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Controlled light-induced gas phase nitric oxide release from S-nitrosothiol-doped silicone rubber films.

ABSTRACT: The light induced nitric oxide (NO) release properties of S-nitroso-N-acetylpenicillamine (SNAP) and S-nitrosoglutathione (GSNO) NO donors doped within polydimethylsiloxane (PDMS) films (PDMS-SNAP and PDMS-GSNO respectively) for potential inhaled NO (iNO) applications is examined. To achieve photolytic release of gas phase NO from the PDMS-SNAP and PDMS-GSNO films, narrow-band LED light sources are employed and the NO concentration in a N₂ sweep gas above the film is monitored with an electrochemical NO sensor. The NO release kinetics using LED sources with different nominal wavelengths and optical power densities are reported. The effect of the NO donor loading within the PDMS films is also examined. The NO release levels can be controlled by the LED triggered release from the NO donor-doped silicone rubber films in order to generate therapeutic levels in a sweep gas for suitable durations potentially useful for iNO therapy. Hence this work may lay the groundwork for future development of a highly portable iNO system for treatment of patients with pulmonary hypertension, hypoxemia, and cystic fibrosis.

SUBMITTER: Lautner G

PROVIDER: S-EPMC8740643 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Feedback-controlled photolytic gas phase nitric oxide delivery from S-nitrosothiol-doped silicone rubber films.

Project description:Constant therapeutic gas phase nitric oxide (NO) delivery is achieved from S-nitrosothiol (RSNO) type NO donor doped silicone rubber films using feedback-controlled photolysis. For photo-release of the NO gas, the intensity of the LED light source is controlled via a PID (proportional-integral-derivative) controller implemented on a microcontroller. The NO concentration within the emitted gas phase is monitored continuously with a commercial amperometric NO gas sensor. NO release was accurately adjustable up to 10?ppm across a broad range of setpoints with response times of roughly 1?min or less. When NO is generated into an air recipient stream, lower NO yields and a comparable level of toxic nitrogen dioxide (NO2) formation is observed. However, NO gas generated into an N2 recipient gas stream can be blended into pure O2 with very low NO2 formation. Following scale-up, this technology could be used for point-of-care gas phase NO generation as an alternative for currently used gas cylinder technology for treatment of health conditions where inhaled NO is beneficial, such as pulmonary hypertension, hypoxemia, and cystic fibrosis.

| S-EPMC7895313 | biostudies-literature

Electrochemically Modulated Nitric Oxide Release From Flexible Silicone Rubber Patch: Antimicrobial Activity For Potential Wound Healing Applications.

Project description:Herein, we report a novel design and the antimicrobial efficacy of a flexible nitric oxide (NO) releasing patch for potential wound healing applications. The compact sized polydimethylsiloxane (PDMS) planar patch generates NO via electrochemical reduction of nitrite ions mediated by a copper(II)-ligand catalyst using a portable power system and an internal gold coated stainless steel mesh working electrode. Patches are fabricated via soft lithography and 3-D printing. The devices can continuously release NO over 4 days and exhibit potent bactericidal effects on both Escherichia coli and Staphylococcus aureus. The device may provide an effective, safe, and less costly alternative for treating chronic wounds.

| S-EPMC5022776 | biostudies-literature

Biodegradable crosslinked polyesters derived from thiomalic acid and S-nitrosothiol analogues for nitric oxide release.

Project description:Crosslinked polyesters with Young's moduli similar to that of certain soft biological tissues were prepared via bulk polycondensation of thiomalic acid and 1,8-octanediol alone, and with citric or maleic acid. The copolymers were converted to nitric oxide (NO)-releasing S-nitrosothiol (RSNO) analogues by reaction with tert-butyl nitrite. Additional conjugation steps were avoided by inclusion of the thiolated monomer during the polycondensation to permit thiol conversion to RSNOs. NO release at physiological pH and temperature (pH 7.4, 37 °C) was determined by chemiluminescence-based NO detection. The average total NO content for poly(thiomalic-co-maleic acid-co-1,8-octanediol), poly(thiomalic-co-citric acid-co-1,8-octanediol), and poly(thiomalic acid-co-1,8-octanediol) was 130 ± 39 ?mol g-1, 200 ± 35 ?mol g-1, and 130 ± 11 ?mol g-1, respectively. The antibacterial properties of the S-nitrosated analogues were confirmed against Escherichia coli and Staphylococcus aureus. The hydrolytic degradation products were analyzed by time-of-flight mass spectrometry after a 10-week study to investigate their composition. Tensile mechanical tests were performed on the non-nitrosated polymers as well as their S-nitrosated derivatives and suggested that the materials have appropriate Young's moduli and elongation values for biomedical applications.

| S-EPMC6675467 | biostudies-literature

S-nitrosothiol-modified dendrimers as nitric oxide delivery vehicles.

Project description:The synthesis and characterization of two generation-4 polyamidoamine (PAMAM) dendrimers with S-nitrosothiol exteriors are reported. The hyperbranched macromolecules were modified with either N-acetyl-D, L-penicillamine (NAP) or N-acetyl-L-cysteine (NACys) and analyzed via 1H and 13C NMR, UV absorption spectroscopy, MALDI-TOF mass spectrometry, and size exclusion chromatography. Treatment of the dendritic thiols with nitrite solutions yielded the corresponding S-nitrosothiol nitric oxide (NO) donors (G4-SNAP, G4-NACysNO). Chemiluminescent NO detection demonstrated that the dendrimers were capable of storing approximately 2 micromol NO x mg (-1) when exposed to triggers of S-nitrosothiol decomposition (e.g., light and copper). The kinetics of NO release were found to be highly dependent on the structure of the nitrosothiol (i.e., tertiary vs primary) and exhibited similar NO release characteristics to classical small molecule nitrosothiols reported in the literature. As a demonstration of utility, the ability of G4-SNAP to inhibit thrombin-mediated platelet aggregation was assayed. At equivalent nitrosothiol concentrations (25 microM), the G4-SNAP dendrimer resulted in a 62% inhibition of platelet aggregation, compared to only 17% for the small molecule NO donor. The multivalent NO storage, the dendritic effects exerted on nitrosothiol stability and reactivity, and the utility of dendrimers as drug delivery vehicles highlight the potential of these constructs as clinically useful S-nitrosothiol-based therapeutics.

| S-EPMC3564213 | biostudies-literature

Photoinitiated nitric oxide-releasing tertiary S-nitrosothiol-modified xerogels.

Project description:The synthesis of a tertiary thiol-bearing silane precursor (i.e., N-acetyl penicillamine propyltrimethoxysilane or NAPTMS) to enable enhanced NO storage stability at physiological temperature is described. The novel silane was co-condensed with alkoxy- or alkylalkoxysilanes under varied synthetic parameters (e.g., water to silane ratio, catalyst and solvent concentrations, and reaction time) to evaluate systematically the formation of stable xerogel films. The resulting xerogels were subsequently nitrosated to yield tertiary RSNO-modified coatings. Total NO storage ranged from 0.87 to 1.78 μmol cm(-2) depending on the NAPTMS concentration and xerogel coating thickness. Steric hindrance near the nitroso functionality necessitated the use of photolysis to liberate NO. The average NO flux for irradiated xerogels (20% NAPTMS balance TEOS xerogel film cast using 30 μL) in physiological buffer at 37 °C was ∼23 pmol cm(-2) s(-1). The biomedical utility of the photoinitiated NO-releasing films was illustrated by their ability to both reduce Pseudomonas aeruginosa adhesion by ∼90% relative to control interfaces and eradicate the adhered bacteria.

| S-EPMC3288218 | biostudies-literature

Diazeniumdiolate-doped poly(lactic-co-glycolic acid)-based nitric oxide releasing films as antibiofilm coatings.

Project description:Nitric oxide (NO) releasing films with a bilayer configuration are fabricated by doping dibutyhexyldiamine diazeniumdiolate (DBHD/N2O2) in a poly(lactic-co-glycolic acid) (PLGA) layer and further encapsulating this base layer with a silicone rubber top coating. By incorporating pH sensitive dyes within the films, pH changes in the PLGA layer are visualized and correlated with the NO release profiles (flux vs. time). It is demonstrated that PLGA acts as both a promoter and controller of NO release from the coating by providing protons through its intrinsic acid residues (both end groups and monomeric acid impurities) and hydrolysis products (lactic acid and glycolic acid). Control of the pH changes within the PLGA layer can be achieved by adjusting the ratio of DBHD/N2O2 and utilizing PLGAs with different hydrolysis rates. Coatings with a variety of NO release profiles are prepared with lifetimes of up to 15 d at room temperature (23 °C) and 10 d at 37 °C. When incubated in a CDC flow bioreactor for a one week period at RT or 37 °C, all the NO releasing films exhibit considerable antibiofilm properties against gram-positive Staphylococcus aureus and gram-negative Escherichia coli. In particular, compared to the silicone rubber surface alone, an NO releasing film with a base layer of 30 wt% DBHD/N2O2 mixed with poly(lactic acid) exhibits an ∼98.4% reduction in biofilm biomass of S. aureus and ∼99.9% reduction for E. coli at 37 °C. The new diazeniumdiolate-doped PLGA-based NO releasing coatings are expected to be useful antibiofilm coatings for a variety of indwelling biomedical devices (e.g., catheters).

| S-EPMC3432167 | biostudies-literature

Extended Nitric Oxide-Releasing Polyurethanes via S-Nitrosothiol-Modified Mesoporous Silica Nanoparticles.

Project description:S-Nitrosothiol (RSNO)-modified mesoporous silica nanoparticles (MSNs) were doped into polyurethane (PU) to achieve extended NO-releasing coatings. Parameters influencing the synthesis of RSNO-functionalized nitric oxide (NO)-releasing MSNs were evaluated to elucidate the impact of pore structure on NO release characteristics. The porous particles were characterized as having larger NO payloads and longer NO release durations than those of nonporous particles, a feature attributed to the recombination of the NO radical in confined intraporous microenvironments. NO release kinetics, particle leaching, and thermal stability of the RSNO-modified MSNs dispersed in PU were evaluated as a function of PU structure to determine the feasibility of preparing a range of NO-releasing polymers for biomedical device-coating applications. The NO release kinetics from the PUs proved to be highly extended (>30 d) and consistent over a range of PU properties. Furthermore, RSNO-modified MSN leaching was not observed from the PUs. The NO release payloads were also maintained for 4 days for polymers stored at 0 °C.

| S-EPMC6773253 | biostudies-literature

The preparation and characterization of nitric oxide releasing silicone rubber materials impregnated with <i>S</i>-nitroso-<i>tert</i>-dodecyl mercaptan.

Project description:Recently, considerable research efforts have focused on increasing the biocompatibility a nd bactericidal activity of biomedical polymeric devices (e.g., catheters, etc.) through incorporation of nitric oxide (NO) releasing molecules. NO is an important endogenous molecule that is well known for enhancing blood flow via its vasodilatory activity, but it also exhibits potent antithrombotic and antimicrobial properties. In this work, we demonstrate that silicone rubber tubing can be impregnated with a tertiary S-nitrosothiol (RSNO), S-nitroso-tert-dodecylmercaptan, via a simple solvent swelling method. We further characterize the NO release and RSNO leaching from the tubing over time via use of chemiluminescence and UV/Vis spectroscopy, respectively. The tubing is shown to maintain an NO flux above the physiological levels released by endothelial cells, 0.5-4.0 × 10-10 molcm-2min-1, for more than 3 weeks while stored at 37 °C and exhibit minimal leaching. Finally, the RSNO impregnated tu bing exhibits significant antimicrobial activity over a 21 d period (vs. controls) during incubation in a CDC bioreactor after inoculation of media with S. aureus bacteria. The use of such lipophilic RSNO impregnated silicone rubber tubing could dramatically reduce the risk of catheter-related infections, which are a common problem associated with placement of intravascular or urinary catheters.

| S-EPMC4826759 | biostudies-literature

Light-triggered nitric oxide (NO) release from photoresponsive polymersomes for corneal wound healing.

Project description:Polymersomes have been extensively used in the delivery of both small and macromolecular payloads. However, the controlled delivery of gaseous therapeutics (e.g., nitric oxide, NO) remains a grand challenge due to its difficulty in loading of gaseous payloads into polymersomes without premature leakage. Herein, NO-releasing vesicles could be fabricated via the self-assembly of NO-releasing amphiphiles, which were synthesized by the direct polymerization of photoresponsive NO monomers (abbreviated as oNBN, pNBN, and BN). These monomers were rationally designed through the integration of the photoresponsive behavior of N-nitrosoamine moieties and the self-immolative chemistry of 4-aminobenzyl alcohol derivatives, which outperformed conventional NO donors such as diazeniumdiolates (NONOates) and S-nitrosothiols (SNOs) in terms of ease of preparation, stability of storage, and controllability of NO release. The unique design made it possible to selectively release NO by a light stimulus and to regulate the NO release rates. Importantly, the photo-mediated NO release could be manipulated in living cells and showed promising applications in the treatment of corneal wounds. In addition to delivering NO, the current design enabled the synergistic delivery of NO and other therapeutic payloads by taking advantage of NO release-mediated traceless crosslinking of the vesicles.

| S-EPMC7012058 | biostudies-literature

Nitric oxide induces Zn2+ release from metallothionein by destroying zinc-sulphur clusters without concomitant formation of S-nitrosothiol.

Project description:The reaction of nitric oxide (NO) with metallothionein (MT) has been investigated at neutral pH under strictly anaerobic conditions. It is observed that NO mediates zinc release from MT by destroying zinc-sulphur clusters, but that it does not by itself S-nitrosylate MT in contrast to common belief. Zinc release and loss of thiolate groups under anaerobic conditions is found to be much slower than under aerobic conditions. The observed percentage loss of Zn(2+) and thiolate groups after 3 h of NO treatment are 62 and 39%, respectively. The reaction of NO with cysteine is reinvestigated and it is found that cysteine is quantitatively converted to cystine after 5 min of NO treatment at pH 7.3. At lower pH, a much lower rate of conversion is observed confirming the base-catalysed nature of the reaction of NO with thiols. On the basis of these results, a reaction mechanism involving electrophilic attack of NO on thiolate groups and subsequent formation of a nitrogen-centred radical, MTSN(. )OH, as intermediate is proposed for the reaction of NO with MT that leads to zinc release.

| S-EPMC1220638 | biostudies-other

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