engleski

Synthesis and antimicrobial potential of quaternary 3-aminoquinuclidinium salts with long alkyl chains

Emerging antibiotic resistance is one of the biggest threats to public health and there is a crucial need for development of new effective antibiotics. Quaternary ammonium compounds (QACs), as cationic amphiphiles, have been recognized as broad-spectrum antibacterial agents. In this paper, we have designed and synthesized cationic surfactant systems based on quinuclidine bearing an amino group and a long side alkyl chain (C12 and C14) assuming that amino group would upgrade ability of bacterial membrane disruption (Figure 1). These compounds are characterized by FT-IR, 1H NMR and 13C NMR analysis and are evaluated for antimicrobial activity against representative Gram-positive and -negative bacterial strains. The minimal inhibitory and bactericidal concentrations (MIC and MBC) are determined by using the method of a serial dilution. Our results show a positive correlation between antimicrobial activity and an alkyl chain length. Tested compounds exhibit noteworthy antibacterial activity, especially, QNH2-C14 with considerably low minimal inhibitory concentration against S. aureus (MIC = 3.9 μg mL-1), S. pyogenes (MIC = 3.9 μg mL-1) and E. faecalis (MIC = 1.95 μg mL-1). The work on cytotoxicity measurements toward different human cell lines is currently in progress.

Quaternary ammonium compounds (QAC) ; Antimicrobial activity ; Cytotoxicity

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