Partitioning and localization of spin-labeled amantadine in lipid bilayers: an EPR study

J Pharm Sci. 1998 Oct;87(10):1249-54. doi: 10.1021/js970381n.

Abstract

EPR was used to study the distribution of the spin-labeled amantadine (AA-SL) between the bulk hydrophobic-hydrocarbon solvent, light paraffin oil, and water and between hydrophobic-hydrocarbon chain region of lipid membranes and water. The AA-SL molecules were soluble in both hydrophobic and polar regions of investigated systems. It was shown that the partition coefficient of AA-SL between the hydrocarbon region of the L-alpha-dimyristoylphosphatidylcholine fluid-phase membrane and water is much higher than between bulk hydrocarbon solvent and water. Furthermore, the partitioning of AA-SL into membranes of multilamellar liposomes made of L-alpha-dimyristoylphosphatidylcholine, L-alpha-dipalmitoylphosphatidylcholine, and L-alpha-distearoylphosphatidylcholine was studied as a function of temperature, indicating no abrupt change at the main phase transition of these membranes. It is also clear from our data that AA-SL can penetrate into the gel-phase membrane practically with the same partitioning as into the fluid-phase membrane. Furthermore, it was shown that at least part of the AA-SL molecule is deeply buried in the hydrocarbon chain region of the membrane.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amantadine / analysis*
  • Antiviral Agents / analysis*
  • Electron Spin Resonance Spectroscopy
  • Lipid Bilayers / chemistry*
  • Liposomes
  • Spin Labels
  • Water

Substances

  • Antiviral Agents
  • Lipid Bilayers
  • Liposomes
  • Spin Labels
  • Water
  • Amantadine