, 2020·Chemical Research in Toxicology·Andrea Ebert, Kai-Uwe Goss
Mar 1, 1981·Chemico-biological Interactions·W N AldridgeJ G Noltes
Feb 1, 1991·International Journal for Parasitology·R O McCracken, W H Stillwell
Jul 18, 2018·Chemical Research in Toxicology·Steven J EnochOvanes G Mekenyan
Nov 21, 2017·Journal of Medicinal Chemistry·Elizabeth S ChildressWebster L Santos

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