Synthesis, characterization, anticancer, and antioxidant activities of chitosan Schiff bases bearing quinolinone or pyranoquinolinone and their silver nanoparticles derivatives

Abstract

In this work, new chitosan-based Schiff bases were synthesized by the reaction of chitosan with quinolinone and pyranoquinolinone giving CSQ, and CSP, respectively. The novel Chitosan Schiff bases were grafted on silver nanoparticles providing CSQ/Ag, CSP/Ag structures. Characterization of isolated compounds was carried out by FT-IR, TGA, XRD, SEM, and TEM. The target compounds CSQ, CSP, CSQ/Ag, and CSP/Ag were evaluated as antitumor agents against three cancer cell lines, liver (HepG-2), colon (HCT-116), and breast (MCF-7). Compound CSQ/Ag disclosed potent cytotoxic effect with IC50 values in the range of 41.9–55.1 μg/ml in comparison with 5-fluorouracil against different cancer cell lines. Besides, the antioxidant activity of chitosan and its quinolinone and pyranoquinolinone analogues was assessed as radical scavengers versus 1,1-diphenyl-2-picrylhydrazyl radicals (DPPH%). The compound CSQ/Ag emerged as the most active member in scavenging the DPPH radicals. The obtained findings proved that the new Schiff bases/silver nanoparticles of chitosan showed higher antiproliferative and antioxidant activities than the blank CS and would be highly applicable in biomedical fields. Graphical abstract

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

“…6B) were determined to be 109.6 and 76.74 μg/mL with SI values of 6.63 ± 0.10 and 6.19 after treatment for 24 and 72 h, respectively. These outcomes prove the significant safety for the prepared CTS-SB toward the normal human cells with high selectivity against hepatoma cancer cells [61,62]. On the other hand, both chitosan (CTS) and berberine (standard drug) showed moderate antitumor activity against HepG-2 cells (Table 3).…”

Developing a new multi-featured chitosan-quinoline Schiff base with potent antibacterial, antioxidant, and antidiabetic activities: design and molecular modeling simulation

“…Hence, chitosan demonstrated acceptable antimicrobial, antioxidant, antiviral, and anti-inflammatory activities 8 , 9 , in addition to its vital role in the cytotoxic profile and targeting of cancer cells 10 . Both OH and NH 2 functional groups of chitosan are considered the key active functional groups for its antioxidant activity since they can inhibit the reactive oxygen species (ROS) from donating hydrogen or the lone pairs of electrons 11 . Further, chitosan and its derivatives have encouraged antidiabetic profits, which are mediated over mechanisms comprising suppression of α-glucosidase and α-amylase activities, amended glucose metabolism, and reduced β-cell dysfunction 12 .…”

Novel Multi-Target Agents Based on the Privileged Structure of 4-Hydroxy-2-quinolinone

“…The quinolinone scaffold is one of the most attractive privileged structures for drug discovery research, exhibiting a wide variety of biological activities, such as antibacterial, anti-inflammatory, anticancer, and neuroprotective [6][7][8][9][10][11][12][13]. In particular, compounds possessing 4-hydroxy-2-quinolinone structural features (Figure 1) have gained interest as an anti-inflammatory, anticancer, and neuroprotective [6][7][8][9][10][11][12][13].…”

“…The quinolinone scaffold is one of the most attractive privileged structures for drug discovery research, exhibiting a wide variety of biological activities, such as antibacterial, anti-inflammatory, anticancer, and neuroprotective [6][7][8][9][10][11][12][13]. In particular, compounds possessing 4-hydroxy-2-quinolinone structural features (Figure 1) have gained interest as an anti-inflammatory, anticancer, and neuroprotective [6][7][8][9][10][11][12][13]. In particular, compounds possessing 4-hydroxy-2-quinolinone structural features (Figure 1) have gained interest as an important class of heterocyclic molecules with well-known reported activity [14][15][16], while several synthetic strategies have been developed [17][18][19][20].…”

“…anti-inflammatory, anticancer, and neuroprotective [6][7][8][9][10][11][12][13]. In particular, compounds possessing 4-hydroxy-2-quinolinone structural features (Figure 1) have gained interest as an important class of heterocyclic molecules with well-known reported activity [14][15][16], while several synthetic strategies have been developed [17][18][19][20].…”