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Water-soluble fluorine-functionalized chitooligosaccharide derivatives: Synthesis, characterization and antimicrobial
Conghao Lin1, Fang Luan2, Shengjia Su3
1Research and Development Center for Efficient Utilization of Coastal Bioresources, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, 264003, China; College of Life Sciences, Yantai University, Yantai, 264005, China.
Carbohydrate Research
|September 17, 2023
Summary
Novel fluorine-functionalized chitooligosaccharide derivatives show potent antimicrobial activity against bacteria and fungi. These biocompatible compounds offer a promising avenue for developing eco-friendly antimicrobial agents.
Area of Science:
- Biochemistry
- Materials Science
- Microbiology
Background:
- Chitooligosaccharides (COS) are biocompatible polysaccharides with potential applications in various fields.
- Developing novel antimicrobial agents is crucial due to rising resistance.
- Fluorine functionalization can enhance the properties of biomaterials.
Purpose of the Study:
- To synthesize and characterize water-soluble fluorine-functionalized chitooligosaccharide derivatives.
- To evaluate the antimicrobial and antifungal activities of these novel derivatives.
- To assess the biocompatibility of the synthesized compounds.
Main Methods:
- Synthesis via nicotinylation and nucleophilic substitution reactions.
- Structural identification using Fourier Transform Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance (NMR).
- Antimicrobial and antifungal assays including broth dilution, Kirby-Bauer, and mycelium growth rate methods. Cytotoxicity assessed via MTT assay.
Main Results:
- Fluorine-functionalized COS derivatives, particularly those with benzyl or fluorobenzyl groups, demonstrated significant antimicrobial activity.
- The 2,3,4-trifluorobenzyl derivative showed high efficacy against Botrytis cinerea (84.35% inhibition) and Staphylococcus aureus (MIC: 0.03125 mg/mL, MBC: 0.0625 mg/mL).
- All synthesized derivatives exhibited no toxicity towards Huvec cells, indicating good biocompatibility.
Conclusions:
- Incorporating pyridinium cations and fluorine enhances the antimicrobial efficacy of chitooligosaccharides.
- These fluorine-functionalized COS derivatives possess rapid microbicidal properties and excellent biocompatibility.
- The study presents promising prospects for developing effective and environmentally friendly antimicrobial agents from modified chitooligosaccharides.
