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Diels−Alder Click Cross-Linked Hyaluronic Acid Hydrogels for Tissue Engineering

2011; American Chemical Society; Volume: 12; Issue: 3 Linguagem: Inglês

10.1021/bm101446k

1526-4602

Chelsea M. Nimmo, Shawn C. Owen, Molly S. Shoichet,

3D Printing in Biomedical Research

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.