Diels−Alder Click Cross-Linked Hyaluronic Acid Hydrogels for Tissue Engineering
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, inc...
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| Veröffentlicht in: | Biomacromolecules 2011-03, Vol.12 (3), p.824-830 |
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| container_title | Biomacromolecules |
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| creator | Nimmo, Chelsea M Owen, Shawn C Shoichet, Molly S |
| description | 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. |
| doi_str_mv | 10.1021/bm101446k |
| format | Article |
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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. 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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.</description><subject>Applied sciences</subject><subject>Biocompatible Materials</subject><subject>Biological and medical sciences</subject><subject>Click Chemistry - methods</subject><subject>Cross-Linking Reagents - chemistry</subject><subject>Exact sciences and technology</subject><subject>Hyaluronic Acid - chemistry</subject><subject>Hydrogels - chemical synthesis</subject><subject>Hydrogels - chemistry</subject><subject>Medical sciences</subject><subject>Natural polymers</subject><subject>Physicochemistry of polymers</subject><subject>Starch and polysaccharides</subject><subject>Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases</subject><subject>Technology. Biomaterials. 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Transplantations, organ and tissue grafts. Graft diseases</topic><topic>Technology. Biomaterials. 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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.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>21314111</pmid><doi>10.1021/bm101446k</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Applied sciences Biocompatible Materials Biological and medical sciences Click Chemistry - methods Cross-Linking Reagents - chemistry Exact sciences and technology Hyaluronic Acid - chemistry Hydrogels - chemical synthesis Hydrogels - chemistry Medical sciences Natural polymers Physicochemistry of polymers Starch and polysaccharides Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases Technology. Biomaterials. Equipments Tissue Engineering - methods |
| title | Diels−Alder Click Cross-Linked Hyaluronic Acid Hydrogels for Tissue Engineering |
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