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Fluorescent probe for distinguishing GSH (Glutathione), Cys (Cysteine) and SO2 as well as preparation method and application of fluorescent probe

A technology of fluorescent probes and synthesis methods, applied in the field of organic small molecule fluorescent probes, can solve problems such as insufficient discrimination, and achieve the effect of broad application prospects

Inactive Publication Date: 2018-06-29
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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  • Fluorescent probe for distinguishing GSH (Glutathione), Cys (Cysteine) and SO2 as well as preparation method and application of fluorescent probe
  • Fluorescent probe for distinguishing GSH (Glutathione), Cys (Cysteine) and SO2 as well as preparation method and application of fluorescent probe
  • Fluorescent probe for distinguishing GSH (Glutathione), Cys (Cysteine) and SO2 as well as preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0032] At 0℃, DMF (15 mL, 10.0 mmol) was added to a 100 mL single-necked flask, and POCl 3 (2 mL,) was added dropwise to the flask. After stirring for 30 min at 0℃, the compound 7-diethylamino-4-hydroxycoumarin was dissolved in DMF and added dropwise to the above solution. The temperature was gradually increased to 80°C and reacted for 4 hours. After the reaction, the reaction solution was cooled to room temperature, and then poured into ice water, adjusted to neutral pH to obtain a large amount of solids. The solids were filtered and purified by column chromatography (2 Chloroform: methanol=40:1, v / v), the yellow compound Co-SO2 is finally obtained; its 1 The H NMR spectrum is shown as figure 1 Shown.

Embodiment 2

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

[0034] The Co-SO in Example 1 2 The fluorescent probe was prepared into a mother liquor with a concentration of 1 mM.

[0035] 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, Cys are prepared with phosphate buffer (0.01 mM, pH=7.4) to prepare 5 mL mother liquor 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 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 the solution, perform fluorescen...

Embodiment 3

[0037] Example 3 Different concentrations of SO 2 Down Co-SO 2 Fluorescence intensity and wavelength change

[0038] Prepare 10 mL of 100 mM SO 2 The mother liquor was diluted with water to a total of 17 arithmetic concentrations of 0-40 μM, with water as the control. The Co-SO in Example 2 2 The mother liquor is diluted to 5 μM, and different concentrations of SO are added respectively 2 , After reacting for 5s, perform fluorescence detection (λex = 460 nm, λem = 575 nm), and detect the fluorescence intensity in each system. Use fluorescence intensity-SO 2 Concentration curve, such as image 3 Shown. It can be seen from the figure that with SO 2 As the concentration increases, not only the fluorescence intensity of the reaction system increases, but the emission wavelength also undergoes a red shift. 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 present invention relates to a method for distinguishing GSH, Cys, SO in cells 2 A fluorescent probe and a preparation method and application thereof belong 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) 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 can not only cause many respiratory diseases, but also lung cancer, vascular diseases, and many neurological diseases, such as migraine, stroke and brain cancer. Medical research has shown that abnormal physiological concentrations may cause many diseases, such as renal failure, Alzheimer’s disease, Parkinson’s disease, cardiovascular disease, coron...

Claims

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Application Information

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Patent Type & Authority Applications(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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