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

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 azobisiso­but­yronitrile as an initiator with 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 (T_g) of copolymers was found in the range of 139–145 °C. The highest T_g was found for IA–TAG2 copolymers, whereas IA–TAG4 copolymer showed lowest T_g. 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.