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Fluorescent probe, nerve agent detection element, preparation method and application

A fluorescent probe and detection element technology, applied in the field of fluorescent probes, can solve the problems of low detection sensitivity, long response time, poor selectivity, etc., and achieve the effects of high product yield, efficient detection, and high selectivity

Active Publication Date: 2021-02-02
中国人民解放军61699部队
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the problems of poor selectivity, low detection sensitivity and long response time in existing fluorescent probes used for nerve agent detection, the present invention provides a fluorescent probe, nerve agent detection element, preparation method and application

Method used

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  • Fluorescent probe, nerve agent detection element, preparation method and application
  • Fluorescent probe, nerve agent detection element, preparation method and application
  • Fluorescent probe, nerve agent detection element, preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0069] This embodiment provides a method for preparing a fluorescent probe, comprising the following steps:

[0070] (1) Synthesis of 5-ethynyl-2-hydroxybenzaldehyde:

[0071] In the reaction flask, add 5-bromosalicylaldehyde (3.00g, 14.92mmol), two (triphenylphosphine) palladium dichloride PdCl 2 (PPh 3 ) 2 (315.0mg, 0.449mmol), cuprous iodide (85.0mg, 0.446mmol), triethylamine 20mL, trimethylsilyl acetylene (2.20g, 22.40mmol) and 50mL tetrahydrofuran, stirred at 50 ° C, TLC detection After the raw material disappears, the reaction solution is spin-dried, and then column chromatography is performed with methylene chloride and n-hexane with a volume ratio of 1:2 as the eluent, and the collected eluent is spin-dried at 30-60°C under low pressure , to obtain a white product, the product was dissolved in 90mL tetrahydrofuran, 1mL tetrabutylammonium fluoride (TBFA) was added, stirred and reacted at 25°C for 18h, the reaction solution was spin-dried, and then dichloromethane wit...

Embodiment 2

[0087] Application of fluorescent probes in the detection of nerve agent VX:

[0088] Using acetonitrile as a solvent, the fluorescent probe prepared in Example 1 was formulated into a concentration of 1.0×10 -3 Fluorescent probe stock solution of M, VX made up to 1.0 x 10 -2 Stock solution of the nerve agent VX of M.

[0089] Add 20 μL of fluorescent probe stock solution to a cuvette containing 60 μL of triethylamine and 2 mL of acetonitrile, add 2 μL of VX stock solution drop by drop, shake for 2 min after each drop, and then measure the UV-visible absorption spectrum and fluorescence spectrum. Measurement results such as Figure 5 and Figure 6 shown.

[0090] Depend on Figure 5It can be seen that with the addition of VX, the absorption peak of the solution blue-shifts from 527nm to 523nm, and the absorption intensity is significantly enhanced. Depend on Figure 5 As can be seen in the inset of , the color of the solution is purple visible to the naked eye when VX ...

Embodiment 3

[0093] Selective detection of neurotoxic agents with fluorescent probes:

[0094] With acetonitrile as the solvent, the concentrations were prepared to be 1.0×10 -2 Organophosphorus interferents of M: stock solutions of dimethyl methylphosphonate, triphenyl phosphate, trimethyl phosphate, acephate, isocarbophos, dimethoate, and parathion.

[0095] Using acetonitrile as a solvent, the fluorescent probe prepared in Example 1 was formulated into a concentration of 1.0×10 -3 Fluorescent probe stock solution of M, VX made up to 1.0 x 10 -2 Stock solution of the nerve agent VX of M.

[0096] Take 9 sample vials, add 1.89 mL of acetonitrile, 20 μL of fluorescent probe stock solution, and 60 μL of triethylamine to each vial, and then add one of the above-prepared vials to each of the previous 7 sample vials. 30 μL of the interfering substance stock solution, and 30 μL of the LVX stock solution was added to the eighth sample bottle, and the ninth sample bottle was a fluorescent prob...

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Abstract

The invention relates to the technical field of fluorescent probes, and particularly discloses a fluorescent probe, a nerve agent detection element, a preparation method and application. The structureof the fluorescent probe is shown as a formula 3. According to the fluorescent probe with a novel structure, salicylaldoxime is bridged with BODIPY fluorescent chromophores through alkynyl to form arigid planar molecular structure, and a photoinduced electron transfer pathway between the chromophores and reaction groups is constructed, so that the self-fluorescence of probe molecules can be effectively reduced, the background noise is weakened, and the detection effect is enhanced. The fluorescent probe molecule of the nerve agent provided by the invention is high in response speed, high indetection sensitivity and good in selectivity, the detection limit can reach 4.0 * 10 <-9 > mol, a detection element prepared from the fluorescent probe can detect nerve agent molecules in a gas phaseand a liquid phase at the same time, and the fluorescent probe molecule can be applied to visual detection of the nerve agent in a real environment; and good application prospects are realized.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a fluorescent probe, a nerve agent detection element, a preparation method and an application. Background technique [0002] Nerve agents are a class of highly toxic organophosphate or organophosphonate compounds, which are divided into class G nerve agents and class V nerve agents. Class G nerve agents are alkyl fludronates or alkyl dialkylaminocyanidronates, the main representatives of which are tabun (GA), sarin (GB) and soman (GD). Class V neurotoxins refer to S-dialkylaminoethylmethylphosphonothioate alkyl esters, the main representative of which is Viex (VX). When the nerve agent enters the human body through inhalation or skin contact, it can quickly combine with the serine on the acetylcholinesterase to destroy the enzyme activity, thereby causing convulsions and even death. Therefore, it is of great significance to find fast, simple, highly sensitive and hig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/6428C09K2211/1055G01N2021/6432
Inventor 李盛菘郑永超胡张雁赵冲林张法恒刘丹丹孙付兵
Owner 中国人民解放军61699部队
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