期刊
CHEMICAL SCIENCE
卷 5, 期 9, 页码 3617-3626出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc01629g
关键词
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资金
- EPSRC [EP/J009687/1]
- ARC [DP140100227]
- China Scholarship Council
- University of Southampton
- European Cooperation in Science and Technology (COST) action [CM1005]
- Royal Society
- Wolfson Foundation
- Engineering and Physical Sciences Research Council [EP/J009687/1] Funding Source: researchfish
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1401783, 1058699] Funding Source: National Science Foundation
- EPSRC [EP/J009687/1] Funding Source: UKRI
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 thjosquaramides was synthesised and their pH-dependent chloride binding and anion transport behaviour was investigated using H-1 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 pK(a) 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.
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