Supramolecular and dynamic covalent hydrogel scaffolds: from gelation chemistry to enhanced cell retention and cartilage regeneration

Teng, Lijing; Chen, Yunhua; Jia, Yong‐Guang; Li, Ren

doi:10.1039/c9tb01698h

Cited by 59 publications

(36 citation statements)

References 303 publications

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“…The stability of the DCB endows the hydrogels with proper mechanical properties, while the dynamic nature of the DCB provides both self-healing and controllable stimuli-responsive properties [4,5]. Recently, the DCBs-based materials with controllable properties and multiple responsiveness have become increasingly popular because of their application prospects in some complex environments [6,7]. To this end, considerable research has been devoted to the incorporation of multiple DCBs in a single system to enhance the performance and complexities of the material [8,9].…”

Section: Introductionmentioning

confidence: 99%

Doubly Dynamic Hydrogel Formed by Combining Boronate Ester and Acylhydrazone Bonds

Liu

Wang

et al. 2020

Polymers

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The incorporation of double dynamic bonds into hydrogels provides an effective strategy to engineer their performance on demand. Herein, novel hydrogels were PREPARED by combining two kinetically distinct dynamic covalent bonds, boronate ester and acylhydrazone bonds, and the synergistic properties of the hydrogels were studied comprehensively. The functional diblock copolymers P(N-isopropyl acrylamide-co-N-acryloyl-3-aminophenylboronic acid)-b-(N-isopropyl acrylamide-co-diacetone acrylamide) (PAD) were prepared via reversible addition−fragmentation chain transfer (RAFT) polymerization. The hydrogel was constructed by exploiting dynamic reaction of phenyboronic acid moieties with polyvinyl alcohol (PVA) and ketone moieties with adipic dihydrazide (ADH) without any catalyst. The active boronate ester linkage endows the hydrogel with fast gelation kinetics and self-healing ability, and the stable acylhydrazone linkage can enhance the mechanical property of the hydrogel. The difference in kinetics endows that the contribution of each linkage to mechanical strength of the hydrogel can be accurately estimated. Moreover, the mechanical property of the hydrogel can be readily engineered by changing the composition and solid content, as well as by controlling the formation or dissociation of the dynamic linkages. Thus, we provide a promising strategy to design and prepare multi-responsive hydrogels with tunable properties.

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Section: Introductionmentioning

confidence: 99%

Doubly Dynamic Hydrogel Formed by Combining Boronate Ester and Acylhydrazone Bonds

Liu

Wang

et al. 2020

Polymers

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“…Reversible Schiff base (imine) linkages formed between aldehyde and amine functional groups offer unique properties including self‐healing and injectability in the so‐called dynamic hydrogels. [ 1–5 ] Hence, Schiff base‐based dynamic hydrogels have found application in regenerative medicine, drug delivery, [ 6,7 ] wound dressing. [ 8,9 ]…”

Section: Introductionmentioning

confidence: 99%

Amylopectin Multiple Aldehyde Crosslinked Hydrogel as an Injectable and Self‐Healing Cell Carrier for Bone Tissue Engineering

Vahedi

Shokrolahi

Barzin

et al. 2020

Macro Materials & Eng

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linkages formed between aldehyde and amine functional groups offer unique properties including self-healing and injectability in the so-called dynamic hydrogels. [1][2][3][4][5] Hence, Schiff base-based dynamic hydrogels have found application in regenerative medicine, drug delivery, [6,7] wound dressing. [8,9] Cell delivery for regenerative medicine is one of the marvelous applications of dynamic hydrogels based on natural polymers which are addressed in recent scientific reports. For example, chitosan crosslinked using polyethylene glycol dibenzaldehyde through Schiff base linkages were found to be an injectable and self-healing hydrogel. Such prepared hydrogels have been used as a cell delivery vehicle for encapsulation of neural stem cells for promoting nerve regeneration. [3] Another self-healing/injectable hydrogel was reported as a cell carrier for cardiac cell therapy by Schiff base linkages between chitosan chains and polyethylene glycol dibenzaldehyde. [10] As another example, a self-healing and injectable hydrogel cell carrier for myoblast cell therapy was reported prepared by Schiff base linkages between N-carboxyethyl chitosan and dextran-graft-aniline tetramer-graft-4-formylbenzoic acid. [11] Such studies have been focused on the formation of Schiff base linkages via benzaldehyde derivatives for crosslinking chitosan as the amine sharing part and the obtained hydrogels support both injectability and self-healing characteristics as the cell delivery systems.On the other hand, there are some reports on fabrication of injectable and self-healing dynamic hydrogels based on Schiff base linkages by aliphatic aldehyde sharing parts for cell delivery applications. For example, an injectable and self-healing hydrogel was prepared via formation of Schiff base linkages between N-succinyl-chitosan and chondroitin sulfate multiple aldehyde. The reported hydrogel was used for encapsulation of Hela cells. [12] Also, a hydrogel with mentioned characteristics was reported which was fabricated by the formation of Schiff base linkages between N-carboxyethyl chitosan and oxidized sodium alginate and was used as a cell carrier for neural stem cells. [13] Moreover, another injectable and self-healing hydrogel Despite excellent processing and biological properties of gelatin for use as a cell carrier, none of the gelatin-based hydrogel cell carriers reported to date offer all characteristics including quick formation, injectability, self-healing, and durability, which are simultaneously required for an ideal system. Here, a gelatin-based hydrogel with dynamic Schiff base linkages, so-called "dynamic hydrogel," as an injectable cell carrier consisting of gelatin and amylopectin multiple aldehyde (AMPA), with all the required characteristics is reported. Biocompatibility and osteoinductivity of the hydrogel are verified through the culture of human bone marrow-derived mesenchymal stem cells (hBMSCs). As live/dead results show, hBMSCs are alive and highly viable ≈85-90% within the hydrogel after 5 days. According to bromodeo...

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“…On the other hand, gels are interesting soft materials owing to their functional properties, leading to potential applications (Yao et al, 2017). Using gels as drug carriers has attracted tremendous attention for their numerous advantages in medical treatments, including prolonged drug release time, reduced side effects of drugs, and maintained effective plasma concentration (Nishimura et al, 2019;Teng et al, 2019;Thamizhanban et al, 2019). For example, Prof. Yao and co-workers prepared a soft gel based on pillar[5]arene by using a carbazone reaction and found that dyes such as TPP or TPPE can be incorporated into this gel and then released in a sustained way in water due to solvent exchange (Yao et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water

et al. 2020

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P -tert-butyldihomooxacalix[4]arene is a well-known calix [4]arene analog in which one CH 2 bridge is replaced by one -O-group. Thus, dihomooxacalix[4]arene has a slightly larger cavity than that of calix[4]arene and usually possesses a more flexible cone conformation, and the bridged oxygen atom might provide additional binding sites. Here, we synthesized a new functional p-tert-butyldihomooxacalix[4]arene 1 through Ugi reaction with good yield (70%), starting from condensed p-tert-butyldihomooxacalix [4]arene O-alkoxy-substituted benzaldehydes, benzoic acid, benzylamine, and cyclohexyl isocyanide. Proton nuclear magnetic resonance spectroscopy ( 1 H NMR), 13 C NMR, IR, and diffusion-ordered 1 H NMR spectroscopy (DOSY) methods were used to characterize the structure of 1. Then soft gel was prepared by adding 1 into cyclohexane directly. It shows remarkable thermoreversibility and can be demonstrated for several cycles. As is revealed by scanning electron microscopy (SEM) images, xerogel showed highly interconnected and homogeneous porous network structures, and hence, the gel is suitable for storage and controlled release. . (2019). Enzyme-mediated dynamic combinatorial chemistry allows out-of-equilibrium template-directed synthesis of macrocyclic oligosaccharides. Chem. Sci. 10, 9981-9987.

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Supramolecular and dynamic covalent hydrogel scaffolds: from gelation chemistry to enhanced cell retention and cartilage regeneration

Abstract: This review highlights the most recent progress in gelation strategies of biomedical supramolecular and dynamic covalent crosslinking hydrogels and their applications for enhancing cell retention and cartilage regeneration.

Cited by 59 publications

References 303 publications

Doubly Dynamic Hydrogel Formed by Combining Boronate Ester and Acylhydrazone Bonds

Doubly Dynamic Hydrogel Formed by Combining Boronate Ester and Acylhydrazone Bonds

Amylopectin Multiple Aldehyde Crosslinked Hydrogel as an Injectable and Self‐Healing Cell Carrier for Bone Tissue Engineering

A p-tert-Butyldihomooxacalix[4]arene Based Soft Gel for Sustained Drug Release in Water

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