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

Record type: Article

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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Citation

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), pp. 103-117. (doi:10.1039/C2SC21112B).

More information

e-pub ahead of print date: 29 August 2012
Published date: January 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 342469
URI: http://eprints.soton.ac.uk/id/eprint/342469
ISSN: 1478-6524
PURE UUID: b8f06380-d4a8-4427-ad6a-f3b683913dc4
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Julie Herniman: ORCID iD orcid.org/0000-0003-4834-1093
ORCID for John Langley: ORCID iD orcid.org/0000-0002-8323-7235
ORCID for Philip Gale: ORCID iD orcid.org/0000-0001-9751-4910

Catalogue record

Date deposited: 31 Aug 2012 13:19
Last modified: 18 Jul 2017 05:28

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Contributors

Author: Stephen Moore
Author: Cally Haynes
Author: Jorge González
Author: Jennifer Sutton
Author: Simon Brooks
Author: Mark Light ORCID iD
Author: Julie Herniman ORCID iD
Author: John Langley ORCID iD
Author: Vanessa Soto-Cerrato
Author: Ricardo Pérez-Tomás
Author: Igor Marques
Author: Paulo Costa
Author: Vitor Felix
Author: Philip Gale ORCID iD

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