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Updated: Oct 29, 2026

Self-Assembly of Hybrid Lipid Membranes Doped with Hydrophobic Organic Molecules at the Water/Air Interface
Published on: May 1, 2020
Structure-property relationships in series of hydroxypropyl-functionalized imidazolium surfactants: linking
Darya A Kuznetsova1, Denis M Kuznetsov1, Veronica S Kolbasina1
1Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov Str. 8, 420088 Kazan, Russia.
Abstract:
Hydroxyalkyl-functionalized cationic surfactants are promising membrane-active compounds with potential antimicrobial applications. In this work, a homologous series of hydroxypropyl-substituted imidazolium surfactants (HPIm-n, n = 12, 14, 16, and 18) was investigated with respect to self-assembly, solubilization, membrane interactions, and antimicrobial activity. The surfactants exhibited pronounced amphiphilic properties and formed positively charged aggregates in aqueous solution, with the critical micelle concentration decreasing from 2.6 to 0.17 mM with increasing alkyl chain length. Self-assembly was strongly affected by the ionic environment, with lower aggregation thresholds and altered aggregate properties observed in phosphate-buffered saline compared with deionized water. The surfactants showed chain-length-dependent solubilization of hydrophobic compounds, while their interactions with DPPC and DPPC/DPPG (70,30 mol%) liposomes revealed pronounced effects on lipid phase behavior and membrane surface charge. Calcein leakage from DPPC/DPPG liposomes demonstrated a structure-dependent membrane-permeabilizing effect, with HPIm-14 showing the highest activity. Antimicrobial activity also depended strongly on alkyl chain length, with HPIm-14 and HPIm-16 showing the highest activity and MIC values as low as 0.9 μM against Staphylococcus aureus and methicillin-resistant S. aureus. Overall, the results demonstrate that alkyl chain length and ionic environment are important determinants of the self-assembly, solubilization, membrane interactions, and antimicrobial activity of hydroxypropyl-substituted imidazolium surfactants.
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