Membrane interactions and metal ion effects on bilayer permeation of the lipophilic ion modulator DP-109

Biochemistry. 2005 Sep 13;44(36):12077-85. doi: 10.1021/bi050718x.

Abstract

DP-109, a lipophilic bivalent metal ion modulator currently under preclinical development for neurodegenerative disorders, was designed to have membrane-associated activity, thereby restricting its action to the vicinity of cell membranes. We describe the application of a colorimetric phospholipid/polydiacetylene (PDA) biomimetic membrane assay in elucidating DP-109 membrane interactions and penetration into lipid bilayers. In this membrane model, visible quantifiable color changes were monitored in studying membrane interactions. The colorimetric data identified a biphasic concentration-dependent interaction, with a break point around the critical micelle concentration (CMC) of DP-109. The kinetics and colorimetric dose-response profile of DP-109 indicate that the compound inserts into the lipid bilayers rather than being localized at the bilayer surface. Analysis of interactions of DP-109 with phospholipid/PDA vesicles in which ionic gradients were imposed indicates that membrane activity of DP-109 is strongly affected by electrochemical gradients imposed by K+ and Zn2+. The ionic gradient effects suggest that the insertion of DP-109 into the membrane may depend on the membrane potential.

MeSH terms

  • Egtazic Acid / analogs & derivatives*
  • Egtazic Acid / chemistry
  • Egtazic Acid / pharmacology
  • Ions / chemistry
  • Lipid Bilayers / chemistry*
  • Lipid Bilayers / metabolism*
  • Molecular Structure
  • Potassium / chemistry
  • Potassium / pharmacology*
  • Sodium / chemistry
  • Sodium / pharmacology*
  • Zinc / chemistry
  • Zinc / pharmacology*

Substances

  • DP-109
  • Ions
  • Lipid Bilayers
  • 1,2-bis(2-aminophenoxy)ethane N,N,N',N'-tetraacetic acid acetoxymethyl ester
  • Egtazic Acid
  • Sodium
  • Zinc
  • 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid
  • Potassium