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

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 isolat...

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Bibliographic Details
Published in:Polymer bulletin (Berlin, Germany) Germany), 2023-04, Vol.80 (4), p.4035-4059
Main Authors: Mostafa, Mai A., Ismail, Mostafa M., Morsy, Jehan M., Hassanin, Hany M., Abdelrazek, Marwa M.
Format: Article
Language:English
Subjects:
Anticancer properties
Antimicrobial agents
Antioxidants
Breast cancer
Cell cycle
Characterization and Evaluation of Materials
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chitosan
Complex Fluids and Microfluidics
Imines
Nanocomposites
Nanoparticles
Organic Chemistry
Original Paper
Pharmaceuticals
Physical Chemistry
Polymer Sciences
Scavenging
Silver
Soft and Granular Matter
Toxicity
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Summary: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 IC 50 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
ISSN:0170-0839
1436-2449
DOI:10.1007/s00289-022-04238-7