The University of Southampton
University of Southampton Institutional Repository

Selective anion transport mediated by strap-extended calixpyrroles

Selective anion transport mediated by strap-extended calixpyrroles
Selective anion transport mediated by strap-extended calixpyrroles
Synthetic anion receptors that facilitate transmembrane chloride transport are of interest as potential therapeutic agents for cancer and cystic fibrosis. Transporters selective for chloride over protons are desired for therapeutic applications to avoid autophagy inhibition and cytotoxicity. Examples of such compounds are rare because the majority of anion transporters can interact with the carboxylate head groups of fatty acids leading to proton leakage. In this paper, we report the synthesis, anion binding and transmembrane anion transport properties of two novel bis-triazole-functionalized calixpyrroles with extended straps, and compare them to previously reported shorter-strap analogues known to exhibit high Cl>H+ selectivity. We demonstrate improved chloride transport activities of the strap-extended compounds that likely benefit from increased lipophilicity, and reduced Cl>H+ selectivity due to the larger anion binding cavities facilitating interaction with fatty acids. The results are instructive for future design of ideal anion transporters with potent activity and high selectivity against proton leakage.
anion coordination chemistry, transmembrane anion transporters, chloride transport, calixpyrrole
1088-4246
Clarke, Harriet
f5c240ce-625a-47b4-a835-8b7cb44681d2
Wu, Xin
bb3a0609-dae5-4ba5-b650-86b064f7771d
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Gale, Philip
c840b7e9-6847-4843-91af-fa0f8563d943
Clarke, Harriet
f5c240ce-625a-47b4-a835-8b7cb44681d2
Wu, Xin
bb3a0609-dae5-4ba5-b650-86b064f7771d
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Gale, Philip
c840b7e9-6847-4843-91af-fa0f8563d943

Clarke, Harriet, Wu, Xin, Light, Mark and Gale, Philip (2019) Selective anion transport mediated by strap-extended calixpyrroles. Journal of Porphyrins and Phthalocyanines. (doi:10.1142/S1088424619501591).

Record type: Article

Abstract

Synthetic anion receptors that facilitate transmembrane chloride transport are of interest as potential therapeutic agents for cancer and cystic fibrosis. Transporters selective for chloride over protons are desired for therapeutic applications to avoid autophagy inhibition and cytotoxicity. Examples of such compounds are rare because the majority of anion transporters can interact with the carboxylate head groups of fatty acids leading to proton leakage. In this paper, we report the synthesis, anion binding and transmembrane anion transport properties of two novel bis-triazole-functionalized calixpyrroles with extended straps, and compare them to previously reported shorter-strap analogues known to exhibit high Cl>H+ selectivity. We demonstrate improved chloride transport activities of the strap-extended compounds that likely benefit from increased lipophilicity, and reduced Cl>H+ selectivity due to the larger anion binding cavities facilitating interaction with fatty acids. The results are instructive for future design of ideal anion transporters with potent activity and high selectivity against proton leakage.

Text
manuscript - Accepted Manuscript
Download (649kB)

More information

Accepted/In Press date: 9 October 2019
e-pub ahead of print date: 16 October 2019
Keywords: anion coordination chemistry, transmembrane anion transporters, chloride transport, calixpyrrole

Identifiers

Local EPrints ID: 436046
URI: http://eprints.soton.ac.uk/id/eprint/436046
ISSN: 1088-4246
PURE UUID: 9ec5f847-1761-4553-88a0-b24a4585bdf5
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Philip Gale: ORCID iD orcid.org/0000-0001-9751-4910

Catalogue record

Date deposited: 27 Nov 2019 17:30
Last modified: 18 Feb 2021 16:55

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×