Antibacterial polymeric micelles based on kojic acid/acrylic acid/chitosan

In the present study, antibacterial micelles based on poly [5-(benzyloxy)-4-oxo-4H-pyran-2-yl] methyl acrylate/polyacrylic acid/chitosan(PBOPMA-PAA-Cs) terpolymer with suspended kojic acid groups was synthesized. For this purpose, first, protected kojic acid (BOP) was prepared by reaction of 5-hydroxy-2-hydroxymethyl-4 H-pyran-4-one with benzyl chloride. Subsequently, [5-(benzyloxy)-4-oxo-4H-pyran-2-yl] methyl acrylate(BOPMA) was prepared by esterification reaction between protected kojic acid hydroxyl groups and carboxylic groups related to acrylic acid. The initiator, [5-(benzyloxy)-4-oxo-4H-pyran-2-yl] methyl-2-bromo-2-methylpropanoate (BOPBr), was synthesized via acyl nucleophilic substitution. Polymerization of BOPMA by ATRP polymerization using initiator (BOPBr) was performed. The PBOPMA-PAA copolymer was prepared by free radical polymerization. In the final step, PBOPMA-PAA-Cs terpolymer was prepared by esterification reaction of the N-phthaloylated chitosan hydroxyl group with the carboxylic acid groups of the PBOPMA-PAA copolymer. Micelles with a size of 20 +/- 5 nm were prepared from amphiphilic terpolymers and their morphology and size were evaluated by TEM and DLS, respectively. The structure, thermal stability, and morphology of synthesized compounds were confirmed by FT-IR, 1H-NMR, TGA, and SEM. Furthermore, in the study of antibacterial properties against gram-positive and negative bacteria, PBPMA, PBPMA-PAA, and PBPMA-PAA-Cs behaved differently, however, all three had good antibacterial properties compared to gentamicin and ampicillin.