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Fluorescent probes and application thereof to detection of neurotoxic agents

A fluorescent probe and nerve agent technology, applied in the field of fluorescent probes, can solve the problems that the detection limit of fluorescent probes is difficult to meet the needs of practical applications, and the substrate selectivity is limited, so as to achieve rapid nerve agent response and specific recognition , the effect of high sensitivity

Inactive Publication Date: 2020-04-10
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing fluorescence detection is based on the resonance energy transfer mechanism, the photoinduced electron transfer mechanism or the energy trap mechanism. The detection limit is still difficult to meet the needs of practical applications

Method used

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  • Fluorescent probes and application thereof to detection of neurotoxic agents
  • Fluorescent probes and application thereof to detection of neurotoxic agents
  • Fluorescent probes and application thereof to detection of neurotoxic agents

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0038] Synthesis of Preparation Example 1 TPA-HTAZ (Fluorescent Probe 1)

[0039] Step (1): Synthesis of the intermediate bromobenzoyl hydrazide (Br-2O-Br)

[0040] Weigh 4-bromobenzoyl chloride, hydrazine hydrate and triethylamine in a molar ratio of about 2-3:1:2-3. At 0°C, dissolve 4-bromobenzoyl chloride in chloroform. After it is completely dissolved, add triethylamine with a dropper, and then slowly add hydrazine hydrate into the mixed solution with a syringe. It can be observed that a white precipitate appears, stirred under this condition for 0.5-1 hour, then returned to room temperature and continued to stir for 3-5 hours. After the reaction, the product is suction-filtered, thoroughly washed with petroleum ether and deionized water, and dried. The structural characterization is as follows: Mass Spectrum: MW 398.05, m / z=398.05 (M+). 1 H NMR (500 MHz, DMSO) δ 10.64 (s, 2H), 7.87 (d, J = 8.6 Hz, 4H), 7.76 (d, J = 8.5 Hz, 4H).

[0041]

[0042] Step (2): Synthesis...

preparation Embodiment 2

[0051] Synthesis of Preparation Example 2 TPA-BTAZ (fluorescent probe 2)

[0052] The preparation of step (1) and (2) intermediate product is respectively the same as step (1) and (2) among the embodiment 1.

[0053] Step (3): Synthesis of intermediate product Br-TAZ-B

[0054] The chloroazobromotoluene and aniline were weighed in a molar ratio of 1:1-1.8. Dissolve the weighed raw materials in degassed N-methylpyrrolidone (or N,N-dimethylformamide), and stir for 10-14 hours under nitrogen protection at 130-140°C under anhydrous and oxygen-free conditions. After cooling, add about 10-15mL of 2M dilute hydrochloric acid, and a precipitate can be observed during the dropwise addition of dilute hydrochloric acid. After continuing to stir at room temperature for 30-60 minutes, the product is suction filtered, washed with a large amount of deionized water, and dried. The structural characterization is as follows: Mass Spectrum: MW454.97, m / z=454.95 (M+). 1 H NMR (500MHz, DMSO) δ...

preparation Embodiment 3

[0058] Synthesis of Preparation Example 3 TPA-CNTAZ (fluorescent probe 3)

[0059] The synthesis of step (1) and (2) intermediate product is respectively the same as step (1) and (2) among the embodiment 1.

[0060] Step (3): Synthesis of intermediate product Br-TAZ-CN

[0061] Weigh chloroazobromotoluene and 4-aminobenzonitrile at a molar ratio of 1:1-1.8. Dissolve the weighed raw materials in degassed N-methylpyrrolidone (or N,N-dimethylformamide), and stir for 10-14 hours under nitrogen protection at 130-140°C under anhydrous and oxygen-free conditions. After cooling, add about 10-15mL of 2M dilute hydrochloric acid, and a precipitate can be observed during the dropwise addition of dilute hydrochloric acid. After continuing to stir at room temperature for 30-60 minutes, the product is suction filtered, washed with a large amount of deionized water, and dried. Mass spectrum: MW808.67, m / z=808.99 (M+). 1 H NMR (500MHz, Chloroform-d) δ7.81–7.75(m,2H),7.60–7.53(m,4H),7.52–7...

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Abstract

The invention relates to fluorescent probes represented by a general formula I or II which is described in the specification, and application of the fluorescent probes in detection of neurotoxic agents. The fluorescent probes can be used for efficiently detecting neurotoxic agents including of sarin, soman, tabun, ethyl sarin and the like of the G series and VX, VG, VM, VE and the like of the V series on the basis of a hybrid local area-charge transfer excited state and a dehybridization mechanism, and has the advantages of excellent detection limit, high sensitivity, good selectivity and recyclability.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular, the invention relates to a fluorescent probe and its application for detecting nerve agents. Background technique [0002] Nerve agents such as Sarin (Sarin), Soman (Soman), and Tabun (Tabun) can quickly destroy human nerve conduction function at very low concentrations, causing severe poisoning symptoms and even death, and can even directly Used as chemical weapons, it seriously endangers public security and even international security. Although the international community has issued documents such as the "Convention on the Prohibition of the Use of Chemical Weapons" to curb the application of nerve agents as chemical weapons, vicious crimes such as the sarin gas incident in the Japanese subway and the assassination of Kim Jong-nam in the past three decades still have a negative impact on the use of nerve agents. Rapid and efficient detection puts forward urgent realis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/02C09K11/06G01N21/64
CPCC07D249/02C09K11/06C09K2211/1059G01N21/643G01N2021/6432
Inventor 张诗童王曼李迪杨兵马洪伟程志勇
Owner JILIN UNIV
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