Journal article
Thiosquaramides: pH switchable anion transporters
Chemical science (Cambridge), Vol.5(9), pp.3617-3626
09/01/2014
DOI: 10.1039/C4SC01629G
PMCID: PMC4486358
PMID: 26146535
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
1
H 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 p
K
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.
Details
- Title: Subtitle
- Thiosquaramides: pH switchable anion transporters
- Creators
- Nathalie Busschaert - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaRobert B. P Elmes - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaDawid D Czech - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaXin Wu - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaIsabelle L Kirby - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaEvan M Peck - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaKevin D Hendzel - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaScott K Shaw - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaBun Chan - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaBradley D Smith - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaKatrina A Jolliffe - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi ArabiaPhilip A Gale - Chemistry, University of Southampton, Southampton, SO17 1BJ, UK School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana, 46556, USA Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
- Resource Type
- Journal article
- Publication Details
- Chemical science (Cambridge), Vol.5(9), pp.3617-3626
- DOI
- 10.1039/C4SC01629G
- PMID
- 26146535
- PMCID
- PMC4486358
- NLM abbreviation
- Chem Sci
- ISSN
- 2041-6520
- eISSN
- 2041-6539
- Language
- English
- Date published
- 09/01/2014
- Academic Unit
- Chemistry
- Record Identifier
- 9984216723802771
Metrics
11 Record Views