A catechol-chitosan-based adhesive and injectable hydrogel resistant to oxidation and compatible with cell therapy

Guyot, Capucine; Adoungotchodo, Atma; Taillades, Werner; Cerruti, Marta; Lerouge, Sophie

doi:10.1039/d1tb00807b

Cited by 13 publications

(15 citation statements)

References 82 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This is the case for the dhba-CH/SHC hydrogels. Not only are these hydrogels cytocompatible at cat levels up to 8%, but also, as we previously showed, they have excellent mechanical and bioadhesive properties, which makes them excellent candidates as adhesive vehicles for cell therapy.…”

Section: Discussionmentioning

confidence: 63%

See 1 more Smart Citation

How to Design Catechol-Containing Hydrogels for Cell Encapsulation Despite Catechol Toxicity

Guyot,

Malaret,

Touani Kameni

et al. 2023

ACS Appl. Bio Mater.

Self Cite

View full text Add to dashboard Cite

Catechol (cat) is a highly adhesive diphenol that can be chemically grafted to polymers such as chitosan (CH) to make them adhesive as well. However, catechol-containing materials experimentally show a large variability of toxicity, especially in vitro. While it is unclear how this toxicity emerges, most concerns are directed toward the oxidation of catechol into quinone that releases reactive oxygen species (ROS) which can, in turn, cause cell apoptosis through oxidative stress. To better understand the mechanisms at play, we examined the leaching profiles, hydrogen peroxide (H 2 O 2 ) production, and in vitro cytotoxicity of several cat-chitosan (cat-CH) hydrogels that were prepared with different oxidation levels and cross-linking methods. To create cat-CH with different propensities toward oxidation, we grafted either hydrocaffeic acid (HCA, more prone to oxidation) or dihydrobenzoic acid (DHBA, less prone to oxidation) to the backbone of CH. Hydrogels were cross-linked either covalently, using sodium periodate (NaIO 4 ) to trigger oxidative cross-linking, or physically, using sodium bicarbonate (SHC). While using NaIO 4 as a cross-linker increased the oxidation levels of the hydrogels, it also significantly reduced in vitro cytotoxicity, H 2 O 2 production, and catechol and quinone leaching in the media. For all gels tested, cytotoxicity could be directly related to the release of quinones rather than H 2 O 2 production or catechol release, showing that oxidative stress may not be the main reason for catechol cytotoxicity, as other pathways of quinone toxicity come into play. Results also suggest that the indirect cytotoxicity of cat-CH hydrogels fabricated through carbodiimide chemistry can be reduced if (i) catechol groups are chemically bound to the polymer backbone to prevent leaching or (ii) the chosen cat-bearing molecule has a high resistance to oxidation. Coupled with the use of other cross-linking chemistries or more efficient purification methods, these strategies can be adopted to synthesize various types of cytocompatible cat-containing scaffolds.

show abstract

Section: Discussionmentioning

confidence: 63%

“…HCA and DHBA were grafted to CH by carbodiimide chemistry using previously published protocols. , Briefly, 1.2 mg of CH was dissolved in 0.1 M HCl to reach a pH of 2.5. Then, the pH was increased to 5 using 1 M NaOH.…”

Section: Methodsmentioning

confidence: 99%

How to Design Catechol-Containing Hydrogels for Cell Encapsulation Despite Catechol Toxicity

Guyot,

Malaret,

Touani Kameni

et al. 2023

ACS Appl. Bio Mater.

Self Cite

View full text Add to dashboard Cite

show abstract

“…[ 214 ] Dihydroxybenzoic acid‐ grafted ‐chitosan–catechol, with a high catechol content, shows strong mucoadhesive properties in mucin. [ 215 ] The conjugation of polyphenolic compounds with chitin nanostructures improves adhesion and hemostasis further. [ 216 ] The adhesion of a gallol‐conjugated chitin nanofiber to porcine skin is up to 10 times higher than that of a chitosan–catechol or pyrogallol polymer (Figure 7f–h).…”

Section: Applications Of Chitin and Chitosan Nanostructures With Mult...mentioning

confidence: 99%

Nanochitin and Nanochitosan: Chitin Nanostructure Engineering with Multiscale Properties for Biomedical and Environmental Applications

et al. 2022

View full text Add to dashboard Cite

Nanochitin and nanochitosan (with random‐copolymer‐based multiscale architectures of glucosamine and N‐acetylglucosamine units) have recently attracted immense attention for the development of green, sustainable, and advanced functional materials. Nanochitin and nanochitosan are multiscale materials from small oligomers, rod‐shaped nanocrystals, longer nanofibers, to hierarchical assemblies of nanofibers. Various physical properties of chitin and chitosan depend on their molecular‐ and nanostructures; translational research has utilized them for a wide range of applications (biomedical, industrial, environmental, and so on). Instead of reviewing the entire extensive literature on chitin and chitosan, here, recent developments in multiscale‐dependent material properties and their applications are highlighted; immune, medical, reinforcing, adhesive, green electrochemical materials, biological scaffolds, and sustainable food packaging are discussed considering the size, shape, and assembly of chitin nanostructures. In summary, new perspectives for the development of sustainable advanced functional materials based on nanochitin and nanochitosan by understanding and engineering their multiscale properties are described.

show abstract

“…39 Therefore, bio-functional modification strategies are commonly employed to enhance the antibacterial and antioxidant properties of these single natural polymer hydrogels, which are conducive to complete wound closure. [40][41][42][43][44] In this work, hybrid hydrogels generated by rhCol III and CS were developed to serve as an ECM-mimicking hydrogel for cutaneous wound healing without additional therapeutic agents or cells. rhCol III was conjugated with methacrylic anhydride (MA) through amide bonds (denoted as rhCol III-MA), which may emulate the structure of natural ECM to mediate cell adhesion, migration and proliferation, as well as provide essential amino acids for collagen formation.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Injectable hydrogels of recombinant human collagen type III and chitosan with antibacterial and antioxidative activities for wound healing

et al. 2023

View full text Add to dashboard Cite

show abstract

A catechol-chitosan-based adhesive and injectable hydrogel resistant to oxidation and compatible with cell therapy

Abstract: Injectable hydrogels designed for cell therapy need to be adhesive to the surrounding tissues to maximize their retention and the communication between the host and the encapsulated cells. Catechol grafting...

Cited by 13 publications

References 82 publications

How to Design Catechol-Containing Hydrogels for Cell Encapsulation Despite Catechol Toxicity

How to Design Catechol-Containing Hydrogels for Cell Encapsulation Despite Catechol Toxicity

Nanochitin and Nanochitosan: Chitin Nanostructure Engineering with Multiscale Properties for Biomedical and Environmental Applications

Injectable hydrogels of recombinant human collagen type III and chitosan with antibacterial and antioxidative activities for wound healing

Contact Info

Product

Resources

About