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A pyrrole dihydrazone derivative fluorescent probe and its preparation method and application

A fluorescent probe, pyrrole dihydrazone technology, applied in the field of pyrrole dihydrazone derivatives and its preparation, can solve the problems of complex purification process, limited application, high cost of raw materials, etc., and achieve simple synthesis and post-processing methods and high fluorescence recognition performance , the effect of extensive application value

Inactive Publication Date: 2021-02-05
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Today's Hg targeting lysosomes 2+ The number of reported fluorescent probes is limited, and existing lysosomes target Hg 2+ Fluorescent probes usually have high raw material costs, long synthetic routes, and complicated purification processes, which limit their further applications.

Method used

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  • A pyrrole dihydrazone derivative fluorescent probe and its preparation method and application
  • A pyrrole dihydrazone derivative fluorescent probe and its preparation method and application
  • A pyrrole dihydrazone derivative fluorescent probe and its preparation method and application

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Embodiment 1

[0031] The preparation method of the pyrrole dihydrazone derivative fluorescent probe in this embodiment is as follows:

[0032] 2.79 g (10 mmol) N-morpholine ethyl-2,4-dimethyl-5-formylpyrrole-3-carboxamide and 0.50 g (10 mmol) hydrazine hydrate were dissolved in 0.05L ethanol, and 0.012 g acetic acid (0.2 mmol) was used as a catalyst, stirred under reflux at 80°C for 3-4 hours, cooled to room temperature, filtered under reduced pressure, and the obtained solid was washed with ethanol to obtain the pyrrole dihydrazone derivative fluorescent probe. The yield of the target product was 88%.

[0033] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the pyrrole dihydrazone derivative that makes, the result is as follows:

[0034] 1 H NMR (400 MHz, DMSO- d 6 ), δ (ppm): 11.35 (s, 1H, NH), 8.40 (s, 1H,CH), 7.24 (s, 1H, NH), 3.57 (t, 4H, 2CH 2 ), 2.41-2.44 (m, 8H, 4CH 2 ), 2.35 (s,3H, CH 3 ), 2.25 (s, 3H, CH 3 ). See the specific...

Embodiment 2

[0037] Determination of Optical Properties of Pyrrole-Containing Dihydrazone Derivatives to Mercury Ions

[0038] The pyrrole dihydrazone derivative prepared in Example 1 above was used as a fluorescent probe in an acetonitrile / HEPES buffer solution (v:v, 7:3, 0.02 mol / L, pH = 5) to prepare a molar concentration of 1×10 -5 mol / L solution, respectively, at a molar concentration of 2×10 -5 mol / L metal ion (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 Zn 2+ ) solution, adding an equal amount of the above-mentioned fluorescent probe solution, and using a UV-Vis spectrophotometer or a fluorescence spectrometer for analysis (excitation wavelength is 410 nm), the resulting UV and fluorescence spectra are shown in image 3 . pass image 3 It can be seen that the pyrrole dihydrazone derivatives prepared in the present invention have obvious responses only to mercury ions as probes, and both the ...

Embodiment 3

[0041] Detection experiment of pyrrole dihydrazone derivative fluorescent probe in intracellular mercury ion

[0042] 1 x 10 for HeLa cells -5 mol / L pyrrole dihydrazone derivative fluorescent probe prepared in Example 1 above was incubated at 37°C for 30 minutes, and Hg 2+ (2×10 -5 mol / L) and then incubated for 30 minutes to obtain the fluorescence imaging image of HeLa cells, as shown in Figure 5 As shown, wherein: a is the fluorescence imaging image of the blue channel of the above-mentioned fluorescent probe; b is the bright-field image of the above-mentioned fluorescent probe; c is the superimposed picture of the above-mentioned fluorescent probe bright-field image and fluorescence image; d is the above-mentioned fluorescence Probe + Hg 2+ Fluorescence imaging image of the blue channel; e is the above fluorescent probe + Hg 2+ Imaging image under bright field; f is the above-mentioned fluorescent probe Hg 2+ Superimposed images of brightfield and fluorescence image...

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Abstract

The present invention provides a pyrrole dihydrazone derivative fluorescent probe and its preparation method and application, wherein the chemical structural formula of the pyrrole dihydrazone derivative is as follows:; the preparation method is: N-morpholine ethyl-2,4 -Dimethyl-5-formylpyrrole-3-carboxamide and hydrazine hydrate were dissolved in an organic solvent; the resulting solution was added dropwise with acetic acid as a catalyst, and then refluxed and stirred at 80°C for 3-4h; the resulting solution was cooled to room temperature, Suction filtration under reduced pressure, and the obtained solid residue was washed with ethanol to obtain the pyrrole dihydrazone derivative fluorescent probe. The pyrrole dihydrazone derivative fluorescent probe of the present invention can selectively interact with mercury ions under physiological conditions, and the solution changes from colorless to green, while the blue fluorescence is significantly enhanced, especially as a fluorescent probe in the cell lysosome Applications for the convenient detection of mercury ions.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to pyrrole dihydrazone derivatives and their preparation methods and applications. Background technique [0002] Mercury is an essential heavy metal element used in electronics, chemical industry, pharmaceuticals, biology, etc. Mercury is widely distributed in soil, water, and air, and can be released into the environment through various human activities such as metallurgy, use of fossil fuels, and incineration of solid waste, and natural activities such as volcanic eruptions. Water-soluble mercury ions can be converted into methylmercury by bacteria, absorbed by organisms, and enriched in the human body through the food chain. Excessive accumulation of mercury in the body can cause cell dysfunction, leading to a series of diseases in forebrain, nervous system, kidney, cognition, mitosis, endocrine, and movement. Cell lysosomes contain a variety of acid hydrolases, whic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/34C09K11/06G01N21/64
CPCC07D207/34C09K11/06C09K2211/1029C09K2211/1033G01N21/6428G01N2021/6417
Inventor 王元吴伟娜赵晓雷李晓红刘盼郭芳芳
Owner HENAN POLYTECHNIC UNIV
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