Catalytic generation of nitric oxide from S-nitrosothiols using immobilized organoselenium species
Abstract
Novel nitric oxide (NO) generating polymeric materials possessing immobilized organoselenium species are described. These materials mimic the capability of small organoselenium molecules as well as a known selenium-containing enzyme, glutathione peroxidase (GPx), by catalytically decomposing S-nitrosothiols (RSNO) into NO and the corresponding free thiol. Model polymeric materials, e.g., cellulose filter paper and polyethylenimine, are modified with an appropriate diselenide species covalently linked to the polymeric structures. Such organoselenium (RSe)-derivatized polymers are shown to generate NO from RSNO species in the presence of an appropriate thiol reducing agent (e.g., glutathione). The likely involvement of both immobilized selenol/selenolate and diselenide species for NO production is suggested via a catalytic pathway, as deduced in separate homogeneous solution phase experiments using non-immobilized forms of small organodiselenide species. Preliminary experiments with the new RSe-polymers clearly demonstrate the ability of such materials to generate NO from RSNO species even after the contact with fresh animal plasma. It is anticipated that such NO generation from endogenous S-nitrosothiols in blood could render RSe-containing polymeric materials more thromboresistant when in contact with flowing blood, owing to NO's ability to inhibit platelet adhesion and activation.
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Enzymes such as CuZn-SOD or GPx can convert RSNO to NO in the presence of a reducing agent like GSH.
“Further, certain enzymes such as copper-containing superoxide dismutase (CuZn-SOD)140,176 or the selenium-containing enzyme glutathione peroxidase (GPx)140,171,173 can also convert RSNO to NO in the presence of a reducing agent, such as glutathione (GSH)”
From Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO) (2016) · cites this paper as [171]
Metal ions such as copper or ferrous ions, or organoselenium compounds, can catalyze RSNO decomposition.
“Metal ions (such as copper or ferrous ions)169,170 or organoselenium compounds can catalyze RSNO decomposition.114,171–173”
From Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO) (2016) · cites this paper as [171]
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- Authors
- Cha, W., & Meyerhoff, M. E.
- Affiliations
- University of Michigan (US)
- Corresponding author
- Meyerhoff, Mark E.
- Venue
- Biomaterials
- Publisher
- Elsevier BV
- Published
- 2007-01
- Volume
- 28
- Issue
- 1
- Pages
- 19-27
- ISSN
- 0142-9612 (ISSN-L)
- OpenAlex
- W2164428662
- Cited by
- 140
- References
- 38
- Citations by year
- 2026: 4 · 2025: 10 · 2024: 8 · 2023: 6 · 2022: 16 · 2021: 12 · 2020: 10 · 2019: 9 · 2018: 9 · 2017: 11 · 2016: 6 · 2015: 7 · 2014: 6 · 2013: 3 · 2012: 4
- FWCI
- 5.57
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biomaterials (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Institute of Biomedical Imaging and Bioengineering (EB 004527, R01EB004527, EB-000783, R01EB000783)
- Eunice Kennedy Shriver National Institute of Child Health and Human Development (R01HD015434)
- Topics
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Organoselenium and organotellurium chemistry
- Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
- Physical Sciences › Materials Science › Surfaces, Coatings and Films › Polymer Surface Interaction Studies
- Keywords
- nitric oxide production, S-nitrosothiols, organoselenium compounds, diselenides, glutathione peroxidase mimicry, polyethyleneimine, cellulose filter paper, thromboresistance, platelet adhesion, hemocompatibility, catalytic decomposition
- MeSH terms
- Animals, Catalysis, Nitric Oxide, Polymers, Solutions, Swine, Molecular Structure, Organoselenium Compounds, S-Nitrosothiols
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