Summary
The physical effects of 3-phenylindole, an antimicrobial compound which interacts with phospholipids, on ion transport across phosphatidylcholine-cholesterol bilayers have been investigated using three lipophilic ions and one ion-carrier complex. It was found that 3-phenylindole increased membrane electrical conductance of positively charged membrane probes and decreased electrical conductance of negatively charged probes. The enhancement of conductance detected by nonactin-K+ complex and tetraphenylarsonium+ was several orders of magnitude, whereas the suppression of conductance due to tetraphenylborate− and dipicrylamine− was less than a factor of ten. Presence of 3-phenylindole in aqueous phase slightly decreased adsorption of tetraphenylborate− and dipicrylamine− at the membrane surface. From the voltage dependence of the steady-state conductance it was shown that 3-phenylindole induced kinetic limitation of membrane transport of potassium mediated by nonactin. No such limitation was found in the case of tetraphenylarsonium+ transport. These results are shown to be consistent with the present concept of ion diffusion in membranes and the assumption that 3-phenylindole decreases the electric potential in the membrane interior. The asymmetry of the effect of 3-phenylindole on the magnitude of conductance changes for positively and negatively charged membrane permeable ions is also discussed as a reflection of the discreteness of both the adsorbed 3-phenylindole and lipid dipoles.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Andersen, O.S., Feldberg, S., Nakadomari, H., Levy, S., McLaughlin, S. 1978. Electrostatic interactions among hydrophobic ions in lipid bilayer membranes.Biophys. J. 21:35–70
Andersen, O.S., Finkelstein, A., Katz, I., Cass, A. 1976. Effect of phloretin on the permeability of thin lipid membranes.J. Gen. Physiol. 67, 749–771
Andersen, O.S., Fuchs, M. 1975. Potential energy barriers to ion transport within lipid bilayers.Biophys. J. 15:795–830
Barratt, M.D., Weaver, A.C. 1979. The interaction of 3,3′,4′,5-tetrachlorosalicylanilide with phosphatidylcholine bilayers.Biochim Biophys. Acta 555:337–348
Benz, R., Gisin, B.F. 1978. Influence of membrane structure on ion transport through lipid bilayer membranes.J. Membrane Biol. 40:293–314
Bruner, L.J. 1975. The interaction of hydrophobic ions with lipid bilayer membranes.J. Membrane Biol. 22:125–141
Cousin, J. L., Motais, R. 1978. Effect of phloretin on chloride permeability: A structure-activity study.Biochim. Biophys Acta 507:531–538
Dekker, W.H., Selling, H.A., Overeem, J.O. 1975. Structure-activity relationships of some antifungal indoles.J. Agric. Food Chem. 23:785–791
Fischer, E., Schmidt, T. 1888. Ueber Pr. 3-Phenylindol.Berichte Deutschen Chemischen Gesellschaft 21:1811–1812
Hanai, T., Haydon, D.A., Taylor, J. 1965. The variation of capacitance and conductance of biomolecular lipid membranes with area.J. Theor. Biol. 9:433–443
Haydon, D.A., Myers, V.B. 1973. Surface charge, surface dipoles and membrane conductance.Biochim. Biophys. Acta 307:429–443
Hladky, S.B. 1972. The steady-state theory of the carrier transport of ions.J. Membrane Biol. 10:67–91
Hladky, S.B. 1973. The effect of stirring on the flux of carriers into black lipid membranes.Biochim. Biophys. Acta 307:261–269
Hladky, S.B. 1975. Tests of the carrier model for ion transport by nonactin and trinactin.Biochim. Biophys. Acta 375:327–349
Hladky, S.B. 1979. The carrier mechanism.In: Current Topics in Membranes and Transport. F. Bronner and A. Kleinzeller, editors. pp. 53–164. Academic Press, New York
Hoppe, H.H., Kerkenaar, A., Sijpesteijn, A.K. 1976a. On the mode of action of 3-phenylindole towardsAspergillus niger.Pest. Biochem. Physiol. 6:413–421
Hoppe, H.H., Kerkenaar, A., Sijpesteijn, A.K. 1976b. Interaction with phospholipids as a possible mode of action of 3-phenylindole onAspergillus niger.Pest Biochem. Physiol. 6:422–429
Ketterer, B., Neumcke, B., Läuger, P. 1971. Transport mechanism of hydrophobic ions through lipid bilayer membranes.J. Membrane Biol. 5:225–245
Liberman, Y.A., Topaly, V.P. 1969. Permeability of bimolecular phospholipid membranes for fat-soluble ions.Biophysics 14:477–487
McClellan, A.L. 1974. Tables of Experimental Dipole Moments. Vol. 2. p. 288. Rahara Enterprises, El Cerrito (Calif.)
McLaughlin, S. 1973. Salicylates and phospholipid bilayer membranes.Nature (London) 243:234–236
McLaughlin, S., Eisenberg, M. 1975. Antibiotics and membrane biology.Annu. Rev. Biophys. Bioeng. 4:335–366
McLaughlin, S., Dilger, J.P. 1980. Transport of protons across membranes by weak acids.Physiol. Rev. 60:825–863
Mueller, P., Rudin, D.O., Tien, H., Wescott, W.C. 1963. Methods for the formation of single bimolecular lipid membranes in aqueous solution.J. Phys. Chem. 67:534–535
Owen, J.D. 1974. The effect of phloretin on the potassium conductance inAplysia giant neurons.J. Membrane Biol. 16:65–78
Pickar, A.D., Benz, R. 1978. Transport of oppositely charged lipophilic probe ions in lipid bilayer membranes having various structures.J. Membrane Biol. 44:353–376
Sinha, B. 1981. Physical effects of 3-phenylindole on ion transport across bilayer lipid membranes. Ph. D. Dissertation. Portland State University, Portland, Oregon
Smejtek, P., Paulis-Illangasekare, M. 1979a. Modification of ion transport in lipid bilayer membranes in the presence of 2,4-dichlorophenoxyacetic acid (2,4-D). I. Enhancement of cationic conductance and changes of the kinetics of nonactin-mediated transport of potassium.Biophys. J. 26:441–466
Smejtek, P., Paulis-Illangasekare, M. 1979b. Modification of ion transport in lipid bilayer membranes in the presence of 2,4-dichlorophenoxyacetic acid (2,4-D). II. Suppression of tetraphenylborate conductance and changes of interfacial potentials.Biophys. J. 26:467–488
Stark, G., Benz, R. 1971. The transport of potassium through lipid bilayer membranes by the neutral carriers valinomycin and monactin.J. Membrane Biol. 5:133–153
Szabo, G. 1974. Dual mechanism for the action of cholesterol on membrane permeability.Nature (London) 257:47–49
Szabo, G. 1976. The influence of dipole potentials on the magnitude and the kinetics of ion transport in lipid bilayer membranes.In: Extreme Environments: Mechanisms of Microbial Adaptation. M.R. Heinrich, editor. pp. 321–348. Academic Press, New York
Szabo, G., Eisenman, G., McLaughlin, S.G.A., Krasne, S. 1972. Ionic probes of membrane structures.Ann. N. Y. Acad. Sci. 193:273–290
Wang, C.C., Bruner, L.J. 1978a. Dielectric saturation of the aqueous boundary layer adjacent to charged bilayer membranes.J. Membrane Biol. 38:311–331
Wang, C.C., Bruner, L.J. 1978b. Evidence for a discrete charge effect within lipid bilayer membranes.Biophys. J. 24:749–764
Wieth, J.O., Dalmark, M., Gunn, R.Z., Tosteson, D.C. 1973. The transfer of monovalent inorganic anions through the red cell membrane.In: Erythrocytes, Thrombocytes, Leucocytes. E. Gerlach, K. Moses, E. Deutsch, and W. Wilmanns, editors. pp. 71–76. Georg Thieme Verlag KG, Stuttgart
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sinha, B.A., Smejtek, P. Effect of 3-phenylindole on lipophilic ion and carrier-mediated ion transport across bilayer lipid membranes. J. Membrain Biol. 71, 119–130 (1983). https://doi.org/10.1007/BF01870680
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF01870680