Towards “drug-like” indole-based transmembrane anion transporters
Towards “drug-like” indole-based transmembrane anion transporters
A series of mono-ureas and mono-thioureas, some incorporating a trifluoromethyl group, have been synthesised and their ability to facilitate ion transport assessed using a combination of ion selective electrode and fluorescence techniques. Chloride/nitrate and chloride/bicarbonate antiport and HCl symport processes were examined using phospholipid vesicles as a model system. In general, the trifluoromethyl functionalised receptors showed greater transport activity than unfluorinated analogous systems, corresponding with increased clogP. The most active transporter facilitated chloride efflux from phospholipid vesicles at receptor to lipid ratios as low as 1:20,000. In addition, in vitro fluorescence and viability assays indicated that the most potent anion transporters induced apoptosis in human cancer cell lines.
Gale, Philip A
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Pérez Tomás, Ricardo
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Wenzel, Marco
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Light, Mark E.
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Morley, Rebeka
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Bradberry, Samuel
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Soto Cerrato, Vanessa
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Gomez Iglesias, Patricia
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1 June 2012
Gale, Philip A
c840b7e9-6847-4843-91af-fa0f8563d943
Pérez Tomás, Ricardo
e4d62d99-65b5-4ae9-83e0-3434359a3639
Wenzel, Marco
d1c2d66d-80a9-4d77-88c6-5c25fbaac546
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Morley, Rebeka
a0b2a9c1-7480-49b1-9e3c-a27c42623dd7
Bradberry, Samuel
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Soto Cerrato, Vanessa
0763c9c0-ad9b-438c-8752-cd10f3221646
Gomez Iglesias, Patricia
bad6656c-b989-4405-9394-e0e5e31364e4
Gale, Philip A, Pérez Tomás, Ricardo, Wenzel, Marco, Light, Mark E., Morley, Rebeka, Bradberry, Samuel, Soto Cerrato, Vanessa and Gomez Iglesias, Patricia
(2012)
Towards “drug-like” indole-based transmembrane anion transporters.
Chemical Science.
(doi:10.1039/C2SC20551C).
Abstract
A series of mono-ureas and mono-thioureas, some incorporating a trifluoromethyl group, have been synthesised and their ability to facilitate ion transport assessed using a combination of ion selective electrode and fluorescence techniques. Chloride/nitrate and chloride/bicarbonate antiport and HCl symport processes were examined using phospholipid vesicles as a model system. In general, the trifluoromethyl functionalised receptors showed greater transport activity than unfluorinated analogous systems, corresponding with increased clogP. The most active transporter facilitated chloride efflux from phospholipid vesicles at receptor to lipid ratios as low as 1:20,000. In addition, in vitro fluorescence and viability assays indicated that the most potent anion transporters induced apoptosis in human cancer cell lines.
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Published date: 1 June 2012
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
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Local EPrints ID: 340034
URI: http://eprints.soton.ac.uk/id/eprint/340034
ISSN: 1478-6524
PURE UUID: 3b48e2c4-975e-4e1a-9404-cab2b50f1d15
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Date deposited: 07 Jun 2012 12:42
Last modified: 15 Mar 2024 03:06
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Contributors
Author:
Philip A Gale
Author:
Ricardo Pérez Tomás
Author:
Marco Wenzel
Author:
Rebeka Morley
Author:
Samuel Bradberry
Author:
Vanessa Soto Cerrato
Author:
Patricia Gomez Iglesias
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