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Analytic application and method of thiol nucleophilic substitution derivatization reagent

A derivatization reagent and derivatization technology, applied in the field of analytical chemistry, can solve the problems of difficult real content, difficult and accurate determination of mustard gas prototypes, and unsuitable biological sample analysis.

Active Publication Date: 2014-12-10
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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Problems solved by technology

[0003] However, mustard gas is a highly active alkylating agent. In complex environmental samples or biological samples, most of its prototype molecules are easily degraded, hydrolyzed or rapidly undergo biotransformation such as addition, which makes it difficult to accurately determine the prototype mustard gas. True content in complex samples has been a major challenge associated with this field of analysis
[0004] At present, gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) are the main methods for the detection of mustard gas and its related compounds, but there are shortcomings such as poor stability of the analytical method, complicated sample pretreatment, and unsuitability for biological sample analysis.
Although liquid chromatography (LC) and liquid chromatography-mass spectrometry (LC-MS) have the advantages of simple sample pretreatment and high sensitivity, due to the combination of mustard gas and its oxidation product mustard sulfone, etc. Alkylation or hydrolysis reactions occur in the column packing and flow phase, so it is generally believed that liquid chromatography cannot be directly used to analyze mustard gas prototypes and related compounds

Method used

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  • Analytic application and method of thiol nucleophilic substitution derivatization reagent

Examples

Experimental program
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Effect test

preparation example 1

[0070] Preparation Example 1: Preparation and Characterization of S,S'-Diacetyltrithiodiglycol

[0071] 5% mustard gas acetonitrile solution was added to 0.1g / mL PTA aqueous solution in portions or once, sealed with a polytetrafluoroethylene (PTFE) bottle cap, and reacted at 100°C for 1 hour; the reaction mixture was extracted with 2mL dichloromethane , the extract was subjected to silica gel column chromatography, the eluting solvent was n-hexane:dichloromethane=1:3, the collected fractions were subjected to vacuum distillation to obtain the derivative product S,S'-diacetyl trisulfide of mustard gas and PTA Diethylene glycol.

[0072] figure 1 S,S'-Diacetyltrithiodiglycol 1 H NMR spectrum. The characterization results showed that the purity of the refined S,S'-diacetyltrithiodiglycol could meet the experimental requirements.

preparation example 2

[0073] Preparation Example 2: Preparation and Characterization of 3,5-Dimercaptomethyl-Phenoxyacetic Acid

[0074] The preparation method of 3,5-dimercaptomethyl-aromatic compound is as follows:

[0075]

[0076] The dithiol derivatization reagent 3,5-dimercaptomethyl-phenoxyacetic acid (DSH) was prepared and purified according to the above synthetic route.

[0077] figure 2 for DSH 1 H NMR spectrum. The characterization results showed that the purity of the prepared DSH could meet the experimental requirements.

Embodiment 1

[0078] Embodiment 1: the instrument parameter optimization of PTA derivatization method

[0079] Prepare PTA aqueous solution and d4-mustard acetonitrile internal standard solution with a concentration of 0.1 mg / mL and 1 mg / mL respectively, mix the sample containing mustard gas with PTA solution and internal standard solution, vortex and mix, and place in a water bath at 50°C Reacted for 30min, the reaction solution was centrifuged at 14000rpm for 10 minutes, and 50 μL of the supernatant was put into the intubation tube of the sampling bottle, and the chromatograms of mustard gas and d4-mustard gas were measured with a triple quadrupole linear ion trap tandem mass spectrometer (LC / MS Hyphenated instrument 5500QTRAP, equipped with TurboV electrospray ionization source (ESI) and ACQUITY TM ultra-high performance liquid chromatography (UPLC).

[0080] The detection conditions of liquid chromatography-mass spectrometry are as follows:

[0081] Chromatographic conditions Chroma...

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Abstract

The invention belongs to the field of analytic chemistry, and relates to an application of a thiol derivatization reagent to detection of mustard gas and related compounds of the mustard gas. The invention also relates to a method for detecting the mustard gas and / or related compounds of the mustard gas. Specifically, the detection method comprises the following steps: using the thiol derivatization reagent or adding the thiol derivatization reagent to a treated or untreated sample to be tested. The application and the method are suitable for the detection of the prototypes of the high-reaction activity mustard gas and the related compounds of the mustard gas, have the advantage of overcoming the abuses that the prototypes cannot be detected and the content detection is incorrect as the mustard gas and nitrogen mustard in the complicated samples undergo rapid prototype or alkylation conversion, have simplicity in operation and good reproducibility and stability, and can be applied to the liquid chromatogram-mass spectrum combined detection of the mustard gas with reaction activity and the related compounds in the environment samples and biological samples and applied to the related virus pharmacological researches.

Description

technical field [0001] The invention belongs to the field of analytical chemistry and relates to the application of mercapto derivatization reagents in the detection of mustard gas and its related compounds. The invention also relates to a method of detecting mustard gas and / or its related compounds. Background technique [0002] Mustard gas (sulfur mustard, SM), whose chemical name is 2,2'-dichlorodiethyl sulfide, is a difficult-to-prevent and intractable chemical warfare agent. It has been used many times in wars, causing a large number of casualties . At present, SM is still the main filler for the world's existing chemical weapons, and it is also the main component of Japan's abandoned chemical weapons in China. Therefore, the rapid and accurate detection of mustard gas and its related compounds has important research significance in terms of responding to public emergencies, clinical diagnosis, treatment, prognosis assessment and poisoning mechanism research of mustar...

Claims

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Application Information

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IPC IPC(8): G01N30/02
Inventor 谢剑炜徐斌吴剑峰郭磊宗成齐美玲
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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