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Adamantane appended antimicrobial supramolecular self-associating amphiphiles

Rutkauskaite, Andzelika, White, Lisa-Jane, Boles, Jessica E., Hilton, Kira L.F., clifford, Melanie, Patenall, Bethany L., Streather, Bree, Mulvihill, Daniel P., Henry, Samantha A., Shepherd, Mark, and others. (2023) Adamantane appended antimicrobial supramolecular self-associating amphiphiles. Supramolecular Chemistry, . pp. 1-10. ISSN 1061-0278. (KAR id:99274)

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Herein, we present the synthesis of two novel adamantane appended supramolecular selfassociating amphiphiles. The antimicrobial efficacy of these compounds is determined against both clinically relevant Gram-positive methicillin-resistant Staphylococcus aureus and Gramnegative Escherichia coli. We also explore the self-associative properties of these amphiphiles in both polar organic DMSO-d6 0.5% H2O and H2O (D2O)/EtOH 19:1 solutions, confirming aggregate stability through the determination of zeta potential values, aggregate size through a combination of 1 H NMR DOSY and dynamic light scattering studies as appropriate, and critical aggregate concentration through the derivation of concentration-dependent surface tension values. We also perform a variety of 1 H NMR dilution studies and in-silico modelling to further explore the roles of intermolecular hydrogen bonding and lipophilicity within aggregate formation and antimicrobial efficacy. Finally, we perform haemolysis and Galleria mellonella toxicity assays to establish the potential of these compounds to undergo further development as antibiotic agents.

Item Type: Article
Additional information: For the purpose of open access, the author has applied a CC BY public copyright licence (where permitted by UKRI, an Open Government Licence or CC BY ND public copyright licence may be used instead) to any Author Accepted Manuscript version arising
Uncontrolled keywords: Hydrogen bond; antimicrobial; self-association; amphiphile
Subjects: Q Science
Q Science > QD Chemistry
Divisions: Divisions > Division of Natural Sciences > Chemistry and Forensics
Funders: UK Research and Innovation (
UK Health Security Agency (
Depositing User: Jennifer Hiscock
Date Deposited: 21 Dec 2022 14:42 UTC
Last Modified: 20 Jan 2023 11:22 UTC
Resource URI: (The current URI for this page, for reference purposes)
Mulvihill, Daniel P.:
Shepherd, Mark:
Hiscock, Jennifer R.:
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