title: Substitution of ether linkage for ester bond in phospholipids increases permeability of bilayer lipid membrane for SkQ1-type penetrating cations.
abstract: Using dialkylphospholipid (diphytanyl phosphatidylcholine) instead of the conventional diacylphospholipid (diphytanoyl phosphatidylcholine) in planar lipid bilayer membranes (BLM) led to an increase in the diffusion potential of the penetrating cation plastoquinonyl-decyl-triphenylphosphonium (SkQ1), making it close to the Nernst value, and accelerated translocation of SkQ1 across the BLM as monitored by the kinetics of a decrease in the transmembrane electric current after applying a voltage (current relaxation). The consequences of changing from an ester to an ether linkage between the head groups and the hydrocarbon chains are associated with a substantial reduction in the membrane dipole potential known to originate from dipoles of tightly bound water molecules and carbonyl groups in ester bonds. The difference in the dipole potential between BLM formed of the ester phospholipid and that of the ether phospholipid was estimated to be 100 mV. In the latter case, suppression of SkQ1-mediated proton conductivity of the BLM was also observed.
authors.affiliation: Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, 119991 Moscow, Russia.
authors.forename: T M
authors.initials: TM
authors.lastname: Il'yasova
authors.forename: T I
authors.initials: TI
authors.lastname: Rokitskaya
authors.forename: I I
authors.initials: II
authors.lastname: Severina
authors.forename: Y N
authors.initials: YN
authors.lastname: Antonenko
authors.forename: V P
authors.initials: VP
authors.lastname: Skulachev
mesh_terms: D002412:Cations / Q000737:chemistry / Q000494:pharmacology; D002463:Cell Membrane Permeability / Q000187:drug effects*; D004952:Esters / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D008051:Lipid Bilayers / Q000737:chemistry*; D015394:Molecular Structure; D010743:Phospholipids / Q000737:chemistry*; D010971:Plastoquinone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
chemical_list: C532038:10-(6'-plastoquinonyl)decyltriphenylphosphonium; D002412:Cations; D004952:Esters; D004987:Ethers; D008051:Lipid Bilayers; D010743:Phospholipids; D010971:Plastoquinone