Daniel A. McNaughton

ORCID: 0000-0002-9320-4568
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About
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Research Areas
  • Molecular Sensors and Ion Detection
  • X-ray Diffraction in Crystallography
  • Crystallization and Solubility Studies
  • Lipid Membrane Structure and Behavior
  • DNA and Nucleic Acid Chemistry
  • Cancer therapeutics and mechanisms
  • Synthesis and Biological Evaluation
  • Mass Spectrometry Techniques and Applications
  • Supramolecular Chemistry and Complexes
  • Chemical Synthesis and Analysis
  • Crystallography and molecular interactions
  • Radioactive element chemistry and processing
  • Drug Transport and Resistance Mechanisms
  • Phenothiazines and Benzothiazines Synthesis and Activities
  • Amino Acid Enzymes and Metabolism
  • Luminescence and Fluorescent Materials
  • Advanced biosensing and bioanalysis techniques
  • Neuroscience and Neuropharmacology Research
  • Synthesis and biological activity
  • Chemical Reaction Mechanisms
  • Metal-Organic Frameworks: Synthesis and Applications
  • Supramolecular Self-Assembly in Materials
  • Analytical Chemistry and Chromatography
  • ATP Synthase and ATPases Research
  • Analytical Chemistry and Sensors

The University of Sydney
2019-2025

University of Technology Sydney
2023-2025

Designing molecular receptors that bind anions in water is a significant challenge, and an even greater difficulty lies using these to remove from without resorting the hazardous liquid–liquid extraction approach. We here demonstrate effective synthetically simple strategy toward goals by exploiting ion-pair assembly of macrocycles. Our anion binding ensemble consists octa-chloro tetra-urea macrocyclic receptor (ClTU), which forms water-dispersible aggregates, tetra-cationic fluorescent dye...

10.1021/jacs.4c14194 article EN Journal of the American Chemical Society 2025-01-13

A potent squaramide-based anion transporter was used to evaluate how vesicles prepared with tailored lipid compositions, which mimic organelle membranes, can impact transmembrane transport.

10.1039/d5cc00409h article EN Chemical Communications 2025-01-01

A five-membered central scaffold was used to develop a series of anion receptors. The library perturbed liposomal pH gradients through H + /Cl − transmembrane transport and elicited variety cytotoxicities against normal cancerous cell lines.

10.1039/d3qo01956j article EN Organic Chemistry Frontiers 2024-01-01

Mitochondrial uncoupling by small molecule protonophores is a promising strategy for developing novel anticancer agents. Recently, aryl urea substituted fatty acids (aryl ureas) were identified as new class of protonophoric To mediate proton transport these molecules self-assemble into membrane-permeable anionic dimers in which intermolecular hydrogen bonds between the carboxylate and aryl-urea anion receptor delocalise negative charge across aromatic π-system. In this work, we extend...

10.1002/chem.202400931 article EN cc-by-nc-nd Chemistry - A European Journal 2024-06-05

Targeting the cancer cell mitochondrion is a promising approach for developing novel anticancer agents. The experimental agent N,N′-bis(3,5-dichlorophenyl)urea (SR4) induces apoptotic death in several lines by uncoupling mitochondrial oxidative phosphorylation (OxPhos) using protein-free mechanism. However, precise mechanism which SR4 depolarizes mitochondria unclear because lacks an acidic functional group typically found protein-independent uncouplers. Recently, it was shown that...

10.1021/acschembio.1c00807 article EN ACS Chemical Biology 2022-07-19

A series of fluorescent coumarin-based bis-ureas have been synthesised. These compounds show strong HCl cotransport properties in model vesicle systems. Cellular localisation studies that cytotoxic compound 4 localises lysosomes and perturbs cellular pH.

10.1039/d3ob00128h article EN Organic & Biomolecular Chemistry 2023-01-01

The conformational change accompanying the N , ′-dimethylation of a diphenylsquaramide has been exploited to form series potent anionophores with convergent anion binding sites. compounds were demonstrated transport H + /Cl − across lipid bilayers in model vesicles and dissipate pH gradient.

10.1039/d4ob00703d article EN Organic & Biomolecular Chemistry 2024-01-01

Synthetic anion transporters provide a promising avenue to treat diseases like cystic fibrosis and cancer. Anion binding site preorganisation is one aspect of transporter design which can be manipulated enhance binding. Macrocycles possess preorganised cavities, enabling more stable, selective, efficient transport. In this study, we build on macrocyclic tetralactam scaffold by preparing series fluorinated non-fluorinated transporters. The macrocycles were functionalised with variety...

10.26434/chemrxiv-2024-nf2rh preprint EN 2024-07-17

Synthetic anion transporters provide a promising avenue to treat diseases like cystic fibrosis and cancer. Anion binding site preorganisation is one aspect of transporter design which can be manipulated enhance binding. Macrocycles possess preorganised cavities, enabling more stable, selective, efficient transport. In this study, we build on macrocyclic tetralactam scaffold by preparing series fluorinated non-fluorinated transporters. transport assays were used analyse the substituent...

10.26434/chemrxiv-2024-nf2rh-v2 preprint EN cc-by-nc 2024-08-12

A series of chloride receptors has been synthesized containing an amide hydrogen bonding site and a hydroquinone motif. It was anticipated that oxidation the unit to quinone would greatly diminish binding affinity these receptors. conformational switch is promoted in form through formation intramolecular bond between carbonyl, which blocks site. The reversibility this process highlighted potential systems for use as redox-switchable 1H-NMR studies confirmed stronger capabilities compared...

10.3390/chemistry1010007 article EN cc-by Chemistry 2019-07-11

Cyclodextrins have been employed as delivery agents for lipophilic anion transporters, which allow their incorporation into lipid bilayers without using an organic solvent or pre-incorporation.

10.1039/d1ob02041b article EN Organic & Biomolecular Chemistry 2021-01-01

In respiring mitochondria, the proton gradient across inner mitochondrial membrane is used to drive ATP production. Mitochondrial uncouplers, which are typically weak acid protonophores, can disrupt this process induce dysfunction and apoptosis in cancer cells. We have shown that bisaryl urea-based anion transporters also mediate uncoupling through a novel fatty acid-activated transport mechanism, where urea promotes transbilayer movement of deprotonated acids transport. paper, we...

10.3390/biom13081202 article EN cc-by Biomolecules 2023-07-31

Synthetic anion transporters provide a promising avenue to treat diseases like cystic fibrosis and cancer. Anion binding site preorganisation is one aspect of transporter design which can be manipulated enhance binding. Macrocycles possess preorganised cavities, enabling more stable, selective, efficient transport. In this study, we build on macrocyclic tetralactam scaffold by preparing series fluorinated non-fluorinated transporters. transport assays were used analyse the substituent...

10.26434/chemrxiv-2024-nf2rh-v3 preprint EN 2024-09-17

The arrangement of hydrogen bond donors around a central lipophilic scaffold has proven to be successful strategy in the development potent chloride transporters. In this work, we revisit an acridinone 1,9-bis(thio)urea motif which had previously shown promise as anion sensor and expand series compounds by appending variety electron-withdrawing groups peripheral phenyl moieties. High levels activity were achieved most effective series, facilitated strictly electroneutral transport.

10.1039/d1ob01545a article EN Organic & Biomolecular Chemistry 2021-01-01

The arrangement of hydrogen bond donors around a central lipophilic scaffold has proven successful strategy in the development potent chloride transporters. In this work, we revisit an acridinone 1,9-bis(thio)urea motif which had previously shown promise as anion sensor and expand series compounds by appending variety electron-withdrawing groups to peripheral phenyl moieties. HIgh levels activity were achieved most effective series, facilitated strictly electroneutral transport.

10.33774/chemrxiv-2021-6b4tx preprint EN cc-by 2021-08-06
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