Water-soluble fluorine-functionalized chitooligosaccharide derivatives: Synthesis, characterization and antimicrobial activity.

In this work, a series of water-soluble fluorine-functionalized chitooligosaccharide derivatives were synthesized by conjugating nicotinic acid to chitooligosaccharide via nicotinylation reaction, followed by nucleophilic reaction with ethyl bromide, benzyl bromide and fluorobenzyl bromides. Synthesized derivatives were identified structurally by Fourier Transform Infrared Spectroscopy and Nuclear Magnetic Resonance. In addition, the antibacterial activities of chitooligosaccharide derivatives against several disease-causing bacteria were assessed by the broth dilution method and Kirby-Bauer method, the mycelium growth rate method was used to assessing the antifungal properties of samples against three plant-threatening fungi. Among the chitooligosaccharide derivatives, those containing benzyl or fluorobenzyl exhibited noteworthy antimicrobial activity. Specifically, the chitooligosaccharide derivative containing 2,3,4-trifluorobenzyl displayed remarkable antimicrobial activity, with an inhibition index of 84.35% against Botryis cinerea at a concentration of 1.0 mg/mL. Additionally, its MIC value against Staphylococcus aureus was found to be 0.03125 mg/mL, while the MBC value was determined to be 0.0625 mg/mL. The findings of the study revealed that the incorporation of pyridinium cations and fluorine into the chitooligosaccharide backbone may play a critical role in strengthening its ability to combat harmful microorganisms. Furthermore, the cytotoxicities of chitooligosaccharide derivatives against Huvec cells were evaluated through MTT assay, and all samples were not toxic. As a consequence, the water-soluble fluorine-functionalized chitooligosaccharide derivatives possessed rapid microbicidal properties and good biocompatibility, which provided promising prospects for the development of a more effective and environmentally friendly antimicrobial agent.

Redox-sensitive self-assembled micelles based on low molecular weight chitosan-lipoic acid conjugates for the delivery of doxorubicin: Effect of substitution degree of lipoic acid.

Amphiphilic low molecular weight chitosan-lipoic acid (LC-LA) conjugates with different degrees of substitution (DS) of LA were synthesized by N, N'­carbonyldiimidazole (CDI) catalysis to self-assemble into redox-sensitive micelles. Critical micelle concentration (CMC), size, zeta potential, biocompatibility and redox-sensitive behavior of blank micelles were investigated. The results indicated that blank micelles with low CMC, nanoscale size and positive zeta potential showed excellent biocompatibility and redox-sensitive behavior. Doxorubicin (Dox) loaded micelles were prepared by encapsulating Dox into blank micelles. The loading ability, trigger-release behavior, antitumor activity and cellular uptake of Dox loaded micelles were studied. The results demonstrated that Dox loaded micelles with superior loading ability exhibited redox-trigger behavior, strong antitumor activity and increased cellular uptake efficiency against A549 cell. Besides, the effect of DS of LA on above properties was estimated. An increase in DS of LA reduced the CMC and cumulative release amount of Dox, but improved the loading efficiency, antitumor activity, and cellular uptake of Dox loaded micelles, which resulted from stronger interaction of hydrophobic groups in micelles with the DS of LA increased. Overall, self-assembled LC-LA micelles with good biosecurity and redox-sensitive behavior hold promising application prospects in Dox delivery and improving cancer therapeutic effect of Dox.

Self-assembled low molecular weight chitosan-based cationic micelle for improved water solubility, stability and sustained release of α-tocopherol.

New amphiphilic low molecular weight chitosan-graft-nicotinic acid bearing decyl groups (LCND) was synthesized by two-step reaction and spontaneously assembled into cationic micelle by ultra-sonication method to improve water solubility and photostability properties of α-tocopherol. The chemical structure of LCND was characterized and physical properties of cationic micelle were evaluated. Results displayed that cationic micelle exhibited strong self-assemble ability with nanoscale spherical morphology and showed best loading ability with loading content of 18.50% when the feeding ratio of LCND to α-tocopherol reached 10:3. Meanwhile, the greatly enhanced water solubility, photostability and sustained release behavior of α-tocopherol in cationic micelle were observed. The cumulative release of α-tocopherol in cationic micelle reached up 82.18% within 96 h while free α-tocopherol was completely released within 10 h. Additionally, release kinetics models were also fitted. The LCND cationic micelle could be promising nanocarrier for improving the physicochemical properties of α-tocopherol in food fields.