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In this study, the chitosan backbone was functionalized with 2,2',4,4'-tetrahydroxybenzophenone by Schiff base, bonding the molecules into the repeating amine groups. The use of 1 H NMR, FT-IR, and UV-Vis analyses provided compelling evidence of the structure of the newly developed derivatives. The deacetylation degree was calculated to be 75.35 %, and the degree of substitution was 5.53 % according to elemental analysis. The thermal analysis of samples using TGA demonstrated that CS-THB derivatives are more stable than chitosan itself. SEM was used to investigate the change in surface morphology. The improvement of the biological properties of chitosan was investigated in terms of its antibacterial activity against pathogenic antibiotic-resistant bacteria. The antioxidant properties showed an improvement in activity compared to chitosan by two times against ABTS radicals and four times against DPPH radicals. Furthermore, the cytotoxicity and anti-inflammatory properties were investigated using normal skin cells (HBF4) and WBCs. Quantum chemistry calculations revealed that combining polyphenol with chitosan makes it more effective as an antioxidant than either chitosan or polyphenol alone. Our findings suggest that the new chitosan Schiff base derivative could be utilized for tissue regeneration applications., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023. Published by Elsevier B.V.)