Synthesis of ciprofloxacin-coupled AoM esters as pre-cursors for antibacterial applications utilizing click chemistry

Abstract

Biofilm-forming bacteria pose significant challenges in the realm of drug synthesis and delivery, due to their ability to acclimate to extreme environmental conditions and resist effective antibiotics. Ciprofloxacin has traditionally been employed to combat Pseudomonas aeruginosa, a bacterium implicated in diseases such as cystic fibrosis and tuberculosis. However, the increasing resistance to this drug necessitates modification to enhance its efficacy upon cellular entry. One approach involves appending various molecules to the piperazine moiety of ciprofloxacin, thereby altering its antibacterial activity against P. aeruginosa and Staphylococcus aureus. Here, the inclusion of 1,2,3-triazoles and acetoxymethyl (AoM) esters are implemented to the base ciprofloxacin drug, tested against P. aeruginosa and S. aureus, and compared to the base drug for observations of improved potency. The techniques of the copper-catalyzed azide-alkyne cycloaddition (CuAAC) is primarily used to synthesize these novel 1,2,3-triazole compounds.