C6-Modifications on chitosan to develop chitosan-based glycopolymers and their lectin-affinities with sigmoidal binding profiles

Koshiji, Kazuhiro; Nonaka, Yoichi; Iwamura, Maho; Dai, Fumiko; Matsuoka, Ryoji; Hasegawa, Takeshi

doi:10.1016/j.carbpol.2015.10.073

Cited by 19 publications

(10 citation statements)

References 42 publications

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“…Compared with the characteristic absorbance bands of pristine chitosan at 3417 cm −1 (the NeH and OeH stretching vibrations), 2877 cm −1 (the C-H stretching vibration), 1600 cm −1 (the NeH bending vibration), and 1072 cm −1 (the C-OeC stretching vibration), the FTIR spectrum of N-phthaloyl chitosan (3) in Fig. 1 shows the new characteristic peaks of imide at 1778, 1712, 1388, and 721 cm −1 which demonstrates the successful introduction of N-phthaloyl groups (Koshiji et al, 2016). The new resonances appeared at 7.81 ppm are assigned to the protons of phthaloyl group for N-phthaloyl chitosan derivatives 3, 4, 5, 6a-6c, and 8a-8c shown in Fig.…”

Section: Resultsmentioning

confidence: 95%

“…The proton assignments of chitosan are observed at 3.13 ppm (H 2 of GlcN) and 3.40-4.00 ppm (H 3 , H 4 , H 5 , and H 6 of GlcN) (Liu, Xia, Jiang, Yu, & Yue, 2018). Whereas after the Huisgen cycloaddition, the new downfield signals at 8.03, 8.13, and 8.48 ppm (a in the spectra of chitosan derivatives 7a, 7b, and 7c) are assigned to hydrogen atoms at 5-H position of 1,2,3-triazole rings (Koshiji et al, 2016). Besides, the other newly formed characteristic proton signals of methylene of chitosan derivatives bearing 1,2,3-triazole at 4.65 and 4.29 ppm (b in the spectra of chitosan derivatives 7a and 7b) and 3.53, 3.50, and 3.54 ppm (c in the spectra of chitosan derivatives 7a, 7b, and 7c) are also observed.…”

Section: -Deoxy Chitosan Derivatives (7a-7c and 9a-9c)mentioning

confidence: 97%

“…The procedure was adapted from a previously reported method (Koshiji et al, 2016). To a 500 mL round-bottomed flask equipped with a magnetic stir bar and a condenser was charged chitosan 2 (4.83 g, 30 mmol of glucosamine), phthalic anhydride (13.32 g, 90 mmol), and DMF containing 5% (v/v) water (200 mL).…”

Section: Synthesis Of N-phthaloyl Chitosan (3)mentioning

confidence: 99%

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Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation

Tan

Zhang

Zhao

et al. 2018

Carbohydrate Polymers

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Amino functionality has been paid growing attention in chemical modification of polysaccharides due to their potential biomedical applications. Here, the preparation of novel antioxidant materials based on chitosan derivatives bearing amino-containing groups equipped with 1,2,3-triazole and 1,2,3-triazolium by Cuprous-catalyzed azide-alkyne cycloaddition and N-methylation was described for the first time. The structural characteristics of the synthesized derivatives were examined by FTIR, H NMR, and elemental analysis. The antioxidant activities of the chitosan derivatives were assessed in vitro. The results indicated that chitosan derivatives bearing 1,2,3-triazoles displayed superior antioxidant activity over pristine chitosan, especially against superoxide anion radical. Moreover, antioxidant efficiency of chitosan derivatives further enhanced after N-methylation of 1,2,3-triazole moieties with iodomethane, which is comparative to that of ascorbic acid. Notably, of all chitosan derivatives bearing 1,2,3-triazole or 1,2,3-triazolium moieties, acylhydrazine-functionalized and amino-functionalized chitosan showed the stronger antioxidant capacity than hydroxyl-modified chitosan at the test concentration. Besides, the cytotoxicities of them were also evaluated in vitro on HaCaT cells. These results suggested that amino and acylhydrazine-functionalized chitosan derivatives with 1,2,3-triazolium could be used as novel antioxidant biomaterials.

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Section: Resultsmentioning

confidence: 95%

Section: -Deoxy Chitosan Derivatives (7a-7c and 9a-9c)mentioning

confidence: 97%

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Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation

Tan

Zhang

Zhao

et al. 2018

Carbohydrate Polymers

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“…Furthermore, there are other chitosan derivatives developed via click chemistry reactions [32,50,65,66,67,68,69,70,71,72,73,74], some of which exhibit diverse properties like antimicrobial, antifungal, enhanced solubility in acidic and basic conditions, and an antigen detection system initiated by click chemistry, etc. Other materials synthesized are a cellulose-click-chitosan material [75], click-coupled graphene sheet with chitosan [76], and chitosan functionalized multiwalled carbon nanotubes [77].…”

Section: Click Chemistry Reactionsmentioning

confidence: 99%

Chitosan Derivatives: Introducing New Functionalities with a Controlled Molecular Architecture for Innovative Materials

et al. 2018

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The functionalization of polymeric substances is of great interest for the development of innovative materials for advanced applications. For many decades, the functionalization of chitosan has been a convenient way to improve its properties with the aim of preparing new materials with specialized characteristics. In the present review, we summarize the latest methods for the modification and derivatization of chitin and chitosan under experimental conditions, which allow a control over the macromolecular architecture. This is because an understanding of the interdependence between chemical structure and properties is an important condition for proposing innovative materials. New advances in methods and strategies of functionalization such as the click chemistry approach, grafting onto copolymerization, coupling with cyclodextrins, and reactions in ionic liquids are discussed.

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“…Thus, they can easily react with various amines to obtain novel C6 substituted amino chitosan. Moreover, 6-deoxy-6-tosyl chitosan and 6-deoxy-6-halogeno chitosan are both important intermediates preparing 6-deoxy-6-azido chitosan, which can yield terminal primary amines via Staudinger reaction and Staudinger ligation (Fox & Edgar, 2012;Koshiji et al, 2016;Luan et al, 2018). However, it is necessary to use triphenylphosphane and remove the resulting triphenylphosphaneoxide, which is not very environmentally friendly.…”

Section: Introducing Polyamino Groupsmentioning

confidence: 99%

Cationic chitosan derivatives as potential antifungals: A review of structural optimization and applications

Qin

Guo

2020

Carbohydrate Polymers

137

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The increasing resistance of pathogen fungi poses a global public concern. There are several limitations in current antifungals, including few available fungicides, severe toxicity of some fungicides, and drug resistance. Therefore, there is an urgent need to develop new antifungals with novel targets. Chitosan has been recognized as a potential antifungal substance due to its good biocompatibility, biodegradability, non-toxicity, and availability in abundance, but its applications are hampered by the low charge density results in low solubility at physiological pH. It is believed that enhancing the positive charge density of chitosan may be the most effective approach to improve both its solubility and antifungal activity. Hence, this review mainly focuses on the structural optimization strategy of cationic chitosan and the potential antifungal applications. This review also assesses and comments on the challenges, shortcomings, and prospect of cationic chitosan derivatives as antifungal therapy.

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C6-Modifications on chitosan to develop chitosan-based glycopolymers and their lectin-affinities with sigmoidal binding profiles

Cited by 19 publications

References 42 publications

Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation

Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation

Chitosan Derivatives: Introducing New Functionalities with a Controlled Molecular Architecture for Innovative Materials

Cationic chitosan derivatives as potential antifungals: A review of structural optimization and applications

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