Issue 3, 2014

Lipophilic balance – a new design principle for transmembrane anion carriers

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.

Graphical abstract: Lipophilic balance – a new design principle for transmembrane anion carriers

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Oct 2013
Accepted
11 Nov 2013
First published
10 Jan 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2014,5, 1128-1134

Lipophilic balance – a new design principle for transmembrane anion carriers

H. Valkenier, C. J. E. Haynes, J. Herniman, P. A. Gale and A. P. Davis, Chem. Sci., 2014, 5, 1128 DOI: 10.1039/C3SC52962B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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