Aromatic derivative of chitosan improves regenerative properties

The antioxidant, bacteriostatic and antinflammatory properties of chitosan ensure that it is highly suitable for regenerative medicine applications such as wound dressings. In the presented study, a chitosan derivatized via a Schiff base is introduced to further improve these properties.

 

 

Chitosan derivative with 2,2',4,4'-tetrahydroxybenzophenone exhibits stronger antibacterial, anti-inflammatory and antioxidant properties

Tamer M. Tamer, Mervat M. ElTantawy, Arina Brussevich, Anna Nebalueva, Alexander Novikov, Ivan V. Moskalenko, Marwa M. Abu-Serie, Mohamed A. Hassan, Svetlana Ulasevich, Ekaterina V. Skorb, Functionalization of chitosan with poly aromatic hydroxyl molecules for improving its antibacterial and antioxidant properties: Practical and theoretical studies, International Journal of Biological Macromolecules, Volume 234, 2023, 123687, ISSN 0141-8130, https://doi.org/10.1016/j.ijbiomac.2023.123687

Interest in antioxidants has increased greatly in recent years as numerous studies have shown the link between oxidative stress and chronic degenerative diseases such as atherosclerosis. One antioxidant recently isolated from plants is tetrahydroxybenzophenone. In the study presented, this was bound to the amino group of chitosan via a Schiff base. Chitosan with a molecular weight between 100 and 300 kDa and a degree of deacetylation of about 75% was used. You can also find similar products in our online store.

The exact antioxidant mechanism of chitosan is unknown, but it is assumed that free radicals can be scavenged via the positive charges. In the case of the derivative synthesized in the study, it is suspected that the phenolic groups additionally act as electron donors, thereby enhancing the antioxidant effect. Oxidative stress can not only cause direct damage, but also activates an immune response via various signaling pathways. To confirm the anti-inflammatory effect of the derivative, it was verified whether the level of the proinflammatory cytokine TNF-alpha was lowered. However, the bacteriostatic effect of chitosan is also significant for its use in regenerative medicine. Due to the positive charge of chitosan at the amine group, it can attach itself to the cell wall and cell membrane of bacteria and thus damage them. This can be enhanced by the hydrophobic properties of the chitosan. Derivatization with 2,2',4,4'-tetrahydroxybenzophenone increases the hydrophobic character of the chitosan, resulting in stronger interactions with the hydrophobic cell wall. Multi-resistant bacterial strains from hospitals were used to verify whether this also enhances the antibacterial effect of chitosan.

Results

• increased antibacterial activity against multi-resistant bacteria
• better wound healing properties
• tronger antioxidant and anti-inflammatory activity
• higher thermal stability
• lower solubility

Conclusion: The derivative of chitosan with tetrahydroxybenzophenone may be more suitable than normal chitosan for regenerative medicine application. However, it is much more complex to produce compared to regular chitosan.

Link to article: https://www.sciencedirect.com/science/article/abs/pii/S0141813023005809?via%3Dihub