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

• Published in: Carbohydrate polymers 2019-09, Vol.219, p.240-250
• Main Authors: Gularte, Matheus S., Anghinoni, João M., Abenante, Laura, Voss, Guilherme T., de Oliveira, Renata L., Vaucher, Rodrigo A., Luchese, Cristiane, Wilhelm, Ethel. A., Lenardão, Eder J., Fajardo, André R.
• Format: Article
• Language: English
• Subjects: Antimicrobial activity; Atopic dermatitis; Chitosan; Organoselenium; Organosulfur; Schiff base
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2019.05.040

[Display omitted] •Schiff bases of CS were synthesized using organoselenium and organosulfur compounds.•The conversion degrees of CS-derivatives containing selenium and sulfur were >20%.•Films prepared by the blending the CS-derivatives and PVA showed antimicrobial activity.•The sulfur-containing film was the most active against the tested pathogens.•In vivo assays showed that this film has anti-inflammatory and antioxidant activities. 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 coli, Staphylococcus 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.