Hydrophobic ion probe studies of membrane dipole potentials

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Hydrophobic anions of dipicrylamine and of sodium tetraphenylborate have been employed as probes of interfacial dipole potential variations in lipid bilayer membranes. Systematic variation of dipole potentials has been achieved by introduction of compounds incorporating N + and B − charge centers. Distribution of hydrophilic and and hydrophobic groups relative to these charge centers has been shown to control the orientation in the membrane/solution interface of the electric dipole moment formed by these centers. Thus triphenyl-[4-trimethylphenylammonium] borate orients with the B − center, surrounded by phenyl groups, embedded in the membrane, while the smaller methylated N + center is directed toward the aqueous phases. This orientation has been confirmed using dipicrylamine probe ions. Results obtained in this system have been interpreted quantitatively using a previously developed model incorporating discrete charge effects. A second class of compounds, tri-n- alkylamine borane (T n AB) complexes having the generic formula (C n H 2n+1 ) 3N +B −H 3, have also been synthesized for this study, using even-carbon alkyls ranging from ethyl to decyl. Molecular orientation of the complex is with the N + center and its associated alkyl groups directed into the membranes, while the protonated B − center is directed toward the aqueous phases, as confirmed by use of tetraphenylborate ions as probes.