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Mitochondria-targeted pH and viscosity dual-channel detection fluorescent probe as well as preparation method and application thereof

A fluorescent probe, mitochondrial technology, applied in chemical instruments and methods, fluorescence/phosphorescence, material analysis by optical means, etc., can solve the problem of less specific imaging of cell mitochondria

Active Publication Date: 2021-11-02
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In recent years, fluorescence imaging methods have been widely used to monitor biological processes, but there are still very few specific imaging for cell mitochondria, especially with dual detection functions of viscosity and pH, so the development of fluorescent probes for dual-channel detection of cell pH and viscosity is very urgent and important

Method used

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  • Mitochondria-targeted pH and viscosity dual-channel detection fluorescent probe as well as preparation method and application thereof
  • Mitochondria-targeted pH and viscosity dual-channel detection fluorescent probe as well as preparation method and application thereof
  • Mitochondria-targeted pH and viscosity dual-channel detection fluorescent probe as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of CMPV

[0026] 1. Dissolve 3g (18.5mmol) 7-hydroxycoumarin and 5mL acetic anhydride in 25mL dichloromethane, activate at 25°C for half an hour, then add 0.1mL piperidine to continue the reaction for 1 hour; after the reaction, wash with ice water , suction filtration to obtain intermediate 1 as a white solid, 3.02 g, yield 80%.

[0027] 2. Under the condition of ice-water bath, add magneton, 20mL trifluoroacetic acid (TFA) and 3g (21.4mmol) hexamethylenetetramine (HMTA) into the round-bottomed flask, keep stirring in ice-water bath for half an hour, continue at room temperature Reacted for 1 hour, dissolved 2g (9.8mmol) of intermediate 1 in 5mL of TFA and then slowly added to the system, reflux (rf) at 80°C for 48h; after the reaction, purified by column chromatography to obtain light yellow solid intermediate 2 (washed The liquid was removed to petroleum ether:ethyl acetate=8:1, v / v) to obtain light yellow solid intermediate 2, 1.21 g, yi...

Embodiment 2

[0030] Embodiment 2: Spectral test of CMPV in different pH solvents

[0031]In order to explore CMPV in the solvent to detect the ultraviolet and fluorescence changes of different pH and viscosity, the CMPV of the present invention was dissolved in DMSO to prepare 2mM mother solution, and 15μL of the mother solution was put in 3mL of PBS solvent with different pH to obtain 10μM CMPV in different test solutions. The UV and fluorescence spectra in ( figure 1 ). With the decrease of pH, the absorbance of CMPV increased at 370nm and decreased at 500nm, and the fluorescence decreased continuously at 451nm. The above results show that CMPV can effectively detect pH in solution and can be used as a pH detector. Linear fit of pH to fluorescence values figure 2 It was found that the fluorescence value of the probe at pH 6.5 to 8.5 had a good linear relationship with pH (R 2 = 0.99).

Embodiment 3

[0032] Embodiment 3: Spectral test of CMPV in solvents of different viscosities

[0033] Dissolve the CMPV of the present invention in DMSO to prepare a 2mM mother solution, use different proportions of glycerin and distilled water to prepare different viscosity system solvents, add 15 μL of the probe mother solution to prepare a 10 μM viscosity test system, and test the fluorescence spectra of the probe under different viscosity conditions. As the viscosity of the system increases, the maximum fluorescence emission at 519nm increases continuously. The results show that CMPV can effectively detect viscosity in solution.

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Abstract

The invention discloses a mitochondria-targeted pH and viscosity dual-channel detection fluorescent probe as well as a preparation method and application thereof, and the mitochondria-targeted pH and viscosity dual-channel detection fluorescent probe has a structure disclosed in the invention. The fluorescent probe can generate interference-free two-color fluorescent response to pH and viscosity in vitro. A cytotoxicity test shows that the fluorescent probe is good in biocompatibility, a confocal fluorescence microscopic imaging experiment shows that the fluorescent probe is good in light stability for HeLa cells, mitochondria in the cells can be effectively positioned (the positioning coefficient is 0.92), and the fluorescent probe is suitable for confocal fluorescence imaging and dual-channel detection in the cells.

Description

technical field [0001] The present invention relates to a mitochondrial-targeted pH and viscosity dual-channel detection fluorescent probe and its preparation method and application, so as to realize the mitochondrial-targeted pH and viscosity dual-channel detection fluorescent imaging in solution and in cells, with selective specificity. 1. The advantages of high detection efficiency and good biocompatibility. Background technique [0002] Mitochondria are maternally inherited cytoplasmic organelles of eukaryotic cells and are important bioenergy synthesis factories. Mitochondria are involved in cell metabolism, organs, tissues and the whole body including Ca 2+ Regulation of homeostasis, clearance of redundant or damaged organelles, and triggering of cell death all play critical roles. Therefore, the survival of cells requires the maintenance of normal mitochondrial levels. Mitochondrial defects or dysfunction are associated with several cardiovascular and neurological ...

Claims

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Application Information

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IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06G01N21/6428G01N21/6458C09K2211/1088C09K2211/1037
Inventor 孟祥明韦峰陈俊张宛雏杨邦伟
Owner ANHUI UNIVERSITY
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