Chloride, carboxylate and carbonate transport by ortho-phenylenediamine-based bisureas

Gale, Philip A, Felix, Vitor, Pérez Tomás, Ricardo, Soto Cerrato, Vanessa, Haynes, Cally, Moore, Stephen, González, Jorge, Light, Mark E., Sutton, Jennifer, Marques, Igor, Herniman, Julie and Langley, John (2012) Chloride, carboxylate and carbonate transport by ortho-phenylenediamine-based bisureas. Chemical Science, 4, (1), 103-117. (doi:10.1039/C2SC21112B).


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A series of simple ortho-phenylenediamine-based bisureas have been synthesised and their ability to facilitate chloride/nitrate and chloride/bicarbonate antiport, and HCl symport processes assessed using a combination of ion selective electrode and fluorescence techniques. In addition, the transmembrane transport of dicarboxylate anions (maleate and fumarate) by the compounds was examined. The incorporation of electron withdrawing groups into the receptor scaffold was found to enhance transport activity, which correlates with the calculated electrostatic potential surface maxima points (VS,max) of the receptors. The most active compound is able to facilitate chloride efflux at receptor to lipid ratios as low as 1:1,000,000. The molecular dynamics simulations showed that this compound permeates the membrane better than other promising receptors corroborating the experimental efflux data. Moreover, cell based assays revealed that the majority of the compounds showed cytotoxicity in cancer cells, corroborating their ability to function as ion transporters

Item Type: Article
Digital Object Identifier (DOI): doi:10.1039/C2SC21112B
ISSNs: 2041-6520 (print)
2041-6539 (electronic)
Subjects: Q Science > QD Chemistry
Divisions : Faculty of Natural and Environmental Sciences > Chemistry > Organic Chemistry: Synthesis, Catalysis and Flow
ePrint ID: 342469
Accepted Date and Publication Date:
29 August 2012Made publicly available
January 2013Published
Date Deposited: 31 Aug 2012 13:19
Last Modified: 31 Mar 2016 14:33
Synthetic Anionophores with Therapeutic Potential - a Coordinated Two-Centre Approach
Funded by: EPSRC (EP/J009687/1)
Led by: Philip Alan Gale
1 October 2012 to 30 September 2015

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