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Zwitterionic Protonophore Derived from 2-(2-Hydroxyaryl)alkenylphosphonium as an Uncoupler of Oxidative Phosphorylation

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dc.contributor.author Rokitskaya T.
dc.contributor.author Terekhova N.
dc.contributor.author Khailova L.
dc.contributor.author Kotova E.
dc.contributor.author Plotnikov E.
dc.contributor.author Zorov D.
dc.contributor.author Tatarinov D.
dc.contributor.author Antonenko Y.
dc.date.accessioned 2020-01-21T20:45:59Z
dc.date.available 2020-01-21T20:45:59Z
dc.date.issued 2019
dc.identifier.issn 1043-1802
dc.identifier.uri https://dspace.kpfu.ru/xmlui/handle/net/157752
dc.description.abstract © 2019 American Chemical Society. 2-(2-Hydroxyaryl)alkenylphosphonium salts (here coined as PPR) representing derivatives of quaternary phosphonium with two phenyl (P) and one alkyl (R) substituents linked through alkenyl bridge to substituted phenol were applied here to planar bilayer lipid membranes (BLM), isolated mitochondria, and cell culture. PPR with six carbon atoms in R (PP6) induced proton-selective currents across BLM and caused mitochondrial uncoupling. In particular, PP6 at submicromolar concentrations accelerated respiration, decreased membrane potential, and reduced ATP synthesis in isolated rat liver mitochondria (RLM). Methylation of a hydroxyl group substantially suppressed the protonophoric activity of PP6 on BLM and its uncoupling potency in RLM. Of note, the methylated derivative PP6-OMe was synthesized here via a new synthetic route including cyclization of PP6 with subsequent ring opening. PPR were considered as protonophoric uncouplers of a zwitterionic type, capable of penetrating membranes both as a zwitterion composed of a deprotonated phenol and a cationic quaternary phosphonium, and as a protonated cation. The protonophoric and uncoupling properties of PPR found here were speculated to account for their strong antibacterial activity described previously.
dc.relation.ispartofseries Bioconjugate Chemistry
dc.title Zwitterionic Protonophore Derived from 2-(2-Hydroxyaryl)alkenylphosphonium as an Uncoupler of Oxidative Phosphorylation
dc.type Article
dc.relation.ispartofseries-issue 9
dc.relation.ispartofseries-volume 30
dc.collection Публикации сотрудников КФУ
dc.relation.startpage 2435
dc.source.id SCOPUS10431802-2019-30-9-SID85071617906


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  • Публикации сотрудников КФУ Scopus [22633]
    Коллекция содержит публикации сотрудников Казанского федерального (до 2010 года Казанского государственного) университета, проиндексированные в БД Scopus, начиная с 1970г.

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