Synthesis of cross‐linked diazaborine‐based polymeric microparticles with antiquorum sensing, anti‐swarming, antimicrobial, and antibiofilm properties

Abstract

AbstractTransmission of infectious diseases and resistance by microorganisms is a global health threat. Antimicrobial polymers are increasingly being developed as biocides with greater applications than traditional antibiotics. In this study, 3‐(potassiumsulfonyl)propyl methacrylate (SPMA) monomer, ethylene glycol dimethacrylate cross‐linker and ammonium persulfate initiator were reacted to yield poly[3‐(potassiumsulfonyl)propyl methacrylate] microgels (PSPMA). Surface modification of PSPMA with thionyl chloride yielded poly[3‐(chlorosulfonyl)propyl methacrylate microparticle] (PSPMA‐Cl) which was reacted with hydrazinehydrate to obtain poly[3‐(hydrazinylsulfonyl)propyl methacrylate] microparticles (PSPMA‐NH2). Finally, 2‐formyl benzeneboronic acid was added to give the final product poly[3‐((1‐hydroxybenzo(d)(1,2,3)diazaborinin‐2(1H)‐yl)sulfonyl)propyl methacrylate] (PSPMA‐DAZ) microparticles. The modified microparticles were characterized using attenuated total reflectance‐Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy and energy‐dispersive x‐ray analyses. The polymeric microparticles showed good antibiofilm activity against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Candida albicans ATCC 10239 and Candida tropicalis ATCC 13803 while low to moderate biofilm inhibitions were observed against Listeria monocytogenes ATCC 7644, Enterococcus faecalis ATCC 29212, Pseudomonas aeruginosa ATCC 27853 and Salmonella typhi ATCC 14028. Surface group modification from PSPMA, PSPMA‐Cl, PSPMA‐NH2 to PSPMA‐DAZ increased violacein inhibition, quorum‐sensing inhibition and antimicrobial activity but reduced swarming. These polymer microparticles can be used to reduce spread of microbial infections and resistance.