Synthesis, antioxidant and cathepsin D inhibition activity of quaternary ammonium chitosan derivatives

Li, Wenjuan; Duan, Yunfei; Huang, Jianying; Zheng, Qingdong

doi:10.1016/j.carbpol.2015.09.111

Cited by 35 publications

(24 citation statements)

References 60 publications

(48 reference statements)

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“…Based on the work of Hu [9], the decreased scavenging ability of CAIL should be caused by the substitution of ÀOH groups by chloracetyl groups. TAIL has better scavenging ability on hydroxyl radicals than inulin and CAIL, and the scavenging effect is 71.3%, which is in accord with the result of Li [21].…”

Section: Antioxidant Activitysupporting

confidence: 85%

“…For all of the measured samples, IAIL has the best scavenging ability, and the scavenging index is 86.7% at 1.6 mg/mL. It would be reasonable to presume that the imidazole groups should be an important factor that influences the scavenging activity against hydroxyl radicals . Besides, the scavenging activity of MIAIL is soft than IAIL.…”

Section: Resultsmentioning

confidence: 95%

“…After triethylamine, imidazole or 1-methylimidazole grafted on CAIL, the absorbance of C═O at 1747 cm À1 and C-Cl at 790 cm À1 are weakened. New peaks appear at 1461 and 1631 cm À1 for TAIL, which should be assigned to the quaternary ammonium [21,22]. And new peaks appear at about 3154 cm À1 in IAIL and MIAIL, which are related to the characteristic absorption of imidazole group [21].…”

Section: Chemical Analysis Of the Inulin Derivativesmentioning

confidence: 90%

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Antioxidant activity of inulin derivatives with quaternary ammonium

et al. 2017

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Three inulin derivatives with quaternary ammonium, including 2‐(N,N,N‐triethylamine)acetyl inulin chloride (TAIL), 2‐imidazoleacetyl inulin chloride (IAIL), and 2‐(1‐methylimidazole)acetyl inulin chloride (MIAIL) were synthesized via reaction of chloracetyl inulin (CAIL) with tertiary amine. Their antioxidant activity against hydroxyl radicals and superoxide radicals were evaluated in vitro, respectively. The results showed that IAIL had the best scavenging ability on scavenging hydroxyl radicals and superoxide radicals, and the scavenging indices were 86.7 and 67.8% at 1.6 mg/mL, respectively. These data indicate that all of the inulin derivatives have better antioxidant activities than inulin, and the quaternary ammonium and imidazole will improve the antioxidant activity of inulin derivatives.

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Section: Antioxidant Activitysupporting

confidence: 85%

Section: Resultsmentioning

confidence: 95%

Section: Chemical Analysis Of the Inulin Derivativesmentioning

confidence: 90%

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Antioxidant activity of inulin derivatives with quaternary ammonium

et al. 2017

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“…The epoxy-derivative ring-opening process is the reaction of C 2 -NH 2 with GTA or CTA under alkaline conditions. The reaction of chitosan and epoxypropyl trimethyl ammonium chloride gives N-2-Hydroxypropyl trimethyl ammonium chloride chitosan (N-2-HACC) [76,77]. The reaction equation of this is shown in Figure 5C.…”

Section: Quaternary Ammonium Chitosanmentioning

confidence: 99%

Chitosan Derivatives and Their Application in Biomedicine

Wang

Meng

et al. 2020

IJMS

601

326

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Chitosan is a product of the deacetylation of chitin, which is widely found in nature. Chitosan is insoluble in water and most organic solvents, which seriously limits both its application scope and applicable fields. However, chitosan contains active functional groups that are liable to chemical reactions; thus, chitosan derivatives can be obtained through the chemical modification of chitosan. The modification of chitosan has been an important aspect of chitosan research, showing a better solubility, pH-sensitive targeting, an increased number of delivery systems, etc. This review summarizes the modification of chitosan by acylation, carboxylation, alkylation, and quaternization in order to improve the water solubility, pH sensitivity, and the targeting of chitosan derivatives. The applications of chitosan derivatives in the antibacterial, sustained slowly release, targeting, and delivery system fields are also described. Chitosan derivatives will have a large impact and show potential in biomedicine for the development of drugs in future.

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“…Thus, it is necessary to modify the structure of chitosan to create derivatives with improved properties. Although chemical modification of chitosan to generate new bio-functional materials has achieved success (Zhang, Geng, Jiang, Li & Huang, 2012;Geng, Yang, Huang, Zhang & Wang, 2013;Jia, Duan, Fang, Wang & Huang, 2016;Li, Duan, Huang & Zheng, 2016), a strategy to reduce the positive charges of protonated amino groups presented on the polymeric surface, especially the introduction of sulfonate groups (RSO3 − ) on the chitosan chain, is still of great interest.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and antimicrobial activities of sulfonated chitosan

Sun

Shi

Wang

et al. 2017

Carbohydrate Polymers

Self Cite

121

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Sulfonated chitosan (SCS) was prepared via a facile chemical procedure by using 1,3-propane sultone attached to the backbone of chitosan. The resulting chitosan derivative was characterized by Fourier transform-infrared spectroscopy, nuclear magnetic resonance spectroscopy, gel permeation chromatography, elemental analysis, and thermo gravimetric analysis. The antibacterial experiments demonstrated that SCS exhibited higher antibacterial activities against Escherichia coli and Staphylococcus aureus with the minimum inhibitory concentration (MIC) of 0.13mg/mL and 2.00mg/mL than those of water-soluble chitosan (WCS) with MIC of 0.50mg/mL and 4.00mg/mL. However, different antifungal activities of SCS against Arthrinium sacchari (MIC, 64.00mg/mL) and Botrytis cinerea (MIC, 0.25mg/mL) were observed. Scanning electron microscopy revealed that WCS and SCS could damage and deform the structure of fungal hyphae with different action modes. It is worth mentioning that SCS exhibited selective antifungal activity, which was an important parameter to control its biological performance in many fields.

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Synthesis, antioxidant and cathepsin D inhibition activity of quaternary ammonium chitosan derivatives

Cited by 35 publications

References 60 publications

Antioxidant activity of inulin derivatives with quaternary ammonium

Antioxidant activity of inulin derivatives with quaternary ammonium

Chitosan Derivatives and Their Application in Biomedicine

Synthesis, characterization, and antimicrobial activities of sulfonated chitosan

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