Towards the Prediction of Antimicrobial Efficacy for Hydrogen Bonded, Self-Associating Amphiphiles

Nyasha Allen, Lisa White, Jessica Boles, George Williams, Dominique Chu, Rebecca Ellaby, Helena Shepherd, Kendrick Ng, Laura Blackholly, Ben Wilson, Daniel Mulvihill, Jennifer Hiscock

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


Herein we report 50 structurally related supramolecular self-associating amphiphilic (SSA) salts and related compounds. These SSAs are shown to act as antimicrobial agents, active against model Gram-positive (methicillin-resistant Staphylococcus aureus) and/or Gram-negative (Escherichia coli) bacteria of clinical interest. Through a combination of solution-state, gas-phase, solid-state and in silico measurements, we determine 14 different physicochemical parameters for each of these 50 structurally related compounds. These parameter sets are then used to identify molecular structure-physicochemical property-antimicrobial activity relationships for our model Gram-negative and Gram-positive bacteria, while simultaneously providing insight towards the elucidation of SSA mode of antimicrobial action.

Original languageEnglish
Pages (from-to)2193-2205
Number of pages13
Issue number22
Publication statusPublished - Sept 2020

Bibliographical note

Funding Information:
We acknowledge the University of Kent and the Royal Society (RGS\R2\180336) for funding. J. R. Hiscock thanks the UKRI (MR/T020415/1) for funding. G. T. Williams thanks the GCDC at the University of Kent for funding. We also thank T. A. Eastwood (microscopy) and K. Howland (mass spectrometry). J. Boles thanks the University of Kent and Public Health England for PhD studentship funding. J. Hiscock thanks E. Clark (Senior Lecturer in Chemistry, University of Kent) and Max D. Allen for their help in the production of this manuscript.

Publisher Copyright:
© 2020 The Authors. Published by Wiley-VCH GmbH


  • Amphiphiles
  • Antimicrobial
  • Hydrogen bonds
  • Structure-activity relationships
  • Supramolecular Chemistry

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Pharmacology
  • Drug Discovery
  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry


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