title: Synthesis and Characterization of the Novel Nitric Oxide (NO) Donating Compound, S-nitroso-N-acetyl-D-penicillamine Derivatized Cyclam (SNAP-Cyclam).
abstract: Nitric oxide (NO) has been heavily studied over the past two decades due to its multitude of physiological functions and its potential therapeutic promise. Of major interest is the desire to fabricate or coat implanted devices with an NO releasing material that will impart the appropriate dose and duration of NO release to positively mediate the biological response to the medical device, thereby improving its safety and efficacy. To date, this goal has not yet been achieved, despite very promising early research. Herein, we describe the synthesis and NO release properties of a novel NO donor which covalently links the S-nitrosothiol, S-nitroso-N-acetyl-D-penicillamine (SNAP), to the macrocycle, cyclam (SNAP-cyclam). This compound can then be blended into a wide variety of polymer matrices, imparting NO release to the polymer system. This release can be initiated and controlled by transition metal catalysis, thermal degradation or photolytic release of NO from the composite NO-releasing material. SNAP-cyclam is capable of releasing physiologically relevant levels of NO for up to 3 months in vitro when blended into poly(l-lactic acid) thin films.
authors: Department of Biomedical Engineering, Michigan Technological University , Houghton, Michigan 49931, United States.
authors: Connor W
authors: CW
authors: McCarthy
authors: Department of Biomedical Engineering, Michigan Technological University , Houghton, Michigan 49931, United States.
authors: Jeremy
authors: J
authors: Goldman
authors: Department of Biomedical Engineering, Michigan Technological University , Houghton, Michigan 49931, United States.
authors: Megan C
authors: MC
authors: Frost
mesh_terms: D002851:Chromatography, High Pressure Liquid; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007700:Kinetics; D009569:Nitric Oxide / Q000032:analysis / Q000378:metabolism; D020030:Nitric Oxide Donors / Q000138:chemical synthesis* / Q000737:chemistry*; D011091:Polyesters / Q000737:chemistry; D026423:S-Nitroso-N-Acetylpenicillamine / Q000138:chemical synthesis / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D006571:Heterocyclic Compounds; D020030:Nitric Oxide Donors; D011091:Polyesters; C024560:cyclam; D009569:Nitric Oxide; C033616:poly(lactide); D026423:S-Nitroso-N-Acetylpenicillamine
keywords: controlled release; long-term; macrocycle; nitric oxide; poly(l-lactic acid)