Adamantane appended antimicrobial supramolecular self-associating amphiphiles

Andzelika Rutkauskaite, Lisa J. White, Jessica E. Boles, Kira L.F. Hilton, Melanie Clifford, Bethany Patenall, Bree R. Streather, Daniel P. Mulvihill, Samantha A. Henry, Mark Shepherd, J. Mark Sutton, Charlotte K. Hind, Jennifer R. Hiscock*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Herein, we present the synthesis of two novel adamantane appended supramolecular self-associating amphiphiles. The antimicrobial efficacy of these compounds is determined against both clinically relevant Gram-positive methicillin-resistant Staphylococcus aureus and Gram-negative Escherichia coli. We also explore the self-associative properties of these amphiphiles in both polar organic DMSO-d 6 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 1H 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 1H 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.

Original languageEnglish
JournalSupramolecular Chemistry
Publication statusAccepted/In press - 2023
Externally publishedYes

Bibliographical note

Funding Information:
A. Rutkauskaite, L.White, J.Boles, K. Hilton and J. Hiscock would like to thank the University of Kent for funding. Additionally, J. Hiscock and L. White would also like to thank UKRI for the funding of J. Hiscock's Future Leaders Fellowship (MR/T020415/1). J. Boles thank UKHSA for the funding of her PhD studentship.

Publisher Copyright:
© 2023 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.


  • Hydrogen bond
  • amphiphile
  • antimicrobial
  • self-association


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