81739-40-4

Usage

InChI:InChI=1/C7H12N2O4S/c1-4(10)8-5(6(11)12)7(2,3)14-9-13/h5H,1-3H3,(H,8,10)(H,11,12)/t5-/m1/s1

Upstream product

• 2510-38-5 N-acetyl-L-penicillamine 
• 359699-80-2 C₁₇H₂₃N₃O₃S₂ 
• 59-53-0 NAP 
• 60285-31-6 N,N'-diphenyl-N-nitroso-urea 
• 67616-44-8 2-hydroxy-S-nitrosoethanethiol 
• 52-66-4 DL-Penicillamin 
• 79032-48-7 S-nitroso-N-acetylpenicillamine 
• 67616-42-6 S-nitroso-2-aminoethanethiol 
• 67616-46-0 S-nitroso-3-mercaptopropionic acid 
• 57564-91-7 S-Nitrosoglutathione 
• 166667-89-6 (S)-nitroso-L-cysteine ethyl ester 
• 134469-02-6 S-nitroso-L-cysteine 
• 70015-86-0 1-(2-chloroethyl)-1-nitroso-3-(3-pyridylmethyl)urea N-oxide 
• 273921-90-7 S-nitroso-N-acetyl-penicillamine 

Downstream Products

• 79032-48-7 S-nitroso-N-acetylpenicillamine 
• 70527-85-4 2-Acetylamino-3-methyl-3-(toluene-4-sulfonylsulfanyl)-butyric acid 
• 67809-84-1 N-acetyl-D,L-penicillamine disulfide 

Relevant academic research and scientific papers

Versatile new reagent for nitrosation under mild conditions

Here we report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures and is effective for transnitrosation in multiple solvents. Compared with traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso compounds are accessed here for the first time, including 15N isotopologues. X-ray data confirm that two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization effects.

NITROSATION REAGENTS AND METHODS

Provided are compounds that can find use as nitrosation reagents. Provided are nitrosation methods that include reacting a substrate with one of the provided nitrosation reagents and thereby generating a nitrosation product. Provided are kits including a nitrosation reagent. Provided are compositions wherein the nitrosation reagent is enriched in the 15N isotope.

Nitric oxide-releasing packaging membranes

Biodegradable composite membranes with antimicrobial properties consisting of nanocellulose fibrils, chitosan, and S-Nitroso-N-acetylpenicillamine (SNAP) were developed and tested for food packaging applications. Nitric oxide donor, SNAP was encapsulated into completely dispersed chitosan in 100 mL, 0.1N acetic acid and was thoroughly mixed with nanocellulose fibrils (CNF) to produce a composite membrane. The fabricated membranes had a uniform dispersion of chitosan and SNAP within the nanocellulose fibrils, which was confirmed through Scanning Electron Microscopy (SEM) micrographs and chemiluminescence nitric oxide analyzer. The membranes prepared without SNAP showed lower water vapor permeability than that of the membranes with SNAP. The addition of SNAP resulted in a decrease in the Young's modulus for both 2-layer and 3-layer membrane configurations. Antimicrobial property evaluation of SNAP incorporated membranes showed an effective zone of inhibition against bacterial strains of Enterococcus faecalis, Staphylococcus aureus, and Listeria monocytogenes and demonstrated its potential applications for food packaging.

Direct measurement of actual levels of nitric oxide (NO) in cell culture conditions using soluble NO donors

Applying soluble nitric oxide (NO) donors is the most widely used method to expose cells of interest to exogenous NO. Because of the complex equilibria that exist between components in culture media, the donor compound and NO itself, it is very challenging to predict the dose and duration of NO cells actually experience. To determine the actual level of NO experienced by cells exposed to soluble NO donors, we developed the CellNO Trap, a device that allows continuous, real-time monitoring of the level of NO adherent cells produce and/or experience in culture without the need to alter cell culturing procedures. Herein, we directly measured the level of NO that cells grown in the CellNO Trap experienced when soluble NO donors were added to solutions in culture wells and we characterized environmental conditions that effected the level of NO in in vitro culture conditions. Specifically, the dose and duration of NO generated by the soluble donors S-nitroso-N-acetylpenicillamine (SNAP), S-nitrosoglutathione (GSNO), S-nitrosocysteine (CysNO) and the diazeniumdiolate diethyltriamine (DETA/NO) were investigated in both phosphate buffered saline (PBS) and cell culture media. Other factors that were studied that potentially affect the ultimate NO level achieved with these donors included pH, presence of transition metals (ion species), redox level, presence of free thiol and relative volume of media. Then murine smooth muscle cell (MOVAS) with different NO donors but with the same effective concentration of available NO were examined and it was demonstrated that the cell proliferation ratio observed does not correlate with the half-lives of NO donors characterized in PBS, but does correlate well with the real-time NO profiles measured under the actual culture conditions. This data demonstrates the dynamic characteristic of the NO and NO donor in different biological systems and clearly illustrates the importance of tracking individual NO profiles under the actual biological conditions.

Reduction in thrombosis and bacterial adhesion with 7 day implantation of S-nitroso-N-acetylpenicillamine (SNAP)-doped Elast-eon E2As catheters in sheep

Thrombosis and infection are two common problems associated with blood-contacting medical devices such as catheters. Nitric oxide (NO) is known to be a potent antimicrobial agent as well as an inhibitor of platelet activation and adhesion. Healthy endothelial cells that line the inner walls of all blood vessels exhibit a NO flux of 0.5-4 × 10-10 mol cm-2 min-1 that helps prevent thrombosis. Materials with a NO flux that is equivalent to this level are expected to exhibit similar anti-thrombotic properties. In this study, NO-releasing catheters were fabricated by incorporating S-nitroso-N-acetylpenicillamine (SNAP) in the Elast-eon E2As polymer. The SNAP/E2As catheters release physiological levels of NO for up to 20 days, as measured by chemiluminescence. Furthermore, SNAP is stable in the E2As polymer, retaining 89% of the initial SNAP after ethylene oxide (EO) sterilization. The SNAP/E2As and E2As control catheters were implanted in sheep veins for 7 days to examine the effect on thrombosis and bacterial adhesion. The SNAP/E2As catheters reduced the thrombus area when compared to the control (1.56 ± 0.76 and 5.06 ± 1.44 cm2, respectively). A 90% reduction in bacterial adhesion was also observed for the SNAP/E2As catheters as compared to the controls. The results suggest that the SNAP/E2As polymer has the potential to improve the hemocompatibility and bactericidal activity of intravascular catheters, as well as other blood-contacting medical devices (e.g., vascular grafts, extracorporeal circuits). This journal is

THROMBORESISTANT/BACTERICIDAL S-NITROSO-N-ACETYLPENICILLAMINE (SNAP)-DOPED NITRIC OXIDE RELEASE POLYMERS WITH ENHANCED STABILITY

In an example of a method for making an NO-releasing polymeric composition, a discrete RSNO adduct is dissolved in a solvent to form a discrete RSNO adduct solution. A polymer material is soaked in the discrete RSNO adduct solution for a predetermined time to swell the polymer material and impregnate the polymer material with the discrete RSNO adduct.

Synergistic activity of acetohydroxamic acid on prokaryotes under oxidative stress: The role of reactive nitrogen species

One-electron oxidation of acetohydroxamic acid (aceto-HX) initially gives rise to nitroxyl (HNO), which can be further oxidized to nitric oxide (NO) or react with potential biological targets such as thiols and metallo-proteins. The distinction between th

S-nitrosothiol chemistry at the single-molecule level

SNO patrol: S-Nitrosothiols (RSNO) are important molecules involved in cell signaling, which control physiological processes such as vasodilation and bronchodilation. By using the protein pore α-hemolysin as a nanoreactor, the biological chemistry of RSNO has been investigated at the single-molecule level (see scheme). Copyright

Formation of the distinct redox-interrelated forms of nitric oxide from reaction of dinitrosyl iron complexes (DNICs) and substitution ligands

Release of the distinct NO redox-interrelated forms (NO+, NO, and HNO/NO-), derived from reaction of the dinitrosyl iron complex (DNIC) [(NO)2Fe(C12HaN)2]- (1) (C12H8N = carbazolate) and the substitution Iigands (S2CNMe2)2, [SC6H 4-O-NHC(O)(C5H4N)]2, ((PyPepS) 2), and P(C6H3,-3SiMe3-2-SH) 3 ([P(SH)3]), respectively, was demonstrated. In contrast to the reaction of (PyPepS)2 and DNIC 1 in a 1:1 stoichiometry that induces the release of an NO radical and the formation of complex [PPN][Fe(PyPepS)2] (4), the incoming substitution ligand (S 2CNMe2)2 triggered the transformation of DNIC 1 into complex [(NO)Fe(S2CNMe2J2] (2) along with N-nitrosocarbazole (3). The subsequent nitrosation of N-acetylpenicillamine (NAP) by N-nitrosocarbazole (3) to produce S-nitroso-A-acetylpenicillamine (SNAP) may signify the possible formation pathway of S-nitrosothiols from DNICs by means of transnitrosation of N-nitrosamines. Protonation of DNIC 1 by [P(SH)3] triggers the release of HNO and the generation of complex [PPN][Fe(NO)P(C6H3-3-SiMe3-2-S)3] (5). In a similar fashion, the nucleophilic attack of the chelating ligand P(C6H3,-3-SiMe3,-2-SNa)3 ([P(SNa)3]) on DNIC 1 resulted in the direct release of [NO] - captured by [(15NO)Fe(SPh)3]-, thus leading to [(15NO)- (14NO)Fe(SPh) 2]-. These results illustrate one aspect of how the incoming substitution ligands ((S2CNMe2)2 vs. (PyPepS)2 vs. [P(SH)3]/[P(SNa)3]) in cooperation with the carbazolate-coordinated ligands of DNIC 1 function to control the release of NO+, NO, or [NO]- from DNIC 1 upon reaction of complex 1 and the substitution ligands. Also, these results signify that DNICs may act as an intermediary of NO in the redox signaling processes by providing the distinct redox-interrelated forms of NO to interact with different NO-responsive targets in biological systems.

ORGANIC NITRIC OXIDE DONOR SALTS OF ANTIMICROBIAL COMPOUNDS, COMPOSITIONS AND METHODS OF USE

The invention describes novel organic nitric oxide donor salts of a antimicrobial . compounds, and novel compositions and kits comprising at least one organic nitric oxide donor salt of an antimicrobial compound, and, optionally, at least one nitric oxide