RESUMO
This study aimed to enhance the antioxidant activity of carboxymethyl inulin (CMI) by chemical modification. Therefore, a series of cationic Schiff bases bearing heteroatoms were synthesized and incorporated into CMI via ion exchange reactions, ultimately preparing 10 novel CMI derivatives (CMID). Their structures were confirmed by Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy. The radical scavenging activities and reducing power of inulin, CMI, and CMID were studied. The results revealed a significant enhancement in antioxidant activity upon the introduction of cationic Schiff bases into CMI. Compared to commercially available antioxidant Vc, CMID demonstrated a broader range of antioxidant activities across the four antioxidant systems analyzed in this research. In particular, CMID containing quinoline (6QSCMI) exhibited the strongest hydroxyl radical scavenging activity, with a scavenging rate of 93.60 % at 1.6 mg mL-1. The CMID bearing imidazole (2MSCMI) was able to scavenge 100 % of the DPPH radical at 1.60 mg mL-1. Furthermore, cytotoxicity experiments showed that the products had good biocompatibility. These results are helpful for evaluating the feasibility of exploiting these products in the food, biomedical, and cosmetics industries.
Assuntos
Antioxidantes , Sequestradores de Radicais Livres , Inulina , Bases de Schiff , Bases de Schiff/química , Inulina/química , Inulina/síntese química , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Sequestradores de Radicais Livres/síntese química , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/síntese química , Cátions/química , Radical Hidroxila/química , Humanos , Técnicas de Química Sintética , Espectroscopia de Infravermelho com Transformada de Fourier , Compostos de Bifenilo/química , Compostos de Bifenilo/antagonistas & inibidores , PicratosRESUMO
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.
Assuntos
Antineoplásicos , Quitosana , Doxorrubicina , Glutationa , Micelas , Peso Molecular , Estresse Oxidativo , Quitosana/química , Quitosana/farmacologia , Doxorrubicina/farmacologia , Doxorrubicina/química , Glutationa/metabolismo , Humanos , Estresse Oxidativo/efeitos dos fármacos , Antineoplásicos/farmacologia , Antineoplásicos/química , Cátions/química , Portadores de Fármacos/química , Espécies Reativas de Oxigênio/metabolismo , Liberação Controlada de Fármacos , Linhagem Celular TumoralRESUMO
To improve the antioxidant activity, sulfhydryl groups (-SH) were introduced into chitosan. Acylated chitosan derivatives, chitosan cationic salt derivatives, hydroxypropyl trimethylammonium chloride chitosan quaternary ammonium salt (HACC) derivatives and N,N,N-trimethyl chitosan iodine (TMC) derivatives were obtained. The chitosan derivatives were characterized by FTIR and 1H NMR to confirm the successful synthesis. Ellman's reagent was used to determine that the compound contained free sulfhydryl groups. The water solubility and thermal stability of chitosan and derivatives were evaluated. The antioxidant activities of the derivatives were verified, including DPPH radical scavenging activity, superoxide anion radical scavenging activity and reducing power activity. The novel chitosan derivatives showed excellent antioxidant activities. Toxicity assay used L929 cells proved that the derivatives had no significant toxic. The results showed that the chitosan derivatives bearing sulfhydryl groups described in this paper has a certain antioxidant effect, which provides a practical approach for further study of chitosan.
Assuntos
Antioxidantes , Quitosana , Antioxidantes/farmacologia , Antioxidantes/química , Quitosana/química , Espectroscopia de Ressonância Magnética , Compostos de Amônio Quaternário/farmacologia , Compostos de Amônio Quaternário/química , SolubilidadeRESUMO
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.
Assuntos
Quitosana , Neoplasias Pulmonares , Polietilenoglicóis , Polietilenoimina , Polifosfatos , Humanos , Animais , Camundongos , Nanogéis , Antioxidantes/farmacologia , Cloreto de Amônio , Benzimidazóis , Doxorrubicina/farmacologia , Compostos de Amônio Quaternário/farmacologiaRESUMO
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.
Assuntos
Antioxidantes , Quitosana , Nanogéis , Antioxidantes/farmacologia , Quitosana/química , Liberação Controlada de Fármacos , Espectroscopia de Infravermelho com Transformada de Fourier , Doxorrubicina/farmacologia , Doxorrubicina/química , Concentração de Íons de Hidrogênio , Sódio , Portadores de Fármacos/químicaRESUMO
As a promising biological material, chitooligosaccharide (COS) has attracted increasing attention because of its unique biological activities. In this study, fourteen novel phenolic acid functional COS derivatives were successfully prepared using two facile methods. The structures of derivatives were characterized by FT-IR and 1H NMR spectra. The in vitro antioxidant activity experiment results demonstrated that the derivatives presented stronger 1,1-Diphenyl-2-picryl-hydrazyl (DPPH), superoxide, hydroxyl radical scavenging activity and reducing power, especially the N,N,N-trimethylated chitooligosaccharide gallic acid salt (GLTMC), gallic acid esterified N,N,N-trimethylated chitooligosaccharide (GL-TMC) and caffeic acid N,N,N-trimethylated chitooligosaccharide (CFTMC) derivatives. Furthermore, the antifungal assay was carried out and the results indicated that the salicylic acid esterified N,N,N-trimethylated chitooligosaccharide (SY-TMC) had much better inhibitory activity against Botrytis cinerea and Fusarium graminearum. Additionally, the results of the bacteriostasis experiment showed that the caffeic acid esterified N,N,N-trimethylated chitooligosaccharide (CF-TMC) had the potential ability to inhibit Escherichia coli and Staphylococcus aureus bacteria. Altogether, this study may provide a neoteric method to produce COS derivatives with significantly increased biological activities, which have potential use in food, medicine, and health care products and other related industries.
Assuntos
Antioxidantes , Quitosana , Antioxidantes/farmacologia , Antioxidantes/química , Antifúngicos/farmacologia , Antifúngicos/química , Espectroscopia de Infravermelho com Transformada de Fourier , Quitosana/química , Quitina/farmacologia , Ácido Gálico , Antibacterianos/farmacologia , Antibacterianos/químicaRESUMO
Natural polysaccharides are abundant and renewable resource, but their applications are hampered by limited biological activity. Chemical modification can overcome these drawbacks by altering their structure. Three series of polysaccharide derivatives with coumarins were synthesized to obtain polysaccharide derivatives with enhanced biological activity. The biological activities were tested, including antioxidant property, antifungal property, and antibacterial property. Based on the results, the inhibitory properties of the coumarin-polysaccharide derivatives were significantly improved over the raw polysaccharide. The IC50 of the inhibition of DPPH, ABTSâ¢+, and superoxide (O2â¢-) radical-scavenging was 0.06-0.15 mg/mL, 2.3-15.9 µg/mL, and 0.03-0.25 mg/mL, respectively. Compared with the raw polysaccharides, coumarin- polysaccharide derivatives exhibited higher efficacy in inhibiting the growth of tested phytopathogens, showing inhibitory indices of 60.0-93.6 % at 1.0 mg/mL. Chitosan derivatives with methyl and chlorine (Compound 10B and 10C) exhibited significant antibacterial activity against S. aureus (MIC = 31.2 µg/mL), E. coli (MIC = 7.8 µg/mL), and V. harveyi (MIC = 15.6 µg/mL), respectively. The results of the cytotoxicity assay showed no observed cytotoxicity when the RAW 264.7 cells were incubated with the synthesized polysaccharide derivatives at the tested concentrations.
Assuntos
Cumarínicos , Staphylococcus aureus , Cumarínicos/farmacologia , Cumarínicos/química , Escherichia coli , Antioxidantes/farmacologia , Antioxidantes/química , Antibacterianos/farmacologia , Antibacterianos/química , Polissacarídeos/farmacologiaRESUMO
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.
Assuntos
Quitosana , Ácido Tióctico , Micelas , Quitosana/química , Ácido Tióctico/química , Portadores de Fármacos/química , Peso Molecular , Doxorrubicina/farmacologia , Doxorrubicina/química , Oxirredução , Sistemas de Liberação de Medicamentos/métodos , Concentração de Íons de HidrogênioRESUMO
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.
Assuntos
Quitosana , Micelas , alfa-Tocoferol/química , Solubilidade , Quitosana/química , Preparações de Ação Retardada , Peso Molecular , Portadores de Fármacos/química , Água/química , Tamanho da PartículaRESUMO
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.
Assuntos
Antioxidantes , Quitosana , Antioxidantes/farmacologia , Antioxidantes/química , Quitosana/química , Staphylococcus aureus , Espectroscopia de Infravermelho com Transformada de Fourier , Escherichia coli , Sais , Superóxidos , Imidazóis/farmacologia , Antibacterianos/farmacologia , Antibacterianos/químicaRESUMO
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.
Assuntos
Quitosana , Micelas , Liberação Controlada de Fármacos , Sistemas de Liberação de Medicamentos , Doxorrubicina/farmacologia , OxirreduçãoRESUMO
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 O2â¢- radical scavenging activity, 91.23% of â¢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.
Assuntos
Anticoagulantes , Heparina , Humanos , Heparina/farmacologia , Heparina/química , Anticoagulantes/farmacologia , Anticoagulantes/química , Antioxidantes/farmacologia , Antioxidantes/química , Glucosamina/farmacologia , Glucosamina/química , Cloreto de Sódio , Íons , EletrólitosRESUMO
A series of phenolic acid chitooligosaccharide (COS) derivatives synthesized by two mild and green methods were illuminated in this paper. Seven phenolic acids were selected to combine two kinds of COS derivatives: the phenolic acid chitooligosaccharide salt derivatives and the phenolic-acid-acylated chitooligosaccharide derivatives. The structures of the derivatives were characterized by FT-IR and 1H NMR spectra. The antioxidant experiment results in vitro (including DPPH-radical scavenging activity, superoxide-radical scavenging activity, hydroxyl-radical scavenging ability, and reducing power) demonstrated that the derivatives exhibited significantly enhanced antioxidant activity compared to COS. Moreover, the study showed that the phenolic acid chitooligosaccharide salts had stronger antioxidant activity than phenolic-acid-acylated chitooligosaccharide. The cytotoxicity assay of L929 cells in vitro indicated that the derivatives had low cytotoxicity and good biocompatibility. In conclusion, this study provides a possible synthetic method for developing novel and nontoxic antioxidant agents which can be used in the food and cosmetics industry.
Assuntos
Antioxidantes , Hidroxibenzoatos , Antioxidantes/química , Antioxidantes/farmacologia , Quitosana , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacologia , Oligossacarídeos , Espectroscopia de Infravermelho com Transformada de FourierRESUMO
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.
Assuntos
Quitosana , Nanopartículas , Antioxidantes/farmacologia , Preparações de Ação Retardada , Doxorrubicina/farmacologia , Portadores de Fármacos , Concentração de Íons de Hidrogênio , beta-CiclodextrinasRESUMO
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.
Assuntos
Antifúngicos , Quitosana , Antifúngicos/química , Antifúngicos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Quitosana/química , Fungos , Testes de Sensibilidade Microbiana , Bases de Schiff/químicaRESUMO
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.
Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antioxidantes/farmacologia , Quitosana/análogos & derivados , Compostos de Amônio Quaternário/farmacologia , Antibacterianos/química , Antifúngicos/química , Antioxidantes/química , Quitosana/química , Quitosana/farmacologia , Espectroscopia de Ressonância Magnética , Compostos de Amônio Quaternário/química , Bases de Schiff/química , Solubilidade , Espectroscopia de Infravermelho com Transformada de FourierRESUMO
In this study, to investigate the influence of glyoxylate bearing Schiff base on bioactivity to chitosan quaternary ammonium salts, different chitosan derivatives were synthesized by ion exchange of glyoxylate bearing Schiff base with chitosan quaternary ammonium salts (TMCI and HACC). For this purpose, glyoxylate was prepared by Schiff base reaction of glyoxylic acid and amino heterocycles and it was further ionization to substitute iodide ions and chloride ions. After structural characterization by FTIR and 1H NMR, the antifungal and antioxidant activities were measured. Results indicated that glyoxylate bearing Schiff base could improve the bioactivity of TMCI and HACC obviously. Specifically, anionic TMCI with Schiff base of amino pyridines possessed best antioxidant activity >92.40% at 1.6 mg/mL against DPPH radicals. Meanwhile, they showed antifungal activity >84.88% at 1.0 mg/mL against G. cingulate. Furthermore, the cytotoxicity was evaluated, and all samples showed good cell viability >80.14% at 1000 µg/mL.
Assuntos
Antifúngicos/farmacologia , Antioxidantes/farmacologia , Quitosana/farmacologia , Fungos/efeitos dos fármacos , Glioxilatos/farmacologia , Compostos de Amônio Quaternário/farmacologia , Antifúngicos/síntese química , Antifúngicos/química , Antioxidantes/síntese química , Antioxidantes/química , Compostos de Bifenilo/antagonistas & inibidores , Quitosana/química , Glioxilatos/química , Testes de Sensibilidade Microbiana , Picratos/antagonistas & inibidores , Compostos de Amônio Quaternário/química , Bases de Schiff/química , Bases de Schiff/farmacologiaRESUMO
A series of novel carboxymethyl inulin derivatives bearing thiosemicarbazide salts, aminoguanidine salts, and aniline salts were prepared via a facile method and employed to evaluate in vitro antioxidant activity and antibacterial activity. Their structures were characterized by Fourier-transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR). The characterization results confirmed the successful synthesis of carboxymethyl inulin salt derivatives. The in vitro antioxidant activity evaluation results presented a significant improved superoxide radical scavenging ability, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging ability, and reducing ability of carboxymethyl inulin salt derivatives as compared to inulin and carboxymethyl inulin. In particular, the series of carboxymethyl inulin derivatives containing thiosemicarbazide salts and aminoguanidine salts showed remarkable free radical scavenging ability and reducing ability. Moreover, the carboxymethyl inulin derivatives containing thiosemicarbazide salts and aniline salts displayed potential antibacterial activity against Escherichia coli and Staphylococcus aureus bacteria. The cytotoxicity assay was also carried out on L929 cells by CCK-8 method, and all samples showed weak cytotoxicity. Furthermore, hemolysis results showed no hemolytic activity of most prepared inulin derivatives. In summary, the inulin derivatives containing thiosemicarbazide salts exhibited outstanding antioxidant activity, antibacterial activity, and biocompatibility, and the all-inclusive properties highlighted their potential use in food and medical applications.
Assuntos
Antioxidantes , Inulina , Antibacterianos/química , Antioxidantes/química , Sequestradores de Radicais Livres/química , Espectroscopia de Infravermelho com Transformada de Fourier , Superóxidos/químicaRESUMO
In this paper, adriamycin-incorporated chitosan nanoparticles were synthesized by ionic gelation using negatively charged carboxymethyl chitosan and positively charged 2-hydroxypropyltrimethyl ammonium chloride chitosan. The method was efficient to obtain nanoparticles with low polydispersity index and small hydrodynamic diameter. And high zeta potential value indicated that nanoparticles had good stability. The adriamycin release of nanoparticles represented a significant response to pH, with the fastest release in phosphate buffer solution at pH 6.8. Meanwhile, the antioxidant efficiency of nanoparticles was assayed, and nanoparticles represented significant enhancement in radicals scavenging activity. The assay of cell viability by CCK-8 test exhibited that nanoparticles led to statistically significant decrease in cell viability for four kinds of cancer cells (HEPG-2, A549, MCF-7, and BGC-823). It was indicated that the nanoparticles with enhanced biological activity, reduced cytotoxicity, and pH-sensitive release could be served as potential drug carrier in drug delivery system.
Assuntos
Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Doxorrubicina/farmacologia , Portadores de Fármacos/química , Nanopartículas/química , Antineoplásicos/química , Antioxidantes/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Quitosana/química , Doxorrubicina/química , Liberação Controlada de Fármacos , Humanos , Concentração de Íons de HidrogênioRESUMO
Chitosan nanoparticles have been considered as potential candidates for drug loading/release in drug delivery systems. In this paper, nanoparticles (HACAFNP) loading adriamycin based on 2-hydroxypropyltrimethyl ammonium chloride chitosan grafting folic acid (HACF) were synthesized. The surface morphology of the novel nanoparticles was spherical or oval, and the nanoparticles exhibited a relatively small hydrodynamic diameter (85.6 ± 2.04 nm) and positive zeta potential (+21.06 ± 0.96 mV). The drug release of nanoparticles was assayed and represented a burst effect followed by a long-term steady release. Afterward, the antioxidant efficiencies of nanoparticles were assayed. In particular, the target nanoparticles exhibited significant enhancement in radical scavenging activities. Cytotoxicities against cancer cells (MCF-7, BGC-823, and HEPG-2) were estimated in vitro, and results showed nanoparticles inhibited the growth of cancer cells. It's worth noting that the inhibition index of HACAFNP against BGC-823 cells was 71.19% with the sample concentration of 25 µg/mL, which was much higher than the inhibitory effect of ADM. It was demonstrated that the novel nanoparticles with dramatically enhanced biological activity, reduced cytotoxicity, and steady release could be used as the practical candidates for drug loading/release in a delivery system.