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

Moore, Stephen, Haynes, Cally, González, Jorge, Sutton, Jennifer, Brooks, Simon, Light, Mark, Herniman, Julie, Langley, John, Soto-Cerrato, Vanessa, Pérez-Tomás, Ricardo, Marques, Igor, Costa, Paulo, Felix, Vitor and Gale, Philip (2013) Chloride, carboxylate and carbonate transport by ortho-phenylenediamine-based bisureas. Chemical Science, 4 (1), 103-117. (doi:10.1039/C2SC21112B).

Abstract

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

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Contributors

Author: Mark Light

Author: Julie Herniman

Author: John Langley

Author: Philip Gale

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