Synthesis, Characterization, and Antibacterial Activities of Novel Methacrylate Polymers Containing Norfloxacin

Abstract

A novel methacrylate monomer containing a quinolone moiety was synthesized and homopolymerized in N,N-dimethylformamide (DMF) by using azobisisobutyronitrile (AIBN) as an initiator. The new monomer was copolymerized with poly(ethylene glycol) methyl ether methacrylate (MPEGMA) in DMF using the same initiator. The monomer, homopolymer, and copolymer were characterized by elemental analysis, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), size exclusion chromatography (SEC), FTIR, (13)C NMR, and (1)H NMR. The antibacterial activities of the monomer as well as polymers were investigated against Staphylococcus aureus and Escherichia coli, which are representative of Gram-positive and Gram-negative bacteria, respectively. All compounds showed excellent antibacterial activities against these two types of bacteria. The antibacterial activities were determined using the shaking flask method, where 25 mg/mL concentrations of each compound were tested against 10(5) CFU/mL bacteria solutions. The number of viable bacteria was calculated by using the spread plate method, where 100 microL of the incubated antibacterial agent in bacteria solutions were spread on agar plates and the number of viable bacteria was counted after 24 h of incubation period at 37 degrees C.

Antimicrobial Polymers in Solution and on Surfaces: Overview and Functional Principles

“…However, the conjugates exhibited full antimicrobial activity if the biocides were tethered via a hydrolytically labile bond, which proved that the antibiotics are reactivated upon release. On the other hand recent examples indicate the possibility to polymerize antibiotics retaining their activity at the polymer backbone, e.g., by copolymerization of methacrylate modified Norfloxacin and PEG-methacrylates [27]. Direct modification of Vancomycin with PEG-methacrylate and subsequent polymerization resulted in active polymers that are at least 6-fold less active when comparing them to the unmodified antibiotic [28].…”

Development of biomaterial surfaces with and without microbial nanosegments

“…Biocidal active polymers were reportedly formed by direct modification of vancomycin with polyethylene glycol methyl ether methacrylate and subsequent polymerization [17]. However, the polymeric biocides are generally described as extremely low-activity biocides compared with the unmodified antibiotic [18].…”

Novel Antimicrobial Polyelectrolytes Nanofilm Coatings Using the Layer By Layer Technique~!2008-08-26~!2008-10-09~!2008-11-26~!

“…However, immobilizing these molecules for prolonged biocide effect was another challenging issue. Researchers developed polymeric macromolecules with antibacterial properties which was proved to be more efficient than the antibacterial monomer [4][5][6]. These polymers had quaternary ammonium salts, biguanide groups, quaternary pyridinium salts, sulphonium salts, phosphonium salts, and other antibacterial groups.…”