Development and validation of a sensitive gas chromatography–ammonia chemical ionization mass spectrometry method for the determination of tabun enantiomers in hemolysed blood and plasma of different species

Tenberken, Oliver; Worek, Franz; Thiermann, Horst; Reiter, Georg

doi:10.1016/j.jchromb.2009.09.002

Cited by 19 publications

(4 citation statements)

References 41 publications

(45 reference statements)

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“…Similar research was done in 2010 by H. John for sarin, soman, tabun, cyclosarin, VX, Chinese VX, Russian VX, chlorpyrifos-oxon, DFP, paraoxonethyl, and profenofos . LC-MS/MS was also used as detection technique for VX in blood plasma and microdialysates. , Chiral quantification of tabun enantiomers in swine blood was carried out by O. Tenberken by GC-PCI-MS . Developed GC-MS can allow for the detection of nerve agents at an exposure level of 1% BuChE inhibition, where ChE activity assay cannot be verified …”

Section: Sensing and Detectionmentioning

confidence: 95%

Destruction and Detection of Chemical Warfare Agents

et al. 2011

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Section: Sensing and Detectionmentioning

confidence: 95%

Destruction and Detection of Chemical Warfare Agents

et al. 2011

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“…The peak at 902.2 m/z in negative mode represents aging through deamination, whereas the peak at 874.2 m/z represents aging by dealkylation. This result shows that both stereoisomers of tabun inhibit human BChE (Tenberken et al, 2010b) and that adducts with racemic tabun age by deamination and by dealkylation. The relative concentrations of adducts (Fig.…”

Section: Aging Of Authentic Tabun-bche Adductmentioning

confidence: 70%

Mass Spectrometry Method to Identify Aging Pathways of Sp- and Rp-Tabun Adducts on Human Butyrylcholinesterase Based on the Acid Labile P-N Bond

Jiang

Cashman

Nachon³

et al. 2013

Toxicological Sciences

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The phosphoramidate nerve agent tabun inhibits butyrylcholinesterase (BChE) and acetylcholinesterase by making a covalent bond on the active site serine. The adduct loses an alkyl group in a process called aging. The mechanism of aging of the tabun adduct is controversial. Some studies claim that aging proceeds through deamination, whereas crystal structure studies show aging by O-dealkylation. Our goal was to develop a method that clearly distinguishes between deamination and O-dealkylation. We began by studying the tetraisopropyl pyrophosphoramide adduct of BChE because this adduct has two P-N bonds. Mass spectra showed that the P-N bonds were stable during trypsin digestion at pH 8 but were cleaved during pepsin digestion at pH 2. The P-N bond in tabun was also acid labile, whereas the P-O bond was stable. A scheme to distinguish aging by deamination from aging by O-dealkylation was based on the acid labile P-N bond. BChE was inhibited with Sp- and Rp-tabun thiocholine nerve agent model compounds to make adducts identical to those of tabun with known stereochemistry. After aging and digestion with pepsin at pH 2, peptide FGES198AGAAS from Sp-tabun thiocholine had a mass of 902.2 m/z in negative mode, indicating that it had aged by deamination, whereas peptide FGES198AGAAS from Rp-tabun thiocholine had a mass of 874.2 m/z in negative mode, indicating that it had aged by O-dealkylation. BChE inhibited by authentic, racemic tabun yielded both 902.2 and 874.2 m/z peptides, indicating that both stereoisomers reacted with BChE and aged either by deamination or dealkylation.

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“…Within the first minute, approximately half of the labeled sarin was in the form of IMPA. The highest concentrations of sarin and its (Nakajima et al, 1998;Katagi et al, 1999;Jokanović, 2001Jokanović, , 2009Evans et al, 2008;Black, 2010;Tenberken et al, 2010;Reiter et al, 2011;Black and Read, 2013;Kranawetvogl et al, 2013). metabolites were found in the kidneys. Lower concentrations of IMPA and MPA were detected in the liver, suggesting a minor role for the liver in detoxification of sarin.…”

Section: Chemical Aspects Of Biotransformation Of Wnasmentioning

confidence: 98%

“…Of the G-agents, tabun gives rise to the greatest number of degradation products. The metabolites of tabun EDMPA and EPCA (Figure 59.1) are apparently unstable, whereas the EPA is an excretion metabolite of tabun as well as of certain pesticides and plasticisers (Tenberken et al, 2010;Black and Read, 2013). The final metabolite of tabun is a phosphate (Black, 2010).…”

Section: Chemical Aspects Of Biotransformation Of Wnasmentioning

confidence: 99%

Biotransformation of Warfare Nerve Agents

Jokanović¹

2015

Handbook of Toxicology of Chemical Warfare Agents

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Development and validation of a sensitive gas chromatography–ammonia chemical ionization mass spectrometry method for the determination of tabun enantiomers in hemolysed blood and plasma of different species

Cited by 19 publications

References 41 publications

Destruction and Detection of Chemical Warfare Agents

Destruction and Detection of Chemical Warfare Agents

Mass Spectrometry Method to Identify Aging Pathways of Sp- and Rp-Tabun Adducts on Human Butyrylcholinesterase Based on the Acid Labile P-N Bond

Biotransformation of Warfare Nerve Agents

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