The exploitation of fluorescence in the development of novel membrane transporters and chemical sensors

Abstract

This thesis reports the development of novel transmembrane anion transporters and chemical sensors in which fluorescence spectroscopy and/or microscopy was utilised to provide information about the function and/or applications of said compounds.

Firstly, a series of transmembrane anion transporters based on an isophthalamide scaffold with phenyl, naphthyl or anthracenyl central rings were investigated. Hill analysis, along with fluorescent spectroscopy was employed to show that these compounds aggregate inside lipid bilayer membranes, and a cooperative transporting mechanism was proposed.

Next, a series of fluorescent anion transporters consisting of urea or thiourea groups linked to a naphthalimide fluorophore were evaluated. The compounds functioned as moderate anion transporters in POPC vesicle experiments and fluorescent microscopy was utilised to show, for the first time, where these compounds localised in A549 cancer cells. The most potent anionophore was investigated further and shown to induce apoptosis in cancer cells, showing potential for development of future antineoplastic drugs.

Finally, a novel, highly specific and selective chemical sensor for Al3+ was prepared. Through screening in various solvent systems and pH’s, the optimal conditions for sensing were uncovered. 1H NMR, UV-vis, LCMS and fluorescence experiments allowed the sensing mechanism to be fully described and fluorescence microscopy confirmed this compound could be utilised to detect Al³⁺ in living cells.

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Identifiers

ORCID for Philip Gale: orcid.org/0000-0001-9751-4910

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