Synthesis and physicochemical properties of an aromatic chitosan derivative: In vitro antibacterial, antioxidant, and anticancer evaluations, and in silico studies

This study was designed to synthesize a functionalized chitosan by coupling the amine groups of chitosan with 2,4,6-Trimethoxybenzaldehyde, producing a chitosan Schiff base (Cs-TMB). The development of Cs-TMB was verified employing FT-IR, 1H NMR, the electronic spectrum, and elemental analysis. Antioxidant assays exhibited significant ameliorations of Cs-TMB, reporting scavenging activities of 69.67 +/- 3.48 % and 39.65 +/- 1.98 % for ABTS center dot+ and DPPH, respectively, while native chitosan showed scavenging ratios of 22.69 +/- 1.13 % and 8.24 0.4.1 % toward ABTS center dot+ and DPPH, respectively. Besides, Cs-TMB exerted significant antibacterial activity up 90 % with remarkable bactericidal capacity against virulent gram-negative and gram-positive bacteria compared to the original chitosan. Furthermore, Cs-TMB exhibited a safe profile against normal fibroblast cells (HFB4). Interestingly, flow cytometric analysis showed that Cs-TMB demonstrated prominent anticancer properties 52.35 +/- 2.99 % against human skin cancer cells (A375), compared to 10.66 +/- 0.55 % for Cs-treated cells. Moreover, Python and PyMOL in-house scripts were used to predict the interaction of Cs-TMB with the adenosine A1 receptor and visualized as a protein-ligand system submerged in a lipid membrane. Overall, these findings accentuate that Cs-TMB could be a favorable representative for wound dressing formulations and skin cancer treatment.

Automated summary

This study aimed to synthesize a functionalized chitosan, Cs-TMB, by coupling the amine groups of chitosan with 2,4,6-Trimethoxybenzaldehyde. Cs-TMB showed improved antioxidant and antibacterial activities compared to native chitosan. It also exhibited a safe profile against normal fibroblast cells and demonstrated prominent anticancer properties against human skin cancer cells.