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A kind of carboxy-containing coumarin derivative and its synthesis method and application

The technology of a coumarin derivative and a synthesis method is applied in the field of coumarin derivatives and achieves the effects of good selectivity, broad application prospects and simple detection means

Active Publication Date: 2022-03-18
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, there have been no reports on specific fluorescent probes for highly efficient detection of cysteine ​​in the cytoplasm
it's still a challenge

Method used

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  • A kind of carboxy-containing coumarin derivative and its synthesis method and application
  • A kind of carboxy-containing coumarin derivative and its synthesis method and application
  • A kind of carboxy-containing coumarin derivative and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation and characterization of XI-2

[0049]1) Ethyl chloroformate (0.488g, 4.50mmol) and sodium bicarbonate (0.315g, 3.75mmol) were dissolved in 10mL of tetrahydrofuran, and slowly added dropwise to the mixture containing m-hydroxyphenylpiperazine (0.535 g, 3.00mmol) in a volume ratio of 1:1 tetrahydrofuran and deionized water solution (40mL) in a round bottom flask, stirred overnight at room temperature; after the reaction was completed, extracted with dichloromethane, dried over anhydrous sodium sulfate, and evaporated under reduced pressure White needle crystals A: ethyl 4-(3-hydroxyphenyl)piperazine-1-carboxylate were obtained.

[0050] 2) Slowly add phosphorus oxychloride (5mL) dropwise into 10mL N,N-dimethylformamide in an ice-water bath, and after stirring for 30min, dissolve 0°C in 10mL N,N-dimethylformamide A (0.500g, 2.00mmol) in methyl formamide was slowly added to the above solution, and stirred for 2h after mixing completely; the system was introduce...

Embodiment 2

[0056] Prepare PBS buffer solution with pH=7.4 and concentration of 10mM, prepare 2mM XI-2 DMSO solution, prepare 20mM cysteine ​​aqueous solution; take 2mL of PBS-DMSO (10mM, pH=7.4, 4:1, v / v ) solution and 10 μL XI-2 DMSO solution were added to the fluorescence cuvette, and the volume of cysteine ​​solution was gradually added to 0, 5, 10, 15, 20, 25, 30, 35, 40, 45 μL, and at the same time The fluorescence intensity at 500nm measured by the fluorescence spectrometer was 50.23, 898.8, 1590, 1917, 2360, 2567, 2754, 2952, 2962, 3081, and the fluorescence intensity gradually increased. Fluorescence emission map see Figure 4 .

Embodiment 3

[0058] Prepare a PBS buffer solution with a pH of 7.4 and a concentration of 10 mM, prepare a 2 mM XI-2 DMSO solution, prepare a 0.2 M cysteine ​​aqueous solution, and prepare a 0.2 M N-ethylmaleimide (NEM) solution; Add 10μL of XI-2 DMSO solution to 2mL PBS-DMSO (10mM, pH=7.4, 4:1, v / v) fluorescence cuvette, take 10μL of cysteine ​​solution, add to the above buffer solution, When the fluorescence intensity of the system no longer changes, take 0.5 μL NEM solution and add it to the above solution. When the fluorescence intensity of the system no longer changes, continue to add 2 μL NEM solution. When the fluorescence intensity of the system no longer changes, add 2 μL NEM solution was used 4 times until the fluorescence intensity of the system did not change; adding 10 μL of cysteine ​​solution again made the fluorescence of the system increase again. Fluorescence emission map see Figure 5 . Take another fluorescence cuvette, add 10μL XI-2 DMSO solution to 2mL PBS-DMSO (10m...

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Abstract

The invention discloses a carboxyl-containing coumarin derivative and its synthesis method and application. The Chinese name of the derivative is (Z)-2-cyano-3-(4-((E)-3-( 7-(4-(ethoxycarbonyl)piperazin-1-yl)-2-oxo-2H-chromene-3-yl)-3-oxoprop-1-en-1-yl)phenyl) Acrylic acid, the English name is (Z)‑2‑cyano‑3‑(4‑((E)‑3‑(7‑(4‑(ethoxycarbonyl)piperazin‑1‑yl)‑2‑oxo‑2H‑chromen‑3 ‑yl)‑3‑oxoprop‑1‑en‑1‑yl)phenyl)acrylic acid, named XI‑2. The invention provides a method for the specific detection of derivative XI-2 to cysteine, in the solution of PBS-DMSO (4:1, v / v, pH 7.4), quantitatively detects half cysteine ​​by fluorescence spectrophotometer cystine content. The detection process is recyclable, simple, sensitive, fast, and the detection result is accurate. The present invention also provides the application of the derivative XI-2 in the preparation of a reagent for detecting cysteine ​​in cells, that is, under the regulation of NEM, XI-2 can efficiently penetrate the cell membrane to detect cysteine ​​in the cytoplasm.

Description

technical field [0001] The present invention relates to coumarin derivatives, in particular to a carboxyl-containing coumarin derivative and its synthesis method, and under the regulation and control of N-ethylmaleimide (NEM), it efficiently penetrates cell membranes and differentiates and detects cell membranes and cytoplasm The application of cysteine. Background technique [0002] Alterations of cysteine ​​homeostasis are associated with a variety of diseases and cellular functions. Therefore, real-time live-cell intracellular imaging and quantitative analysis of cysteine ​​dynamics are important for understanding pathological and physiological processes. Therefore, whether cysteine ​​probes have high permeability is crucial. [0003] Studies have shown that cell membranes are composed of phospholipid bilayers and embedded proteins, which pass through the cell membrane and are adsorbed on the surface of the cell membrane. Integral membrane proteins in membrane proteins ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCG01N21/6428G01N21/6486C09K11/06C07D311/16C09K2211/1044C09K2211/1088
Inventor 阴彩霞解茜茜霍方俊
Owner SHANXI UNIV
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