An injectable hyaluronic acid/PEG hydrogel for cartilage tissue engineering formed by integrating enzymatic crosslinking and Diels–Alder “click chemistry”

Yu, Feng; Cao, Xiaodong; Li, Yuli; Zeng, Lei; Yuan, Bo; Chen, Xiaofeng

doi:10.1039/c3py00869j

Cited by 159 publications

(111 citation statements)

References 46 publications

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“…The DA/rDA equilibrium has been exploited, e.g., for the synthesis of recyclable, mendable or self-healing materials. 10 In a slightly different approach, furan-modied hyaluronic acid (HA) derivatives were cross-linked with dimaleimide PEG 11,24 or maleimide-functionalized HA. [18][19][20] The rDA fragmentation has also been explored for the purpose of binding and release drugs from macromolecular carriers.…”

Section: Introductionmentioning

confidence: 99%

New insights into the cross-linking and degradation mechanism of Diels–Alder hydrogels

et al. 2015

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Eight-armed poly(ethylene glycol) was functionalized with furyl and maleimide groups. The two macromonomers were cross-linked by Diels-Alder (DA) reactions and the degradation behavior of the formed hydrogels was investigated. UV spectroscopy showed that maleimide groups were subject to ring-opening hydrolysis above pH 5.5, with the reaction rate depending on the pH and temperature. As a result of this, the gelation kinetics and stiffness of DA hydrogels were dependent on the temperature and the pH of the cross-linking medium, as demonstrated by rheological experiments. The gel time varied between 87.8 min (pH 3.0, 37 C) and 374.7 min (pH 7.4, 20 C). Values between 420 Pa (pH 9.0, 37 C) and 3327 Pa (pH 3.0, 37 C) were measured for the absolute value of the complex shear modulus. Hydrogel swelling and degradation were influenced by the same parameters. With increasing pH and temperature the degradation time was reduced from 98 days (pH 7.4, 20 C) to 2 days (pH 7.4, 50 C); no degradation was observed at pH 3.0 and 5.5. Molecular modeling studies of the DA and retro-Diels-Alder (rDA) moieties revealed that hydrogel degradation occurred by rDA reaction followed by OH Àcatalyzed ring-opening hydrolysis of maleimide groups to unreactive maleamic acid derivatives.

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Section: Introductionmentioning

confidence: 99%

New insights into the cross-linking and degradation mechanism of Diels–Alder hydrogels

et al. 2015

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“…Other investigations of similar chemistry include the synthesis of injectable HA/PEG hydrogel [108], interpenetrating HA/gelatin/chondroitin sulfate hydrogel [109], and hydroxylpropyl methylcellulose-based hydrogels [110].…”

Section: Classic Diels-alder Reactionmentioning

confidence: 99%

“Click” reactions in polysaccharide modification

Meng

Edgar

2016

Progress in Polymer Science

183

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Polysaccharide chemistry is enjoying accelerating development thanks to advances in synthetic techniques, biochemistry and solvents, which enable polysaccharide materials to be useful in a variety of demanding applications. Among the synthetic advances, click chemistry has reconfigured the realm of polysaccharide modification that previously was dominated by conventional synthetic approaches such as esterification and etherification. "Click" reactions provide mild, modular, and efficient modification pathways, and equally importantly allow us to synthesize derivatives with novel functionality, architecture, and properties, that are otherwise difficult to obtain via conventional methods. Herein, we review application in polysaccharide modification of six groups of click reactions; CuAAC (copper catalyzed alkyne/azide cycloaddition), metal-free [3+2] cycloaddition, Diels-Alder reaction, oxime click, thiol-Michael reaction, and thiol-ene reaction, as well as one click-like reaction that is the subject of our own research, olefin cross-metathesis.

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“…HA hydrogels have been widely applied in the biomedical field because of their good biocompatibility and structural diversity (Collins & Birkinshaw, 2013a,b). On the other side, polyethylene glycol (PEG) has been widely used to synthesize many types of hydrogels for tissue engineering due to its good biocompatibility, ability to promote tissue regeneration and longterm in vivo security (Byeon et al, 2014;Burdick & Anseth, 2002;Yu et al, 2014;Yu, Cao, Zeng, Zhang, & Chen, 2013;Rufaihah et al, 2013). A gentle hydrazone bond crosslinking method was recently reported to synthesize HA hydrogels by reacting HA aldehyde with HA adipic dihydrazide (Oommen et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Hyaluronic acid hydrogel scaffolds with a triple degradation behavior for bone tissue engineering

Cui

Qian

Liu

et al. 2015

Carbohydrate Polymers

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An injectable hyaluronic acid/PEG hydrogel for cartilage tissue engineering formed by integrating enzymatic crosslinking and Diels–Alder “click chemistry”

Abstract: Injectable HA/PEG hydrogel was crosslinked by integrating the enzymatic crosslinking and Diels–Alder click chemistry and showed excellent shape recovery and anti-fatigue properties at a high compressive stress.

Cited by 159 publications

References 46 publications

New insights into the cross-linking and degradation mechanism of Diels–Alder hydrogels

New insights into the cross-linking and degradation mechanism of Diels–Alder hydrogels

“Click” reactions in polysaccharide modification

Hyaluronic acid hydrogel scaffolds with a triple degradation behavior for bone tissue engineering

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