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Chromene-pyridine derivative fluorescent probe, preparation method and application

A technology of fluorescent probes and derivatives, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as the inability to realize hypochlorite, pH working range research, and limit practical applications, so as to improve selectivity and sensitivity, easy availability of raw materials, and wide application value

Active Publication Date: 2022-02-01
HENAN POLYTECHNIC UNIV
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Problems solved by technology

However, most of the existing fluorescent probes for hypochlorite require organic co-solvents (>10%), and cannot recognize hypochlorite in a pure aqueous environment. There is no detailed study on the working range of pH, which limits its further development. practical application, and there are not many reports on lysosome-targeted hypochlorite fluorescent probes

Method used

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  • Chromene-pyridine derivative fluorescent probe, preparation method and application
  • Chromene-pyridine derivative fluorescent probe, preparation method and application
  • Chromene-pyridine derivative fluorescent probe, preparation method and application

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Embodiment 1

[0031] The preparation method of the chromene-pyridine derivative fluorescent probe of this embodiment is as follows:

[0032] 2.102 g of 3H-benzo[f]chromene-2-carbaldehyde (10 mmol) and 2.87 g of 4-methyl-1-(2-morpholin-4-yl-ethyl)-pyridine bromide (10 mmol ) was dissolved in 0.05L ethanol, 0.017 g piperidine (0.2 mmol) was added dropwise as a catalyst, refluxed and stirred at 80°C for 4-5h, cooled and left to room temperature, filtered under reduced pressure, the obtained solid was washed with ethanol, and then ethanol The chromene-pyridine derivative fluorescent probe was obtained by recrystallization. The yield of the target product was 84%.

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

[0034] 1 H NMR (400 MHz, DMSO- d 6), δ (ppm): 8.87-8.89 (2H, d, Ar-H), 8.11-8.15(3H, m, Ar-H), 7.85-7.96 (4H, m, Ar-H), 7.61-7.63 ( 1H, t, Ar-H), 7.44-7....

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Abstract

The invention provides a chromene-pyridine derivative fluorescent probe, a preparation method and an application. The structural formula of the fluorescent probe is as follows:. The specific preparation method is to dissolve 3H-benzo[f]chromene-2-formaldehyde and 4-methyl-1-(2-morpholin-4-yl-ethyl)-pyridine bromide in ethanol, drop Add piperidine as a catalyst, reflux and stir at 80°C for 4-5 hours, cool and stand to room temperature, filter under reduced pressure, wash the obtained solid with ethanol to obtain the chromene-pyridine derivative fluorescent probe. The chromene-pyridine derivative fluorescent probe of the present invention can selectively interact with hypochlorite under pure aqueous physiological conditions, the yellow color of the solution fades, and the red fluorescence is significantly weakened, especially as a fluorescent probe in the cell lysosome Application for convenient detection of hypochlorite. The working environment of the probe does not require any organic solvent to solubilize, which is very beneficial to be applied to biological systems and has a wide range of potential application values.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a chromene-pyridine derivative fluorescent probe, a preparation method and an application. Background technique [0002] Hypochlorous acid (HClO) is usually known as hypochlorite (ClO − ) exists in the physiological environment, 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. Inflammation in some tissues has been linked to hypochlorite, 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 produced by lysosomal metabolism, 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 selec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06G01N21/6402G01N21/64G01N21/6428G01N21/6458C09K2211/1029C09K2211/1033C09K2211/1088G01N2021/6417G01N2021/6439G01N2021/6443
Inventor 吴伟娜王元郭芳芳宋雨飞刘爽爽
Owner HENAN POLYTECHNIC UNIV
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