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Fluorescent probe for specifically identifying hydrogen polysulphide and bio-thiol

A technology of polyhydrogen sulfide and fluorescent probes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of not being able to distinguish at the same time, and achieve the effect of simple preparation methods

Active Publication Date: 2019-07-16
南宁师范大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In regulating various physiological processes, H 2 S n Has high potency, including activation of ion channels, transcription factors and tumor suppressors; how to detect biothiols and polyhydrogen sulfides has attracted much attention. In recent years, a large number of fluorescent probes, including fluorescent proteins and fluorescent dyes, have been used It is used for the detection of certain objects in organisms, but most of the current probes do not have the ability to simultaneously distinguish H 2 S n and biothiols, so it is of great significance to develop a probe that can distinguish them at the same time

Method used

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  • Fluorescent probe for specifically identifying hydrogen polysulphide and bio-thiol
  • Fluorescent probe for specifically identifying hydrogen polysulphide and bio-thiol
  • Fluorescent probe for specifically identifying hydrogen polysulphide and bio-thiol

Examples

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Embodiment 1

[0040] A fluorescent probe that specifically recognizes hydrogen polysulfide and biological thiols. The structural formula of the fluorescent probe is as follows:

[0041]

[0042] The preparation method of a fluorescent probe that specifically recognizes hydrogen polysulfide and biological thiols includes the following steps:

[0043] Step 1: Dissolve 3-aldehyde-4-chloro-7-diethylaminocoumarin (labeled 1,1mmol, 279mg) in 5mL of anhydrous acetonitrile, and then add 4-dimethylaminophenolate Acid salt (1mmol, 173mg), and finally triethylamine (NEt 3 ) (1mmol, 139μL) as a base, protected by argon, and reacted at 80°C under reflux for 4h. The solvent was spin-dried to obtain a mixture. The mixture was purified to obtain compound A. The mixture was a reddish-brown solid and was purified to obtain dark brown compound A, totaling 304 mg , The yield is 80%;

[0044] The main product in the mixture is compound A;

[0045] The reaction equation is:

[0046]

[0047] Step two, dissolve compound ...

Embodiment 2

[0052] A fluorescent probe that specifically recognizes hydrogen polysulfide and biological thiols. The structural formula of the fluorescent probe is as follows:

[0053]

[0054] The preparation method of a fluorescent probe that specifically recognizes hydrogen polysulfide and biological thiols includes the following steps:

[0055] Step 1. Dissolve 3-aldehyde-4-chloro-7-diethylaminocoumarin (labeled 1,1mmol, 279mg) in 10mL of anhydrous acetonitrile, and add 4-dimethylaminophenolate Acid salt (2mmol, 346mg), and finally triethylamine (NEt 3 ) (2mmol, 278μL) as a base, protected by argon, and reacted under reflux at 100°C for 4.5 hours. The solvent was spin-dried to obtain a mixture. The mixture was purified to obtain compound A. The mixture was a reddish brown solid and was purified to obtain dark brown compound A. Total 291.8mg, the yield was 76.8%;

[0056] The main product in the mixture is compound A;

[0057] The reaction equation is:

[0058]

[0059] Step two, dissolve compo...

Embodiment 3

[0063] A fluorescent probe that specifically recognizes hydrogen polysulfide and biological thiols. The structural formula of the fluorescent probe is as follows:

[0064]

[0065] The preparation method of a fluorescent probe that specifically recognizes hydrogen polysulfide and biological thiols includes the following steps:

[0066] Step 1: Dissolve 3-aldehyde-4-chloro-7-diethylaminocoumarin (labeled 1,1mmol, 279mg) in 15mL of anhydrous acetonitrile, and then add 4-dimethylaminophenolate Salt (3mmol, 519mg), and finally triethylamine (NEt 3 ) (3mmol, 417μL) as a base, protected by argon, and reacted at 90°C for 5 hours by rotating the solvent to dryness. The mixture was purified to obtain compound A, where the mixture was a reddish-brown solid and was purified to obtain dark brown compound A, totaling 297.2 mg, the yield is 78.2%;

[0067] The main product in the mixture is compound A;

[0068] The reaction equation is:

[0069]

[0070] Step 2: Dissolve compound A (297.2304mg, 0.7...

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Abstract

The invention discloses a fluorescent probe for specifically identifying hydrogen polysulphide and bio-thiol. The fluorescent probe has a structural formula shown in the description. A preparation method of the fluorescent probe for specifically identifying hydrogen polysulphide and bio-thiol includes the following steps: (1) dissolving 3-aldehyde-4-chloro-7-diethylamino coumarin in anhydrous acetonitrile, then adding 4-dimethylaminophenol hydrochloride and triethylamine sequentially, adopting inert gas for protection, performing reflux for a reaction, and performing spin drying on a solvent so as to obtain a compound A; and (2) dissolving the compound A and malononitrile in anhydrous dichloromethane, then adding triethylamine as base, performing a reaction in an ice bath under the protection of inert gas, and performing separation so as to obtain the fluorescent probe. The fluorescent probe has the advantage of specifically identifying hydrogen polysulphide and bio-thiol.

Description

Technical field [0001] The invention relates to the technical field of fluorescent probe preparation. More specifically, the present invention relates to a fluorescent probe that specifically recognizes hydrogen polysulfide and biological thiols. Background technique [0002] Biological thiols (Cysteine ​​(Cys), Homocysteine ​​(Hcy), Glutataione (GSH)) are important components of many proteins and small molecules, which are active in cell life. Play an important role in the process. Among them, cysteine ​​is not only the precursor of glutathione, acetyl-coenzyme and taurine, but also the provider of sulfur ligands in the sulfide-iron complex of organisms. The lack of cysteine ​​in the human body will cause slow growth. , Hair decolorization, edema, lethargy, liver damage, muscle relaxation, physical weakness and other symptoms. Abnormal cysteine ​​concentration may also cause Alzheimer's disease, cardiovascular disease, and cancer. Glutathione is the most abundant non-protein...

Claims

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Application Information

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IPC IPC(8): C07D311/56C09K11/06G01N21/64
CPCC07D311/56C09K11/06G01N21/6428C09K2211/1007C09K2211/1088
Inventor 谌文强盛家荣傅立
Owner 南宁师范大学
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