Busschaert, Nathalie and Elmes, Robert B.P. and Czech, Dawid D. and Wu, Xin and Kirby, Isabelle L. and Peck, Evan M. and Hendzel, Kevin D. and Shaw, Scott J. and Chan, Bun and Smith, Bradley D. and Jolliffe, Katrina A. and Gale, Philip A. (2014) Thiosquaramides: pH switchable anion transporters. Chemical Science, 5 (9). pp. 3617-3626. ISSN 2041-6539

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Abstract

The transport of anions across cellular membranes is an important biological function governed by specialised proteins. In recent years, many small molecules have emerged that mimick the anion transport behaviour of these proteins, but only a few of these synthetic molecules also display the gating/switching behaviour seen in biological systems. A small series of thiosquaramides was synthesised and their pH-dependent chloride binding and anion transport behaviour was investigated using 1H NMR titrations, single crystal X-ray diffraction and a variety of vesicle-based techniques. Spectrophotometric titrations and DFT calculations revealed that the thiosquaramides are significantly more acidic than their oxosquaramide analogues, with pKa values between 4.0 and 9.0. This led to the observation that at pH 7.2 the anion transport ability of the thiosquaramides is fully switched OFF due to deprotonation of the receptor, but is completely switched ON at lower pH.

Item Type:	Article
Additional Information:	This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Keywords:	Thiosquaramides; pH switchable anion transporters; cellular membranes;
Academic Unit:	Faculty of Science and Engineering > Chemistry
Item ID:	5638
Identification Number:	https://doi.org/10.1039/c4sc01629g
Depositing User:	Robert Elmes
Date Deposited:	18 Dec 2014 17:31
Journal or Publication Title:	Chemical Science
Publisher:	Royal Society of Chemistry
Refereed:	Yes
URI:	http://pubs.rsc.org/en/Journals/JournalI...
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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