Fabrication and characterization of a new eco-friendly sulfonamide-chitosan derivative with enhanced antimicrobial and selective cytotoxicity properties.

Chitosan (CH) exhibits low antimicrobial activity. This study addresses this issue by modifying the chitosan with a sulfonamide derivative, 3-(4-(N,N-dimethylsulfonyl)phenyl)acrylic acid. The structure of the sulfonamide-chitosan derivative (DMS-CH) was confirmed using Fourier transform infrared spectroscopy and Nuclear magnetic resonance. The results of scanning electron microscopy, thermal gravimetric analysis, and X-ray diffraction indicated that the morphology changed to a porous nature, the thermal stability decreased, and the crystallinity increased in the DMS-CH derivative compared to chitosan, respectively. The degree of substitution was calculated from the elemental analysis data and was found to be moderate (42%). The modified chitosan exhibited enhanced antimicrobial properties at low concentrations, with a minimum inhibitory concentration (MIC) of 50 µg/mL observed for B. subtilis and P. aeruginosa, and a value of 25 µg/mL for S. aureus, E. coli, and C. albicans. In the case of native chitosan, the MIC values doubled or more, with 50 µg/mL recorded for E. coli and C. albicans and 100 µg/mL recorded for B. subtilis, S. aureus, and P. aeruginosa. Furthermore, toxicological examinations conducted on MCF-7 (breast adenocarcinoma) cell lines demonstrated that DMS-CH exhibited greater toxicity (IC50 = 225.47 µg/mL) than pure CH, while still maintaining significant safety limits against normal lung fibroblasts (WI-38). Collectively, these results suggest the potential use of the newly modified chitosan in biomedical applications.

Synthesis, characterization, and biological evaluation of new chitosan derivative bearing diphenyl pyrazole moiety.

This work reports the synthesis of a new pyrazole derivative by reacting 5-amino-1,3-diphenyl pyrazole with succinic anhydride and bearing the product chemically on the chitosan chains via amide linkage to achieve a new chitosan derivative (DPPS-CH). The prepared chitosan derivative was analyzed by IR, NMR, elemental analysis, XRD, TGA-DTG, and SEM. As compared with chitosan, DPPS-CH showed an amorphous and porous structure. Coats-Redfern results showed that the thermal activation energy for the first decomposition of DPPS-CH is 43.72 KJ mol-1 lower than that required for chitosan (88.32 KJ mol-1), indicating the accelerating effect of DPPS on the thermal decomposition of DPPS-CH. The DPPS-CH manifested a powerful wide spectrum antimicrobial potential against pathogenic gram-positive and gram-negative bacteria and Candida albicans at minute concentrations (MIC = 50 µg mL-1) compared to chitosan (MIC = 100 µg mL-1). The MTT assay proved the toxic properties of DPPS-CH against a cancer cell line (MCF-7) at a minute concentration (IC50 = 15.14 µg mL-1) while affecting normal cells (WI-38) at seven times this concentration (IC50 = 107.8 µg mL-1). According to the current findings, the chitosan derivative developed in this work appears to be a promising material for use in biological domains.