Method: A model antimicrobial, Ciprofloxacin (CF) was reacted with triphenyl chloride in dry chloroform, in the presence of triethylamine for a period of five hours to protect active functional groups. Methanol was subsequently added to deprotect the carboxylic acid group. (N)-trityl-Ciprofloxacin was consequently reacted with triethylene glycol, using 4-dimethylaminopyridine (DMAP) and 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (EDC) as catalysts in dichloromethane under dry conditions for ten days. The product was isolated and reacted with trifluoroacetic acid in chloroform, in the presence of water for four hours to release the secondary amine groups. The deprotected product was then reacted with methacrylic acid in the presence of EDC and DMAP in N,N-dimethylformamide under dry conditions for five days.
Result: The final monomer was successfully synthesized (approximately 37% yield) and structures confirmed by 1H and 19F NMR. Although initial polymerization studies have begun, optimization of the polymerization conditions is still ongoing. Similarly, characterization of the resulting polymers’ physical and chemical properties and antibiotic release rate is still in progress.
Conclusion: The synthesis of a novel antimicrobial monomer was successful.
Keywords: Antimicrobials, Biomaterials, Dental materials and Polymers
See more of: Dental Materials 6: Polymer-based Materials-Chemistry and Composition