Lipophilic balance - a new design principle for transmembrane anion carriers

Hennie Valkenier, Cally J. E. Haynes, Julie Herniman, Philip A. Gale*, Anthony P. Davis

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

57 Citations (Scopus)

Abstract

Despite extensive interest in transmembrane anion carriers (anionophores), the factors that govern activity are still only partly understood. Herein we report a study which identifies a new principle for anionophore design, that of "lipophilic balance'. A series of simple thioureas with identical molecular formulae has been prepared and assayed for chloride/nitrate transport activity in synthetic vesicles. The molecules differ only in the positioning of the phenylthiourea binding unit within an 11-carbon linear chain. They are shown to possess very similar lipophilicities and anion affinities, while a test for leaching establishes that they locate almost exclusively in the vesicle membranes. Notwithstanding their close similarities, activities across the series show >5-fold variation, peaking when the phenylthiourea group is centrally located. The results suggest that transport is favoured by a balanced array of lipophilic substituents, possibly because this arrangement facilitates transfer of the complexed anion into the apolar membrane interior.

Original languageEnglish
Pages (from-to)1128-1134
Number of pages7
JournalChemical Science
Volume5
Issue number3
DOIs
Publication statusPublished - Mar 2014

Keywords

  • CHLORIDE TRANSPORT
  • MEMBRANE TRANSPORTERS
  • PI INTERACTIONS
  • CELL-MEMBRANES
  • CHANNELS
  • VESICLE

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