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Naunyn-Schmiedeberg's Archives of Pharmacology

, Volume 316, Issue 3, pp 266–272 | Cite as

Transport of organic ions through lipid bilayers

  • Peter G. Ruifrok
  • Dirk K. F. Meijer
Article

Summary

The transport of a series of charged drugs and other organic ions through lipid bilayers was studied, using single-bilayer liposomes. Monovalent organic cations and organic anions could carry charge into the liposomes independent of the nature of their counter ion. Ion-pair formation, following the addition of an excess of I or Br, did not facilitate this transport. However the passage of organic cations and anions across the membrane required the presence of the organic anion tetraphenylborate in the lipid bilayer. This effect of tetraphenylborate is probably due to a lowering of an intra-membrane potential energy hill, the principal barrier for transport, and not to ion-pair formation.

It is concluded that organic ions that posses sufficiently lipophilic structures to mask their charged character, can pass lipid bilayers in charged form.

Key words

Organic ions Liposomes Transport 

List of Abbreviations

CCCP

carbonylcyanide-m-chlorophenylhydrazone

DDA+

dibenzyldimethylammonium

DNP

dinitrophenol

DPA

dipicrylamine

F

ferrocene

F+

ferricinium

FCCP

p-trifluoromethoxycarbonylcyanide-phenylhydrazone

MDT+

N-methyldeptropine

PCB

phenyl-dicarbaundecaborane

SCN

thiocyanate

S13

3-t-butyl,5-chloro,2′-chloro,4′ nitro-salicylanilid

TBA+

tetrabutylammonium

TPAs+

tetraphenylarsonium

TPMP+

triphenylmethylphosphonium

TPP+

tetraphenylphosphonium

TPB

tetraphenylborate

TTFB

tetrachlorotrifluoromethylbenzimidazole

X+

an organic cation

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Copyright information

© Springer-Verlag 1981

Authors and Affiliations

  • Peter G. Ruifrok
    • 1
  • Dirk K. F. Meijer
    • 1
  1. 1.Department of Pharmacology and Pharmacotherapeutics, Faculty of PharmacyState University of GroningenGroningenThe Netherlands

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