Ion Conductors Derived From Cholic Acid and Spermine: Importance of Facial Hydrophilicity on NA(+) Transport and Membrane Selectivity

J Am Chem Soc. 2001 Aug 8;123(31):7691-6. doi: 10.1021/ja010926m.


A series of ion conductors have been synthesized in which the degree of facial hydrophilicity has been systematically varied. Specifically, conjugates have been prepared from cholic acid and spermine in which the hydrophilic face of each sterol bears methoxy (1), hydroxy (2), carbamate (3), or sulfate groups (4). The ability of these conjugates to promote the transport of Na(+) across phosphatidylcholine membranes of varying thickness has been investigated by (23)Na NMR spectroscopy. Examination of observed activities in three different phosphatidylcholine membranes has provided evidence for membrane-spanning dimers as the transport-active species. In the thinnest membranes investigated, made from 1,2-dimyristoleoyl-sn-glycero-3-phosphocholine (C14), Na(+)-transport activity was found to increase, substantially, with increasing facial hydrophilicity. In thicker membranes, made from 1,2-dioleoyl-sn-glycero-3-phosphocholine (C18), observed activities were found to decrease with increasing facial hydrophilicity; with a membrane of intermediate thickness, prepared from 1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine (C16), ion-conducting activity increased and then decreased, with continuous increases in facial hydrophilicity. The possible origins for these variations in activity are briefly discussed.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cholic Acid / chemistry*
  • Drug Design
  • Magnetic Resonance Spectroscopy
  • Membranes, Artificial
  • Molecular Structure
  • Sodium / chemistry*
  • Spermine / chemistry*


  • Membranes, Artificial
  • Spermine
  • Sodium
  • Cholic Acid