Polyurethane with tethered copper(II)–cyclen complex: Preparation, characterization and catalytic generation of nitric oxide from S-nitrosothiols

Hwang, Sangyeul; Meyerhoff, Mark E.

doi:10.1016/j.biomaterials.2008.02.004

Cited by 82Nitric Oxide and Endothelin EffectsPolymer Surface Interaction StudiesConducting polymers and applications

Polyurethane with tethered copper(II)–cyclen complex: Preparation, characterization and catalytic generation of nitric oxide from S-nitrosothiols

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Hwang, Sangyeul, Meyerhoff, Mark E.·2008·Biomaterials

DOI 10.1016/j.biomaterials.2008.02.004PMC PMC2408722

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Abstract

The preparation and characterization of a commercial biomedical-grade polyurethane (Tecophilic((R)), SP-93A-100) material possessing covalently linked copper(II)-cyclen moieties as a nitric oxide (NO) generating polymer are described. Chemiluminescence NO measurements demonstrate that the prepared polymer can decompose endogenous S-nitrosothiols (RSNOs) such as S-nitrosoglutathione and S-nitrosocysteine to NO in the presence of thiol reducing agents (RSHs; e.g., glutathione and cysteine) at physiological pH. Since such RSNO and RSH species already exist in blood, the proposed polymer is capable of spontaneously generating NO when in contact with fresh blood. This is demonstrated by utilizing the polymer as an outer coating at the distal end of an amperometric NO sensor to create a device that generates response toward the RSNO species in the blood. This polymer possesses the combined benefits of a commercial biomedical-grade polyurethane with the ability to generate biologically active NO when in contact with blood, and thus may serve as a useful coating to improve the hemocompatibility of various medical devices.

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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 [170]
Meyerhoff and coworkers first covalently attached copper(II)-cyclen onto commercial biomedical grade polyurethane, which generates physiological levels of NO (1-2 × 10−10 mol cm−2 min−1) when in contact with endogenous RSNO and RSH species such as 10 μM GSNO/GSH in PBS with 3 μM EDTA.
“Meyerhoff and coworkers were the first to covalently attach copper(II)-cyclen onto commercial biomedical grade polyurethane, which can generate physiological levels of NO (1–2 × 10−10 mol cm−2 min−1) when in contact with endogenous RSNO and RSH species, such as 10 µM GSNO/GSH in PBS buffer containing 3 µM EDTA.170”
From Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO) (2016) · cites this paper as [170]
This polymer was used as an outer coating at the distal end of an amperometric NO sensor that generates an electrochemical response toward RSNO species in whole blood.
“This polymer has also been used as an outer coating at the distal end of an amperometric NO sensor that can generate electrochemical response toward the RSNO species in whole blood.170”
From Recent advances in thromboresistant and antimicrobial polymers for biomedical applications: just say yes to nitric oxide (NO) (2016) · cites this paper as [170]

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Metal ion‐mediated nitric oxide generation from polyurethanes via covalently linked copper(II)‐cyclen moieties
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Nitric Oxide Generating Polymers (NOGPs).
Hwang, S. (2007) · Deep Blue (University of Michigan)
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Biomimetic nitric oxide (NO) generation at interface of polymeric materials doped with lipophilic copper(II)-complex.
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Organoditelluride-tethered polymers that spontaneously generate nitric oxide when in contact with fresh blood
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Authors: Hwang, S., & Meyerhoff, M. E.
Affiliations: University of Michigan (US)
Corresponding author: Meyerhoff, Mark E.
ORCID: Meyerhoff, Mark E.
Venue: Biomaterials
Publisher: Elsevier BV
Published: 2008-06
Volume: 29
Issue: 16
Pages: 2443-2452
ISSN: 0142-9612 (ISSN-L)
DOI: 10.1016/j.biomaterials.2008.02.004
PMC: PMC2408722
OpenAlex: W1990869971
Cited by: 82
References: 55
Citations by year: 2026: 2 · 2025: 3 · 2024: 3 · 2023: 3 · 2022: 6 · 2021: 4 · 2020: 9 · 2019: 5 · 2018: 3 · 2017: 7 · 2016: 10 · 2015: 5 · 2014: 6 · 2013: 2 · 2012: 4
FWCI: 2.26
Type: journal article
Language: en
Open access: green
europepmc.org
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
doi.org/10.15223/policy-017 (stm-asf)
doi.org/10.15223/policy-037 (stm-asf)
doi.org/10.15223/policy-012 (stm-asf)
doi.org/10.15223/policy-029 (stm-asf)
doi.org/10.15223/policy-004 (stm-asf)
Locations: Biomaterials (publishedVersion)
PubMed (publishedVersion)
Europe PMC (PubMed Central) (acceptedVersion)
PubMed Central (acceptedVersion)
Funders: National Institutes of Health (EB-000783, EB-004527)
U.S. Army (W81XWH-05-1-0602)
Topics: Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
Physical Sciences › Materials Science › Surfaces, Coatings and Films › Polymer Surface Interaction Studies
Physical Sciences › Materials Science › Polymers and Plastics › Conducting polymers and applications
Keywords: polyurethane, nitric oxide production, S-nitrosothiols, S-nitrosoglutathione, S-nitrosocysteine, thiol reducing agents, chemiluminescence, hemocompatibility, medical device coatings
MeSH terms: Cyclams, Animals, Biocompatible Materials, Catalysis, Copper, Heterocyclic Compounds, Nitric Oxide, Polyurethanes, Sheep, S-Nitrosothiols

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Polyurethane with tethered copper(II)–cyclen complex: Preparation, characterization and catalytic generation of nitric oxide from S-nitrosothiols

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