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Preparation and characterization of an improved Cu(2+)-cyclen polyurethane material that catalyzes generation of nitric oxide from S-nitrosothiols.

ABSTRACT: A new, stable and highly efficient Cu(2+)-cyclen-polyurethane material is described and shown to exhibit improved performance compared to prior materials for the catalytic decomposition of S-nitrosothiols to physiologically active nitric oxide.

SUBMITTER: Liu K

PROVIDER: S-EPMC3462352 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Preparation and characterization of an improved Cu(2+)-cyclen polyurethane material that catalyzes generation of nitric oxide from S-nitrosothiols.

Liu Kun K Meyerhoff Mark E ME

Journal of materials chemistry 20120101 36

A new, stable and highly efficient Cu(2+)-cyclen-polyurethane material is described and shown to exhibit improved performance compared to prior materials for the catalytic decomposition of S-nitrosothiols to physiologically active nitric oxide. ...[more]

PMID: 23049170

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

Project description: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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Photochemistry of nitric oxide and S-nitrosothiols in human skin.

Project description:Nitric oxide (NO) is related to a wide range of physiological processes such as vasodilation, macrophages cytotoxicity and wound healing. The human skin contains NO precursors (NOx). Those are mainly composed of nitrite (NO2-), nitrate (NO3-), and S-nitrosothiols (RSNOs) which forms a large NO store. These NOx stores in human skin can mobilize NO to blood stream upon ultraviolet (UV) light exposure. The main purpose of this study was to evaluate the most effective UV light wavelength to generate NO and compare it to each NO precursor in aqueous solution. In addition, the UV light might change the RSNO content on human skin. First, we irradiated pure aqueous solutions of NO2- and NO3- and mixtures of NO2- and glutathione and NO3- and S-nitrosoglutathione (GSNO) to identify the NO release profile from those species alone. In sequence, we evaluated the NO generation profile on human skin slices. Human skin was acquired from redundant plastic surgical samples and the NO and RSNO measurements were performed using a selective NO electrochemical sensor. The data showed that UV light could trigger the NO generation in skin with a peak at 280-285 nm (UVB range). We also observed a significant RSNO formation in irradiated human skin, with a peak at 320 nm (UV region) and at 700 nm (visible region). Pre-treatment of the human skin slice using NO2- and thiol (RSHs) scavengers confirmed the important role of these molecules in RSNO formation. These findings have important implications for clinical trials with potential for new therapies.

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Synthesis and nitric oxide releasing properties of novel fluoro S-nitrosothiols.

Project description:A series of new fluoro S-nitrosothiols is reported as potential nitric oxide (NO) donors. A three-step synthesis and the NO releasing kinetic profiles of these species are presented. The stoichiometric release of NO, with the clean formation of corresponding disulfides, confirms that these new species can facilitate their application as NO donors for various applications including creating novel antimicrobial and thromboresistant fluoropolymer-based medical devices.

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Nitric oxide-releasing silica nanoparticle-doped polyurethane electrospun fibers.

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Fabrication of nitric oxide-releasing polyurethane glucose sensor membranes.

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Active Release of Nitric Oxide-Releasing Dendrimers from Electrospun Polyurethane Fibers.

Project description:The fabrication of electrospun composite polyurethane fibers capable of dual-action antibacterial dendrimer release is reported. Generation 4 (G4) poly(amidoamine) dendrimers were functionalized with octyl alkyl chain or quaternary ammonium (QA) moieties followed by modification of the resulting secondary amines with N-diazeniumdiolate nitric oxide (NO) donors to produce dual-action antibacterial dendrimers. Control and NO-releasing dendrimers were doped into polyurethane solutions prior to electrospinning of the polymer to yield well-defined dendrimer-doped composite polyurethane fibers. The fiber mats were semi-porous (?30% porosity) and exhibited high water uptake (>100% relative to fiber mass). Dendrimer- and NO-release characteristics (rates and totals) were dependent on the dendrimer modification and polyurethane composition, with total dendrimer- and NO-release amounts ranging from 10 - 80 ?g/mg and 0.027 - 0.072 ?mol NO/mg, respectively. The antibacterial action of the fibers was evaluated against Gram-negative and Gram-positive bacterial strains. Nitric oxide-releasing fibers demonstrated broad-spectrum bactericidal action at short (2 h) and long (24 h) timescales.

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S-nitrosothiols regulate nitric oxide production and storage in plants through the nitrogen assimilation pathway.

Project description:Nitrogen assimilation plays a vital role in plant metabolism. Assimilation of nitrate, the primary source of nitrogen in soil, is linked to the generation of the redox signal nitric oxide (NO). An important mechanism by which NO regulates plant development and stress responses is through S-nitrosylation, that is, covalent attachment of NO to cysteine residues to form S-nitrosothiols (SNO). Despite the importance of nitrogen assimilation and NO signalling, it remains largely unknown how these pathways are interconnected. Here we show that SNO signalling suppresses both nitrate uptake and reduction by transporters and reductases, respectively, to fine tune nitrate homeostasis. Moreover, NO derived from nitrate assimilation suppresses the redox enzyme S-nitrosoglutathione Reductase 1 (GSNOR1) by S-nitrosylation, preventing scavenging of S-nitrosoglutathione, a major cellular bio-reservoir of NO. Hence, our data demonstrates that (S)NO controls its own generation and scavenging by modulating nitrate assimilation and GSNOR1 activity.

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Design Considerations for Silica-Particle-Doped Nitric-Oxide-Releasing Polyurethane Glucose Biosensor Membranes.

Project description:Nitric oxide (NO)-releasing polymers have proven useful for improving the biocompatibility of in vivo glucose biosensors. Unfortunately, leaching of the NO donor from the polymer matrix remains a critical design flaw of NO-releasing membranes. Herein, a toolbox of NO-releasing silica nanoparticles (SNPs) was utilized to systematically evaluate SNP leaching from a diverse selection of biomedical-grade polyurethane sensor membranes. Glucose sensor analytical performance and NO-release kinetics from the sensor membranes were also evaluated as a function of particle and polyurethane (PU) chemistries. Particles modified with N-diazeniumdiolate NO donors were prone to leaching from PU membranes due to the zwitterionic nature of the NO donor modification. Leaching was minimized (<5% of the entrapped silica over 1 month) in low water uptake PUs. However, SNP modification with neutral S-nitrosothiol (RSNO) NO donors lead to biphasic leaching behavior. Particles with low alkanethiol content (<3.0 wt % sulfur) leached excessively from a hydrogel PU formulation (HP-93A-100 PU), while particles with greater degrees of thiol modification did not leach from any of the PUs tested. A functional glucose sensor was developed using an optimized HP-93A-100 PU membrane doped with RSNO-modified SNPs as the outer, glucose diffusion-limiting layer. The realized sensor design responded linearly to physiological concentrations of glucose (minimum 1-21 mM) over 2 weeks incubation in PBS and released NO at >0.8 pmol cm-2 s-1 for up to 6 days with no detectable (<0.6%) particle leaching.

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Fabrication of nitric oxide-releasing porous polyurethane membranes-coated needle-type implantable glucose biosensors.

Project description:The active release of pharmaceutical agents and the use of porous sensor membranes represent the two most promising strategies for addressing the poor tissue biocompatibility of implantable glucose biosensors. Herein, we describe the combination of these approaches to create nitric oxide (NO)-releasing porous fiber mat-modified sensor membranes. An electrospinning method was used to directly modify needle-type glucose biosensors with the NO donor-loaded fibers. The resulting NO-releasing fiber mat (540 ± 139 nm fiber diameter, 94.1 ± 3.7% porosity) released ~100 nmol of NO per mg of polyurethane over 6 h while maintaining a porous structure without leaching of the NO donor, even in serum. The porous fiber membrane did not influence the analytical performance of the biosensor when ?50 ?m thick.

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Nitric oxide-releasing polyurethane/<i>S</i>-nitrosated keratin mats for accelerating wound healing.

Project description:Nitric oxide (NO) plays an important role in wound healing, due to its ability to contract wound surfaces, dilate blood vessels, participate in inflammation as well as promote collagen synthesis, angiogenesis and fibroblast proliferation. Herein, keratin was first nitrosated to afford S-nitrosated keratin (KSNO). As a NO donor, KSNO was then co-electrospun with polyurethane (PU). These as-spun PU/KSNO biocomposite mats could release NO sustainably for 72 h, matching the renewal time of the wound dressing. Moreover, these mats exhibited excellent cytocompatibility with good cell adhesion and cell migration. Further, the biocomposite mats exhibited antibacterial properties without inducing severe inflammatory responses. The wound repair in vivo demonstrated that these mats accelerated wound healing by promoting tissue formation, collagen deposition, cell migration, re-epithelialization and angiogenesis. Overall, PU/KSNO mats may be promising candidates for wound dressing.

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