Novel synthesis of N‐acrylamidociprofloxacin and related polymers: Bioactivity, drug resistance, and drug release

Abstract

AbstractTwo new ciprofloxacin (CF) monomers, (ACF) and (MCF) were designed and synthesized. Both ACF and MCF were polymerized using a redox‐initiated polymerization process, yielding the polymers PACF and PMCF, respectively. Three co‐polymers were prepared by polymerizing ACF with acrylamide (AcA), acrylonitrile (AcN), or N‐(thiazol‐2‐yl) acrylamide (NTA) monomers in a 1:3 molar ratio. Elemental analysis, X‐ray, IR, 1H and 13C NMR, and mass spectrometry were used to characterize the obtained monomers, polymers, and co‐polymers. The biological activities of the prepared monomers, polymers, and co‐polymers against Gram‐positive and Gram‐negative bacteria were investigated. Newly prepared compounds had a severe‐to‐mild impact on the microorganisms that were tested. Additionally, CF‐resistant bacteria were tested against newly prepared monomers and polyciprofloxacin. These data demonstrated that novel CF derivatives can overcome bacterial mutations that result in resistance to quinolone derivatives. Under acidic and basic conditions at 40°C, the sustained drug release of CF from polymeric chains and co‐polymers was studied. Drug release in the absence and presence of a catalytic quantity of potassium chloride at different concentrations, was studied and showed an increase in extended release. Drug release from the polymer and co‐polymer chains was measured by UV–visible spectroscopy. Morphologies and thermal stability of the prepared polymers and co‐polymers have also been reported.