Tuning the lipophilicity of new ciprofloxacin derivatives in selected ESKAPE bacteria with emphasis on E. coli mutants
Abstract
The objective of the present study was to improve the antimicrobial profile of ciprofloxacin by introducing a peptidomimetic function. A ciprofloxacin C3 carboxyl group was modified by a three-component Passerini reaction conducted under micellar conditions. The series of newly synthesized peptidomimetics was evaluated for their possible in vitro antibacterial activity toward including selected LPS-varied E. coli strains. A preliminary exploration of ciprofloxacin-based peptidomimetic analogues as novel antimicrobial agents was carried out to determine the basic characteristics of the structure responsible for the observed biological activity. The collected data demonstrated that an appropriate modification of the C3 position of ciprofloxacin significantly extends and improves antimicrobial activity, particularly against LPS-varied E. coli strains, which may cause various diseases such as urinary tract infections (UTI), enteric / diarrheal disease, and sepsis/meningitis. Furthermore, the antimicrobial activities of peptidomimetics against selected Gram-positive and Gram-negative bacterial strains belonging to ESKAPE bacteria (A. baumannii, P. aeruginosa, E. cloacae, and S. aureus) were investigated. All synthesized ciprofloxacin derivatives were found to be more potent antibacterial agents than the native compound. Most importantly, the introduction of a short aliphatic substituent into the peptidomimetic structure allowed to enhance and extend the activity of modified…
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