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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. [ABSTRACT FROM AUTHOR]

A novel and green method for the preparation of chitosan derivatives bearing organic acids was reported in this paper. In order to improve the antioxidant activity of chitosan, eight different hydroxypropyltrimethyl ammonium chitosan derivatives were successfully designed and synthesized via introducing of organic acids onto chitosan by mild and non-toxic ion exchange. The data of Fourier Transform Infrared (FTIR), 13C Nuclear Magnetic Resonance (NMR), 1H NMR, and elemental analysis for chitosan derivatives indicated the successful conjugation of organic acid salt with hydroxypropyltrimethyl ammonium chloride chitosan (HACC). Meanwhile, the antioxidant activity of the chitosan derivatives was evaluated in vitro. The results indicated that the chitosan derivatives possessed dramatic enhancements in DPPH-radical scavenging activity, superoxide-radical scavenging activity, hydroxyl radical scavenging ability, and reducing power. Furthermore, the cytotoxicity of the synthesized compounds was investigated in vitro on L929 cells and showed low cytotoxicity. Thus, the enhanced antioxidant property of all novel chitosan products might be a great advantage, while applied in a wide range of applications in the form of antioxidant in biomedical, food, and cosmetic industry. [ABSTRACT FROM AUTHOR]

In this study, starch was chemically modified to improve its antioxidant activity. Five novel cationic 1,2,3-triazole functionalized starch derivatives were synthesized by using "click" reaction and N-alkylation. A convenient method for pre-azidation of starch was developed. The structures of the derivatives were analyzed using FTIR and 1H NMR. The radicals scavenging abilities of the derivatives against hydroxyl radicals, DPPH radicals, and superoxide radicals were tested in vitro in order to evaluate their antioxidant activity. Results revealed that all the cationic starch derivatives (2a–2e), as well as the precursor starch derivatives (1a–1e), had significantly improved antioxidant activity compared to native starch. In particular, the scavenging ability of the derivatives against superoxide radicals was extremely strong. The improved antioxidant activity benefited from the enhanced solubility and the added positive charges. The biocompatibility of the cationic derivatives was confirmed by the low hemolytic rate (<2%). The obtained derivatives in this study have great potential as antioxidant materials that can be applied in the fields of food and biomedicine. [ABSTRACT FROM AUTHOR]

A new class of chitosan derivatives possessing thiourea salts were synthesized to improve the solubility and the antioxidant activity of chitosan. Firstly, chitosan was modified to carboxymethyl chitosan, combining carboxymethyl chitosan with thiourea salts that have different structures to form new chitosan derivatives. The chitosan and chitosan derivatives were characterized by FT-IR, 13C NMR, TGA, and elemental analyses. The new peaks of thiourea salts could be clearly observed at about 1240 cm–1 in the IR spectra, and the peak of C=S was clearly observed at around 180 ppm in the 13C NMR. IR spectra and 13C NMR of the structural units of these polymers validated the chitosan derivatives possessing thiourea salts were successfully synthesized. Their antioxidant properties were tested, including DPPH-radical scavenging ability, superoxide-radical scavenging ability, and hydroxyl-radical scavenging ability. Our results suggested the increase of thiourea salt groups in chitosan derivatives promotes the scavenging effect. The scavenging activity of 4TMCMCS, TMCMCS. 4,4DCMCS, and 4ACMCS against DPPH-radical and superoxide-radical were more than 90% at 1.6 mg/mL, respectively. In the cytotoxicity assay, no cytotoxicity was observed for the L929 cells with chitosan and its derivatives at all testing concentrations. These results demonstrated that the combination of chitosan and thiourea salt groups improved the antioxidant activity of chitosan, and the antioxidants or free radical scavengers based on natural polymers and thiourea salts showed potential applications. [ABSTRACT FROM AUTHOR]

In this paper, we report chemical modifications of inulin by seven kinds of aromatic Schiff bases, which are different from their substituent groups. The obtained inulin derivatives were confirmed by FTIR, 1H NMR, and 13C NMR. Then, we studied their antifungal activity against four kinds of plant pathogens involving Botrytis cinerea, Fusarium oxysporum f. sp. cucumerium Owen, Fusarium oxysporum f. sp. niveum, and Phomopsis asparagi by the mycelium growth rate method. The results revealed that all inulin derivatives were endowed with significant antifungal activity compared to inulin. Among them, 6-amino-(N-4-chlorobenzylidene)-6-deoxy-3,4-di-O-acetyl inulin (4CBSAIL) and 6-amino-(N-3,4-dichlorobenzylidene)-6-deoxy-3,4-di-O-acetyl inulin (3,4DCBSAIL), which were synthesized from p-chlorobenzaldehyde and 3,4-dichlorobenzaldehyde, could completely inhibit the growth of the test fungi at 1.0 mg/mL. The inhibitory indices of the inulin derivatives were related to the type, position, and number of substituent groups (halogens) on the Schiff bases. The results confirmed that it was feasible to chemically modify inulin with Schiff bases to confer high antifungal activity to inulin. The products described in this paper have great potential as alternatives to some harmful pesticides used for plant disease control. [ABSTRACT FROM AUTHOR]

As a renewable, biocompatible, and biodegradable polysaccharide, inulin has a good solubility in water and some physiological functions. Chemical modification is one of the important methods to improve the bioactivity of inulin. In this paper, based on 6-amino-6-deoxy-3,4-acetyl inulin (3), three kinds of Schiff bases of inulin bearing pyridine rings were successfully designed and synthesized. Detailed structural characterization was carried out using FTIR, 13C NMR, and 1H NMR spectroscopy, and elemental analysis. Moreover, the antifungal activity of Schiff bases of inulin against three plant pathogenic fungi, including Botrytis cinerea, Fusarium oxysporum f.sp.niveum, and Phomopsis asparagi, were evaluated using in vitro hypha measurements. Inulin, as a natural polysaccharide, did not possess any antifungal activity at the tested concentration against the targeted fungi. Compared with inulin and the intermediate product 6-amino-6-deoxy-3,4-acetyl inulin (3), all the synthesized Schiff bases of inulin derivatives with >54.0% inhibitory index at 2.0 mg/mL exhibited enhanced antifungal activity. 3NS, with an inhibitory index of 77.0% exhibited good antifungal activity against Botrytis cinerea at 2.0 mg/mL. The synthesized Schiff bases of inulin bearing pyridine rings can be prepared for novel antifungal agents to expand the application of inulin. [ABSTRACT FROM AUTHOR]

Many saccharides are attractive targets for biomaterial applications, due to their abundance, biocompatibility, and biodegradability. In this article, a synthesis process of 6-N-substituted cationic inulin derivatives, including 6-pyridyl-6-deoxyinulin bromide (PIL), 6-(2-amino-pyridyl)-6-deoxyinulin bromide (2APIL), 6-(3-amino-pyridyl)-6-deoxyinulin bromide (3APIL), 6-(4-amino-pyridyl)-6-deoxyinulin bromide (4APIL), 6-(2,3-diamino-pyridyl)-6-deoxyinulin bromide (2,3DAPIL), 6-(3,4-diamino-pyridyl)-6-deoxyinulin bromide (3,4DAPIL), and 6-(2,6-diamino-pyridyl)-6-deoxyinulin bromide (2,6DAPIL) was described. The C6-OH of inulin was first activated by PPh3/N-bromosuccinimide (NBS) bromination. Then, pyridine and different kinds of amino-pyridine groups (different position and different numbers of amino) were grafted onto inulin, respectively, via nucleophilic substitution. Then, we confirmed their structure by Fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance (NMR) spectroscopy. After this, their radical scavenging activities against hydroxyl radical and diphenylpicryl phenylhydrazine (DPPH) radical were tested in vitro. Each derivative showed a distinct improvement in radical scavenging activity when compared to inulin. The hydroxyl-radical scavenging effect decreased in the following order: 3APIL > PIL > 3,4DAPIL > 4APIL > 2,3DAPIL > 2,6DAPIL > 2APIL. Amongst them, 3APIL revealed the most powerful scavenging effect on hydroxyl radicals, as well as DPPH radicals. At 1.6 mg/mL, it could completely eliminate hydroxyl radicals and could clear 65% of DPPH radicals. The results also showed that the steric hindrance effect and the substitute position of the amino group had an effect on the radical scavenging activity. Moreover, the application prospects of inulin derivatives as natural antioxidant biomaterials are scientifically proven in this paper. [ABSTRACT FROM AUTHOR]

We successfully synthesized the water-soluble chitosan derivatives propane sulfonated chitosan (PSCS) and dipropane sulfonated chitosan (DPSCS) in this paper. These derivatives were characterized by FTIR, 1H NMR, and 13C NMR. Moreover, the antioxidant activity of the chitosan derivatives was evaluated by free radical scavenging ability (against DPPH-radical, hydroxyl-radical, and superoxide-radical) and ferric reducing power. Meanwhile, inhibitory effects against two fungi were also tested. Our results suggested antioxidant abilities and antifungal properties were in order of DPSCS > PSCS > CS, which were consistent with the number of propane sulfonated groups. The scavenging activity of DPSCS against superoxide-radical and DPPH-radical were 94.1% and 100% at 1.6 mg/mL, respectively. The inhibitory indices of DPSCS against P. asparagi and F. oxysporum were up to 82.2% and 94% at 1.0 mg/mL, respectively. Obviously, the number of propane sulfonated groups of chitosan derivatives not only contributes to antioxidant activity, but also to antifungal activity. Therefore, DPSCS with more propane sulfonated groups endowed with antioxidant and antifungal activity that can be used as a candidate material in the food and pharmaceutical industries. [ABSTRACT FROM AUTHOR]