Preparation and application of boron-dipyrromethene-based diethyl chlorophosphate fluorescent probe

A technology of diethyl chlorophosphate and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of limited use of fluorescent probes, high detection limit of fluorescent probes, low selectivity of fluorescent probes, etc., and achieves good application prospects, The effect of good sensitivity and selectivity, and simple synthesis steps

Inactive Publication Date: 2017-04-26
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the existing fluorescent probe technology, there are some fluorescent probes for detecting DCP, but these fluorescent probes still have some shortcomings. Some of the DCP fluorescent probes have relatively low selectivity, insufficient detection sensitivity, and relatively long detection time.
For example, Fluorescein is a fluorescent probe for detecting DCP. This fluorescent probe is a fluorescent quenching probe, and the detection limit of this fluorescent probe is relatively high, which limits the use of this fluorescent probe.

Method used

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  • Preparation and application of boron-dipyrromethene-based diethyl chlorophosphate fluorescent probe
  • Preparation and application of boron-dipyrromethene-based diethyl chlorophosphate fluorescent probe
  • Preparation and application of boron-dipyrromethene-based diethyl chlorophosphate fluorescent probe

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Embodiment 1, the synthesis of probe molecule I

[0046](a) Nitrogen protection, take 6.24g (about 32mmol) of cyanobiphenol and 4.56g (about 48mmol) of anhydrous MgCl 2 , add 80 mL of anhydrous acetonitrile, then add 16.32 mL (about 122 mmol) of triethylamine and 12.3 g (about 440 mmol) of paraformaldehyde (excess). Mixture 70 o C for 5 hours. After the reaction was complete, it was quenched with water and acidified with 6M hydrochloric acid. Crude product with CH 2 Cl 2 Extraction, liquid separation, desolventization under reduced pressure, and separation by column chromatography gave 3.5 g of white solid III, with a yield of about 50%.

[0047] (b) Under nitrogen protection, 2.00 g (8.96 mmol) of compound III was dissolved in 50 mL of dry dichloromethane, and stirred at room temperature. Add 12.0 mL (174.4 mmol) of pyrrole and react under the catalysis of 0.03 mL of trifluoroacetic acid for 1 hour. The crude product was then purified by column chromatography to...

Embodiment 2

[0049] Embodiment 2, probe selectivity experiment

[0050] The fluorescent probe compound prepared in Example 1 was prepared into a DMF solution containing the probe, triethylamine (20 μM) and DMAP (10 μM) for later use.

[0051] Take the fluorescent probe DMF solution and divide it into 6 groups, 10 ml in each group. One group does not add detection species, and the remaining 5 groups are added with solutions containing HCl, TFA, triphosgene, Phosgene, DCP, so that each group of solutions contains probes The concentration of I is 10 μM, the concentration of the detection species is 100 μM, so that the molar ratio of the detection species to the probe compound is 10:1; under the excitation of light with a wavelength of 480 nm, the fluorescence intensity of the fluorescence is tested. Such as image 3 As shown, the probe solution of the present invention has no fluorescence itself. Once DCP is added, the fluorescence of the solution at 530nm increases rapidly, but the fluoresce...

Embodiment 3

[0052] Embodiment 3, probe sensitivity experiment

[0053] Take the fluorescent probe solution prepared in Example 2, and divide it into 12 groups, each with 10 milliliters, add DCP solutions of different concentrations respectively, adjust the concentration of the probe compound contained in the solution to be 10 μM, and the concentration of DCP to be 0, 5, 10, 15, 20, 25...60 μM. Under the excitation of light with a wavelength of 480nm, test its fluorescence intensity, such as Figure 4 shown. The results showed that the fluorescence of the solution increased rapidly at 530nm, and the fluorescence intensity was linearly related to the concentration. According to the calculation, the minimum detection limit of this probe compound is 1.3×10 -8 mol / L.

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Abstract

The invention relates to a detection diethyl chlorophosphate (DCP) fluorescent probe compound based on boron dipyrromethene (BODIPY) and preparation and application of the detection diethyl chlorophosphate (DCP) fluorescent probe compound. The detection diethyl chlorophosphate (DCP) fluorescent probe compound has the structure shown in the formula I. A preparation method includes the steps that an acetonitrile solution containing 4-(4-hydroxyphenyl)benzonitrile, anhydrous magnesium chloride, paraformaldehyde and triethylamine is subjected to heating and refluxing under protection of nitrogen to obtain white solid III; the obtained solid III and pyrrole are mixed and dissolved in dichloromethane; grey white solid II is obtained under catalysis of trifluoroacetic acid; and the obtained grey white solid II is subjected to DDQ oxydehydrogenation and boron trifluoride diethyl etherate coupling to obtain orange solid I. The probe compound has very good selectivity and sensitivity for DCP, the detection limit is low, and the probe compound can be applied to DCP content measurement.

Description

technical field [0001] The invention relates to the preparation and application of a fluorescent probe compound based on BODIPY for detecting diethyl chlorophosphate, and belongs to the technical field of fluorescent probes. [0002] technical background [0003] Diethyl chlorophosphate (DCP) is a colorless liquid with a pungent, malodorous odor that reacts violently with moisture in the air before converting to a nontoxic compound. The structure of DCP is similar to the nerve agent sarin, and it is an excellent low-toxicity nerve agent mimic molecule. Its toxicology is: when DCP is absorbed by the organism, it will attack the active site of acetylcholinesterase. Acetylcholinesterase is a key enzyme in the central nervous system, mainly responsible for the hydrolysis of the neurotransmitter acetylcholine. When the active site of acetylcholinesterase is attacked by nucleophiles, its activity is inhibited, causing fatal effects. In the past, the poisonous gas accident on the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02G01N21/64
CPCC07F5/022G01N21/643
Inventor 吕正亮范文龙范春华王艳青孟可馨张陆艳
Owner UNIV OF JINAN
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