Lipophilic ion aromaticity is not important for permeability across lipid membranes

Autor: Vadim N. Tashlitsky, Elena A. Kotova, Yuri N. Antonenko, Victor B. Luzhkov, Tatyana I. Rokitskaya, Galina A. Korshunova, Ekaterina V. Aleksandrova, Roman S. Kirsanov
Rok vydání: 2020
Předmět:
Zdroj: Biochimica et biophysica acta. Biomembranes. 1863(1)
ISSN: 1879-2642
Popis: To clarify the contribution of charge delocalization in a lipophilic ion to the efficacy of its permeation through a lipid membrane, we compared the behavior of alkyl derivatives of triphenylphosphonium, tricyclohexylphosphonium and trihexylphosphonium both in natural and artificial membranes. Exploring accumulation of the lipophilic cations in response to inside-negative membrane potential generation in mitochondria by using an ion-selective electrode revealed similar mitochondrial uptake of butyltricyclohexylphosphonium (C4TCHP) and butyltriphenylphosphonium (C4TPP). Fluorescence correlation spectroscopy also demonstrated similar membrane potential-dependent accumulation of fluorescein derivatives of tricyclohexyldecylphosphonium and decyltriphenylphosphonium in mitochondria. The rate constant of lipophilic cation translocation across the bilayer lipid membrane (BLM), measured by the current relaxation method, moderately increased in the following sequence: trihexyltetradecylphosphonium ([P6,6,6,14])
Databáze: OpenAIRE