Diels-Alder Click cross-linked hyaluronic acid hydrogels for tissue engineering

Biomacromolecules. 2011 Mar 14;12(3):824-30. doi: 10.1021/bm101446k. Epub 2011 Feb 11.

Abstract

Hyaluronic acid (HA) is a naturally occurring polymer that holds considerable promise for tissue engineering applications. Current cross-linking chemistries often require a coupling agent, catalyst, or photoinitiator, which may be cytotoxic, or involve a multistep synthesis of functionalized-HA, increasing the complexity of the system. With the goal of designing a simpler one-step, aqueous-based cross-linking system, we synthesized HA hydrogels via Diels-Alder "click" chemistry. Furan-modified HA derivatives were synthesized and cross-linked via dimaleimide poly(ethylene glycol). By controlling the furan to maleimide molar ratio, both the mechanical and degradation properties of the resulting Diels-Alder cross-linked hydrogels can be tuned. Rheological and degradation studies demonstrate that the Diels-Alder click reaction is a suitable cross-linking method for HA. These HA cross-linked hydrogels were shown to be cytocompatible and may represent a promising material for soft tissue engineering.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocompatible Materials
  • Click Chemistry / methods*
  • Cross-Linking Reagents / chemistry
  • Hyaluronic Acid / chemistry
  • Hydrogels / chemical synthesis*
  • Hydrogels / chemistry
  • Tissue Engineering / methods*

Substances

  • Biocompatible Materials
  • Cross-Linking Reagents
  • Hydrogels
  • Hyaluronic Acid