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A kind of lysosome targeting fluorescent probe and preparation method thereof

A technology of fluorescent probes and lysosomes, applied in fluorescence/phosphorescence, carboxylic acid amide preparation, cyanide reaction preparation, etc., can solve the problems of few types, high price, large background signal interference, etc. The effect of reducing interference and background interference is small

Active Publication Date: 2019-07-23
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, commercially available lysosome-labeled fluorescent probes have disadvantages such as high price, few types, and large background signal interference. Therefore, there is an urgent need for a low-priced, targeted labeling, low background interference, and a sensitive, simple, and fast method. Fluorescent probe targeting lysosomes with good labeling effect

Method used

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  • A kind of lysosome targeting fluorescent probe and preparation method thereof
  • A kind of lysosome targeting fluorescent probe and preparation method thereof
  • A kind of lysosome targeting fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the synthesis of formula I

[0037]

[0038] (1) Synthesis of intermediate M1: under argon protection, compound 3-(tert-butylacetyl)acetylacetone (1.40g, 6.53mmol), diboron trioxide (0.46g, 6.61mmol) and tributyl borate (3.01g, 13.07mmol) was dissolved in 5mL DMF (solvent Ⅰ), heated to 75°C and stirred for 15 minutes, then added 4-dimethylaminobenzaldehyde (2.05g, 13.74mmol) and piperidine (40μL) (catalyst Ⅰ ), heated up to 90°C (reaction temperature I) and reacted for 4 hours (reaction time I). After the reaction, cool to 70°C, add 50mL of 20% acetic acid aqueous solution and continue to stir for 1 hour. After cooling to room temperature, 100 mL of chloroform was added for extraction, the organic phase was washed three times with water, dried by adding anhydrous sodium sulfate, concentrated and separated with a silica gel column, the eluent was chloroform / ethanol (100:1), and compound M1 (2.86 g), is a red solid with a yield of 92%.

[0039] (2) Syn...

Embodiment 8

[0043] Embodiment 8, lysosome co-localization experiment of formula I

[0044]In order to investigate the ability of Formula I to localize to lysosomes in cells, we conducted a lysosome co-localization experiment on Formula I. HeLa cells were stained with LysoSensor Green DND-189 (1 μM, a commercial lysosome stain) and Formula I (5 μM), as shown in the attached image 3 shown. from image 3 In a, green punctate fluorescence from LysoSensor Green DND-189 can be observed. from image 3 In b, bright punctate red fluorescence can be observed in the area around the nucleus of HeLa cells. Will image 3 a and 3b are superimposed to get image 3 c, It is found that the coincidence degree of the two is as high as 95%, which proves that the probe formula I can selectively localize in the lysosome and emit strong red fluorescence.

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Abstract

The invention discloses a lysosomal targeting fluorescent probe and a preparation method thereof. A D-Pi-A-Pi-D (donor-Pi-receptor-Pi-donor)-type large Pi conjugated system is constructed by alpha, beta-unsaturated ketone as a receptor. Through intramolecular charge transfer, compared with the existing many fluorescent probes for lysosome, lysosomal targeting fluorescent probe can realize large red shift of the excitation wavelength and emission wavelength of the molecule produce so that background signal interference is effectively reduced. The compound provided by the invention is used for fluorescence imaging of lysosome. In the cell environment, red fluorescence can be emitted under acidic conditions, and the maximum emission wavelength is about 625nm so that the lysosome targeting marker is obtained and background interference is small. The preparation method is sensitive, simple and quick.

Description

technical field [0001] The invention relates to a class of fluorescent probes for intracellular lysosome targeting labeling and a preparation method thereof. Background technique [0002] Lysosome is a very important organelle, which exists in almost all eukaryotic cells, and its pH value is about 4.5-5.5. There are many enzymes and proteins in lysosomes, including acid hydrolases, membrane proteases and cathepsins, which not only control the degradation of macromolecules in organisms, but also affect many special endocrine functions, maintaining normal metabolism of cells and defending against microorganisms play an important role in infection. Therefore, it is of great significance to position and image intracellular lysosomes and detect changes in pH value, which can provide useful information for the diagnosis and treatment tracking of many diseases, especially provide an effective way for visual detection of tumor tissues. [0003] Fluorescent probes have the advantag...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/02C07C237/20C09K11/06G01N21/64
CPCC07C227/10C07C227/18C07C231/02C07C237/20C09K11/06C09K2211/1007G01N21/6428G01N21/6486C07C229/44
Inventor 陈杜刚余响林黎俊波屈宏庆
Owner WUHAN INSTITUTE OF TECHNOLOGY
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