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Morpholine-pyridine-merocyanine derivative fluorescent probe as well as preparation method and application thereof

A technology of fluorescent probes and derivatives, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of uncommon CEs ratio fluorescent probes, achieve wide application value, easy access to raw materials, synthesis and The effect of simple post-processing methods

Active Publication Date: 2021-07-02
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, reports of ratiometric fluorescent probes for existing CEs are not common

Method used

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  • Morpholine-pyridine-merocyanine derivative fluorescent probe as well as preparation method and application thereof
  • Morpholine-pyridine-merocyanine derivative fluorescent probe as well as preparation method and application thereof
  • Morpholine-pyridine-merocyanine derivative fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation method of the morpholine-pyridine-merocyanine derivative fluorescent probe of this embodiment is as follows:

[0031] 4.41 g 4-[2-(6-hydroxy-2-naphthyl)-vinyl]-1-[2-(4-morpholinoethyl)]-pyridinium bromide (10 mmol) and 1.23 g ethyl Acid anhydride (12 mmol) was dissolved in 0.2 L of dichloromethane, 3.04 g of triethylamine (30 mmol) was added dropwise as a catalyst, stirred at room temperature for 3-4 h, after the reaction was traced by TLC, rotary evaporation was performed, and the obtained solid was washed with ethyl acetate The ester was washed, and then recrystallized with absolute ethanol to obtain the fluorescent probe of the morpholine-pyridine-merocyanine derivative. The yield of the target product was 65%.

[0032] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the morpholine-pyridine-merocyanine derivative that makes, the result is as follows:

[0033] 1 H NMR (400 MHz, DMSO- d 6 ), δ (ppm): ...

Embodiment 2

[0037] Determination of Optical Properties of Morpholine-Pyridine-Merocyanine Derivatives on CEs

[0038] The morpholine-pyridine-merocyanine derivatives prepared in the above-mentioned Example 1 were used as fluorescent probes in PBS sodium buffer solution (0.01 mol / L, pH=7.4) to prepare a molar concentration of 1×10 -5 mol / L solution, respectively, at a molar concentration of 2×10 -5 mol / L anion (AcO − , ClO − , CO 3 2− , S 2− and HCO 3 − ), cations (Ca 2+ , Mg 2+ 、Al 3+ and Fe 3+ ) reactive oxygen species (H 2 o 2 ) and amino acids (Cys, Ala, Ary, Ser, Asp) were added with an equal amount of the above fluorescent probe solution, and analyzed with a UV-Vis spectrophotometer or a fluorescence spectrometer (excitation wavelength is 360 nm), and the obtained UV and fluorescence Spectrum see Figure 4 . pass Figure 4 It can be seen that the morpholine-pyridine-merocyanine derivatives prepared in the present invention have obvious responses only to CEs as pro...

Embodiment 3

[0041] Detection experiment of morpholine-pyridine-merocyanine derivative fluorescent probe in intracellular CEs

[0042] 1 x 10 for HeLa cells -5 mol / L of the morpholine-pyridine-merocyanine derivative fluorescent probe prepared in Example 1 above was incubated at 37°C for 30 minutes, and CEs were added to ensure that the concentration of CEs was 1×10 -3 U / L, and then cultivated for 30 minutes to obtain the fluorescence imaging map of HeLa cells, specifically as follows Image 6 As shown, where: a is the fluorescence imaging image of the green channel of the fluorescent probe; b is the fluorescence imaging image of the red channel of the fluorescent probe; c is the overlay image of the green channel and the red channel of the fluorescent probe; d is the bright field image of the fluorescent probe; e The green channel, red channel and bright field overlay of the fluorescent probe; f is the fluorescence imaging image of the green channel after the fluorescent probe + CEs; g t...

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Abstract

The invention provides a morpholine-pyridine-merocyanine derivative fluorescent probe as well as a preparation method and application thereof. The chemical structural formula of a morpholine-pyridine-merocyanine derivative is shown in the specification. The morpholine-pyridine-merocyanine derivative fluorescent probe disclosed by the invention can selectively act with carboxylesterase (CEs) under pure water phase physiological conditions. The fluorescence color of the solution is changed from green to orange yellow, and a typical ratio fluorescence signal is presented. The invention particularly relates to application of the fluorescent probe as a CEs fluorescent probe in cell lysosome fluorescence imaging.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to morpholine-pyridine-merocyanine derivatives and their preparation methods and applications. Background technique [0002] Carboxylesterases (CEs), as an important hydrolytic metabolic enzyme distributed in the human body, play a non-negligible role in maintaining the balance of human lipid metabolism and metabolic clearance of drugs and poisons. However, the abnormal changes of CEs are closely related to the occurrence of many diseases, such as hyperlipidemia, fatty liver, cancer and other diseases. Therefore, it is of great significance to develop rapid, sensitive and accurate detection methods for CEs. [0003] In recent years, fluorescent molecular probe technology has become an important means to detect important metal ions, anions, small molecules and biological enzyme activities due to its high sensitivity, simple operation and low cost. However, most of the ex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/36C09K11/06G01N21/64
CPCC07D213/36C09K11/06G01N21/6428C09K2211/1033C09K2211/1029C09K2211/1011
Inventor 韩学锋吴伟娜郭芳芳宋雨飞刘爽爽王元
Owner HENAN POLYTECHNIC UNIV
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