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

Capucine Guyot1,2, Tommy Malaret1,2, Francesco Touani Kameni2

  • 1Department of Mechanical Engineering, Ecole de Technologie Superieure, Montreal H3C 1K3, Canada.

ACS Applied Bio Materials
|June 20, 2023
PubMed
Summary
This summary is machine-generated.

This study reveals that quinone release, not oxidative stress, drives catechol-chitosan hydrogel toxicity. Strategies like chemical binding and oxidation-resistant molecules can improve biocompatibility for advanced materials.

Keywords:
CatecholROScarbodiimide chemistrychitosancytocompatibilityhydrogelsoxidationquinone

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Area of Science:

  • Biomaterials Science
  • Polymer Chemistry
  • Cell Biology

Background:

  • Catechol (cat) grafting enhances chitosan (CH) polymer adhesion.
  • Catechol-containing materials exhibit variable in vitro toxicity, often attributed to quinone oxidation and reactive oxygen species (ROS) release.
  • The precise mechanisms underlying catechol-induced cytotoxicity remain unclear.

Purpose of the Study:

  • To investigate the relationship between oxidation levels, cross-linking methods, and the in vitro cytotoxicity of catechol-chitosan (cat-CH) hydrogels.
  • To elucidate the primary mechanisms of cytotoxicity, focusing on leaching profiles, hydrogen peroxide (H2O2) production, and quinone release.

Main Methods:

  • Synthesized cat-CH hydrogels by grafting hydrocaffeic acid (HCA) or dihydrobenzoic acid (DHBA) to chitosan.
  • Employed oxidative cross-linking with sodium periodate (NaIO4) or physical cross-linking with sodium bicarbonate (SHC).
  • Assessed hydrogel oxidation levels, leaching of catechol and quinone, H2O2 production, and in vitro cytotoxicity.

Main Results:

  • NaIO4 cross-linking increased hydrogel oxidation but significantly reduced cytotoxicity, H2O2 production, and leaching of catechol and quinones.
  • Cytotoxicity correlated directly with quinone release, independent of H2O2 production or catechol leaching.
  • Oxidative stress is likely not the primary driver of catechol cytotoxicity; other quinone toxicity pathways are implicated.

Conclusions:

  • Reducing indirect cytotoxicity of cat-CH hydrogels is achievable by chemically immobilizing catechol groups or using oxidation-resistant catechol derivatives.
  • Optimizing cross-linking chemistry and purification methods are crucial for developing cytocompatible catechol-containing scaffolds.
  • These findings offer strategies for engineering safer and more effective adhesive biomaterials.