Antimicrobial and anticancer activities of copolymers of tri-O-acetyl-D-glucal and itaconic anhydride

Abstract

This paper reports the synthesis and characterization of monomers itaconic anhydride (IA) and tri-O-acetyl-D-glucal (TAG) as well as 4,6-di-O-acetyl-D-glucal (PSG). The homopolymers and copolymers of IA and TAG were synthesized via free radical copolymerization in bulk using azobisiso-butyronitrile as an initiator using different feed ratios of monomers. Their structural, molecular, and thermal characterization was done using 1H-NMR spectroscopy, gel permeation chromatography, and differential scanning calorimetry, respectively. The glass transition temperature (Tg) of copolymers was found in the range of 139-145 ?C. The highest Tg was found for IA-TAG2 copolymers, whereas IA-TAG4 copolymer showed lowest Tg. The molecular weight of the copolymers was in the range 5157-5499 g mol-1. The monomer TAG undergoes Ferrier rearrangement in water to give PSG. The antimicrobial activity of IA, TAG, PSG and IA-TAG copolymers was studied using the minimum microbicidal concentration-broth dilution method. TAG, IA, and PSG, as well as homopolymer and copolymers of IA and TAG are excellent antimicrobial agents.