Synthesis and Correlation of Aggregation and Antimicrobial Properties of Homochiral Quaternary Ammonium Bromides Derived from Camphoric Acid

Abstract

A group of homochiral quaternary ammonium salts bearing hydrophobic camphoric acid-derived moiety was synthesized and characterized. The aggregation properties of the prepared compounds were evaluated by surface tension measurements, and the critical micelle concentration (CMC) was calculated. The novel quaternary ammonium bromides were tested as antimicrobial and antifungal agents, and their minimal inhibitory concentration (MIC) was evaluated and compared to clinically used benzalkonium bromide (BAB). Correlation of MIC with CMC reveals that monomers of prepared cationic surfactants, instead of micelles, are primarily responsible for antimicrobial activity.

Keywords

• quaternary ammonium salts
• antimicrobial activity
• camphoric acid
• critical micelle concentration