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Coumarin-based fluorescent probe as well as preparation method and application thereof

A fluorescent probe, coumarin technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of background fluorescence interference, inapplicable cells, tissues and living imaging, etc., to avoid fluorescence quenching , avoid self-absorption effect, good solubility effect

Inactive Publication Date: 2021-02-09
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Coumarin is a typical ICT fluorescent dye and has the potential to be sensitive to polarity. However, the dye emits in the short wavelength (400-520nm) region and is easily interfered by background fluorescence. It is not suitable for cell, tissue and in vivo imaging. application

Method used

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  • Coumarin-based fluorescent probe as well as preparation method and application thereof
  • Coumarin-based fluorescent probe as well as preparation method and application thereof
  • Coumarin-based fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation of fluorescent probe comprises the following steps ( figure 1 ):

[0034] (1) Synthesis of compound 2: Br 2 (0.26mL, 5.0mmol) was added dropwise to a solution of 7-diethylaminocoumarin (compound 1, 1.58g, 5.0mmol) in acetic acid (25mL), and stirred at room temperature for 1h. A white solid was obtained by filtration, washed three times with acetic acid, and dried in the air. Compound 2, 7-diethylamine-3-bromocoumarin, was obtained as a white solid after recrystallization from acetone (yield: 60%).

[0035] (2) Synthesis of compound 3: under nitrogen protection, PdCl 2 (PPh 3 ) 2 (91.2mg, 0.13mmol, 5.0mol%), CuI (24.8mg, 0.13mmol, 5.0mol%), triethylamine (770L, 5.5mmol), and trimethylsilylacetylene (469L, 5.0mmol) were added to Compound 2 (740mg, 2.5mmol) in anhydrous DMF (25mL) solution. The resulting mixture was reacted at 60°C for 5 hours. After the reaction solution was cooled, 150 mL of water was added and extracted with dichloromethane. The...

Embodiment 2

[0039] Spectral testing of fluorescent probe PQA

[0040] (1) Study on the ultraviolet absorption spectrum and fluorescence emission spectrum of probe PQA in different solvents.

[0041] Accurately weigh 3.7411mg compound PQA sample, dissolve it in a 10mL volumetric flask with dichloromethane solvent to prepare a concentration of 1.0×10 -3 mol / L mother solution, and then use a pipette gun to draw 100 μL of the mother solution into a 10mL volumetric flask. -5 mol / L of the solution to be tested. The ultraviolet absorption spectrum and fluorescence emission spectrum of the probe PQA in different solvents were measured with the solution to be tested.

[0042] Table 1 The data of the ultraviolet absorption and fluorescence emission spectra of PQA in different solvents

[0043]

[0044] from Figure 4 It is concluded that the maximum absorption spectrum of the probe PQA has a strong red shift with the increase of the solution polarity. For example, among the above solvents, ...

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Abstract

The invention belongs to the field of small organic molecule fluorescent probes, and particularly relates to a coumarin-based fluorescent probe as well as a preparation method and application thereof.Aiming at the condition that the existing fluorescent probes with long emission wavelength and high light quantum yield are fewer, the invention synthesizes the fluorescent probe PQA capable of beingused for detecting the polarity in the microenvironment through a series of reactions on the basis of 7-diethylamino coumarin. The fluorescence probe has large Stokes displacement in solvents with different polarities and non-polar solvents, good solubility, a larger emission wavelength area and high light quantum yield, fluorescence quenching caused by dye self-absorption and molecular aggregation can be avoided, and interference of autofluorescence of cells or tissues can be reduced.

Description

technical field [0001] The invention belongs to the field of organic small molecule fluorescent probes, and relates to a fluorescent probe containing benzoheterocyclic aromatic sulfide compounds for detecting intracellular polarity changes and its application, in particular to a coumarin-based fluorescent probe And its preparation method and application. Background technique [0002] Polarity is an important parameter in chemical and chemical production, and it is also an important environmental factor that determines the characteristics of the local environment (microenvironment). Many organic and inorganic reaction processes are dependent on the polarity of the surrounding environment; at the cellular level in biological systems, polarity controls cellular function proteins by separating proteins and their inhibitors to activate protein functions; polarity can initiate signal transduction processes ; Since hydrophobic interactions play an important role in physiological a...

Claims

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Application Information

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IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06C09K2211/1037C09K2211/1088G01N21/6428G01N2021/6439
Inventor 苗俊峰翁嘉劲刘昱池郭炜
Owner SHANXI UNIV
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