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Fluorescent probe for identifying cysteine and glutathione as well as preparation method and application thereof

A technology of glutathione and cysteine, applied in the field of chemical analysis and detection, can solve the problem of not having the function of targeting lysosomes, and achieve the effects of high sensitivity, mild reaction conditions and simple synthesis route

Active Publication Date: 2018-11-02
南宁师范大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most of the probes used to detect and distinguish cysteine ​​and glutathione do not have the function of targeting lysosomes. Therefore, a probe that can target lysosomes and recognize cysteine Probes for amino acid and glutathione are of great significance

Method used

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  • Fluorescent probe for identifying cysteine and glutathione as well as preparation method and application thereof
  • Fluorescent probe for identifying cysteine and glutathione as well as preparation method and application thereof
  • Fluorescent probe for identifying cysteine and glutathione as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0051] Preparation of intermediates

[0052] React with 3-carboxy-4-chloro-7-diethylaminocoumarin and 3-hydroxy-N-(2-ethylmorpholine) benzamide as raw materials to obtain an intermediate, and the specific process includes:

[0053] Step 1: Add anhydrous dichloromethane (5mL) to 3-carboxy-4-chloro-7-diethylaminocoumarin (295mg, 1mmol) and stir to dissolve, then add oxalyl chloride (0.9mL, 10mmol) in sequence , anhydrous DMF (5 μ L), reacted at room temperature under the protection of argon for 2.5 hours, distilled off the solvent under reduced pressure, then added anhydrous dichloromethane to dissolve (5 mL), and obtained the first reaction solution;

[0054] Step 2. Add 3-hydroxy-N-(2-ethylmorpholine) benzamide (1mmol) and anhydrous triethylamine (4.4mL, 30mmol) into anhydrous dichloromethane (5mL) and stir to dissolve to obtain the Second reaction solution;

[0055] Step 3: Add the first reaction solution to the second reaction solution at ℃, react in an ice-water bath for ...

Embodiment 2

[0057] Preparation of fluorescent probes:

[0058] The specific process of obtaining the probe by reacting the intermediate and p-nitrophenol as raw materials is as follows:

[0059] Add anhydrous acetonitrile (7mL1) to the intermediate (577mg, 1mmol), p-nitrophenol (139mg, 1mmol) and stir to dissolve (specifically add the intermediate and nitrophenol to the reactor first, and then add Anhydrous acetonitrile), then added triethylamine (5 μ L, 1 mmol), under argon protection, refluxed and stirred for 1.5 h, distilled off the solvent under reduced pressure, obtained a light yellow solid through column chromatography, and the light yellow solid was the probe ( probe), yield 577mg, 85%, 1 HNMR spectrum as Figure 4 as shown, 13 CNMR spectrum such as Figure 5 As shown, the mass spectrogram is as Image 6 shown.

Embodiment 3

[0061] Application of Fluorescent Probes

[0062] Dissolve the fluorescent probe in the buffer solution (V DMSO / V PBS =2 / 8, Ph=7.4), and formulated into groups of 1.0×10 - 5 mol / L solution, and then add Cys, GSH, Tyr, Val, Gly, Ala, Asp, Arg, Iso, Lys, Met, His, Phe, Thr, Ser, Pro, Glu to multiple solutions respectively , KCl, CaCl 2 , MgCl 2 , ZnCl 2 , NaCl, H 2 S, and H 2 o 2 , and test the fluorescence intensity of each solution, the test results are as follows Figure 7 with Figure 8 shown;

[0063] Dissolve the fluorescent probe in the buffer solution (V DMSO / V PBS =2 / 8, Ph=7.4), and formulated into groups of 1.0×10 - 5 mol / L solution, and then add different masses of cysteine ​​(Cys) to multiple groups of solutions one by one to prepare a solution with a cysteine ​​concentration of 0-300 μM, and finally test the fluorescence intensity respectively. The results are as follows Figure 9 As shown, the arrow in the figure indicates that the concentration o...

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Abstract

The invention discloses a fluorescent probe for identifying cysteine and glutathione. The structure of the probe is a chemical formula: the formula is shown in the description. The preparation methodof the fluorescent probe for identifying the cysteine and the glutathione comprises the following steps: S1, performing reaction by taking 3-carboxyl-4-chlorine-7-diethylamine coumarin and 3-hydroxyl-N-(2-ethyl morpholine)benzamide as raw materials to obtain an intermediate; and S2, performing reaction by taking the intermediate and p-nitrophenol as raw materials to obtain a probe. The fluorescentprobe can identify the cysteine and the glutathione from various kinds of amino acid and some common substances, has a lysosome targeted function at the same time, can directionally detect the cysteine and the glutathione in the lysosome, has good selectivity and high sensitivity on the cysteine and the glutathione, and has a good application prospect in detection and analysis of the cysteine andthe glutathione in environments or biological samples.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection. More specifically, the present invention relates to a fluorescent probe for recognizing cysteine ​​and glutathione, a preparation method and an application method. Background technique [0002] Biothiols are important components of many proteins and small molecules, and play an important role in the process of cell life. Biothiols include cysteine ​​(Cysteine, Cys), homocysteine ​​(Homocysteine, Hcy) and glutathione (Glutataione, GSH) and so on. Cysteine ​​is not only the precursor of glutathione, acetyl coenzyme and taurine, but also the provider of sulfur ligands in the sulfur-iron complex of organisms. The lack of cysteine ​​in the human body will lead to slow growth, Symptoms such as hair depigmentation, edema, lethargy, liver function damage, muscle relaxation, and physical weakness. At the same time, abnormal concentrations of cysteine ​​may also cause Alzheimer's ...

Claims

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Application Information

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IPC IPC(8): C07D311/56C09K11/06G01N21/64
CPCG01N21/6486C09K11/06C07D311/56C09K2211/1007C09K2211/1088C09K2211/1033
Inventor 盛家荣谌文强徐丽珍张会
Owner 南宁师范大学
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