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Fluorescence probe capable of distinguishing GSH, Cys and NAC as well as preparation method and application of fluorescence probe

A fluorescent probe and reaction technology, applied in fluorescence/phosphorescence, chemical instruments and methods, analytical materials, etc., can solve the problems of insufficient discrimination of GSH, Cys, NAC, etc., and achieve the effect of broad application prospects

Inactive Publication Date: 2018-07-13
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problem that existing probes are insufficient for distinguishing GSH, Cys and NAC in cells, the present invention provides a fluorescent probe with sensitive response, low detection limit and good specificity that can distinguish GSH, Cys and NAC in cells Co-NA can be used to evaluate and study the physiological functions of GSH, Cys, NAC in cells

Method used

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  • Fluorescence probe capable of distinguishing GSH, Cys and NAC as well as preparation method and application of fluorescence probe
  • Fluorescence probe capable of distinguishing GSH, Cys and NAC as well as preparation method and application of fluorescence probe
  • Fluorescence probe capable of distinguishing GSH, Cys and NAC as well as preparation method and application of fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Synthesis of Co-NA fluorescent probe:

[0033] Combine compound 2,3,3-trimethylindole quaternary ammonium salt (1.9 g, 10.0 mmol), compound 7-diethylamino-3chloro-4-aldehyde coumarin (2.6 mL, 12.0 mmol) with Piperidine (1 mL, 10.0 mmol) was added to 20ml ethanol solution and heated to reflux for 8 h. After the reaction, the solvent was removed and purified by column chromatography (dichloromethane: methanol=40:1, v / v), and finally obtained Compound Co-NA; its 1 The H NMR spectrum is shown as figure 1 Shown.

Embodiment 2

[0034] Example 2 Selectivity of Co-NA fluorescent probe to different molecules or ions

[0035] The Co-NA fluorescent probe in Example 1 was formulated into a mother solution with a concentration of 1 mM.

[0036] 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, NAC, GSH, Hcy, Cys are prepared with phosphate buffer (0.01 mM, pH=7.4) to prepare 5 mL of 40 mM mother liquor.

[0037] Take 28 test tubes, add 25 μL probe mother solution, 225 μL DMSO, and the mother solution of each ion or molecule respectively, and use the same amount of water instead of interfering substances; dilute to 5 mL with phosphate buffer (0.01 mM, pH=7.4) , The final concentration of each ion or amino acid is 3 mM, and the final concentration of reactive oxygen and reactive nitrogen is 100 mM. After shaking up the solutions, perform fluorescence detection (λex = 614 ...

Embodiment 3

[0038] Example 3 Changes in the fluorescence intensity and wavelength of Co-NA under different concentrations of GSH

[0039] Prepare 10 mL mother liquor with a concentration of 100 mM GSH, and dilute with water to a total of 17 arithmetic concentrations of 1-9 mM, with water as the control. Dilute the Co-NA mother solution in Example 2 to 5 μM, add different concentrations of GSH, and perform fluorescence detection (λex = 480 nm, λem = 700-500 nm) after reacting for 40 minutes. Detect the fluorescence intensity in each system. Intensity-GSH concentration curve, such as image 3 Shown. It can be seen from the figure that when the GSH concentration is the lowest test concentration (2 μM), Co-NA has a fluorescence response; as the GSH concentration increases, not only the fluorescence intensity of the reaction system increases, but the emission wavelength also blue shifts. When the GSH concentration When it reaches 40 μM, the fluorescence intensity of the reaction system reaches s...

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Abstract

The invention provides a fluorescence probe Co-Na for detecting glutathione of a cell and capable of distinguishing GSH, NAC and Cys, the response of the fluorescence probe is sensitive, the detectionlimit of the fluorescence probe is low, the specificity of the fluorescence probe is good, and the fluorescence probe can be used for evaluating and studying the physiological functions of GSH, NAC and Cys in the cell. The fluorescence probe Co-Na is an agent capable of distinguishing GSH, NAC and Cys simply, rapidly and sensitively; the fluorescence probe can specifically react with GSH, NAC andCys at the low concentration, can resist the interference of various reactive oxygen, amino acids and sulfhydryl compounds, and has a broad application prospect in the fields of biomolecule detection.

Description

Technical field [0001] The invention relates to a fluorescent probe for distinguishing GSH, Cys and NAC in cells, and a preparation method and application thereof, belonging to the field of organic small molecule fluorescent probes. Background technique [0002] Amino acids are the basic substances that constitute proteins and are closely related to the life activities of organisms. Cysteine ​​(Cys), N-acetylcysteine ​​(NAC) and glutathione (GSH) are common sulfhydryl compounds in organisms, which play an important role in maintaining the normal physiological activities of organisms. Medical research shows that abnormal physiological concentrations may cause many diseases, such as kidney failure, Alzheimer's disease, Parkinson's disease, cardiovascular disease, coronary heart disease, muscle damage, skin relaxation, etc., and their changes in the biological content can be used as these diseases Basis for diagnosis. Therefore, it is very important to detect small-molecule biolog...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D491/16G01N21/64
CPCC09K11/06C07D491/16C09K2211/1029C09K2211/1088G01N21/6428
Inventor 林伟英徐高平唐永和徐安
Owner UNIV OF JINAN
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