Tetralactam-based anion transporters

Gilchrist, AM; McNaughton, DA; Fares, M; Wu, X; Hawkins, BA; Butler, SJ; Hibbs, DE; Gale, PA

Tetralactam-based anion transporters

Gilchrist, AM McNaughton, DA Fares, M Wu, X Hawkins, BA Butler, SJ Hibbs, DE Gale, PA

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Publisher:: Elsevier
Publication Type:: Journal Article
Citation:: Chem, 2024
Issue Date:: 2024-01-01

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Field	Value	Language
dc.contributor.author	Gilchrist, AM
dc.contributor.author	McNaughton, DA
dc.contributor.author	Fares, M
dc.contributor.author	Wu, X
dc.contributor.author	Hawkins, BA
dc.contributor.author	Butler, SJ
dc.contributor.author	Hibbs, DE
dc.contributor.author	Gale, PA
dc.date.accessioned	2024-12-12T00:09:48Z
dc.date.available	2024-12-12T00:09:48Z
dc.date.issued	2024-01-01
dc.identifier.citation	Chem, 2024
dc.identifier.issn	2451-9308
dc.identifier.issn	2451-9294
dc.identifier.uri	http://hdl.handle.net/10453/182476
dc.description.abstract	Synthetic anion transporters provide a promising avenue to treat diseases such as cystic fibrosis and cancer. Anion binding site preorganization is one aspect of transporter design that can be manipulated to enhance binding. Macrocycles possess preorganized binding cavities, enabling more selective and efficient anion binding and transport. In this study, we build on a macrocyclic tetralactam scaffold by preparing a series of fluorinated and non-fluorinated tetralactam anion transporters. Anion binding and transport assays were used to analyze the substituent effects on scaffold lipophilicity, selectivity, solubility, binding strength, and transport rates. The series was analyzed for the ability to bind and transport Cl− and F− anions across lipid bilayers. Some highly fluorinated tetralactams display extremely high levels of Cl− and F− transport activity, showing record activities in 8-hydroxypyrene-1,3,6-trisulfonic acid (HPTS) assays and a Eu(III) probe-based F− transport assay.
dc.language	en
dc.publisher	Elsevier
dc.relation	http://purl.org/au-research/grants/arc/DP210100039
dc.relation.ispartof	Chem
dc.relation.isbasedon	10.1016/j.chempr.2024.09.028
dc.rights	info:eu-repo/semantics/embargoedAccess
dc.rights	This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND 4.0). To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.title	Tetralactam-based anion transporters
dc.type	Journal Article
pubs.organisational-group	University of Technology Sydney
pubs.organisational-group	University of Technology Sydney/Faculty of Science
pubs.organisational-group	University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	University of Technology Sydney/UTS Groups
pubs.organisational-group	University of Technology Sydney/UTS Groups/The Kidman Centre (TKC)
utslib.copyright.status	embargoed	*
utslib.copyright.embargo	2026-01-09T00:00:00+1000Z
dc.date.updated	2024-12-12T00:09:46Z
pubs.publication-status	Published

Abstract:

Synthetic anion transporters provide a promising avenue to treat diseases such as cystic fibrosis and cancer. Anion binding site preorganization is one aspect of transporter design that can be manipulated to enhance binding. Macrocycles possess preorganized binding cavities, enabling more selective and efficient anion binding and transport. In this study, we build on a macrocyclic tetralactam scaffold by preparing a series of fluorinated and non-fluorinated tetralactam anion transporters. Anion binding and transport assays were used to analyze the substituent effects on scaffold lipophilicity, selectivity, solubility, binding strength, and transport rates. The series was analyzed for the ability to bind and transport Cl− and F− anions across lipid bilayers. Some highly fluorinated tetralactams display extremely high levels of Cl− and F− transport activity, showing record activities in 8-hydroxypyrene-1,3,6-trisulfonic acid (HPTS) assays and a Eu(III) probe-based F− transport assay.

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http://hdl.handle.net/10453/182476