Pyrrole dihydrazone derivative fluorescent probe as well as preparation method and application thereof

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: 2020-02-04
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 prob

Method used

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  • Pyrrole dihydrazone derivative fluorescent probe as well as preparation method and application thereof
  • Pyrrole dihydrazone derivative fluorescent probe as well as preparation method and application thereof
  • Pyrrole dihydrazone derivative fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

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 0.05 L ethanol, and 0.012 g was added dropwise Acetic acid (0.2 mmol) was used as a catalyst, refluxed and stirred 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...

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 ul...

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 invention provides a pyrrole dihydrazone derivative fluorescent probe as well as a preparation method and an application thereof. The chemical structural formula of a pyrrole dihydrazone derivative is shown in the specification; the preparation method comprises the steps: dissolving N-morpholinoethyl-2,4-dimethyl-5-formylpyrrole-3-formamide and hydrazine hydrate into an organic solvent; dropwise adding acetic acid as a catalyst into the obtained solution, and then carrying out reflux stirring reaction at the temperature of 80 DEG C for 3-4 h; and cooling the obtained solution to room temperature, carrying out reduced pressure suction filtration, and cleaning the obtained solid residue with ethanol to obtain the pyrrole dihydrazone derivative fluorescent probe. The pyrrole dihydrazone derivative fluorescent probe can selectively react with mercury ions under physiological conditions, the solution is changed from colorless to green, meanwhile, blue fluorescence is remarkably enhanced, and the pyrrole dihydrazone derivative fluorescent probe as a fluorescent probe is particularly applied to convenient detection of mercury ions in cytolysosome.

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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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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