J Appl Biomed 12:245-253, 2014 | DOI: 10.1016/j.jab.2014.02.002

Synthesis, antimicrobial activity and physico-chemical properties of some n-alkyldimethylbenzylammonium halides

Salomé El Hage^a, Barbora Lajoie^a, Jean-Luc Stigliani^b, Aurélie Furiga-Chusseau^a, Christine Roques^a, Geneviève Baziard^a,*

^a Université de Toulouse III, INPT, UPS, Laboratoire de Génie Chimique, 35, Chemin des Maraîchers, F-31062 Toulouse Cedex 9, France

^b Université de Toulouse III, Laboratoire de Chimie de Coordination, 205, Route de Narbonne, F-31077 Toulouse Cedex, France

Quaternary ammonium salts (chloride, bromide and iodide; QUATs) with n-alkyl chain lengths between C8 and C18 have been synthesized under optimized experimental conditions. These compounds were tested in vitro for antimicrobial activity against representative bacterial strains (Staphylococcus aureus CIP 4.83, Enterococcus hirae CIP 5855, Pseudomonas aeruginosa CIP 82118, Escherichia coli CIP 53126, Mycobacterium smegmatis CIP 7326) and fungal species (Aspergillus niger ATCC 16404, Candida albicans IP 118079, Trichophyton interdigitale IP 146583). While these compounds showed moderate antifungal activity, several of them (particularly C14-I^-) may be considered as highly potential antibacterial agents against S. aureus, E. hirae and E. coli with MIC values lower than that of commercial benzalkonium chloride and ciprofloxacin used as standards. The relationship between the lipophilicity and the antibacterial activity of the tested QUATs was quantified by a multiple linear regression method.

Keywords: Quaternary ammonium salts; Quaternization; Antimicrobial activity; Lipophilicity

Received: December 19, 2013; Revised: February 12, 2014; Accepted: February 14, 2014; Published: November 1, 2014  Show citation