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Issue 3, 2014
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Lipophilic balance – a new design principle for transmembrane anion carriers

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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

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Publication details

The article was received on 25 Oct 2013, accepted on 11 Nov 2013 and first published on 10 Jan 2014


Article type: Edge Article
DOI: 10.1039/C3SC52962B
Citation: Chem. Sci., 2014,5, 1128-1134
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    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

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