Clicking gallic acid into chitosan prolongs its antioxidant activity and produces intracellular Ca 2+ responses in rat brain cells

Gallic acid is a vegetable-derived and highly bioactive phenolic acid, but its antioxidant capacity is sensitive to environmental conditions. Chitosan is a biopolymer capable of exerting significant protection to various molecules, including phenolic compounds. A chitosan derivative that extends the...

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Bibliographic Details
Published in:International journal of biological macromolecules 2024-10, Vol.277 (Pt 3), p.134343
Main Authors: Pérez-Delgado, Francisco Jonathan, García-Villa, Miriam Denise, Fernández-Quiroz, Daniel, Villegas-Ochoa, Mónica, Domínguez-Avila, Jesús Abraham, Gonzalez-Aguilar, Gustavo Adolfo, Ayala-Zavala, Jesús Fernando, Martínez-Martínez, Alejandro, Montiel-Herrera, Marcelino
Format: Article
Language:English
Subjects:
Animals
Antioxidants - chemistry
Antioxidants - pharmacology
Brain - drug effects
Brain - metabolism
Calcium - metabolism
Chitosan - chemistry
Chitosan - pharmacology
Gallic Acid - analogs & derivatives
Gallic Acid - chemistry
Gallic Acid - pharmacology
Nanoparticles - chemistry
Rats
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Summary:Gallic acid is a vegetable-derived and highly bioactive phenolic acid, but its antioxidant capacity is sensitive to environmental conditions. Chitosan is a biopolymer capable of exerting significant protection to various molecules, including phenolic compounds. A chitosan derivative that extends the antioxidant activity of gallic acid was synthesized by click chemistry and characterized by FT-IR, H NMR, and antioxidant capacity assays. Our results show that synthesized polymeric solutions and nanoparticles of N-(gallic acid) chitosan were both internalized by rat brain cells, processes that were modulated by extracellular Ca and Na . Their internalization was supported by dynamic light scattering and ζ-potential analyses, while Ca imaging recordings performed in brain cells revealed the potential biological effect of N-(gallic acid) chitosan. We conclude that the synthesis of an N-(gallic acid) chitosan derivative through click chemistry is viable and may serve as strategy to prolong its antioxidant activity and to study its biological effects in vivo.
ISSN:1879-0003
DOI:10.1016/j.ijbiomac.2024.134343