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Indole salt-coumarin derivative, and synthesis method and application thereof

A technology of coumarin derivatives and synthesis methods, applied in instruments, analytical materials, organic chemistry, etc., to achieve the effects of good selectivity, simple detection means, and low cost

Inactive Publication Date: 2020-06-02
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many laboratories are currently investigating the fluorescence detection of SO2, there is currently no mitochondria-targeted and reversible detection of SO2 with HCHO. 2 Therefore, the development of mitochondria-targeted, efficient and reversible detection of SO 2 Fluorescent probes are important for the overall health of biological systems

Method used

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  • Indole salt-coumarin derivative, and synthesis method and application thereof
  • Indole salt-coumarin derivative, and synthesis method and application thereof
  • Indole salt-coumarin derivative, and synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0040] Preparation and characterization of Mito-CI

[0041] Diethyl malonate (6.08g, 38mmol), 4-(diethylamino)-2-hydroxybenzaldehyde (3.67g, 19mmol) and piperidine (2.0mL) were mixed with absolute ethanol (60mL), then The mixture was refluxed for 12 hours. After the reaction was completed, the solvent was evaporated under reduced pressure. Next, a mixture of concentrated acetic acid (40 mL) and HCl (40 mL) was added and the reaction was refluxed at 120° C. for 13 hours. Next, after cooling to 25°C, the reaction mixture was poured into 200 ml of water at 0°C. NaOH solution (40%) was added to raise the pH to 5 and a brown precipitate formed immediately. , the mixture was filtered and washed four times with water, dried in vacuo to obtain a yellow-brown solid. (3.92g, Yield: 95%). 1 H NMR (600MHz, DMSO-d 6 )δ7.82(d, J=9.3Hz, 1H), 7.42(d, J=8.8Hz, 1H), 6.68(dd, J=8.8, 2.5Hz, 1H), 6.51(d, J=2.3Hz, 1H), 5.99(d, J=9.3Hz, 1H), 3.42(q, J=7.0Hz, 4H), 1.12(t, J=7.0Hz, 6H). 13 C N...

Embodiment 2

[0046] Prepare a PBS buffer solution with a pH of 7.4 and a concentration of 10 mM, prepare a 2 mM Mito-CI DMSO solution, and prepare a 2 mM sulfur dioxide aqueous solution; take 2 mL of pure PBS buffer solution and 10 μL Mito-CI DMSO solution into a fluorescence cuvette, and take The aqueous solution of sulfur dioxide was gradually added to the cuvette with a micro-injector, and was detected on the fluorescence spectrophotometer while adding the sample. With the addition of sulfur dioxide, the fluorescence intensity at 481nm gradually increased, and the fluorescence intensity at 655nm gradually decreased. Fluorescence emission map see Figure 4 .

Embodiment 3

[0048] Prepare PBS buffer solution with pH=7.4 and concentration of 10mM, prepare 2mM Mito-CI DMSO solution, prepare 2mM sulfur dioxide aqueous solution, prepare 2mM formaldehyde aqueous solution, take 2mL pure PBS buffer solution, 10μL Mito-CI DMSO solution and add to a fluorescent Add 100 μL of sulfur dioxide aqueous solution to the cuvette to make Mito-CI-SO 3 2－ DMSO solution, take the aqueous solution of formaldehyde, gradually add it to the cuvette with a micro-injector, and detect it on the fluorescence spectrophotometer while adding the sample. The fluorescence intensity gradually increased. Fluorescence emission map see Figure 5 .

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Abstract

The invention provides an indole salt-coumarin derivative, and a synthesis method and an application thereof. The English name of the derivative is (E)-1-(2-carboxyethyl)-2-(2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium, and the reagent is named as Mito-CI. The reagent can be used for efficiently and reversibly detecting sulfur dioxide. A detection method is characterized in that sulfur dioxide is detected through a fluorospectro photometer in a pure PBS buffer solution with the pH value of 7.4. The detection process is simple, sensitive and rapid, and the detection result is accurate.

Description

technical field [0001] The invention relates to coumarin derivatives, in particular to an indole salt-coumarin derivative and a synthesis method thereof, and the application of the derivative in ratiometric reversible detection of sulfur dioxide. Background technique [0002] A variety of reactive sulfur compounds exist in nature, such as the primary air pollutant SO 2 And small molecules such as cysteine ​​(Cys), homocysteine ​​(Hcy) and reduced glutathione (GSH). Among them, under the physiological condition of pH=7.4, SO 2 It can be hydrolyzed into sulfite ion and bisulfite ion (3:1, M / M), which play a vital role in the process of life activities. Endogenous sulfur dioxide has been confirmed to be related to many physiological and pathological processes, such as antibacterial, antihypertensive, antioxidative, and protective effects on myocardial ischemia-reperfusion injury, etc. It can also enhance the antioxidant effect of cells and play a role in signal transduction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06G01N21/64
CPCC07D405/06G01N21/643G01N2021/6417G01N2021/6432
Inventor 霍方俊张涛阴彩霞
Owner SHANXI UNIV
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