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A kind of α-pinene-based nuclear fluorescent probe and its preparation method and application

A pinene-based cell nucleus and fluorescent probe technology, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, and can solve problems such as high price, limited applicability, and photobleaching

Active Publication Date: 2022-04-05
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing nuclear stains such as DAPI and Hoechst suffer from photobleaching and self-quenching, which limit their applicability in long-term observations and are expensive

Method used

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  • A kind of α-pinene-based nuclear fluorescent probe and its preparation method and application
  • A kind of α-pinene-based nuclear fluorescent probe and its preparation method and application
  • A kind of α-pinene-based nuclear fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Preparation of α-pinene-based nuclear fluorescent probe

[0031] 1) Preparation of α-pinenyl-4-methylthiosemicarbazone:

[0032] Add 10mmol of myrtenal, 12mmol of p-4-methylthiosemicarbazide, 3mL of 10% hydrochloric acid aqueous solution and 10mL of ethanol into a three-necked flask equipped with a stirrer, a thermometer and a reflux condenser, and react at 85°C ; The reactant was extracted 3 times with 60mL ethyl acetate, and the combined organic phases were washed to neutrality with saturated brine; the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to recover the solvent to obtain α-pinenyl-4-methyl The crude product of α-pinenyl-4-methylthiosemicarbazone was washed with water and dried to obtain α-pinenyl-4-methylthiosemicarbazone with a yield of 80% and a purity of 99%. The characterization data of the product are as follows: 1 H NMR (400MHz, CDCl 3 )δ: 10.42(s, 1H), 7.63(s, 1H), 7.32(s, 1H), 6.02(s, 1H), 3.21(d, J=4....

Embodiment 2

[0037] Example 2 Application of α-pinene-based nuclear fluorescent probe

[0038] 1) Take the Hela cells in the logarithmic growth phase, digest with trypsin, adjust the cell concentration with culture medium, and use 1×10 cells per well. 5 The amount of cells was seeded in a 6-well plate, and 1×10 4 The amount of cells was seeded in a 96-well plate at 37°C, 5% CO 2 and incubated under saturated humidity conditions.

[0039] 2) After the cells grow on the wall, remove the culture medium, wash twice with PBS, add the drug diluted with complete medium to each well, and continue to incubate for a period of time.

[0040] 3) Add 10 μL CCK-8 reagent to the 96-well plate, continue to incubate for 2 hours, and detect the OD value at 450 nm.

[0041] 4) Discard the culture medium, wash the adherent cells twice with pre-cooled PBS to remove drugs not taken up by the cells, and fix with 4% paraformaldehyde for 30 min.

[0042] 5) Add an appropriate amount of commercial nuclear probe...

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Abstract

The invention discloses an α-pinene-based cell nucleus fluorescent probe, a preparation method and application thereof. The invention utilizes the natural renewable resource α-pinene derivative myrtleenal as a raw material to condense with 4-methylthiosemicarbazide to generate α-pinene-based thiosemicarbazone; α-pinene-based thiosemicarbazone Cyclize with chloroacetic acid to obtain α-pinenyl thiazolidinone; α-pinenyl thiazolidinone is condensed with 3-indole formaldehyde to obtain α-pinene-based nuclear fluorescent probe, which can The cell nucleus is specifically imaged in situ and emits green fluorescence under 390nm ultraviolet light irradiation. As a new type of cell nucleus fluorescent probe, it has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a novel α-pinene-based nuclear fluorescent probe and its preparation method and application. Background technique [0002] The nucleus plays a key role in various cellular activities such as metabolism, reproduction and inheritance, so nuclear stains are an important means to study the morphology and function of the nucleus. The nucleolus is an important subnuclear structure whose dynamic morphology reflects pathophysiological conditions. Existing nuclear stains such as DAPI and Hoechst suffer from photobleaching and self-quenching, which limit their applicability in long-term observation and are expensive. Therefore, the development of a new generation of nuclear fluorescent probes with low cytotoxicity and high photosensitivity is highly valued. Contents of the invention [0003] Purpose of the invention: Aiming at the deficiencies in the prior art, the purpose...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06G01N21/6428C09K2211/1011C09K2211/1029C09K2211/1037
Inventor 王石发王芸芸赵雨珣阮树堂王忠龙杨海燕杨益琴徐徐谷文
Owner NANJING FORESTRY UNIV
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