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Chromene-pyridine 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 no pH working range research, inability to identify hypochlorite, and limit practical applications, etc., to improve the selection The effect of stability and sensitivity, wide application value, and small background interference

Active Publication Date: 2021-03-19
HENAN POLYTECHNIC UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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

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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 as well as a preparation method and application thereof. The structural formula of the fluorescent probe is shown in the specification. The specific preparation method comprises the following steps: dissolving 3H-benzo[f]chromene-2-formaldehyde and 4-methyl-1-(2-morpholine-4-ethyl)-pyridine bromide in ethanol, dropwise addingpiperidine as a catalyst, carrying out reflux stirring at 80 DEG C for 4-5 hours, cooling, standing to room temperature, carrying out reduced pressure suction filtration, and cleaning the obtained solid with ethanol to obtain the chromene pyridine derivative fluorescent probe. The chromene pyridine derivative fluorescent probe can selectively react with hypochlorite under pure water phase physiological conditions, the solution is yellow and fades, meanwhile, red fluorescence is remarkably weakened, and the chromene pyridine derivative fluorescent probe is particularly applied to convenient detection of hypochlorite in cytolysosome as a fluorescent probe. The probe does not need any organic solvent for hydrotropy in a working environment, is very beneficial to being applied to a biologicalsystem, and has wide potential application value.

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 Applications(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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