Issue 1, 2014

Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding

Abstract

Small molecule synthetic anion transporters may have potential application as therapeutic agents for the treatment of diseases including cystic fibrosis and cancer. Understanding the factors that can dictate the anion transport activity of such transporters is a crucial step towards their application in biological systems. In this study a series of acylthiourea anion transporters were synthesised and their anion binding and transport properties in POPC bilayers have been investigated. The transport activity of these receptors is dominated by their lipophilicity, which is in turn dependent on both substituent effects and the formation and strength of an intramolecular hydrogen bond as inferred from DFT calculations. This is in contrast to simpler thiourea systems, in which the lipophilicity depends predominantly on substituent effects alone.

Graphical abstract: Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding

Supplementary files

Article information

Article type
Paper
Submitted
24 Jul 2013
Accepted
04 Sep 2013
First published
12 Sep 2013
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2014,12, 62-72

Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding

C. J. E. Haynes, N. Busschaert, I. L. Kirby, J. Herniman, M. E. Light, N. J. Wells, I. Marques, V. Félix and P. A. Gale, Org. Biomol. Chem., 2014, 12, 62 DOI: 10.1039/C3OB41522H

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