Recent research progress on preparation and application of N, N, N-trimethyl chitosan

Wu, Meiyan; Long, Zhu; Xiao, Huining; Dong, Chune

doi:10.1016/j.carres.2016.08.002

Cited by 68 publications

(37 citation statements)

References 98 publications

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“…The interaction starts with the electrostatic attraction between protonated amino groups of chitosan and derivatives and the negatively charged components of the bacterial cell surface. This surface may become decorated with chitosan and be permeabilized leaking the intracellular content (Naberezhnykh et al, 2009;Verlee et al, 2017;Wu, Long, Xiao, & Dong, 2016). The results of the present work also point out to this mechanism of action, which has been often associated with antimicrobial peptides.…”

Section: Discussionsupporting

confidence: 57%

“…It has been reported that chitosan with approximately the same characteristics of Mw and deacetylation degree as our CH2 exhibits MIC around 200 × 10 −3 g L −1 for S. aureus and E. coli at pH 6.9 (Kulikov et al, 2016), however, in the present work we did not find antimicrobial activity for CH2 even at 500 × 10 −3 g L −1 . It was also the case with MeCH2, while the literature reports that fully quaternized chitosan has higher antibacterial activity than the parent chitosan (Wu et al, 2016). Nevertheless, CH30 and CH50 exhibited antibacterial activity at comparable levels toward Gram-negative E. coli and Grampositive S. aureus, mimicked respectively by PCPG and PGCL.…”

Section: Discussionmentioning

confidence: 78%

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Chitosan derivatives targeting lipid bilayers: Synthesis, biological activity and interaction with model membranes

Martins

Nasário²,

Silva-Gonçalves

et al. 2018

Carbohydrate Polymers

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The antimicrobial activity of chitosan and derivatives to human and plant pathogens represents a high-valued prospective market. Presently, two low molecular weight derivatives, endowed with hydrophobic and cationic character at different ratios were synthesized and characterized. They exhibit antimicrobial activity and increased performance in relation to the intermediate and starting compounds. However, just the derivative with higher cationic character showed cytotoxicity towards human cervical carcinoma cells. Considering cell membranes as targets, the mode of action was investigated through the interaction with model lipid vesicles mimicking bacterial, tumoral and erythrocyte membranes. Intense lytic activity and binding are demonstrated for both derivatives in anionic bilayers. The less charged compound exhibits slightly improved selectivity towards bacterial model membranes, suggesting that balancing its hydrophobic/hydrophilic character may improve efficiency. Observing the aggregation of vesicles, we hypothesize that the "charge cluster mechanism", ascribed to some antimicrobial peptides, could be applied to these chitosan derivatives.

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Section: Discussionsupporting

confidence: 57%

Section: Discussionmentioning

confidence: 78%

Chitosan derivatives targeting lipid bilayers: Synthesis, biological activity and interaction with model membranes

Martins

Nasário²,

Silva-Gonçalves

et al. 2018

Carbohydrate Polymers

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“…Therefore, with an increase in positive charge, the antibacterial activity of TMC is enhanced. The antibacterial activity of TMC decreases with the decrease of pH under acidic conditions, and the antibacterial activity is lower under weak alkaline conditions than acidic conditions [72,75,131].…”

Section: Antibacterial Species Applicationmentioning

confidence: 97%

“…TMC can be synthesized by two methods. One method is direct quaternary ammonium substitution ( Figure 5A) [71,72], and the other is the N-alkylation method ( Figure 5B) [73][74][75]. The epoxy-derivative ring-opening process is the reaction of C 2 -NH 2 with GTA or CTA under alkaline conditions.…”

Section: Quaternary Ammonium Chitosanmentioning

confidence: 99%

Chitosan Derivatives and Their Application in Biomedicine

Wang

Meng

et al. 2020

IJMS

607

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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“…Due to the unique biological activity, chitosan has attracted sufficient attention in biotechnology, pharmaceutics, papermaking, wastewater, cosmetology, food science, agriculture, and textiles fields [8][9][10][11][12][13]. Presently used methods for the modification of chitosan mainly include quaternization, alkylation, acetylation, carboxylation, phosphorylation, and grafting [14]. Among the derived products, quaternary ammonium chitosan salt not only maintains the unique characteristics of chitosan but also possesses better solubility and biological activities, so it plays an important role in the development of new functional chitosan derivatives [15,16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of N,N,N-trimethyl-O-(ureidopyridinium)acetyl Chitosan Derivatives with Antioxidant and Antifungal Activities

Zhang

Tan

et al. 2020

Marine Drugs

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Chitosan is an active biopolymer, and the combination of it with other active groups can be a valuable method to improve the potential application of the resultant derivatives in food, cosmetics, packaging materials, and other industries. In this paper, a series of N,N,N-trimethyl-O-(ureidopyridinium)acetyl chitosan derivatives were synthesized. The combination of chitosan with ureidopyridinium group and quaternary ammonium group made it achieve developed water solubility and biological properties. The structures of chitosan and chitosan derivatives were confirmed by FTIR, 1H NMR spectra, and elemental analysis. The prepared chitosan derivatives were evaluated for antioxidant property by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging ability, hydroxyl radical scavenging ability, and superoxide radical scavenging ability. The results revealed that the synthesized chitosan derivatives exhibited improved antioxidant activity compared with chitosan. The chitosan derivatives were also investigated for antifungal activity against Phomopsis asparagus as well as Botrytis cinerea, and they showed a significant inhibitory effect on the selected phytopathogen. Meanwhile, CCK-8 assay was used to test the cytotoxicity of chitosan derivatives, and the results showed that most derivatives had low toxicity. These data suggested to develop analogs of chitosan derivatives containing ureidopyridinium group and quaternary ammonium group, which will provide a new kind of promising biomaterials having decreased cytotoxicity as well as excellent antioxidant and antimicrobial activity.

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Recent research progress on preparation and application of N, N, N-trimethyl chitosan

Cited by 68 publications

References 98 publications

Chitosan derivatives targeting lipid bilayers: Synthesis, biological activity and interaction with model membranes

Chitosan derivatives targeting lipid bilayers: Synthesis, biological activity and interaction with model membranes

Chitosan Derivatives and Their Application in Biomedicine

Synthesis and Characterization of N,N,N-trimethyl-O-(ureidopyridinium)acetyl Chitosan Derivatives with Antioxidant and Antifungal Activities

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