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A way to distinguish gsh, cys, so 2 Fluorescent probe and its preparation method and application

A SO2, applied technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of insufficient discrimination and achieve the effect of broad application prospects

Inactive Publication Date: 2019-09-17
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Differentiate GSH, Cys, SO in cells against existing probe pairs 2 In order to solve the problem of insufficient discrimination, the present invention provides a sensitive, low detection limit, good specificity that can distinguish GSH, Cys, SO in cells 2 fluorescent probe Co-SO 2 , can be used to evaluate and study intracellular GSH, Cys, SO 2 Physiological function

Method used

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  • A way to distinguish gsh, cys, so <sub>2</sub> Fluorescent probe and its preparation method and application
  • A way to distinguish gsh, cys, so <sub>2</sub> Fluorescent probe and its preparation method and application
  • A way to distinguish gsh, cys, so <sub>2</sub> Fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Co-SO 2 Synthesis of fluorescent probes

[0032] At 0°C, DMF (15 mL, 10.0 mmol) was added to a 100 mL one-necked flask, POCl 3 (2mL,) was added dropwise to the flask, and after stirring at 0°C for 30 min, the compound 7-diethylamino-4-hydroxycoumarin was dissolved in DMF and added dropwise to the above solution to bring the temperature to Gradually raise the temperature to 80°C and react for 4 h. After the reaction, cool the reaction solution to room temperature, then pour it into ice water, adjust the pH to neutral to obtain a large amount of solids from the compound, filter the solids, and use column chromatography to purify (dichloro methane:methanol=40:1, v / v), and finally obtain the yellow compound Co-SO2; its 1 H NMR spectrum as figure 1 shown.

Embodiment 2

[0033] Example 2 Co-SO 2 Selectivity of fluorescent probes for different molecules or ions

[0034] Co-SO in Example 1 2 Fluorescent probes were prepared in a stock solution with a concentration of 1 mM.

[0035] The following substances Br - , ClO - , Cu 2+ , F - , Fe 2+ , H 2 o 2 , HClO, Hg 2+ , HPO 4 2- , Mg 2+ , N 3- , Na + , Na 2 S, NaHS, NO 2- , NO 3- , OAC - , ONOO - , S 2 o 3 2- , SCN - , SO 4 2- , Zn 2+ , singlet oxygen, SO 2 , GSH, Hcy and Cys were prepared in phosphate buffer (0.01 mM, pH=7.4) to prepare 5 mL of a stock solution with a concentration of 40 mM.

[0036] Take 28 test tubes, add 25 μL probe mother solution, 225 μL DMSO and the mother solution of each ion or molecule, and control with an equal amount of water instead of interfering substances; dilute to 5 mL with phosphate buffer (0.01 mM, pH=7.4) , so that the final concentration of each ion or amino acid is 3 mM, and the final concentration of reactive oxygen and nitrogen i...

Embodiment 3

[0037] Example 3 Different concentrations of SO 2 Lower Co-SO 2 Fluorescence intensity vs. wavelength variation

[0038] Prepare 10 mL of 100 mM SO 2 The mother solution was diluted with water to a total of 17 equidifferent concentrations of 0-40 μM, and water was used as a control. Co-SO in embodiment 2 2 The mother solution was diluted to 5 μM, and different concentrations of SO were added 2 , after reacting for 5s, perform fluorescence detection (λex = 460 nm, λem = 575 nm), detect the fluorescence intensity in each system, and take the fluorescence intensity -SO 2 Concentration curves, such as image 3 shown. It can be seen from the figure that with SO 2 As the concentration increases, the reaction system not only enhances the fluorescence intensity, but also red shifts the emission wavelength. When SO 2 When the concentration reached 25 μM, the fluorescence intensity of the reaction system reached saturation at 575 nm.

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Abstract

The invention provides a fluorescent probe for distinguishing GSH (Glutathione), Cys (Cysteine) and SO2, and the fluorescent probe is called Co-SO2 for short. The fluorescent probe has a structure asshown in a formula (I) which is shown in the description. A synthesis method of the fluorescent probe comprises the following steps: (1) heating 7-diethylamino-4-hydroxycoumarin and POCl3 in DMF (Dimethyl Formamide) for reacting, and separating and purifying, thus obtaining the fluorescent probe. The Co-SO2 fluorescent probe provided by the invention is a simple, fast and sensitive GSH, SO2 and Cys distinguishing reagent; the fluorescent probe can specifically react with GSH, SO2 and Cys under low concentration, and is capable of resisting interference of various active oxygen, amino acid andsulfydryl-containing compounds.

Description

technical field [0001] The invention relates to a method for distinguishing GSH, Cys, SO in cells 2 A fluorescent probe and its preparation method and application belong to the field of small organic molecule fluorescent probes. Background technique [0002] Amino acids are the basic substances that make up proteins and are closely related to the life activities of organisms. Cysteine ​​(Cys) and glutathione (GSH) are common sulfhydryl compounds in organisms, which play an important role in maintaining the normal physiological activities of organisms. Epidemiological studies have shown that exposure to sulfur dioxide is not only associated with many respiratory diseases, but also with lung cancer, vascular disease and many neurological diseases, such as migraine, stroke and brain cancer. Unmedical studies have shown that abnormal physiological concentrations may cause many diseases, such as renal failure, Alzheimer's disease, Parkinson's disease, cardiovascular disease, co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
Inventor 林伟英徐高平唐永和
Owner UNIV OF JINAN
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