title: S-nitroso-N-acetylpenicillamine (SNAP) derivatization of peptide primary amines to create inducible nitric oxide donor biomaterials.
abstract: An S-nitroso-N-acetylpenicillamine (SNAP) derivatization approach was used to modify existing free primary amines found in fibrin (a natural protein-based biomaterial) to generate a controlled nitric oxide (NO) releasing scaffold material. The duration of the derivatization reaction affects the NO release kinetics, the induction of controlled NO-release, hydrophobicity, swelling behavior, elastic moduli, rheometric character, and degradation behavior. These properties were quantified to determine changes in fibrin hydrogels following covalent attachment of SNAP. NO-releasing materials exhibited minimal cytotoxicity when cultured with fibroblasts or osteoblasts. Cells maintained viability and proliferative character on derivatized materials as demonstrated by Live/Dead cell staining and counting. In addition, SNAP-derivatized hydrogels exhibited an antimicrobial character indicative of NO-releasing materials. SNAP derivatization of natural polymeric biomaterials containing free primary amines offers a means to generate inducible NO-releasing biomaterials for use as an antimicrobial and regenerative support for tissue engineering.
authors: Department of Biomedical Engineering, College of Engineering, Michigan Technological University , 1400 Townsend Drive, Houghton, Michigan 49931, United States.
authors: Michael
authors: M
authors: VanWagner
authors: Jessica
authors: J
authors: Rhadigan
authors: Michael
authors: M
authors: Lancina
authors: Allison
authors: A
authors: Lebovsky
authors: Genevieve
authors: G
authors: Romanowicz
authors: Hal
authors: H
authors: Holmes
authors: Margaret A
authors: MA
authors: Brunette
authors: Katherine L
authors: KL
authors: Snyder
authors: Michael
authors: M
authors: Bostwick
authors: Bruce P
authors: BP
authors: Lee
authors: Megan C
authors: MC
authors: Frost
authors: Rupak M
authors: RM
authors: Rajachar
mesh_terms: D016475:3T3 Cells; D000588:Amines / Q000737:chemistry*; D000818:Animals; D001672:Biocompatible Materials / Q000737:chemistry* / Q000633:toxicity; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D005337:Fibrin / Q000737:chemistry*; D020100:Hydrogels / Q000737:chemistry / Q000633:toxicity; D057927:Hydrophobic and Hydrophilic Interactions; D051379:Mice; D020030:Nitric Oxide Donors / Q000737:chemistry*; D026423:S-Nitroso-N-Acetylpenicillamine / Q000737:chemistry*; D023822:Tissue Engineering
chemical_list: D000588:Amines; D001672:Biocompatible Materials; D020100:Hydrogels; D020030:Nitric Oxide Donors; D026423:S-Nitroso-N-Acetylpenicillamine; D005337:Fibrin