Synthesis, antimicrobial activity, antioxidant activity and molecular docking of novel chitosan derivatives containing glycine Schiff bases as potential succinate dehydrogenase inhibitors.

Succinate dehydrogenase (SDH) is an important inner mitochondrial membrane-bound enzyme involved in redox reactions during the tricarboxylic acid cycle. Therefore, a series of novel chitosan derivatives were designed and synthesized as potential microbicides targeting SDH and precisely characterized by FTIR, 1H NMR and SEM. Their antifungal and antibacterial activities were evaluated against Botrytis cinerea, Fusarium graminearum, Staphylococcus aureus and Escherichia coli. The bioassays revealed that these chitosan derivatives exerted significant antifungal effects, with four of the compounds achieving 100 % inhibition of Fusarium graminearum merely at a concentration of 0.5 mg/mL. Additionally, CSGDCH showed 79.34 % inhibition of Botrytis cinerea at a concentration of 0.1 mg/mL. In vitro antibacterial tests revealed that CSGDCH and CSGDBH have excellent Staphylococcus aureus and Escherichia coli inhibition with MICs of 0.0156 mg/mL and 0.03125 mg/mL, respectively. Molecular docking studies have been carried out to explore the binding energy and binding mode of chitosan and chitosan derivatives with SDH. The analyses indicated that chitosan derivatives targeted the active site of the SDH protein more precisely, disrupting its normal function and ultimately repressing the growth of microbial cells. Furthermore, the chitosan derivatives were also evaluated biologically for antioxidation, and all of these compounds had a greater degree of reducing power, superoxide radical, hydroxyl radical and DPPH-radical scavenging activity than chitosan. This research has the potential for the development of agricultural antimicrobial agents.

Low molecular weight chitosan based GSH-responsive self-assembled cationic micelle with enhanced anti-tumor effect by combining oxidative damage and chemotherapy.

A novel cationic lipoic acid grafted low molecular weight chitosan (LCNE-LA) conjugate was constructed and further self-assembled into GSH-responsive cationic nanocarrier to achieve better antitumor effect by combining encapsulated chemotherapy and oxidative damage induced by ROS. The resultant LCNE-LA cationic micelle exhibited favorable physicochemical properties (low CMC, small size, positively zeta potential and good stability), excellent biosafety and desired redox sensitivity. Next, doxorubicin (Dox) was embedded into hydrophobic core to form stable Dox/LCNE-LA micelle that had superior loading capacity. The GSH-induced release behavior, cellular uptake ability, ROS generation and GSH consumption capacity and in vitro antitumor activity of Dox/LCNE-LA micelle were systematically evaluated. Consequently, Dox/LCNE-LA cationic micelle with positively charged could efficiently enter into cancer cell and redox-sensitive release Dox via disulfide-thiol exchange reaction, which usually expend abundant GSH and disrupt redox homeostasis. Studies further confirmed that Dox/LCNE-LA micelle could increase ROS and reduced GSH content which might cause oxidative damage to tumor cell. Antitumor activity indicated that Dox/LCNE-LA micelle achieved an excellent cancer-killing effect, which might be attributed to combination treatment of Dox and ROS induce oxidative damage. Overall, this research was expected to provide a platform for antitumor treatment by triggering Dox release and promoting ROS generation.

Improvement of the Antioxidant and Antitumor Activities of Benzimidazole-Chitosan Quaternary Ammonium Salt on Drug Delivery Nanogels.

The present study focused on the design and preparation of acid-responsive benzimidazole-chitosan quaternary ammonium salt (BIMIXHAC) nanogels for a controlled, slow-release of Doxorubicin HCl (DOX.HCl). The BIMIXHAC was crosslinked with sodium tripolyphosphate (TPP) using the ion crosslinking method. The method resulted in nanogels with low polydispersity index, small particle size, and positive zeta potential values, indicating the good stability of the nanogels. Compared to hydroxypropyl trimethyl ammonium chloride chitosan-Doxorubicin HCl-sodium tripolyphosphate (HACC-D-TPP) nanogel, the benzimidazole-chitosan quaternary ammonium salt-Doxorubicin HCl-sodium tripolyphosphate (BIMIXHAC-D-TPP) nanogel show higher drug encapsulation efficiency and loading capacity (BIMIXHAC-D-TPP 93.17 ± 0.27% and 31.17 ± 0.09%), with acid-responsive release profiles and accelerated release in vitro. The hydroxypropyl trimethyl ammonium chloride chitosan-sodium tripolyphosphate (HACC-TPP), and benzimidazole-chitosan quaternary ammonium salt-sodium tripolyphosphate (BIMIXHAC-TPP) nanogels demonstrated favorable antioxidant capability. The assay of cell viability, measured by the MTT assay, revealed that nanogels led to a significant reduction in the cell viability of two cancer cells: the human lung adenocarcinoma epithelial cell line (A549) and the human breast cancer cell line (MCF-7). Furthermore, the BIMIXHAC-D-TPP nanogel was 2.96 times less toxic than DOX.HCl to the mouse fibroblast cell line (L929). It was indicated that the BIMIXHAC-based nanogel with enhanced antioxidant and antitumor activities and acidic-responsive release could serve as a potential nanocarrier.

pH-responsive nanogels with enhanced antioxidant and antitumor activities on drug delivery and smart drug release.

pH-responsive nanogels have played an increasingly momentous role in tumor treatment. The focus of this study is to design and develop pH-responsive benzimidazole-chitosan quaternary ammonium salt (BIMIXHAC) nanogels for the controlled release of doxorubicin hydrochloride (DOX) while enhancing its hydrophilicity. BIMIXHAC is crosslinked with carboxymethyl chitosan (CMC), hyaluronic acid sodium salt (HA), and sodium alginates (SA) using an ion crosslinking method. The chemical structure of chitosan derivatives was verified by 1H NMR and FT-IR techniques. Compared to hydroxypropyl trimethyl ammonium chloride chitosan (HACC)-based nanogels, BIMIXHAC-based nanogels exhibit better drug encapsulation efficiency and loading capacity (BIMIXHAC-D-HA 91.76 %, and 32.23 %), with pH-responsive release profiles and accelerated release in vitro. The series of nanogels formed by crosslinking with three different polyanionic crosslinkers have different particle size potentials and antioxidant properties. BIMIXHAC-HA, BIMIXHAC-SA and BIMIXHAC-CMC demonstrate favorable antioxidant capability. In addition, cytotoxicity tests showed that BIMIXHAC-based nanogels have high biocompatibility. BIMIXHAC-based nanogels exhibit preferable anticancer effects on MCF-7 and A549 cells. Furthermore, the BIMIXHAC-D-HA nanogel was 2.62 times less toxic than DOX to L929 cells. These results suggest that BIMIXHAC-based nanogels can serve as pH-responsive nanoplatforms for the delivery of anticancer drugs.

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.

Preparation of chitosan derivatives containing aromatic five-membered heterocycles for efficient antimicrobial and antioxidant activities.

In this study, nine chitosan derivatives containing aromatic five-membered heterocycles were prepared and the effects of different grafting methods on the biological activities of chitosan derivatives were investigated. The structures of all the compounds were characterized by Fourier Transform Infrared (FT-IR) spectroscopy and Nuclear Magnetic Resonance (NMR) spectroscopy, while the antioxidant, antifungal and antibacterial activities of the chitosan derivatives were tested. The experimental data suggested that the chitosan derivatives had outstanding inhibitory ability against Fusarium graminearum, Fusarium oxysporum f.sp.cucumbrum, Staphylococcus aureus and Escherichia coli. At the same time, some of the compounds showed strong scavenging ability against DPPH radical and superoxide radical. Cytotoxicity experiments have demonstrated that some chitosan derivatives are non-toxic to L929 cells. More importantly, compared to chitosan, these chitosan derivatives have good water solubility and can be used as potential polymers for antifungal and antibacterial biomaterials in agriculture.

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.

Preparation of imidazole acids grafted chitosan with enhanced antioxidant, antibacterial and antitumor activities.

Herein, imidazole acids grafted chitosan derivatives were synthesized, including HACC, HACC derivatives, TMC, TMC derivatives, amidated chitosan and amidated chitosan bearing imidazolium salts. The prepared chitosan derivatives were characterized by FT-IR and 1H NMR. The tests evaluated the biological antioxidant, antibacterial, and cytotoxic activities of chitosan derivatives. The antioxidant capacity (DPPH radical, superoxide anion radical and hydroxyl radical) of chitosan derivatives was 2.4-8.3 times higher than that of chitosan. The antibacterial capacity against E. coli and S. aureus of cationic derivatives (HACC derivatives, TMC derivatives, and amidated chitosan bearing imidazolium salts) was more active than only imidazole-chitosan (amidated chitosan). In particular, the inhibition effect of HACC derivatives on E. coli was 15.625 µg/mL. Moreover, the series of chitosan derivatives bearing imidazole acids showed certain activity against MCF-7 and A549 cells. The present results suggest that the chitosan derivatives in this paper seem to be promising carrier materials for use in drug delivery systems.

Effect of Hydrophobic Chain Length in Amphiphilic Chitosan Conjugates on Intracellular Drug Delivery and Smart Drug Release of Redox-Responsive Micelle.

Three redox-sensitive nanocarriers were rationally designed based on amphiphilic low molecular weight chitosan-cystamine-octylamine/dodecylamin/cetylamine (LC-Cys-OA, LC-Cys-DA, LC-Cys-CA) conjugates containing disulfide linkage for maximizing therapeutic effect by regulating hydrophobic interaction. The resultant spherical micelles had the characteristics of low CMC, suitable size, excellent biosafety and desired stability. The drug-loaded micelles were fabricated by embedding doxorubicin (Dox) into the hydrophobic cores. The effect of hydrophobic chain lengths of amphiphilic conjugates on encapsulation capacity, redox sensitivity, trigger-release behavior, cellular uptake efficacy, antitumor effect and antimigratory activity of Dox-loaded micelles was systematically investigated. Studies found that Dox-loaded LC-Cys-CA micelle had superior loading capacity and enhanced redox sensitivity compared with the other two micelles. Release assay indicated that the three Dox-loaded micelles maintained sufficiently stability in normal blood circulation but rapidly disintegrated in tumor cells. More importantly, the LC-Cys-CA micelle with a longer hydrophobic chain length exhibited a higher accumulative Dox release percentage than the other two micelles. Additionally, an increase in hydrophobic chain lengths of amphiphilic conjugates improved cellular uptake efficiency, antitumor effect and antimigration activity of Dox-loaded micelles, which could be explained by enhanced loading ability and redox sensitivity. Our research was expected to provide a viable platform for achieving a desired therapeutic efficacy via the alteration of hydrophobic interaction.

Preparation of l-Arginine Schiff Bases Modified Chitosan Derivatives and Their Antimicrobial and Antioxidant Properties.

We successfully prepared a series of l-arginine Schiff bases acylated chitosan derivatives, aiming to improve the antioxidant activity and antimicrobial activity of chitosan by introducing a furan ring, pyridine ring, and l-arginine structure. The accuracy of the structures of ten compounds was characterized by FT-IR and 1H NMR. In terms of DPPH radical scavenging activity, except for compound CR3PCA, the scavenging rate of other compounds was higher than chitosan, especially CRCF and CRBF had strong scavenging abilities. At the same time, in the superoxide-radical scavenging activity assay, CRCF, CRBF, CR3PCA, CR2C3PCA, and CR2B3PCA were comparable to positive control at 1.60 mg/mL. Simultaneously, CRFF, CRCF, and CRBF had a certain inhibitory effect on Botrytis cinerea. Furthermore, the inhibitory effect of CRFF, CRCF, and CR3PCA on Staphylococcus aureus was very well, close to the positive control at 1.00 mg/mL. CRCF and CR2B3PCA showed better inhibitory effects on Escherichia coli than other compounds. The MTT assay was used to determine the cytotoxicity of the chitosan derivatives, which proved their safety to fibroblast cells. In summary, the study indicated that some of these compounds have the potential for further development and utilization in the preparation of antioxidants and antimicrobial agents.

Preparation, Anticoagulant and Antioxidant Properties of Glucosamine-Heparin Salt.

Excessive inorganic ions in vivo may lead to electrolyte disorders and induce damage to the human body. Therefore, preparation of enhanced bioactivity compounds, composed of activated organic cations and organic anions, is of great interest among researchers. In this work, glucosamine-heparin salt (GHS) was primarily synthesized with positively charged glucosamine hydrochloride (GAH) and negatively charged heparin sodium (Heps) by ion exchange method. Then, the detailed structural information of the GHS was characterized by FTIR, 1H NMR spectroscopy and ICP-MS. In addition, its anticoagulant potency and antioxidant properties were evaluated, respectively. The results demonstrated that GHS salt achieved enhanced antioxidant activities, including 98.78% of O2•- radical scavenging activity, 91.23% of •OH radical scavenging rate and 66.49% of DPPH radical scavenging capacity at 1.6 mg/mL, severally. Meanwhile, anticoagulant potency (ATTP) of GHS strengthened from 153.10 ± 17.14 to 180.03 ± 6.02 at 0.75 µmol/L. Thus, introducing cationic glucosamine residues into GHS could improve its anticoagulant activity. The findings suggest that GHS product with a small amount of inorganic ions can greatly abate the prime cost of antioxidants and anticoagulants, and has significant economic benefits and practical significance.

Preparation and antioxidant activity of novel chitosan oligosaccharide quinolinyl urea derivatives.

In the present study, four new chitosan oligosaccharide derivatives bearing quinolinyl urea groups were synthesized by reaction between 2-methoxyformylated chitosan oligosaccharide and aminoquinoline. The chitosan oligosaccharide derivatives were characterized by Fourier Transform Infrared (FTIR) and 1H Nuclear Magnetic Resonance (1H NMR) spectroscopy. The obtained results confirmed that chitosan oligosaccharide quinolinyl urea derivatives were successfully synthesized. Meanwhile, the antioxidant activities of different chitosan oligosaccharide derivatives were examined in vitro. Experimentally, it was demonstrated that chitosan oligosaccharide quinolinyl urea derivatives had superior antioxidant activity compared with chitosan oligosaccharide and the antioxidant effects were concentration-dependent. Especially, when the concentration was 1.6 mg/mL, their superoxide anion radical scavenging rates could reach to 72.35 ± 0.49%, 100.00 ± 0.21%, 84.63 ± 0.49%, and 87.22 ± 0.32%, respectively. And the hydroxyl radical scavenging rates could reach to 100.00 ± 0.82%, 98.49 ± 4.08%, 100.00 ± 5.76%, and 92.07 ± 5.10%. In addition, the cytotoxic activity of the prepared chitosan derivatives against L929 cells was determined by CCK-8 assay. The cell survival rates were all higher than 90%, which intuitively indicated that the samples had almost no cytotoxicity. The findings indicated that the enhanced antioxidant property and biocompatibility of these chitosan oligosaccharide quinolinyl urea derivatives could enlarge the scope of the application of chitosan oligosaccharide, particularly as an antioxidant in food packaging, biomedical, pharmaceutical, cosmetics industries and other fields.

Preparation of chitosan-rosmarinic acid derivatives with enhanced antioxidant and anti-inflammatory activities.

In present study, several chitosan derivatives grafted with rosmarinic acid，including chitosan-rosmarinic acid conjugate (CS-RA), chitosan rosmarinic acid salt (CSRA), N,N,N-trimethylated chitosan rosmarinic acid salt (TMCRA), and N-[(2-hydroxy-3-trimethylammonium)propyl]chitosan rosmarinic acid salt (HACRA), were prepared and the effects of different grafting methods on bioactivity of these derivatives were investigated. The structural characterization was identified by FTIR and 1H NMR spectroscopy. The chitosan derivatives were also evaluated biologically for antioxidant, cytotoxic, and anti-inflammatory activities. Derivatives CSRA, TMCRA, and HACRA prepared through ion exchange method exhibited significant antioxidant ability. All derivatives remarkably inhibited lipopolysaccharide-induced nitric oxide and TNF-α production in RAW 264.7 cells without cytotoxicity, especially derivative TMCRA, whose inhibition rate was >50 % at only 250 µg/mL. The results suggested that chitosan quaternary ammonium derivatives grafted with rosmarinic acid possessed better antioxidant and anti-inflammatory properties than chitosan, which could be used as drug materials against oxidative and inflammation-related pathological processes.

Water-soluble amino functionalized chitosan: Preparation, characterization, antioxidant and antibacterial activities.

Amino functionalized chitosan has attracted much attention because of the fascinated bioactivities. In our study, a novel water-soluble amino functionalized chitosan bearing free amino group at C-2 and quaternary ammonium moiety contained free amino group at C-6 (5c) was prepared by a four-step method. The structural characterization was identified by FTIR and 1H NMR spectroscopy. The water-solubility and antioxidant activities against hydroxyl, DPPH radicals and reducing power were estimated. The results displayed that amino functionalized chitosan 5c exhibited improved water-solubility and antioxidant ability, especially its DPPH scavenging rate reached about 90 % at the minimum test concentration of 0.10 mg/mL. Besides, antibacterial tests showed that amino functional chitosan 5c had best antibacterial activities, which indicated that amino group made main contribution to the enhanced bioactivities. In short, the novel chitosan 5c possessed enhanced water-solubility and excellent antioxidant and antibacterial activities, which could provide novel strategy for the development of antioxidant and antibacterial agents in biomedicine and food fields.

Synthesis of Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Thioctate and the Potential for Antioxidant Application.

Hydroxypropyltrimethyl ammonium chloride chitosan (HACC) is one of the most important water-soluble chitosan derivatives; its derivatives have gained growing attention due to their potential biomedical applications. Here, hydroxypropyltrimethyl ammonium chitosan derivatives bearing thioctate (HACTs), with different degrees of substitution of thioctate, were prepared using HACC and α-lipoic acid as the reaction precursors, using an ion exchange method. The structural characteristics of the synthesized derivatives were confirmed by FTIR, 1H NMR, and 13C NMR spectroscopy. In addition, their antioxidant behaviors were also investigated in vitro by the assays of reducing power, and scavenging activities against hydroxyl radicals and DPPH radicals. The antioxidant assay indicated that HACTs displayed strong antioxidant activity compared with HACC, especially in terms of reducing power. Besides, the antioxidant activities of the prepared products were further enhanced with the increase in the test concentration and the degrees of substitution of thioctate. At the maximum test concentration of 1.60 mg/mL, the absorbance value at 700 nm of HACTs, under the test conditions, was 4.346 ± 0.296, while the absorbance value of HACC was 0.041 ± 0.007. The aforementioned results support the use of HACTs as antioxidant biomaterials in food and the biomedical field.

Novel coumarin-functionalized inulin derivatives: Chemical modification and antioxidant activity assessment.

In this paper, a series of target derivatives were synthesized by introducing coumarin into inulin structure using three-step chemical modification, and their structures were characterized by FTIR, 1H NMR, and 13C NMR. At the same time, the antioxidant activities of inulin derivatives were determined, including DPPH-radical scavenging activity, superoxide-radical scavenging activity, PTIO-radical scavenging activity and reducing ability. The test results showed that the antioxidant activities of inulin derivatives containing coumarin were significantly increased. Especially, inulin derivatives showed excellent DPPH radical-scavenging ability (IC50 0.09-0.11 mg/mL). Meanwhile, the scavenging ability of PTIO-radical was increased by more than 80%, and the IC50 values were all between 0.23 and 0.26 mg/mL. At the concentration below 1 mg/mL, the scavenging rate of all inulin derivatives could even reach 100%. This study provides a feasible way to synthesize inulin derivatives with significant activity, which may be developed into new antioxidants in medicine and cosmetics.

Preparation of Doxorubicin-Loaded Carboxymethyl-ß-Cyclodextrin/Chitosan Nanoparticles with Antioxidant, Antitumor Activities and pH-Sensitive Release.

In this study, chitosan nanoparticles (HF-CD NPs) were synthesized by an ionic gelation method using negatively charged carboxymethyl-ß-cyclodextrin and positively charged 2-hydroxypropyltrimethyl ammonium chloride chitosan bearing folic acid. The surface morphology of HF-CD NPs was spherical or oval, and they possessed relatively small particle size (192 ± 8 nm) and positive zeta potential (+20 ± 2 mV). Meanwhile, doxorubicin (Dox) was selected as model drug to investigate the prepared nanoparticles' potential to serve as a drug delivery carrier. The drug loading efficiency of drug-loaded nanoparticles (HF-Dox-CD NPs) was 31.25%. In vitro release profiles showed that Dox release of nanoparticles represented a pH-sensitive sustained and controlled release characteristic. At the same time, the antioxidant activity of nanoparticles was measured, and chitosan nanoparticles possessed good antioxidant activity and could inhibit the lipid peroxidation inside the cell and avoid material infection. Notably, CCK-8 assay testified that the nanoparticles were safe drug carriers and significantly enhanced the antitumor activity of Dox. The nanoparticles possessed good antioxidant activity, pH-sensitive sustained controlled release, enhanced antitumor activity, and could be expected to serve as a drug carrier in future with broad application prospects.

Enhanced antifungal and antioxidant activities of new chitosan derivatives modified with Schiff base bearing benzenoid/heterocyclic moieties.

In this work, chitosan derivatives modified with Schiff base bearing benzenoid/heterocyclic moieties were successfully prepared via amidation reaction. Specific structural characterization was implemented using FTIR and 1H NMR, and the DS of chitosan derivatives were quantitatively calculated by ratio of hydrogen proton integral. Meanwhile, the antifungal activity against two common plant pathogenic fungi (Fusarium oxysporum f. sp. cubense and Glomerella cingulata) was assayed in vitro by hyphal measurement, and data proved that the introduction of functional groups including benzene/heterocyclic compounds and Schiff base groups greatly enhanced the antifungal activity. Besides, the antioxidant efficiency was investigated in vitro, and all chitosan derivatives exhibited significantly increased antioxidant activity. Specially, the scavenging effect of 2SATCS was 96.62% at 1.6 mg/mL, which was close to the positive control VC (98.84%). These results indicated that chitosan derivatives with enhanced antifungal and antioxidant activities could serve as potential biomaterial for antifungal and antioxidant applications.

Antimicrobial and Antioxidant Activities of N-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases.

N-2-hydroxypropyltrimethyl ammonium chloride chitosan (HACC), a cationic quaternary ammonium salt polymer exhibiting good solubility in water, is widely used because of its low toxicity and good biocompatibility. Herein, through ion exchange reaction, we prepared N-2-hydroxypropyltrimethyl ammonium chitosan derivatives bearing amino acid Schiff bases with good biological activities. The accuracy of the structures was verified by FT-IR and 1H NMR. The antibacterial activity, antifungal activity, and scavenging ability of DPPH radical and superoxide radical of HACC derivatives were significantly improved compared with that of HACC. In particular, HACGM (HACC-potassium 2-((2-hydroxy-3-methoxybenzylidene)amino)acetate) and HACGB (HACC-potassium 2-((5-bromo-2-hydroxybenzylidene)amino)acetate) showed good inhibitory effect on bacteria and fungi, including Staphylococcus aureus, Escherichia coli, Botrytis cinerea, and Fusarium oxysporum f. sp. cubense. The inhibition rate of HACGB on Staphylococcus aureus and Escherichia coli could reach 100% at the concentration of 0.1 mg/mL, and the inhibition rate of HACGM and HACGB on Botrytis cinerea and Fusarium oxysporum f. sp. cubense could also reach 100% at the concentration of 0.5 mg/mL. Improving antimicrobial and antioxidant activities of HACC could provide ideas and experiences for the development and utilization of chitosan derivatives.