Fluorescent probe for positioning mitochondria as well as preparation method and application of fluorescent probe
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, etc., and achieve the effects of good fast response, high sensitivity, and good optical stability
Active Publication Date: 2021-06-22
TIANJIN UNIVERSITY OF TECHNOLOGY
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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
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[0026] In order to better understand the technical scheme of the present invention, it is described in further detail below through specific examples:
[0027] 1) Synthesis of probe PyQz
[0028] Add pyrene formaldehyde (350mg, 1.5mol) and 2,3-dimethylquinazine chloride salt (300mg, 1.5mol) and 20μL piperidine into a 10mL round-bottomed flask, and put it in a 90°C oil bath 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 performed with acetonitrile to obtain the target product PyQz. Its yield was 447 mg, a 71% yield. Melting point greater than 300°C; 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=8.0Hz), 8.72(d,1...
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Abstract
The invention provides a fluorescent probe for positioning mitochondria as well as a preparation method and application of the fluorescent probe. The probe is prepared from pyrenecarboxaldehyde and 2, 3-dimethyl quinolizine, the steps are simple, purification is convenient, the yield is high, the structural formula is shown in the specification, pyrene and 2, 3-dimethyl quinolizine form a typical D-[pi]-A system through an olefinic bond, pyrene is of a good large conjugate plane frame structure, and therefore, the probe has relatively large Stokes shift and relatively long emission wavelength, and the signal-to-noise ratio can be effectively reduced; the probe shows specific response to viscosity, and has the advantages of high detection sensitivity, high optical stability, wide pH application range and rapid detection.The probe has good cell membrane permeability, and can realize the detection of the viscosity in the cell mitochondria.
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 the metabolism of cells and the process of 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 of the mitochondria itself and the internal environment and to treat the mitochondria in abnormal conditions in time. For chemical researchers, designing and synthesizing novel fluorescent probes to monitor changes in mitochondria and the microenvironment inside mitochondria is a critical issue. Among them, viscosity, an important factor in the internal microenvironment, is a key factor that controls material transfer, signal transduction, and the interaction b...
Claims
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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