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 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 (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.

Keywords

• free radical polymerization
• glass transition temperature
• homopolymer
• ferrier rearrangement
• cytotoxicity
• antibacterial activity