S-Nitrosoglutathione exhibits greater stability than S-nitroso-N-acetylpenicillamine under common laboratory conditions: A comparative stability study

Melvin, Alyssa C.; Jones, William; Lutzke, Alec; Allison, Christopher L.; Reynolds, Melissa M.

doi:10.1016/j.niox.2019.08.002

Cited by 40 publications

(42 citation statements)

References 41 publications

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“…The first transition, observed at 143 (±1) °C, is attributed to homolytic cleavage of the S–N bond resulting in evolution of NO. The decomposition temperature is shifted from the literature reported value for the thermal cleavage of the S–N bond by ∼8 °C, but this shift can be attributed to differences in experimental design and thermal heating parameters. The second transition, observed at 189 (±1) °C, is attributed to thermal decomposition of the remaining residue after loss of NO.…”

Section: Resultscontrasting

confidence: 60%

Thermogravimetric Analysis and Mass Spectrometry Allow for Determination of Chemisorbed Reaction Products on Metal Organic Frameworks

et al. 2020

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Thermogravimetric analysis (TGA) is a technique which can probe chemisorption of substrates onto metal organic frameworks. A TGA method was developed to examine the catalytic oxidation of S-nitrosoglutathione (GSNO) by the MOF H3[(Cu4Cl)3(BTTri)8] (abbr. Cu-BTTri; H3BTTri = 1,3,5-tris(1H-1,2,3-triazol-5-yl)benzene), yielding glutathione disulfide (GSSG) and nitric oxide (NO). Thermal analysis of reduced glutathione (GSH), GSSG, GSNO, and Cu-BTTri revealed thermal resolution of all four analytes through different thermal onset temperatures and weight percent changes. Two reaction systems were probed: an aerobic column flow reaction and an anaerobic solution batch reaction with gas agitation. In both systems, Cu-BTTri was reacted with a 1 mM GSH, GSSG, or GSNO solution, copiously rinsed with distilled–deionized water (dd-H2O), dried (25 °C, < 1 Torr), and assessed by TGA. Additionally, stock, effluent or supernatant, and rinse solutions for each glutathione derivative within each reaction system were assessed by mass spectrometry (MS) to inform on chemical transformations promoted by Cu-BTTri as well as relative analyte concentrations. Both reaction systems exhibited chemisorption of glutathione derivatives to the MOF by TGA. Mass spectrometry analyses revealed that in both systems, GSH was oxidized to GSSG, which chemisorbed to the MOF whereas GSSG remained unchanged during chemisorption. For GSNO, chemisorption to the MOF without reaction was observed in the aerobic column setup, whereas conversion to GSSG and subsequent chemisorption was observed in the anaerobic batch setup. These findings suggest that within this reaction system, GSSG is the primary adsorbent of concern with regards to strong binding to Cu-BTTri. Development of similar thermal methods could allow for the probing of MOF reactivity for a wide range of systems, informing on important considerations such as reduced catalytic efficiency from poisoning, recyclability, and loading capacities of contaminants or toxins with MOFs.

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Section: Resultscontrasting

confidence: 60%

Thermogravimetric Analysis and Mass Spectrometry Allow for Determination of Chemisorbed Reaction Products on Metal Organic Frameworks

et al. 2020

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“…Solid SNAP and GSNO decompose at 133 and 135 °C, respectively, which are lower than the temperature (>150 °C) required for traditional 3D printing of polymers based on fused deposition modeling. 38 These NO donors are also well-known to be sensitive to light. 38 Therefore, our 3D printing method based on the moisture curing silicone without using any heat or light is highly suited for printing of inks containing S-nitrosothiols.…”

Section: T H Imentioning

confidence: 99%

“…38 These NO donors are also well-known to be sensitive to light. 38 Therefore, our 3D printing method based on the moisture curing silicone without using any heat or light is highly suited for printing of inks containing S-nitrosothiols. Notably, our one-step method for the fabrication of devicedrug combination products is inherently different from previous work on 3D printing of drug-free polymer devices followed by coating of a NO donor layer 39 or solvent-assisted impregnation of the NO donor.…”

Section: T H Imentioning

confidence: 99%

“…Herein, we explored 3D printing of NO-releasing silicone rubber devices using a rationally formulated silicone ink containing S -nitrosothiol crystals. Solid SNAP and GSNO decompose at 133 and 135 °C, respectively, which are lower than the temperature (>150 °C) required for traditional 3D printing of polymers based on fused deposition modeling . These NO donors are also well-known to be sensitive to light .…”

Section: Introductionmentioning

confidence: 97%

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3D Printing of Antibacterial Polymer Devices Based on Nitric Oxide Release from Embedded S-Nitrosothiol Crystals

Yang

Ehrhardt

et al. 2021

ACS Appl. Bio Mater.

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Controlled release of drugs from medical implants is an effective approach to reducing foreign body reactions and infections. We report here on a one-step 3D printing strategy to create drug-eluting polymer devices with a drug-loaded bulk and a drug-free coating. The spontaneously formed drug-free coating dramatically reduces the surface roughness of the implantable devices and serves as a protective layer to suppress the burst release of drugs. A high viscosity liquid silicone that can be extruded based on its shear-thinning property and quickly vulcanize upon exposure to ambient moisture is used as the ink for 3D printing. S-Nitrosothiol type nitric oxide (NO) donors in their crystalline forms are selected as model drugs because of the potent antimicrobial, antithrombotic, and anti-inflammatory properties of NO. Direct ink writing of the homogenized polymer-drug mixtures generates rough and ill-defined device surfaces because of the exposed S-nitrosothiol microparticles. When a low-viscosity silicone (polydimethylsiloxane) is added into the ink, this silicone diffuses outward upon deposition to form a drug-free outermost layer without compromising the integrity of the printed structures. S-Nitrosoglutathione (GSNO) or S-nitroso-N-acetylpenicillamine (SNAP) embedded in the printed silicone matrix releases NO under physiological conditions from days to about one month. The microsized drug crystals are well-preserved in the ink preparation and printing processes, which is one reason for the sustained NO release. Biofilm and cytotoxicity experiments confirmed the antibacterial property and safety of the printed NO-releasing devices. This additive manufacturing platform does not require dissolution of drugs and involves no thermal or UV processes and, therefore, offers unique opportunities to produce drug-eluting silicone devices in a customized manner.

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“…On the other hand, SNAP and GSNO, in addition to releasing NO, can act mainly through trans-S-nitrosation reactions. Furthermore, the application of NO donors might result in nitrosative stress since there have been very few attempts to understand the kinetics of NO generation in planta by NO donors [15][16][17]. Thus, the use of mutants with altered endogenous NO content seems to be a more suitable way of assessing NO-modulated responses.…”

Section: Introductionmentioning

confidence: 99%

Nitric Oxide Overproduction by cue1 Mutants Differs on Developmental Stages and Growth Conditions

Lechón

Sanz

Sánchez-Vicente

et al. 2020

Plants

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The cue1 nitric oxide (NO) overproducer mutants are impaired in a plastid phosphoenolpyruvate/phosphate translocator, mainly expressed in Arabidopsis thaliana roots. cue1 mutants present an increased content of arginine, a precursor of NO in oxidative synthesis processes. However, the pathways of plant NO biosynthesis and signaling have not yet been fully characterized, and the role of CUE1 in these processes is not clear. Here, in an attempt to advance our knowledge regarding NO homeostasis, we performed a deep characterization of the NO production of four different cue1 alleles (cue1-1, cue1-5, cue1-6 and nox1) during seed germination, primary root elongation, and salt stress resistance. Furthermore, we analyzed the production of NO in different carbon sources to improve our understanding of the interplay between carbon metabolism and NO homeostasis. After in vivo NO imaging and spectrofluorometric quantification of the endogenous NO levels of cue1 mutants, we demonstrate that CUE1 does not directly contribute to the rapid NO synthesis during seed imbibition. Although cue1 mutants do not overproduce NO during germination and early plant development, they are able to accumulate NO after the seedling is completely established. Thus, CUE1 regulates NO homeostasis during post-germinative growth to modulate root development in response to carbon metabolism, as different sugars modify root elongation and meristem organization in cue1 mutants. Therefore, cue1 mutants are a useful tool to study the physiological effects of NO in post-germinative growth.

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S-Nitrosoglutathione exhibits greater stability than S-nitroso-N-acetylpenicillamine under common laboratory conditions: A comparative stability study

Cited by 40 publications

References 41 publications

Thermogravimetric Analysis and Mass Spectrometry Allow for Determination of Chemisorbed Reaction Products on Metal Organic Frameworks

Thermogravimetric Analysis and Mass Spectrometry Allow for Determination of Chemisorbed Reaction Products on Metal Organic Frameworks

3D Printing of Antibacterial Polymer Devices Based on Nitric Oxide Release from Embedded S-Nitrosothiol Crystals

Nitric Oxide Overproduction by cue1 Mutants Differs on Developmental Stages and Growth Conditions

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