Biscationic Tartaric Acid-Based Amphiphiles: Charge Location Impacts Antimicrobial Activity

Allison Faig, Timothy D. Arthur, Patrick O. Fitzgerald, Michael Chikindas, Evan Mintzer, Kathryn E. Uhrich

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Cationic amphiphiles have received increasing attention as antimicrobials given their unique ability to disrupt bacteria cell membranes. While extensive research has demonstrated that amphiphiles' hydrophobic-to-charge ratio significantly modulates antibacterial activity, less work has focused on elucidating the specific impact of charge location on amphiphile bioactivity. In this study, two series of cationic amphiphiles, termed bola-like and gemini-like, were synthesized with analogous hydrophobic-to-charge ratios yet differing charge location, and their resulting antibacterial activity was assessed. Bola-like amphiphiles exhibited preferential activity against two Gram-positive bacteria, with activity increasing with increasing hydrophobicity, whereas gemini-like amphiphiles were active against both Gram-positive and Gram-negative bacteria, with activity decreasing with increasing hydrophobicity. After identifying lead compounds from each amphiphile series (bola- and gemini-like), biophysical experiments indicated that both amphiphiles were membrane-active; notably, the lead gemini-like amphiphile exhibited a strong dependence on electrostatic interactions for membrane interaction. In contrast, the lead bola-like amphiphile exhibited a reliance on both hydrophobic and electrostatic contributions. These results demonstrate that charge location significantly impacts cationic amphiphiles' antibacterial and membrane activity.

Original languageEnglish (US)
Pages (from-to)11875-11885
Number of pages11
JournalLangmuir
Volume31
Issue number43
DOIs
StatePublished - Nov 3 2015

Fingerprint

Amphiphiles
acids
Acids
bacteria
hydrophobicity
membranes
electrostatics
Bacteria
lead compounds
Hydrophobicity
Membranes
tartaric acid
Lead compounds
interactions
Cell membranes
Coulomb interactions
Bioactivity
Electrostatics

All Science Journal Classification (ASJC) codes

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

Cite this

Faig, A., Arthur, T. D., Fitzgerald, P. O., Chikindas, M., Mintzer, E., & Uhrich, K. E. (2015). Biscationic Tartaric Acid-Based Amphiphiles: Charge Location Impacts Antimicrobial Activity. Langmuir, 31(43), 11875-11885. https://doi.org/10.1021/acs.langmuir.5b03347
Faig, Allison ; Arthur, Timothy D. ; Fitzgerald, Patrick O. ; Chikindas, Michael ; Mintzer, Evan ; Uhrich, Kathryn E. / Biscationic Tartaric Acid-Based Amphiphiles : Charge Location Impacts Antimicrobial Activity. In: Langmuir. 2015 ; Vol. 31, No. 43. pp. 11875-11885.
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Faig, A, Arthur, TD, Fitzgerald, PO, Chikindas, M, Mintzer, E & Uhrich, KE 2015, 'Biscationic Tartaric Acid-Based Amphiphiles: Charge Location Impacts Antimicrobial Activity', Langmuir, vol. 31, no. 43, pp. 11875-11885. https://doi.org/10.1021/acs.langmuir.5b03347

Biscationic Tartaric Acid-Based Amphiphiles : Charge Location Impacts Antimicrobial Activity. / Faig, Allison; Arthur, Timothy D.; Fitzgerald, Patrick O.; Chikindas, Michael; Mintzer, Evan; Uhrich, Kathryn E.

In: Langmuir, Vol. 31, No. 43, 03.11.2015, p. 11875-11885.

Research output: Contribution to journalArticle

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