Synthesis and transmembrane anion/cation symport activity of a rigid bis(choloyl) conjugate functionalized with guanidino groups

Bioorg Med Chem Lett. 2015 Feb 15;25(4):745-8. doi: 10.1016/j.bmcl.2015.01.015. Epub 2015 Jan 14.

Abstract

A rigid bis(choloyl) conjugate functionalized with guanidino groups was synthesized and fully characterized on the basis of NMR ((1)H and (13)C) and ESI MS (LR and HR) data. Its transmembrane ionophoric activity across egg-yolk l-α-phosphatidylcholine-based liposomal membranes was investigated by means of chloride ion selective electrode technique and pH discharge assay. The data indicate that under the assay conditions, this conjugate was capable of promoting the transport of anions, presumably via a cation/anion symport process. A Hill analysis reveals that two molecules of this compound are assembled into the transport-active species.

Keywords: Anionophore; Anionophoric activity; Cholic acid; Guanidino group; Ion selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cations / chemistry
  • Chlorides / chemistry
  • Cholic Acids / chemistry*
  • Cholic Acids / pharmacology*
  • Guanidine / chemistry*
  • Guanidine / pharmacology*
  • Hydrogen-Ion Concentration
  • Ion Transport / drug effects
  • Ionophores / chemistry*
  • Ionophores / pharmacology*
  • Liposomes / chemistry
  • Phosphatidylcholines / chemistry

Substances

  • Cations
  • Chlorides
  • Cholic Acids
  • Ionophores
  • Liposomes
  • Phosphatidylcholines
  • Guanidine