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Carbohydrate Polymers
Volume 219, 2019, Pages: 240-250


Synthesis of chitosan derivatives with organoselenium and organosulfur compounds: Characterization, antimicrobial properties and application as biomaterials

Matheus S.Gulartea, João M.Anghinonib, Laura Abenanteb, Guilherme T.Vossc, Renata L.de Oliveirac, Rodrigo A.Vaucherd, Cristiane Luchesec, Ethel. A.Wilhelmc, Eder J.Lenardãob, André R.Fajardoa

Laboratório de Tecnologia e Desenvolvimento de Compósitos e Materiais Poliméricos (LaCoPol), Universidade Federal de Pelotas (UFPel), Campus Capão do Leão, 96010-900, Pelotas, RS, Brazil.

Abstract

In this study, Schiff bases of chitosan (CS) were synthesized using citronellal, citral, and their derivatives containing selenium and sulfur. Organoselenium and organosulfur compounds show attractive biological and pharmaceutical activities, which can be beneficial to CS-based materials. From the characterization analyses, it was found that the CS-derivatives containing organoselenium and organosulfur compounds exhibited the highest conversion degrees (23 and 28%). Biological assays were conducted using films prepared by the blending of CS-derivatives and poly(vinyl alcohol). The antimicrobial evaluation indicated that the film prepared with the sulfur-containing CS was the most active against the tested pathogens (Escherichia coliStaphylococcus aureus, and Candida albicans) since it reduced considerably their counts (42.5%, 17.4%, and 18.7%). Finally, in vivo assays revealed that this film attenuates atopic dermatitis-like symptoms in mice by suppressing the increase of myeloperoxidase (MPO) activity and reactive species (RS) levels induced by 2,4-dinitrochlorobenzene (DNCB). In summary, CS-derivatives containing chalcogens, mainly organosulfur, are potential candidates for biomedical applications such as for the treatment of chronic skin diseases.

Graphical abstract

Keywords: Chitosan, Organoselenium, Organosulfur, Schiff base, Antimicrobial activity, Atopic dermatitis.

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