Kotak, Hiral Arvind;
(2025)
The Design and Synthesis of Supramolecular Hosts for Biological Anion Recognition.
Doctoral thesis (Ph.D), UCL (University College London).
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Abstract
Anions are essential in everyday life, especially within biological systems. Their significance spans from simple anions used for pH regulation to larger anionic structures like phospholipids and deoxyribonucleic acid (DNA). Consequently, the binding of anions has the potential to aid in the treatment of channelopathies – diseases associated with dysfunctional ion channels. However, designing anion-binding molecules can be challenging, although recent advancements with metal-organic complexes have shown promise. Chapter 2 details the design and synthesis of the tripodal iron(II) complex 52, which incorporates urea groups for anion binding. The anion-binding properties of this metal-organic complex were evaluated against various anions, demonstrating that complex 52 effectively binds several simple anions, including chloride and benzoate. This prompted an investigation into its indicator displacement properties; complex 52 quenched the fluorescence of multiple fluorophores, some of which could be displaced by introducing simple anions. Furthermore, complex 52 displayed potential anion transport capabilities, particularly in chloride/nitrate antiport and M+/chloride symport. Chapter 3 delves deeper into tripodal anion-binding motifs, detailing efforts to synthesise enantiopure tripodal metal-organic complexes for the binding of chiral anions. The synthesis of chiral tripodal amines succeeded through the reductive amination of phenylalanine-derived aldehydes. However, the creation of metal-organic complexes presented difficulties, with spectroscopic analysis indicating that only a small quantity of chiral Zn(II) complexes might have formed. Ultimately, the crude product was neither chemically nor enantiomerically pure. Hence, a chiral cleft for chiral guest recognition was not synthesised. Chapter 4 investigates supramolecular self-associating amphiphiles (SSAs) that exhibit antibacterial properties, using computational chemistry to focus on their interactions with various lipid headgroups. SSAs 75 and 78 displayed a preference for binding to bacterial-type lipid headgroups over mammalian-type lipid headgroups, highlighting the importance of forming SSA-lipid complexes in the mode of action of SSAs against bacteria.
| Type: | Thesis (Doctoral) |
|---|---|
| Qualification: | Ph.D |
| Title: | The Design and Synthesis of Supramolecular Hosts for Biological Anion Recognition |
| Open access status: | An open access version is available from UCL Discovery |
| Language: | English |
| Additional information: | Copyright © The Author 2025. Original content in this thesis is licensed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) Licence (https://creativecommons.org/licenses/by-nc/4.0/). Any third-party copyright material present remains the property of its respective owner(s) and is licensed under its existing terms. Access may initially be restricted at the author’s request. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10207712 |
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