Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding
Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding
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.
62-72
Haynes, Cally J.E.
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Busschaert, Nathalie
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Kirby, Isabelle L.
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Herniman, Julie
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Light, Mark E.
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Wells, Neil J.
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Marques, Igor
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Félix, Vítor
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Gale, Philip A.
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7 January 2014
Haynes, Cally J.E.
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Busschaert, Nathalie
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Kirby, Isabelle L.
5839d488-f346-4741-b757-9ecf30777938
Herniman, Julie
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Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Wells, Neil J.
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Marques, Igor
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Félix, Vítor
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Gale, Philip A.
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Haynes, Cally J.E., Busschaert, Nathalie, Kirby, Isabelle L., Herniman, Julie, Light, Mark E., Wells, Neil J., Marques, Igor, Félix, Vítor and Gale, Philip A.
(2014)
Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding.
Organic & Biomolecular Chemistry, 12 (1), .
(doi:10.1039/c3ob41522h).
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.
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e-pub ahead of print date: 12 September 2013
Published date: 7 January 2014
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 356741
URI: http://eprints.soton.ac.uk/id/eprint/356741
ISSN: 1477-0520
PURE UUID: bc444949-8a8c-4469-b285-71cbe5a8ce9e
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Date deposited: 13 Sep 2013 09:04
Last modified: 15 Mar 2024 03:06
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Contributors
Author:
Cally J.E. Haynes
Author:
Nathalie Busschaert
Author:
Isabelle L. Kirby
Author:
Igor Marques
Author:
Vítor Félix
Author:
Philip A. Gale
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