A pH-responsive, injectable and self-healing chitosan-coumarin hydrogel based on Schiff base and hydrogen bonds

Int J Biol Macromol. 2024 Jan:255:128122. doi: 10.1016/j.ijbiomac.2023.128122. Epub 2023 Nov 18.

Abstract

Smart hydrogels have shown great potential applications in disease treatment due to their controlled and local drug-release ability. Herein, a smart hydrogel with pH-responsive, injectable, and self-healing properties for controlled release of taxifolin (TFL) was prepared by freezing-thawing and photo-crosslinking methods. The crosslinking network of hydrogels (CS-CA hydrogels) was constructed by the hydrogen bonds, Schiff base bonds, and cyclobutane rings using chitosan (CS) and coumarin (CA) as raw materials. The CS-CA hydrogel demonstrated a compressive strength of 1.04 MPa, a self-healing efficiency of 99.9 %, and could maintain structural and functional integrity after injection. In addition, the drug release rate and shape of the CS-CA hydrogels were tunable due to its pH sensitivity. The TFL cumulative release reached 60 % within 12 h at pH = 4, and after equilibration, the cumulative release of TFL at pH = 4 (80 %) was significantly higher than at pH = 9.2 (50 %). The CCK8 experiment showed that the resulting hydrogel had no cytotoxicity. Meanwhile, subcutaneous implantation experiments in mice showed that the CS-CA hydrogels had favorable biodegradability and compatibility.

Keywords: Chitosan-coumarin hydrogel; Injectability; Schiff base bond; pH-responsiveness.

MeSH terms

  • Animals
  • Chitosan* / chemistry
  • Coumarins
  • Hydrogels / chemistry
  • Hydrogen Bonding
  • Hydrogen-Ion Concentration
  • Mice
  • Schiff Bases

Substances

  • Chitosan
  • Hydrogels
  • Schiff Bases
  • Coumarins