Characterization of hydrogels prepared from copolymerization of the different degrees of methacrylate‐grafted chondroitin sulfate macromers and acrylic acid

Tsai, Ming-Fong; Tsai, Hung-Yu; Peng, Yu-Shiang; Wang, Li Fang; Chen, Jenn‐Shing; Lu, Shui Chun

doi:10.1002/jbm.a.31441

Cited by 12 publications

(7 citation statements)

References 30 publications

(30 reference statements)

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“…50 Thus, the degradation activity of chondroitinase is reduced by steric hindrance around cleavage sites. 51,52 Due to the steric hindrance by an increased density of catechol groups on the CS backbone, chondroitinase-mediated degradation seemed to be hampered in the 10× CS-CA hydrogels (Figure 1f).…”

Section: Resultsmentioning

confidence: 99%

“…During CS degradation by chondroitinase, β-elimination occurs on cleavage sites by neutralizing the charge on the carboxyl group of the uronic acid, abstracting the proton from the C-5 carbon, and releasing a 4-linked hexosamine with the generation of an unsaturated 4,5-bond on the uronic acid . Thus, the degradation activity of chondroitinase is reduced by steric hindrance around cleavage sites. , Due to the steric hindrance by an increased density of catechol groups on the CS backbone, chondroitinase-mediated degradation seemed to be hampered in the 10× CS-CA hydrogels (Figure f).…”

Section: Resultsmentioning

confidence: 99%

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Tissue-Adhesive Chondroitin Sulfate Hydrogel for Cartilage Reconstruction

Shin

Kang

Choi

et al. 2021

ACS Biomater. Sci. Eng.

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Chondroitin sulfate (CS), the main component of cartilage extracellular matrix, has attracted attention as a biomaterial for cartilage tissue engineering. However, current CS hydrogel systems still have limitations for application in successful cartilage tissue engineering owing to their unsuitable degradation kinetics, insufficient mechanical similarity, and lack of integration with the native cartilage tissue. In this study, using mussel adhesive-inspired catechol chemistry, we developed a functional CS hydrogel that exhibits tunable physical and mechanical properties as well as excellent tissue adhesion for efficient integration with native tissues. Various properties of the developed catechol-functionalized CS (CS-CA) hydrogel, including swelling, degradation, mechanical properties, and adhesiveness, could be tailored by varying the conjugation ratio of the catechol group to the CS backbone and the concentration of the CS-CA conjugates. CS-CA hydrogels exhibited significantly increased modulus (∼10 kPa) and superior adhesive properties (∼3 N) over conventional CS hydrogels (∼hundreds Pa and ∼0.05 N). In addition, CS-CA hydrogels incorporating decellularized cartilage tissue dice promoted the chondrogenic differentiation of human adipose-derived mesenchymal stem cells by providing a cartilage-like microenvironment. Finally, the transplantation of autologous cartilage dice using tissue-adhesive CS-CA hydrogels enhanced cartilage integration with host tissue and neo-cartilage formation owing to favorable physical, mechanical, and biological properties for cartilage formation. In conclusion, our study demonstrated the potential utility of the CS-CA hydrogel system in cartilage tissue reconstruction.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Tissue-Adhesive Chondroitin Sulfate Hydrogel for Cartilage Reconstruction

Shin

Kang

Choi

et al. 2021

ACS Biomater. Sci. Eng.

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“…No publications examined the swelling characteristics over time of hydrogels solely based on CS(G)MA. However, swelling studies were reported on hydrogels based on CS(G)MA combined with other polymers like polyethylene glycol diacrylate. ,,, The hydrolytic stability of other MA ester-coupled polysaccharides as soluble polysaccharides and polymeric networks has previously been investigated. , MA-esters derivatized onto dextrans were previously found to only degrade as free polysaccharides but not in their cross-linked states. This difference in ester stability is attributed to the hydrophobic groups present in the polymerized MA backbone of the cross-linked network.…”

Section: Resultsmentioning

confidence: 99%

“…However, swelling studies were reported on hydrogels based on CS(G)MA combined with other polymers like polyethylene glycol diacrylate. 8,9,26,27 The hydrolytic stability of other MA ester-coupled polysaccharides as soluble polysaccharides and polymeric networks has previously been investigated. 22,23 MAesters derivatized onto dextrans were previously found to only degrade as free polysaccharides but not in their cross-linked states.…”

Section: Determination Of Methacrylate Hydrolysismentioning

confidence: 99%

Hydrolytic (In)stability of Methacrylate Esters in Covalently Cross-Linked Hydrogels Based on Chondroitin Sulfate and Hyaluronic Acid Methacrylate

et al. 2021

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Chondroitin sulfate (CS) and hyaluronic acid (HA) methacrylate (MA) hydrogels are under investigation for biomedical applications. Here, the hydrolytic (in)stability of the MA esters in these polysaccharides and hydrogels is investigated. Hydrogels made with glycidyl methacrylate-derivatized CS (CSGMA) or methacrylic anhydride (CSMA) degraded after 2− 25 days in a cross-linking density-dependent manner (pH 7.4, 37 °C). HA methacrylate (HAMA) hydrogels were stable over 50 days under the same conditions. CS(G)MA hydrogel degradation rates increased with pH, due to hydroxide-driven ester hydrolysis. Desulfated chondroitin MA hydrogels also degrade, indicating that sulfate groups are not responsible for CS(G)MA's hydrolytic sensitivity (pH 7.0−8.0, 37 °C). This sensitivity is likely because CS(G)MA's N-acetyl-galactosamines do not form hydrogen bonds with adjacent glucuronic acid oxygens, whereas HAMA's Nacetyl-glucosamines do. This bond absence allows CS(G)MA higher chain flexibility and hydration and could increase ester hydrolysis sensitivity in CS(G)MA networks. This report helps in biodegradable hydrogel development based on endogenous polysaccharides for clinical applications.

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“…If the cross peak 'α' is located at the position of some hydrogen peaks, they indicated that the peaks of H 1 , designated as geminal, and H 2 diagonal to H 3 had coupled to the H 3 hydrogen atom. [22][23][24] Next we measured the ratio of peak areas of geminal hydrogen and sum of the peaks of cis and trans hydrogens to verify the existence of the acrylate end group. The symmetry of acrylate end group was destroyed by the attachment of a carbonyl group (C=O) to the acrylate double bond, and three different hydrogen atoms were observed such as H 1 , H 2 and H 3 .…”

Section: Resultsmentioning

confidence: 99%

Development and physicochemical evaluation of chondroitin sulfate-poly(ethylene oxide) hydrogel

Kim

Woo

et al. 2011

Macromol. Res.

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Novel chondroitin sulfate (CS) -poly(ethylene oxide) (PEO) hydrogel was synthesized and evaluated by a mechanism of self cross-linking of CS derivative with PEO with hexa-thiols (PEO-SH). A derivative of CS was synthesized by the sequential grafting of adipic acid dihydrazide (ADH) and acrylic acid: chemical grafting of ADH to the carboxylic acid in CS (CS-ADH) followed by grafting of the acrylic acid to the free amine groups in the CS-ADH (CS-ADH-Ac). The synthesis of CS-ADH-Ac molecules was confirmed by observing new acrylate peaks in CS-ADH-Ac by FTIR, ESCA, and NMR. The CS-PEO hydrogel was self cross-linked through a Michael type addition reaction between the acrylate end groups of CS-ADH-Ac and the thiol end groups of the PEO-SH. the gelation behavior of 10% CS-PEO was evaluated by rheological analyses from the changes in the solution properties, such as phase angles and visco-elasticities. Rheological analysis indicated that the gelation process was complete within 2 min after mixing two polymer solutions of CS-ADH-Ac and PEO-SH. The fabricated CS-PEO hydrogel was analyzed by measuring both its swelling under different water pHs and its mechanical strength against compression. The morphological shapes of both its surface and cross sections were also evaluated after the sequential processes of gel swelling to equilibrium followed by dehydration. Both the gelation time and swelling of the fabricated hydrogel were dependent on the pH of the polymer solutions and swelling medium, showing quicker gel formation and better swelling behaviors under basic conditions than under acidic conditions. The equilibrated gel showed different morphologies depending on its location, i.e. its cross sections demonstrated more homogeneous morphologies than the surfaces. While the dehydrated hydrogel demonstrated 8-10 µm pore sizes on its cross sections, the compression strength of the hydrogel ranged from 1.4 to 2.8 Pa depending on its gel concentration. Toluidine blue molecules as a model drug were released from the hydrogel over a period of more than 5 days. These hydrogel properties, such as formation of in situ gel, release behaviors of toluidine blue, and porous structures and mechanical properties of the fabricated gel, highlighted the potential of a hydrogel as a carrier for local drug delivery and a scaffold for tissue engineering.

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Characterization of hydrogels prepared from copolymerization of the different degrees of methacrylate‐grafted chondroitin sulfate macromers and acrylic acid

Cited by 12 publications

References 30 publications

Tissue-Adhesive Chondroitin Sulfate Hydrogel for Cartilage Reconstruction

Tissue-Adhesive Chondroitin Sulfate Hydrogel for Cartilage Reconstruction

Hydrolytic (In)stability of Methacrylate Esters in Covalently Cross-Linked Hydrogels Based on Chondroitin Sulfate and Hyaluronic Acid Methacrylate

Development and physicochemical evaluation of chondroitin sulfate-poly(ethylene oxide) hydrogel

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