Preparation of highly regioselective amphiprotic chitosan derivative via “click chemistry”

Ifuku, Shinsuke; Matsumoto, Chisato; Wada, Masahiro; Morimoto, Minoru; Saimoto, Hiroyuki

doi:10.1016/j.ijbiomac.2012.08.012

Cited by 18 publications

(21 citation statements)

References 12 publications

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“…1,2,3-Triazole was stable to metabolic degradation and capable of forming hydrogen bonds, which could favor binding to biomolecular targets and improve solubility [23]. The team of Ifuku prepared new chitosan derivatives containing triazolyl moieties at the C 6 position of glucosamine units by coupling between azide and propargyl groups of chitosan via a 1,3-dipolar cycloaddition [24][25][26]. Novel 1,2,3-triazole-linked starch derivatives synthesized via 'click chemistry' exhibited improved antibacterial property and antioxidant property [21,27].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of water soluble chitosan derivatives with halogeno-1,2,3-triazole and their antifungal activity

Tan

Zhang

et al. 2016

International Journal of Biological Macromolecules

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a b s t r a c tChitosan is an abundant and renewable polysaccharide, which exhibits attractive bioactivities and natural properties. Improvement such as chemical modification of chitosan is often performed prior to further utilization. Three novel water soluble chitosan derivatives containing 1,2,3-triazole with or without halogen was designed and synthesized. Their antifungal activity against three kinds of phytopathogens was estimated by hyphal measurement in vitro. The inhibitory property and water solubility of the synthesized chitosan derivatives exhibited a remarkable improvement over chitosan. It is hypothesized that thiazolyl groups enable the synthesized chitosan to possess obviously better antifungal activity. Moreover, CTCTS and BTCTS, which have halogens at the periphery of polymers, inhibited the growth of tested phytopathogens more effectively with inhibitory indices of 81-93% at 1.0 mg/mL. The halogens could have a synergistic effect with triazole as they exhibited antifungal activity and electron-withdrawing capacity, which improve the antifungal activity of chitosan derivatives.

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Section: Introductionmentioning

confidence: 99%

Synthesis of water soluble chitosan derivatives with halogeno-1,2,3-triazole and their antifungal activity

Tan

Zhang

et al. 2016

International Journal of Biological Macromolecules

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“…Furthermore, it had the ability to form nanoparticles in neutral aqueous solution due to the inter-and intra-molecular aggregation. These properties make it possible to be used as drug delivery systems (Ifuku et al 2013). CuACC was also applied to graft methoxy poly(ethylene glycol) (MPEG) onto N-azidated chitosan.…”

Section: Chitosan-based Biomaterialsmentioning

confidence: 99%

"Click" chemistry as a tool to create novel biomaterials: a short review

Barbosa

Martins

Gomes

2017

UPjeng

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In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

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“…The carboxylic acid moiety can be substituted by a bioisostere group, such as triazole, which can be constructed by click chemistry ,. Ifuku et al.…”

Section: Selective Modificationmentioning

confidence: 99%

“…described the O‐6 modification of the N ‐phthaloyl chitosan, which was brominated by using N ‐bromosuccinimide and triphenylphosphine followed by azidation with NaN 3 (Figure ). The azide moiety at the C‐6 position was then successfully converted to a 1,4‐triazole linker with an appropriate R group by a Huisgen cycloaddition between 6‐azido‐6‐deoxy‐ N ‐phthaloyl chitosan and an adequate propiolate in the presence of a Cu I catalyst . The azide moiety placed at O‐6 can also be transformed into an amine group by formation of a triphenylphosphinimine intermediate that is hydrolyzed by using aqueous hydrazine, with simultaneous removal of the N‐phthaloyl group (Figure ).…”

Section: Selective Modificationmentioning

confidence: 99%

Selective Modification of Chitin and Chitosan: En Route to Tailored Oligosaccharides

Carvalho

Queda

Santos

et al. 2016

Chemistry An Asian Journal

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Chitin and chitosan are attractive biopolymers with enormous structural possibilities for chemical modification, creating platforms for new chemical entities with a broad scope of applications, ranging from material science to medicine. During the last few years, incredible efforts have been dedicated to the regioselective modification of these biopolymers paving the way for improved properties and tailored activities. Herein, the most recent advances in chitin/chitosan regioselective modification, reaction conditions, selectivity, and the impact on its applications are highlighted. Moreover, the recent focus on chitooligosaccharides, their regioselective and chemoselective functionalization, as well as their role in biological studies, including molecular recognition with several biological targets are also covered.

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Preparation of highly regioselective amphiprotic chitosan derivative via “click chemistry”

Cited by 18 publications

References 12 publications

Synthesis of water soluble chitosan derivatives with halogeno-1,2,3-triazole and their antifungal activity

Synthesis of water soluble chitosan derivatives with halogeno-1,2,3-triazole and their antifungal activity

"Click" chemistry as a tool to create novel biomaterials: a short review

Selective Modification of Chitin and Chitosan: En Route to Tailored Oligosaccharides

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