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Preparation and application of open-type hydrogen peroxide fluorescent probe compound

A technology of hydrogen peroxide and fluorescent probes, which is applied in the field of fluorescent probes, can solve the problems of few types of hydrogen peroxide probes, difficulty in detecting hydrogen peroxide, interference in hydrogen peroxide detection, etc., and achieve good sensitivity and selectivity, Good promotion prospect, good water solubility effect

Inactive Publication Date: 2017-04-26
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the existing fluorescent probe technology, there are few types of hydrogen peroxide probes, low selectivity, and insufficient detection sensitivity.
For example, DCFH is a probe for detecting ROS in the body, but it is easily oxidized by oxygen in the air, which easily interferes with the detection of hydrogen peroxide and reduces the sensitivity
In addition, because hydrogen peroxide is easy to be oxidized and decomposed in a short time, and it is easy to react with other substances to form new active oxygen species, so there is a certain difficulty in the detection of hydrogen peroxide. Therefore, it is necessary to design a short response time, high sensitivity, Probes with strong selectivity are of great significance

Method used

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  • Preparation and application of open-type hydrogen peroxide fluorescent probe compound
  • Preparation and application of open-type hydrogen peroxide fluorescent probe compound
  • Preparation and application of open-type hydrogen peroxide fluorescent probe compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1, the synthesis of probe I

[0049] (a) In a nitrogen atmosphere, mix 6.24g (about 32mmol) of cyanobiphenol and 4.56g (about 48mmol) of anhydrous MgCl 2 In a three-neck round bottom flask, add 16.32mL (about 122mmol) of triethylamine, then add 80mL of anhydrous acetonitrile as a solvent, and finally add 12.3g (about 440mmol) of dry paraformaldehyde. The mixture was heated to 70 oC reflux for 8 hours. After the reaction was completed, it was cooled to room temperature, and then quenched with a small amount of water. Then add a large amount of 6M hydrochloric acid for acidification. The above crude product was treated with CH 2 Cl 2 For extraction (3*50 mL), the organic layer was washed with anhydrous MgSO 4 After drying, sample preparation and column chromatography purification, 3.5 g of white compound III was obtained with a yield of about 50%.

[0050] (b) Compound III (0.1g, 0.45mmol), bromobenzylboronate (0.133g, 0.45mmol), K 2 CO 3 (0.62g, 0.45m...

Embodiment 2

[0052] Embodiment 2, fluorescence experiment

[0053] Take the fluorescent probe compound prepared in Example 1, dissolve it in an aqueous solution containing 50% DMF, and adjust the pH to 7.4 with PBS buffer solution; obtain a fluorescent probe solution for future use.

[0054] 1. Take the fluorescent probe solution and divide it into 12 groups, 10 ml in each group. Among them, 1 group does not add reactive oxygen species, and 11 groups add CH 3 COOOH, GSH, H 2 o 2 , HOCl, O 2 •- , •OH, otBU, TBHP, Vc solution, so that the concentration of the probe compound contained in each group of solutions is 10 μM, the concentration of the active oxygen species is 200 μM, so that the molar ratio of the active oxygen species to the probe compound is 30:1; The wavelength is 365nm, and the fluorescence intensity is tested by a fluorescence photometer, such as image 3 As shown, the results show that the probe solution of the present invention has no fluorescence itself. Once hydrogen ...

Embodiment 3

[0056] Embodiment 3, cell imaging experiment

[0057] MCF-7 cells were cultured in 1 milliliter of cell culture medium containing 10% bovine fetal serum for 12 hours, then treated with 100 micromoles per liter of fluoride ion for 10 minutes, and then treated with 10 micromoles per liter of the fluorescent probe of the present invention Process for 30 minutes. The cells were excited with a light source with an excitation wavelength of 365, and imaged under a confocal microscope, such as Figure 5 .

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Abstract

The invention relates to preparation and application of an open-type hydrogen peroxide fluorescent probe compound with a formula I structure. The preparation method is as follows: under the protection of nitrogen, cyano biphenylphenol, paraformaldehyde and anhydrous magnesium chloride are reacted by use of triethylamine as a catalyst to obtain a compound III; the compound III and 4-borate benzyl bromide are refluxed in acetonitrile under stirring by use of anhydrous potassium carbonate as a catalyst to obtain a product II, and the product II and 9, 10 Phenanthrenequinone are refluxed in ethanol by use of ammonium acetate as a catalyst to obtain the final probe 1. The probe compound has good hydrogen peroxide selectivity and sensitivity, low detection limit and no toxicity to cells, can be applied to the detection and imaging of intracellular hydrogen peroxide, and can be applied in deep in-vivo tissue imaging.

Description

technical field [0001] The invention relates to an open-type hydrogen peroxide fluorescent probe compound and its preparation and application, belonging to the technical field of fluorescent probes. [0002] technical background [0003] Hydrogen peroxide is one of the active oxygen species in the human body, which can be produced through the metabolism of oxygen and the catalysis of enzymes. An appropriate amount of hydrogen peroxide can promote the activation of immune cells, cell growth and proliferation, but excessive hydrogen peroxide may cause many serious diseases, such as Alzheimer's disease, Parkinson's disease, cardiovascular and cerebrovascular diseases disease and cancer. Therefore, it is of great significance to identify and monitor the content of hydrogen peroxide in cells in real time. [0004] At present, the detection methods of hydrogen peroxide in vivo and its content mainly include electrochemical methods, elemental analysis mass spectrometry and other m...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07F5/025C09K11/06C09K2211/1007C09K2211/1044C09K2211/1096G01N21/643
Inventor 吕正亮史孝民范春华
Owner UNIV OF JINAN
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