The antioxidant and antifungal activity of chitosan derivatives bearing Schiff bases and quaternary ammonium salts

Wei, Liqing; Tan, Wenqiang; Wang, Gang; Li, Qing; Dong, Fang; Guo, Zhanyong

doi:10.1016/j.carbpol.2019.115256

Cited by 119 publications

(68 citation statements)

References 41 publications

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“…Then, the intermediate, CTCS, was synthesized via N,N,N-trimethyl chitosan. Finally, the obtained urea groups were grafted onto CTCS based on the reaction mechanism of that chitosan derivatives with chloride acetyl group could be attacked by pyridine to give N-alkypyridinium salts and four final chitosan derivatives bearing urea groups were achieved [22,23,28]. The structures of all synthesized derivatives were confirmed by FTIR ( Figure 1) and 1 H NMR ( Figure 2).…”

Section: Chemical Synthesis and Characterizationmentioning

confidence: 91%

“…Therefore, the 1 [31]. For the spectrum of CTCS, a new chemical shift (δ3.1 ppm), which could be assigned to the proton signal of -N + (CH 3 ) 3 , was appeared [22,23]. Meanwhile, another new characteristic peak at δ4.4 ppm could be observed easily from the 1 H NMR spectra of CTCS, which was attributed to proton signal of -COCH 2 Cl [27].…”

Section: Chemical Synthesis and Characterizationmentioning

confidence: 94%

“…Wei et al had synthesized several series of N,N,N-trimethyl chitosan derivatives bearing imidazole groups and Schiff bases. They reported that these chitosan derivatives held up fairly well in antifungal and antioxidant activities [22,23]. In addition, N,N,N-trimethyl chitosan derivatives modified with 1,2,3-triazolium groups also had excellent antifungal ability against Colletotrichum lagenarium, Fusarium oxysporum f. sp.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Chemical Synthesis and Characterizationmentioning

confidence: 91%

Section: Chemical Synthesis and Characterizationmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

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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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“…Among the diverse chitosan conjugates, imine-linked chitosan conjugates have recently received considerable attention. The primary amino group contained in the chitosan skeleton can easily undergo a condensation reaction with an acyl compound (aldehyde, ketone) to form a Schiff base [76][77][78][79][80][81]. This reaction can be performed in a green solvent such as water and ethanol, and the reaction conditions are mild and green.…”

Section: Coupling By Forming a Schiff Basementioning

confidence: 99%

Antimicrobial Chitosan Conjugates: Current Synthetic Strategies and Potential Applications

Qin

2020

IJMS

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As a natural polysaccharide, chitosan possesses good biocompatibility, biodegradability and biosafety. Its hydroxyl and amino groups make it an ideal carrier material in the construction of polymer-drug conjugates. In recent years, various synthetic strategies have been used to couple chitosan with active substances to obtain conjugates with diverse structures and unique functions. In particular, chitosan conjugates with antimicrobial activity have shown great application prospects in the fields of medicine, food, and agriculture in recent years. Hence, we will place substantial emphasis on the synthetic approaches for preparing chitosan conjugates and their antimicrobial applications, which are not well summarized. Meanwhile, the challenges, limitations, and prospects of antimicrobial chitosan conjugates are described and discussed.

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“…Una de las posibles soluciones para combatir dichas enfermedades bacterianas son las bases de Schiff (SB por sus siglas en inglés), debido a que presentan un gran número de aplicaciones las cuales van desde agentes farmacéuticos antitumorales (Sâmia et al, 2019), antibacterianos (Rakesh; Kumara; Ullas; Shivakumara; Gowda, 2019) y antifúngicos (Wei et al, 2019). Dichas bases son sintetizadas mediante una reacción de condensación entre una amia primaria y compuestos carbonilos (cetonas y/o aldehídos) tal como lo descubrió en 1864 Hugo Joseph Schiff (Antony; Arun; David, 2019; Harnsaure, n.d.).…”

Section: Introductionunclassified

Métodos de síntesis novedosos para polímeros

2019

inf_tec

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El bisfenol A (BPA) es un monómero empleado en la fabricación de policarbonato y resinas epoxi por lo cual es fabricado extensivamente a nivel mundial. No obstante, el BPA tiene un aspecto poco deseado ya que diversos estudios lo relacionan con distintas enfermedades especialmente por su efecto como disruptor endocrino. Actualmente el BPA es tema de controversia entre comunidades científicas y agentes gubernamentales, específicamente en relación a su ingesta diaria admisible (IDA). Por otra parte, los tickets de papel térmico son agentes de contaminación en plantas de reciclaje de papel, en consecuencia desde el Laboratorio de Química Industrial (LQI) se empleó la extracción Soxhlet con solventes orgánicos con el fin de eliminar BPA contaminante en muestras de papel térmico usado.

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The antioxidant and antifungal activity of chitosan derivatives bearing Schiff bases and quaternary ammonium salts

Cited by 119 publications

References 41 publications

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

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

Antimicrobial Chitosan Conjugates: Current Synthetic Strategies and Potential Applications

Métodos de síntesis novedosos para polímeros

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