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.
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Frost et al. developed a SNAP functionalized polymer matrix that can release NO via light-initiated SNAP decomposition.
“Frost et al. successfully develop a S-nitroso-N-acetyl-D-penicillamine functionalized polymer matrix (e.g., PDMS,226 cyclam243 and gelatin222) that can release NO via light-initiated SNAP decomposition.”
From Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO) (2016) · cites this paper as [243]
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- Authors
- McCarthy, C. W., Goldman, J., & Frost, M. C.
- Affiliations
- Michigan Technological University (US)
- Corresponding author
- Frost, Megan C.
- Venue
- ACS Applied Materials & Interfaces
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-02-26
- Volume
- 8
- Issue
- 9
- Pages
- 5898-5905
- ISSN
- 1944-8244 (ISSN-L)
- 1944-8252
- OpenAlex
- W2286994628
- Cited by
- 30
- References
- 22
- Citations by year
- 2026: 2 · 2025: 4 · 2024: 2 · 2022: 1 · 2021: 4 · 2020: 1 · 2019: 3 · 2018: 6 · 2017: 5 · 2016: 2
- FWCI
- 4.29
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- ACS Applied Materials & Interfaces (publishedVersion)
- PubMed (publishedVersion)
- Digital Commons - Michigan Tech (Michigan Technological University) (submittedVersion)
- Funders
- National Heart, Lung, and Blood Institute (R15HL113954)
- Division of Materials Research (1410192)
- Topics
- Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Medicine › Hydrogels: synthesis, properties, applications
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmaceutical Science › Advanced Drug Delivery Systems
- Keywords
- nitric oxide donors, S-nitrosothiols, NO release kinetics, transition metal catalysis, thermal degradation, polymer composites, medical device coatings, biomedical implants
- MeSH terms
- Chromatography, High Pressure Liquid, Heterocyclic Compounds, Kinetics, Nitric Oxide, Polyesters, Spectrophotometry, Ultraviolet, Spectroscopy, Fourier Transform Infrared, Nitric Oxide Donors, S-Nitroso-N-Acetylpenicillamine
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