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.
keywords
TRANSMEMBRANE CHLORIDE TRANSPORT; N,N-DISUBSTITUTED THIOUREAS; SYNTHETIC CHLORIDE; SOLVENT-EXTRACTION; CRYSTAL-STRUCTURE; CELL-MEMBRANES; ACYL-THIOUREA; COMPLEXES; LIGANDS; BINDING
subject category
Chemistry
authors
Haynes, CJE; Busschaert, N; Kirby, IL; Herniman, J; Light, ME; Wells, NJ; Marques, I; Felix, V; Gale, PA
our authors
Igor Oliveira Marques
Junior Researcher
Vítor Félix
Associate Professor with Aggregationacknowledgements
We thank the EPSRC for funding (CJEH - EP/J009687/1) and for access to the crystallographic facilities at the University of Southampton. We thank the University of Southampton and A*STAR for a postgraduate scholarship (NB) and the University of Southampton for a teaching assistantship (ILK). PAG thanks the Royal Society and the Wolfson Foundation for a Royal Society Wolfson Research Merit Award. IM thanks the FCT (Fundacao para a Ciencia e a Tecnologia) for the PhD scholarship SFRH/BD/87520/2012. VF acknowledges the funding from QREN-FEDER, through the Operational Program Competitiveness Factors - COMPETE and National Funds through the FCT under project PTDC/QUI-QUI/101022/2008.