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

Chloride, carboxylate and carbonate transport by ortho-phenylenediamine-based bisureas
Chloride, carboxylate and carbonate transport by ortho-phenylenediamine-based bisureas
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
1478-6524
103-117
Moore, Stephen
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Haynes, Cally
54c30472-2ae9-402c-a588-425443df54aa
González, Jorge
b7d9af75-f72a-46ab-a00b-84c3a03400cd
Sutton, Jennifer
366442c8-a564-4df7-8964-4a50ae21527b
Brooks, Simon
fcf66c9a-5e4d-47cf-bc9f-e7c8886a061a
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Herniman, Julie
530b1a36-1386-4602-8df7-defa6eb3512b
Langley, John
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Soto-Cerrato, Vanessa
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Pérez-Tomás, Ricardo
e4d62d99-65b5-4ae9-83e0-3434359a3639
Marques, Igor
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Costa, Paulo
744e6312-9cc6-460a-abcf-1d78fbeeb643
Felix, Vitor
2d812f44-51b9-4359-9f8b-0e644342c0fe
Gale, Philip
c840b7e9-6847-4843-91af-fa0f8563d943
Moore, Stephen
e7a4f98a-ac24-4d29-b1b7-f9ef32d7a63e
Haynes, Cally
54c30472-2ae9-402c-a588-425443df54aa
González, Jorge
b7d9af75-f72a-46ab-a00b-84c3a03400cd
Sutton, Jennifer
366442c8-a564-4df7-8964-4a50ae21527b
Brooks, Simon
fcf66c9a-5e4d-47cf-bc9f-e7c8886a061a
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Herniman, Julie
530b1a36-1386-4602-8df7-defa6eb3512b
Langley, John
7ac80d61-b91d-4261-ad17-255f94ea21ea
Soto-Cerrato, Vanessa
0763c9c0-ad9b-438c-8752-cd10f3221646
Pérez-Tomás, Ricardo
e4d62d99-65b5-4ae9-83e0-3434359a3639
Marques, Igor
97cbc26e-6d94-43e6-a934-1d69dad8de06
Costa, Paulo
744e6312-9cc6-460a-abcf-1d78fbeeb643
Felix, Vitor
2d812f44-51b9-4359-9f8b-0e644342c0fe
Gale, Philip
c840b7e9-6847-4843-91af-fa0f8563d943

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).

Record type: Article

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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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: 15 Mar 2024 03:06

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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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