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A fluorescent probe for detecting intracellular peroxynitrite ion and its synthesis method

A peroxynitrite and fluorescent probe technology, applied in the field of chemistry, can solve the problems of compound synthesis, long reaction time, and short emission wavelength, and achieve the effects of simple structure, short response time, and high sensitivity

Active Publication Date: 2019-03-29
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the chemical sensors currently used to measure peroxynitrite ions have certain defects in practical applications: the emission wavelength is relatively short, most of which are less than 500nm; they are susceptible to interference from other reactive oxygen / nitrogen ions, Especially common are hydrogen peroxide and hypochlorite ions; the long reaction time required and the complex synthesis of compounds; the serious interference of biological bulk autofluorescence all limit their application in the detection of actual biological systems

Method used

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  • A fluorescent probe for detecting intracellular peroxynitrite ion and its synthesis method
  • A fluorescent probe for detecting intracellular peroxynitrite ion and its synthesis method
  • A fluorescent probe for detecting intracellular peroxynitrite ion and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The synthetic route is as follows (formula 2):

[0042]

[0043] 1) Synthesis of 6-dimethylamino-1-tetralone

[0044] Dissolve 6-amino-1,2,3,4-tetrahydro-1-naphthone (325mg, 2mmol) and potassium carbonate (830mg, 6mmol) in 5mL of N,N-dimethylformamide solution, and then Add iodomethane (430 mg, 3 mmol), then heat to 45 ° C, and stir for 24 h to obtain the first mixed solution; after the reaction is completed, the first mixed solution is cooled to room temperature; 10 mL of the first mixed solution is added to the first mixed solution Deionized water, extracted three times with ethyl acetate, and washed several times with a large amount of water and saline, the organic layer after extraction was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and then column chromatography was carried out (with a volume ratio of 6 : 1 mixed solution of petroleum ether and ethyl acetate is eluent), and the white solid obtained is 6-dimethylamino-...

Embodiment 2

[0052] The synthetic route is as shown in (formula 3):

[0053]

[0054] 1) Synthesis of 6-dimethylamino-1-tetralone

[0055] Dissolve 6-amino-1,2,3,4-tetrahydro-1-naphthone (325mg, 2mmol) and potassium carbonate (830mg, 6mmol) in 5mL of N,N-dimethylformamide solution, and then Add 430 mg iodomethane (3 mmol), then heat to 45° C., stir for 24 h to obtain the first mixed liquid. After the reaction was completed, the first mixed solution was cooled to room temperature, 10 mL of deionized water was added to the first mixed solution, extracted three times with ethyl acetate, and washed several times with a large amount of water and saline. The extracted organic phase was dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and then separated by column chromatography (using a mixture of petroleum ether and ethyl acetate with a volume ratio of 6:1 as the eluent) to obtain a white solid It is 6-dimethylamino-1-tetralone, the yield is 160 mg,...

Embodiment 3

[0063] The synthetic route is as follows (formula 4):

[0064]

[0065] 1) Synthesis of 6-dicyclopropylamino-1-tetralone

[0066] Dissolve 6-amino-1,2,3,4-tetrahydro-1-naphthalenone (325 mg, 2 mmol) and potassium hydroxide (336 mg, 6 mmol) in 5 mL of DMSO solution, then add cyclopropane bromide (363mg, 3mmol), heated to 60°C and stirred for 24h to obtain the first mixed solution; after the reaction was completed, the first mixed solution was cooled to room temperature, and 20 mL of deionized water was added to the first mixed solution , extracted three times with ethyl acetate, and washed several times with a large amount of water and saline, the organic phase after the extraction was dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and then separated by column chromatography (with a volume ratio of 8:1 The mixed solution of petroleum ether and ethyl acetate is the eluent), and the white solid obtained is 6-dicyclopropylamino-1-tet...

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Abstract

The invention provides a fluorescent probe for detecting peroxynitrite in a cell. The structural formula of the fluorescent probe is shown in the description, wherein R1 and R2 are selected from hydrogen, linear chain alkyl containing 1 to 5 carbon atoms or naphthenic base containing 3 to 8 carbon atoms respectively and separately; R3 is selected from a cyano group or an ester group. The fluorescent probe has high peroxynitrite selectivity, high cell permeability, extremely-short response time, extremely high detection sensitivity and no toxic and side effects to the cell per se, and is suitable for detecting the concentration change of the peroxynitrite in the cell. The fluorescent probe synthetic method is simple, is high in yield, and is suitable for large-scale production.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a fluorescent probe for detecting intracellular peroxynitrite ions and a synthesis method thereof. Background technique [0002] Since the discovery in the 1980s that NO can be synthesized by enzymes in vivo, people began to study the biomedical aspects of NO. The Nobel Prize in 1998 was awarded to scientists who discovered the special function of NO. It is particularly worth mentioning that NO not only acts as a messenger molecule in biological tissues, NO and O 2 - It can also form peroxynitrite (ONOO - ). Peroxynitrite ion is more effective than NO and O 2 - A potent cytotoxic substance with stronger oxidation and wider effects, which can diffuse a long distance from the production site to reach the target site, causing extensive damage, and is a powerful oxidant that causes cell and tissue damage. Peroxynitrite ion can act on macromolecular substances such as enzymes, proteins...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014G01N21/6428
Inventor 汪鹏飞刘莎刘卫敏张洪艳
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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