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Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding

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.
1477-0520
62-72
Haynes, Cally J.E.
c56ceaa2-ca95-4ef6-bcce-c5cb825c2ca0
Busschaert, Nathalie
bf307f09-0a86-4a03-afd8-4b0a59a8f72b
Kirby, Isabelle L.
5839d488-f346-4741-b757-9ecf30777938
Herniman, Julie
530b1a36-1386-4602-8df7-defa6eb3512b
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Wells, Neil J.
86312185-007b-495b-86da-4e2e5b9b8025
Marques, Igor
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Félix, Vítor
b4098ac2-b86b-48f3-af11-c767e24fac6e
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Haynes, Cally J.E.
c56ceaa2-ca95-4ef6-bcce-c5cb825c2ca0
Busschaert, Nathalie
bf307f09-0a86-4a03-afd8-4b0a59a8f72b
Kirby, Isabelle L.
5839d488-f346-4741-b757-9ecf30777938
Herniman, Julie
530b1a36-1386-4602-8df7-defa6eb3512b
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Wells, Neil J.
86312185-007b-495b-86da-4e2e5b9b8025
Marques, Igor
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Félix, Vítor
b4098ac2-b86b-48f3-af11-c767e24fac6e
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943

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), 62-72. (doi:10.1039/c3ob41522h).

Record type: Article

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

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Local EPrints ID: 356741
URI: http://eprints.soton.ac.uk/id/eprint/356741
ISSN: 1477-0520
PURE UUID: bc444949-8a8c-4469-b285-71cbe5a8ce9e
ORCID for Julie Herniman: ORCID iD orcid.org/0000-0003-4834-1093
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Neil J. Wells: ORCID iD orcid.org/0000-0002-4607-5791
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

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Date deposited: 13 Sep 2013 09:04
Last modified: 18 Feb 2021 16:55

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Contributors

Author: Cally J.E. Haynes
Author: Nathalie Busschaert
Author: Isabelle L. Kirby
Author: Julie Herniman ORCID iD
Author: Mark E. Light ORCID iD
Author: Neil J. Wells ORCID iD
Author: Igor Marques
Author: Vítor Félix
Author: Philip A. Gale ORCID iD

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