Antimicrobial Property of Halogenated Catechols

B Liu, C Zhou, Z Zhang, JD Roland, BP Lee*
July 21, 2020
Chemical Engineering Journal, 403, 126340, 2021.

Bacterial infection associated with multidrug resistance (MDR) bacteria is increasingly becoming a significant public health risk. Herein, we synthesized a series of halogenated dopamine methacrylamide (DMA), which contains a catechol side chain modified with either chloro-, bromo-, or iodo-functional group. Catechol is a widely used adhesive moiety for designing bioadhesives and coating. However, the intrinsic antimicrobial property of catechol has not been demonstrated before. These halogenated DMA were incorporated into hydrogels, copolymers, and coatings and exhibited more than 99% killing efficiencies against Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli. More importantly, hydrogel containing chlorinated DMA demonstrated broad-spectrum antimicrobial activities towards multiple MDR bacteria, which included methicillin resistant S. aureus (MRSA), vancomycin resistant enterococci (VRE), multi antibiotics resistant Pseudomonas aeruginosa (PAER), multi antibiotics resistant Acinetobacter baumannii (AB) and carbapenem resistant Klebsiella pneumoniae (CRKP). These hydrogels also demonstrated the ability to kill bacteria in a biofilm while exhibiting low cytotoxic. Based on molecular docking and molecular dynamics simulation, Cl-functionalized catechol can potentially inhibit bacterial fatty acid synthesis at the enoyl-acyl carrier protein reductase (FabI) step. The combination of moisture-resistant adhesive property, inherent antimicrobial property, and the versatility of incorporating halogenated DMA into different polymeric materials greatly enhanced the potential for using these monomers for designing multifunctional bioadhesives and coatings.

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