GC–MS analysis of S-nitrosothiols after conversion to S-nitroso-N-acetyl cysteine ethyl ester and in-injector nitrosation of ethyl acetate

Tsikas, Dimitrios; Dehnert, Sabine; Urban, Karin; Surdacki, Andrzej; Meyer, H.

doi:10.1016/j.jchromb.2009.06.032

Cited by 26 publications

(26 citation statements)

References 35 publications

(107 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis, purification, mass spectrometry, 1 HNMR infrared spectrometry and polarimetry characterization of NACET (C7H13NO3S, MW 191.2, mp 44.1 -44.5 °C) were reported previously. [2] BUFFER SOLUTIONS The Britton-Robinson buffer solution (pH = 2) was prepared by dissolving 4.94 g of boric acid, mixing with 4.79 g of glacial acetic acid and 5.45 g of phosphoric acid and diluting with deionized water up to 2000 mL yielding the final concentration 4.0 × 10 -2 mol L -1 of the components. Appropriate pH values were adjusted by adding sodium hydroxide solution, {c(NaOH) = 2.0 mol L -1 }.…”

Section: Reagents and Solutionsmentioning

confidence: 99%

“…The purity of synthesized and isolated product was determined by HPLC-UV (215 nm) analysis. [2] Kinetic-based analytical methods are becoming of increasing interest in chemical and pharmaceutical analysis. The application of this kind of methods offers some advantages such as improved selectivity and avoidance of the matrix-interferences due to specific kinetics differing from those of other compounds, besides rapidity and high throughput.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Kinetic Spectrophotometric Determination of N-Acetyl-L-cysteine Ethyl Ester (NACET) Generating Chromogenic Copper(I)Ln Complexes with Different Ligands

Kukoc-Modun¹,

Tsikas²,

Kraljević³

et al. 2017

Croat. Chem. Acta

Self Cite

View full text Add to dashboard Cite

Three simple, sensitive and robust kinetic spectrophotometric methods for the determination of a novel lipophilic thiol compound, N-acetyl-L-cysteine ethyl ester (NACET), have been developed and validated. The methods are based on the reduction of Cu(II)-ligand complex to Cu(I)-ligand complex with the analyte. Studied ligands were neocuproine, bicinchoninic acid (BCA) and bathocuproine disulfonic acid (BCS). The development of chromogenic complexes was followed using kinetic setup with spectrophotometric detection at 458, 562 and 483 nm for the reactions of NACET with neocuproine, BCA and BCS, respectively. The calculated reaction orders with respect to NACET concentration were found to be 1.07, 1.01, 1.07, respectively, thus confirming a first order of reaction. The initial rate and fixed time methods were utilized for constructing calibration curves. Assays limits of detection were 1.4 × 10 -7 , 3.2 × 10 −7 and 6.0 × 10 −8 mol L -1 , respectively. The analytical performance of the methods, in terms of accuracy and precision, was established.

show abstract

Section: Reagents and Solutionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Kinetic Spectrophotometric Determination of N-Acetyl-L-cysteine Ethyl Ester (NACET) Generating Chromogenic Copper(I)Ln Complexes with Different Ligands

Kukoc-Modun¹,

Tsikas²,

Kraljević³

et al. 2017

Croat. Chem. Acta

Self Cite

View full text Add to dashboard Cite

show abstract

“…Sodium nitrite was purchased from Riedel-de-Haën (Seelze, Germany). Synthesis and structural characterization of N-acetyl-cysteine ethyl ester have been described elsewhere [27]. Vivaspin 2 Hydrosart cartridges (2 ml; cut-off, 10 kDa) for ultrafiltration were supplied by Sartorius (Göttingen, Germany).…”

Section: Materials and Chemicalsmentioning

confidence: 99%

HPLC analysis of human erythrocytic glutathione forms using OPA and N-acetyl-cysteine ethyl ester: Evidence for nitrite-induced GSH oxidation to GSSG

Michaelsen

Dehnert

Giustarini

et al. 2009

Journal of Chromatography B

Self Cite

View full text Add to dashboard Cite

“…The objective with this approach is to include an abundant, alternative substrate for nitration. However, a potential shortcoming of this strategy is that artifactual 3‐nitrotyrosine formation during GC‐MS or GC‐MS/MS analysis is possible due to trans‐nitration reactions between nitro‐phenol and tyrosine within the hot injector port of the GC (Tsikas et al, ). Nitration reactions can also occur in the injector between tyrosine and nitrogen oxides (NO x ) or other NO x ‐containing substances derived from endogenous and exogenous sources (e.g., nitrous acid, nitro‐fatty acids, S ‐nitrosothiols) (Tsikas et al, ).…”

Section: Introductionmentioning

confidence: 99%

Mass spectrometry and 3-nitrotyrosine: Strategies, controversies, and our current perspective

Tsikas

Duncan

2013

Mass Spec Rev

Self Cite

View full text Add to dashboard Cite

Reactive-nitrogen species (RNS) such as peroxynitrite (ONOO(-)), that is, the reaction product of nitric oxide ((•)NO) and superoxide (O2(-•)), nitryl chloride (NO2Cl) and (•)NO2 react with the activated aromatic ring of tyrosine to form 3-nitrotyrosine. This modification, which has been known for more than a century, occurs to both the free form of the amino acid (i.e., soluble/free tyrosine) and to tyrosine residues covalently bound within the backbone of peptides and proteins. Nitration of tyrosine is thought to be of biological significance and has been linked to health and disease, but determining its role has proved challenging. Several key questions have been the focus of much of the research activity: (a) to what extent is free/soluble tyrosine nitrated in biological tissues and fluids, and (b) are there specific site(s) of nitration within peptides/proteins and to what extent (i.e., stoichiometry) does this modification occur? These issues have been addressed in a wide range of sample types (e.g., blood, urine, CSF, exhaled breath condensate and various tissues) and a diverse array of physiological/pathophysiological scenarios. The accurate determination of nitrated tyrosine is, however, a stumbling block. Despite extensive study, the extent to which nitration occurs in vivo, the specificity of the nitration reaction, and its importance in health and disease, remain unclear. In this review, we highlight the analytical challenges and discuss the approaches adopted to address them. Mass spectrometry, in combination with either gas chromatography (GC-MS, GC-MS/MS) or liquid chromatography (LC-MS/MS), has played the central role in the analysis of 3-nitrotyrosine and tyrosine-nitrated biological macromolecules. We discuss its unique attributes and highlight the role of stable-isotope labeled 3-nitrotyrosine analogs in both accurate quantification, and in helping to define the biological relevance of tyrosine nitration. We show that the application of sophisticated mass spectrometric techniques is advantageous if not essential, but that this alone is by no means a guarantee of accurate findings. We discuss the important analytical challenges in quantifying 3-nitrotyrosine, possible workarounds, and we attempt to make sense of the disparate findings that have been reported so far.

show abstract

GC–MS analysis of S-nitrosothiols after conversion to S-nitroso-N-acetyl cysteine ethyl ester and in-injector nitrosation of ethyl acetate

Cited by 26 publications

References 35 publications

Kinetic Spectrophotometric Determination of N-Acetyl-L-cysteine Ethyl Ester (NACET) Generating Chromogenic Copper(I)Ln Complexes with Different Ligands

Kinetic Spectrophotometric Determination of N-Acetyl-L-cysteine Ethyl Ester (NACET) Generating Chromogenic Copper(I)Ln Complexes with Different Ligands

HPLC analysis of human erythrocytic glutathione forms using OPA and N-acetyl-cysteine ethyl ester: Evidence for nitrite-induced GSH oxidation to GSSG

Mass spectrometry and 3-nitrotyrosine: Strategies, controversies, and our current perspective

Contact Info

Product

Resources

About