Thiosquaramides: pH switchable anion transporters
Thiosquaramides: pH switchable anion transporters
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 thiosquar-amides 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.
3617-3626
Busschaert, Nathalie
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Elmes, Robert B. P.
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Czech, Dawid D.
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Wu, Xin
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Kirby, Isabelle L.
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Peck, Evan M.
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Hendzel, Kevin D.
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Shaw, Scott K.
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Chan, Bun
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Smith, Bradley D.
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Jolliffe, Katrina A.
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Gale, Philip A.
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2014
Busschaert, Nathalie
bf307f09-0a86-4a03-afd8-4b0a59a8f72b
Elmes, Robert B. P.
67d1c256-18a7-432c-8452-03369b6ddb95
Czech, Dawid D.
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Wu, Xin
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Kirby, Isabelle L.
fb76f041-1cd5-4341-ba61-3e34b0927fc7
Peck, Evan M.
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Hendzel, Kevin D.
1fb35c46-ab8d-4a7b-85c3-50cf63594be2
Shaw, Scott K.
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Chan, Bun
3f56b163-c206-431a-b0a4-402e0935196d
Smith, Bradley D.
fd0bfcd3-c3e7-46ac-a225-60abc125d4e8
Jolliffe, Katrina A.
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Gale, Philip A.
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Busschaert, Nathalie, Elmes, Robert B. P., Czech, Dawid D., Wu, Xin, Kirby, Isabelle L., Peck, Evan M., Hendzel, Kevin D., Shaw, Scott K., Chan, Bun, Smith, Bradley D., Jolliffe, Katrina A. and Gale, Philip A.
(2014)
Thiosquaramides: pH switchable anion transporters.
Chemical Science, 5, .
(doi:10.1039/c4sc01629g).
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 thiosquar-amides 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.
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e-pub ahead of print date: 2014
Published date: 2014
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 366592
URI: http://eprints.soton.ac.uk/id/eprint/366592
ISSN: 1478-6524
PURE UUID: 41086f78-4f0a-4683-9de1-1002afcaa7ff
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Date deposited: 03 Jul 2014 13:00
Last modified: 15 Mar 2024 03:06
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Contributors
Author:
Nathalie Busschaert
Author:
Robert B. P. Elmes
Author:
Dawid D. Czech
Author:
Xin Wu
Author:
Isabelle L. Kirby
Author:
Evan M. Peck
Author:
Kevin D. Hendzel
Author:
Scott K. Shaw
Author:
Bun Chan
Author:
Bradley D. Smith
Author:
Katrina A. Jolliffe
Author:
Philip A. Gale
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