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A kind of pyridine-coumarin derivative fluorescent probe and its preparation method and application

A technology of coumarin derivatives and fluorescent probes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as limiting practical applications

Inactive Publication Date: 2021-05-04
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing copper ion fluorescent probes require organic co-solvents (>10%), which limits their further practical application.

Method used

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  • A kind of pyridine-coumarin derivative fluorescent probe and its preparation method and application
  • A kind of pyridine-coumarin derivative fluorescent probe and its preparation method and application
  • A kind of pyridine-coumarin derivative fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation method of the pyridine-coumarin derivative fluorescent probe in the present embodiment is as follows:

[0029] Dissolve 2.43 g (10 mmol) 7-hydroxy-3-(3-methylisoxazol-5-yl)coumarin and 1.11 g (11 mmol) triethylamine in 0.03 L dichloromethane at 0 °C 0.02 L of a dichloromethane solution containing 1.41 g (10 mmol) of pyridine-2-carbonyl chloride was added dropwise. The reaction mixture was naturally warmed to room temperature, and stirring was continued for 3 h. Filtration under reduced pressure, the filtrate was evaporated to dryness under reduced pressure, and recrystallized with 50% ethanol to obtain the pyridine-coumarin derivative fluorescent probe. The yield of the target product was 69%.

[0030] Mass spectrum ESI-MS: m / z = 349.0881 for [M+H] + ; 371.0562 for [M+Na] + ; 719.1437for [2M+Na] + . For specific mass spectra, see figure 1 ;

[0031] H NMR spectroscopy 1 H NMR (400 MHz, DMSO- d 6 ), δ (ppm): 8.84-8.85 (m, 1H, Ar-H), 8.78 (s, 1H...

Embodiment 2

[0033] Determination of Optical Properties of Pyridine-Coumarin Derivatives on Copper Ion

[0034] The pyridine-coumarin derivative obtained in the above Example 1 was prepared as a fluorescent probe in a DMSO / HEPES buffer solution (v:v, 0.5:99.5, 0.02 mol / L, pH=7.4) to a molar concentration of 1 ×10 -5 mol / L solution, each containing a molar concentration of 2 × 10 -5 mol / L of metal ions (Ag + , Al 3+ , Ca 2+ , Cd 2+ , Co 2+ , Cr 3+ , Cu 2+ , Fe 3 + , Hg 2+ ,K + , Mg 2+ , Mn 2+ , Na + , Ni 2+ , Pb 2+ and Zn2+ ) solution was added with the same amount of the above fluorescent probe solution, and the fluorescence spectrometer was used for analysis (excitation wavelength was 440 nm), and the obtained fluorescence spectrum was shown in image 3 . pass image 3 It can be seen that the pyridine-coumarin derivatives prepared by the present invention only have obvious response to copper ions as probes, and the fluorescence signal can be used for rapid identificat...

Embodiment 3

[0037] Experiments for the detection of intracellular copper ions by fluorescent probes of pyridine-coumarin derivatives

[0038] 1 × 10 for HeLa cells -5 mol / L of the pyridine-coumarin derivative fluorescent probe prepared in Example 1 above was incubated at 37°C for 30 minutes, and Cu was added. 2+ (2×10 -5 mol / L) and then incubate for 30 minutes to obtain a fluorescence image in HeLa cells, as shown in Figure 5 where: a is the fluorescence imaging image of the above fluorescent probe; b is the bright field image of the above fluorescent probe; c is the superimposed image of the above fluorescent probe bright field image and the fluorescent image; d is the above fluorescent probe + Cu 2+ Fluorescence imaging image; e is the above fluorescent probe + Cu 2+ Imaging image under bright field; f is the above fluorescent probe Cu 2+ The superimposed image of the brightfield image and the fluorescence image. Adding a pyridine-coumarin derivative fluorescent probe to HeLa ce...

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Abstract

The present invention provides a pyridine-coumarin derivative fluorescent probe and its preparation method and application, wherein the chemical structural formula of the pyridine-coumarin derivative is as follows: 7-hydroxyl-3-(3-methyl Isoxadiazole-5-yl) coumarin and triethylamine were dissolved in an organic solvent, pyridine-2-formyl chloride was dissolved in an organic solvent, and added dropwise to the above solution at 0°C; the reaction mixture was naturally heated to Keep stirring at room temperature for 3 hours; filter under reduced pressure, evaporate the filtrate to dryness under reduced pressure, and recrystallize with ethanol to obtain the pyridine-coumarin derivative fluorescent probe. The pyridine-coumarin derivative fluorescent probe of the present invention can selectively interact with copper ions under physiological conditions, and the blue fluorescence of the solution is significantly enhanced, especially as a fluorescent probe for convenient detection of intracellular copper ions.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a pyridine-coumarin derivative and a preparation method and application thereof. Background technique [0002] As the third most abundant transition metal ion, copper ion plays an important role in biological systems of plants and humans. However, Cu 2+ When the concentration is too high, it can cause oxidative stress and neurodegenerative diseases such as Alzheimer's, Wilson's and Meck's diseases. In addition, copper ions have also become important metal pollutants due to the large-scale mining and extensive use of copper ore. Scientists have been working on the detection of copper ions in biological and environmental systems using selective fluorescent sensing probes. [0003] In recent years, fluorescent molecular probe technology has become an important method for detecting metal ion pollution due to its high sensitivity, simple operation, and low cost. However, most of t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/14C09K11/06G01N21/64
CPCC07D413/14C09K11/06C09K2211/1029C09K2211/1033C09K2211/1088G01N21/6456G01N21/6486
Inventor 吴伟娜王元郭芳芳李晓红刘盼
Owner HENAN POLYTECHNIC UNIV
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