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A pyrrole-merocyanine derivative fluorescent probe and its preparation method and application

A technology of fluorescent probes and derivatives, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of inability to recognize hypochlorite, not many hypochlorite fluorescent probes, and limited practical application, etc. Achieving the effect of wide application value, simple synthesis and post-processing methods, and high fluorescence recognition performance

Inactive Publication Date: 2020-11-13
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 fluorescent probes for hypochlorite require organic co-solvents (>10%), and cannot recognize hypochlorite in pure aqueous phase, which limits its further practical application.
Moreover, there are not many reports on lysosome-targeted hypochlorite fluorescent probes today.

Method used

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  • A pyrrole-merocyanine derivative fluorescent probe and its preparation method and application
  • A pyrrole-merocyanine derivative fluorescent probe and its preparation method and application
  • A pyrrole-merocyanine derivative fluorescent probe and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0032] The preparation method of the pyrrole-merocyanine derivative fluorescent probe in this embodiment is as follows:

[0033] Dissolve 2.79 g, N-morpholinoethyl-2,4-dimethyl-5-formylpyrrole-3-carboxamide (10 mmol) and 3.05 g of N-ethylbenzothiazole iodide salt (10 mmol) In 0.05L of ethanol, add 0.017 g of piperidine (0.2 mmol) dropwise as a catalyst, reflux and stir at 80°C for 3-4 hours, cool to room temperature, filter under reduced pressure, wash the obtained solid with ethanol, and recrystallize with ethanol The pyrrole-merocyanine derivative fluorescent probe is obtained. The yield of the target product was 82%.

[0034] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the pyrrole-merocyanine derivative that makes, the result is as follows:

[0035] 1 H NMR (400 MHz, D 2O), δ (ppm): 7.85-7.87 (1H, d, Ar-H), 7.75-7.77(1H, d, Ar-H), 7.60-7.63 (d, 1H, CH=), 7.57-7.61 ( 1H, t, Ar-H), 7.45-7.49(1H, t, Ar-H), 6.92-6.96 (1H,...

Embodiment 2

[0038] Determination of Optical Properties of Pyrrole-Merocyanine Derivatives to Hypochlorite

[0039] The pyrrole-merocyanine derivatives prepared in Example 1 above were used as fluorescent probes in citric acid-sodium citrate buffer solution (0.02 mol / L, pH = 4) to prepare a molar concentration of 1×10 -5 mol / L solution, respectively, at a molar concentration of 1×10 -4 mol / L anion (AcO − 、Br − , Cl − , ClO − , ClO 4 − 、CN − , F − 、H 2 PO 4 − 、HPO 4 − , I − 、PO 4 3− , S 2− and SO 3 2− ) or reactive oxygen species (H 2 o 2 , 1 o 2 , OH, NO and O 2 − ) solution, add the same amount of the above-mentioned fluorescent probe solution, and use a UV-visible spectrophotometer or a fluorescence spectrometer to analyze (excitation wavelength is 465 nm), and the obtained UV and fluorescence spectrograms are shown in Figure 4 . pass Figure 4 It can be seen that the pyrrole-merocyanine derivatives prepared by the present invention only have obvious respon...

Embodiment 3

[0042] Detection experiment of pyrrole-merocyanine derivative fluorescent probe in intracellular hypochlorite

[0043] 1 x 10 for HeLa cells -5 The mol / L pyrrole-merocyanine derivative fluorescent probe prepared in Example 1 above and the commercial lysosome localization dye LysoTracker Red were co-incubated at 37°C for 30 minutes to obtain the fluorescence imaging image of HeLa cells, specifically as follows Figure 6 As shown, where: a is the fluorescence imaging image of the green channel; b is the fluorescence imaging image of the red channel; c is the superimposed image of the green channel and the red channel; d is the bright field image; e is the superposition of the green channel, the red channel and the bright field After the picture; f is the overlay map of the intensity distribution of the green channel and the red channel. The green channel fluorescence of the probe in HeLa cells is basically consistent with the LysoTrackerRed red channel fluorescence, with an ov...

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Abstract

The invention provides a pyrrole-merocyanine derivative fluorescent probe, and a preparation method and application thereof. The chemical structural formula of a pyrrole-merocyanine derivative is as shown in the specification. The preparation method comprises the following steps: dissolving N-morpholinoethyl-2,4-dimethyl-5-formylpyrrole-3-formamide and N-ethyl benzothiazole iodate in an organic solvent; dropwise adding piperidine as a catalyst into a solution obtained in the previous step, and then carrying out a reflux stirring reaction at 80 DEG C for 3-4 h; and performing cooling to room temperature, carrying out reduced-pressure suction filtration, cleaning an obtained solid residue with ethanol, and carrying out recrystallizing with ethanol to obtain the pyrrole-merocyanine derivativefluorescent probe. The pyrrole-merocyanine derivative fluorescent probe can selectively react with hypochlorite under pure water phase physiological conditions, allows the yellow color of a solutionto fades while the green fluorescence of the solution to remarkably weaken, and t is particularly applied to convenient detection of hypochlorite in cytolysosome as a fluorescent probe.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to pyrrole-merocyanine derivatives and their preparation methods and applications. Background technique [0002] Hypochlorous acid (HClO) usually exists in the physiological environment in the form of hypochlorite (ClO−), which has a bactericidal effect and also plays an immune role when the body is invaded by microorganisms. However, excessive HClO produced in phagocytes can also cause harm to the human body. Hypochlorite has been implicated in some tissue inflammation, and hypochlorite release from neutrophils is thought to be involved in lung damage, rheumatoid arthritis, hepatic ischemia-reperfusion injury, and kidney disease. Excess hypochlorite in cells is mainly metabolized by lysosomes, and its concentration is closely related to lysosomal redox balance. Hypochlorous acid is also a commonly used disinfectant in daily life. Therefore, the development of selectiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037G01N21/6428G01N21/6458
Inventor 王元吴伟娜赵晓雷郭芳芳李晓红刘盼
Owner HENAN POLYTECHNIC UNIV
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