title: Diels-Alder Click cross-linked hyaluronic acid hydrogels for tissue engineering.
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.
authors.affiliation: The Donnelly Centre for Cellular and Biomolecular Research, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada.
authors.forename: Chelsea M
authors.initials: CM
authors.lastname: Nimmo
authors.forename: Shawn C
authors.initials: SC
authors.lastname: Owen
authors.forename: Molly S
authors.initials: MS
authors.lastname: Shoichet
mesh_terms: D001672:Biocompatible Materials; D057930:Click Chemistry / Q000379:methods*; D003432:Cross-Linking Reagents / Q000737:chemistry; D006820:Hyaluronic Acid / Q000737:chemistry; D020100:Hydrogels / Q000138:chemical synthesis* / Q000737:chemistry; D023822:Tissue Engineering / Q000379:methods*
chemical_list: D001672:Biocompatible Materials; D003432:Cross-Linking Reagents; D020100:Hydrogels; D006820:Hyaluronic Acid