Preparation and characterization of a chitosan-gentamicin derivative and its effect on tropical fruit preservation

Abstract

Applications of chitosan (CS) are hindered by its weak antimicrobial ability, poor solubility in basic and neutral solutions, structural modification is needed to improve its functional properties. Herein, a new chitosan-gentamicin derivative (CS-GT) was successfully synthesized via protection, regioselective bromination, nucleophile substitution reaction, and deprotection. Characterization techniques confirmed the successful introduction of GT onto the C-6 position of CS with a grafting rate of 76.19%. The additional amino groups provided by GT decreased the crystallinity and thermal stability of CS-GT, while enhancing its solubility in neutral and alkaline solutions. Compared to CS, CS-GT exhibited 2.50 and 2.41 times higher antibacterial activities against Escherichia coli and Staphylococcus aureus, respectively. Besides, an active packaging coating was develop by incorporating glycerol into CS-GT. The hydrogen bond networks formed within coatings endowed them good thermal stability and tightly uniform morphology. Furthermore, increasing CS-GT from 1% to 3% improved the coating's ultraviolet resistance and flexibility, but reduced its waterproof performance, visual appearance, and water barrier properties. Preservation experiments with papaya and litchi showed that CS-GT coatings effectively inhibited microbial growth and maintained quality and appearance up to 16 and 8 days of storage, respectively. In conclusion, CS-GT show promising potential for applications in food packaging.