Cited by 30Nitric Oxide and Endothelin EffectsHydrogels: synthesis, properties, applicationsAdvanced Drug Delivery Systems

Synthesis and Characterization of the Novel Nitric Oxide (NO) Donating Compound, S-nitroso-N-acetyl-D-penicillamine Derivatized Cyclam (SNAP-Cyclam)

McCarthy, Connor W., Goldman, Jeremy, Frost, Megan C.·2016·ACS Applied Materials & Interfaces

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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Crossref · 10.1021/acsami.5b12548

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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
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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