Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding
authors Haynes, CJE; Busschaert, N; Kirby, IL; Herniman, J; Light, ME; Wells, NJ; Marques, I; Felix, V; Gale, PA
nationality International
journal ORGANIC & BIOMOLECULAR CHEMISTRY
keywords TRANSMEMBRANE CHLORIDE TRANSPORT; N,N-DISUBSTITUTED THIOUREAS; SYNTHETIC CHLORIDE; SOLVENT-EXTRACTION; CRYSTAL-STRUCTURE; CELL-MEMBRANES; ACYL-THIOUREA; COMPLEXES; LIGANDS; BINDING
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 atone.
publisher ROYAL SOC CHEMISTRY
issn 1477-0520
year published 2014
volume 12
issue 1
beginning page 62
ending page 72
digital object identifier (doi) 10.1039/c3ob41522h
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000329551100007
link 24056984
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journal impact factor 3.423
5 year journal impact factor 3.138
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