Functionalized chitosan with new acrylohydrazide derivative: Synthesis, characterization, DFT calculations, antimicrobial and antiproliferative activities

Abstract

This study presents the modification of the biopolymer chitosan through the attachment of a novel hydrazide derivative to its primary amine groups, aimed at developing alternative strategies to combat microbial infections. The structure of the new derivative was confirmed through FTIR and ¹H NMR analyses. Elemental analysis indicated a degree of substitution of 81.33 %. The biological efficacy of the modified chitosan derivative was investigated in vitro against five pathogenic microbes: Staphylococcus aureus, Klebsiella pneumoniae, Bacillus subtilis, Escherichia coli, and Candida albicans, with inhibition zones ranging from 15.8 to 19.8 mm. Cytotoxicity evaluations of the synthesized derivative on Vero and HFB4 normal cells revealed no significant impact on cell proliferation at low concentrations, with IC<inf>50</inf> values of 831.93 ± 4.82 µg/mL and 639.19 ± 8.69 µg/mL, respectively. Furthermore, density functional theory (DFT) calculations were performed to elucidate the molecular interactions of the modified chitosan (CS-4) with microbial targets. The findings highlight the potential of the functionalized chitosan derivative as a safe and effective antimicrobial agent for diverse biomedical applications, paving the way for innovative treatments against microbial infections.