Novel Cytocompatible Chitosan Schiff Base Derivative as a Potent Antibacterial, Antidiabetic, and Anticancer Agent

Abstract

This study intends to develop a novel bioactive chitosan Schiff base (CTS-SB) derivative via coupling of chitosan (CTS) with 4-((5, 5-dimethyl-3-oxocyclohex-1-en-1-yl) amino) benzene-sulfonamide. The alteration in the chemical structure of CTS-SB was verified using 1H NMR and FT-IR analysis, while the thermal and morphological properties were inspected by TGA and SEM characterization tools, respectively. Ion exchange capacity of the developed CTS-SB derivative recorded a maximal value of 12.1 meq/g compared to 10.1 meq/g for pristine CTS. In addition, antibacterial activity of CTS-SB derivative was greatly boosted against Escherichia coli (E coli) and Staphylococcus aureus (S. aureus) bacteria. Minimum inhibition concentration of CTS-SB derivative was perceived at 50 µg/mL, while the highest concentration (250 µg/mL) could inhibit the growth of S. aureus up to 91%. What’s more, enhanced antidiabetic activity by CTS-SB derivative, which displayed higher inhibitory values of α-amylase (57.9%) and α-glucosidase (63.9%), compared to those of pure CTS (49.8 and 53.4%), respectively Furthermore, cytotoxicity investigation on HepG-2 cell line revealed potential anticancer activity along with good safety margin against primary human skin fibroblasts (HSF cells) and decent cytocompatibility. Collectively, the gained results hypothesized that CTS-SB derivative could be effectively applied as a promising antibacterial, anticancer and antidiabetic agent for advanced biomedical applications.

Metal Complexes with Schiff Bases as Antimicrobials and Catalysts

“…Chitosan SBs have shown interesting biological activities [83] as being anticancer [84,85], antioxidant [86][87][88], antibacterial [89][90][91][92], and antidiabetic [93]. Some chitosan-based SBs are used for the removal of toxic metal ions from the aqueous medium, including Fe(III) [94], Pb(II) [95], Cu(II), Cd(II) [96], Cr(III) [97], and Cr(VI) [98,99].…”

Bactericidal Chitosan Derivatives and Their Superabsorbent Blends with ĸ – Carrageenan

“…Using dialdehydes/diketones such as glutaraldehyde [21], glutaraldehyde-thiourea mixture [22], and dialdehyde cellulose [23] in the cross-linking technique, CsSB gels can be obtained. The chitosan Schiff bases polymers are promising materials with antibacterial [24,25], antifungal [26,27], and anticancer [28,29] properties.…”

Synthesis, Spectral Characterization, Thermal Investigation, Computational Studies, Molecular Docking, and In Vitro Biological Activities of a New Schiff Base Derived from 2-Chloro Benzaldehyde and 3,3′-Dimethyl-[1,1′-biphenyl]-4,4′-diamine

“…Cancer is a hard disease to deal with all over the world for several reasons. One of the biggest problems with getting rid of cancer is that it can become resistant to the drugs used to treat it. − The rate at which cancer responds to cytotoxic drugs is not good enough. Researchers are trying to find a new drug, which has made them think about new agents with less systemic toxicity and better cytotoxicity .…”