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Coumarin-benzopyranium salt derivative as well as synthesis method and application thereof

A technology of benzopyrylium salt and synthesis method, applied in chemical instruments and methods, instruments, analytical materials and other directions, can solve problems such as death, abnormal metabolism of sulfur dioxide, damage to the brain, nervous system organs, etc., and achieves high sensitivity, Simple detection method and simple preparation method

Inactive Publication Date: 2020-06-09
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the lack of intracellular sulfite oxidase will lead to abnormal sulfur dioxide metabolism, and the accumulation of sulfite in the human body will damage important organs such as the brain and nervous system, and even cause death

Method used

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  • Coumarin-benzopyranium salt derivative as well as synthesis method and application thereof
  • Coumarin-benzopyranium salt derivative as well as synthesis method and application thereof
  • Coumarin-benzopyranium salt derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation and Characterization of Coumarin-benzopyrylium Derivative CM-BP

[0049] (1) Dissolve 4-formyl-7 diethylaminocoumarin (0.49g, 2mmol) and cyanoacetic acid (0.255g, 3mmol) in 100mL of absolute ethanol, and heat the mixture at 87°C for 4 hours; After completion, the solution was spin-dried under reduced pressure, and the obtained orange solid was separated by silica gel column chromatography using methanol and dichloromethane with a volume ratio of 1:15 as the eluent to obtain an orange solid powder (0.303 g, yield: 48.7%);

[0050] (2) 4-diethylamino salicylaldehyde (0.386g, 2mmol) and 4-piperazinyl acetophenone (0.408g, 2mmol) were dissolved in 10mL of concentrated sulfuric acid, the mixture was stirred and refluxed at 90°C for 8 hours, cooled After reaching room temperature, the reaction solution was poured into ice water and continued to stir. The resulting precipitate was filtered, washed, and vacuum-dried to obtain a black solid. The resulting orange soli...

Embodiment 2

[0053] Prepare a PBS buffer solution with a pH of 7.4 and a concentration of 10 mM, prepare a 0.2 M glutathione solution, dissolve CM-BP in DMSO to prepare a 2 mM solution; take 2 mL of a PBS solution containing 10% DMSO at a pH of 7.4, Add 10 μL DMSO solution of CM-BP into a fluorescence cuvette, add glutathione to the fluorescence cuvette, with the addition of glutathione to be tested, the fluorescence intensity at 638nm gradually increases; the fluorescence emission picture see Figure 4 .

Embodiment 3

[0055] Prepare a PBS buffer solution with a pH of 7.4 and a concentration of 10mM, prepare a 0.2M glutathione solution, dissolve CM-BP in DMSO to prepare a 2mM solution; add 2mL of 10% to each of the 10 cuvettes DMSO pH 7.4 PBS solution, 10 μL CM-BP DMSO solution, add glutathione solution to the cuvette with volumes of 0, 2, 4, 6, 8, 10, 12, 14, 16, 18 , 20 μL, and then measure the fluorescence intensity at 638nm on the fluorescence spectrometer as 402, 469, 525, 588, 648, 713, 777, 826, 879, 925, 953. Take the concentration of glutathione as the abscissa and the fluorescence intensity as the ordinate to draw a graph to obtain the working curve of the concentration of glutathione; the linear regression equation is: F 638 =283.9c+416.5, the unit of c is 10 -3 mol / L; (see Figure 5 ).

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Abstract

The invention provides a coumarin-benzopyranium salt derivative as well as a synthesis method and application thereof. The Chinese name of the derivative is called (E)-2-(4-(4-(2-cyano-3-(7-(diethylamino)-2-oxo-2H-chrom-3-yl) acryloyl) piperazine-1-yl) phenyl)-7-(diethylamino) chromium perchlorate, the English name is (E)-2-(4-(4-(2-cyano-3-(7-(diethylamino)-2-oxo-2H-chrom-3-yl) acryloyl) piperazine-1-yl) phenyl)-7-(diethylamino) chromenium perchlorate, and the is derivative is named as CM-BP. The invention also provides a synthetic method of the coumarin-benzopyranium salt derivative, a method for distinguishing, identifying and detecting glutathione and sulfur dioxide, and an application of the coumarin-benzopyranium salt derivative in sulfur dioxide metabolic imaging. The contents of glutathione and sulfur dioxide can be quantitatively detected by a fluorospectro photometer in a PBS solution with the pH value of 7.4. The detection process is simple, sensitive and rapid, and the detection result is high in accuracy.

Description

technical field [0001] The invention relates to the synthesis of fluorescent probes and the detection of glutathione and sulfur dioxide, in particular to a coumarin-benzopyrylium salt derivative, its synthesis method and its application in the differential detection of glutathione and sulfur dioxide. Background technique [0002] Studies have shown that glutathione, the most abundant non-protein thiol in cells, plays an important role in maintaining intracellular redox balance, and its concentration imbalance is related to a series of diseases: including immune response, cancer and Alzheimer's disease Wait. There is no doubt that the abnormal metabolism of glutathione in cells is the direct factor causing its concentration imbalance. Glutathione and sodium thiosulfate in mitochondria generate sulfur dioxide under the action of thiosulfate transferase. Sulfur dioxide, as an important small molecule active sulfide, has various pathological activities, such as antibacterial, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/31G01N21/64
CPCC07D311/16C09K11/06G01N21/6428G01N21/314C09K2211/1088C09K2211/1044
Inventor 阴彩霞张伟杰霍方俊
Owner SHANXI UNIV
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