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A fluorescent probe for mitochondrial localization and its preparation method and application

A technology of fluorescent probes and mitochondria, which is applied in the field of molecular fluorescent probes, can solve the problems that are not suitable for measuring the viscosity in living cells, and achieve the effects of good fast response, high sensitivity, and good optical stability

Active Publication Date: 2022-06-03
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] To date, several common viscosity measurement instruments and analytical methods have been developed, including capillary viscometers, rotational viscometers, and electrochemical analysis, but none of them are suitable for measuring viscosity inside living cells

Method used

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  • A fluorescent probe for mitochondrial localization and its preparation method and application
  • A fluorescent probe for mitochondrial localization and its preparation method and application
  • A fluorescent probe for mitochondrial localization and its preparation method and application

Examples

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Embodiment Construction

[0026] In order to better understand the technical scheme of the present invention, the following specific examples are described in further detail:

[0027] 1) Synthesis of probe PyQz

[0028] Pyrene formaldehyde (350 mg, 1.5 mol), 2,3-dimethylquinazine chloride (300 mg, 1.5 mol) and 20 μL piperidine were added to a 10 mL round-bottomed flask, and placed in an oil bath at 90 °C to avoid Light stirring for 72h. After the reaction was completed, the system was cooled to room temperature, and an orange-red precipitate was precipitated. After suction filtration, recrystallization was carried out with acetonitrile to obtain the target product PyQz. The yield was 447 mg, a yield of 71%. Melting point is greater than 300℃; high resolution mass spectrometry (HRMS): theoretical m / z [M-Cl - ] + =370.1612; calculated [M-Cl - ] + :370.1590; the NMR results of the probe are as follows: 1 H NMR (DMSO-d 6 ,400MHz,ppm)δ9.03(d,2H,J=8.0Hz),8.98(d,1H,J=8.0Hz),8.87(s,1H),8.83(d,1H,J=8.0H...

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Abstract

The invention provides a fluorescent probe for mitochondrial localization, a preparation method and application thereof. The probe is prepared from pyrene formaldehyde and 2,3-dimethylquinazine raw materials, the steps are simple, the purification is convenient, and the yield is high. The structural formula is that the probe of the present invention is passed through pyrene and 2,3-dimethylquinazine The olefinic bond constitutes a typical D-π-A system, and pyrene is a better large conjugated planar frame structure, so the probe has a larger Stokes shift and a longer emission wavelength, which can effectively reduce the Signal-to-noise ratio; specific response to viscosity, high detection sensitivity, high optical stability, wide pH range and rapid detection; and the probe has good cell membrane permeability, which can realize cell mitochondria Detection of internal viscosity.

Description

technical field [0001] The invention relates to the technical field of molecular fluorescent probes, in particular to a preparation method and application of a fluorescent probe for mitochondrial localization. Background technique [0002] Mitochondria are important organelles in cells, which play a key role in cell metabolism and supplying ATP to cells. The dysfunction of mitochondria will affect the normal life activities of cells. Therefore, it is of great value to monitor the small changes in the mitochondria itself and its internal environment and to treat mitochondria in time under abnormal conditions. For chemical researchers, designing and synthesizing novel fluorescent probes to monitor mitochondrial and mitochondrial internal microenvironment changes is a very critical issue. Viscosity, an important factor of the internal microenvironment, is a key influencing factor that controls material transfer, signal transduction and the interaction between biological macro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06G01N21/64
CPCC07D471/04C09K11/06G01N21/6458G01N21/6486C09K2211/1011C09K2211/1029
Inventor 刘畅宋金鹏陈阔李季曾宪顺
Owner TIANJIN UNIVERSITY OF TECHNOLOGY