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Preparation and application of hydrogen peroxide fluorescent probe compound

A fluorescent probe and hydrogen peroxide technology, applied in the field of fluorescent probes, can solve the problems of short hydrogen peroxide existence time, few types of hydrogen peroxide probes, and interference in hydrogen peroxide detection, achieving high selectivity and good Effect of sensitivity and selectivity, good water solubility

Inactive Publication Date: 2016-12-14
UNIV OF JINAN
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the existing fluorescent probe technology, the existing hydrogen peroxide probes have problems such as few types, 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, due to the short existence time of hydrogen peroxide, it is easy to react with other substances to form new active oxygen species, so the detection of hydrogen peroxide itself has certain difficulties. Design a short response time, high sensitivity, and strong selectivity Probes are very important

Method used

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  • Preparation and application of hydrogen peroxide fluorescent probe compound
  • Preparation and application of hydrogen peroxide fluorescent probe compound
  • Preparation and application of hydrogen peroxide fluorescent probe compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1, the synthesis of probe molecule I

[0046] (1) Take 1.613 grams of 4-diethylaminosalicylaldehyde, 1.38 grams of bromobenzyl bromide, and 0.533 grams of anhydrous potassium carbonate in a three-necked flask under nitrogen protection. Add 13 ml of acetone into the flask; stir at 50°C Refluxed overnight, evaporated the solvent, and used ethyl acetate:petroleum ether volume ratio of 1:4 as the developing solvent, and separated through the column to obtain 1.004 g of pure product II with a yield of 53%.

[0047] (2) Dissolve 0.339 g of II, 0.285 g of pinacol diborate, and 82 mg of [1,1-bis(diphenylphosphino)ferrocene]palladium dichloride in 10 ml of dry DMF, and dissolve them at 80°C Nitrogen protection was refluxed overnight, the solvent was distilled off, and the compound solvent with a volume ratio of petroleum ether:ethyl acetate of 1:1 was used as a developing solvent, and the compound was separated through a column to obtain 0.369 g of Compound III with...

Embodiment 2

[0049] Embodiment 2, fluorescence experiment

[0050] Take the fluorescent probe compound prepared in Example 1, dissolve it in an aqueous solution containing 5% acetonitrile, and adjust the pH to 7.4 with HEPES buffer solution; obtain a fluorescent probe solution for future use.

[0051] 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, NO, O2•-, •OH, ONOO-, otBU, TBHF, Vc solutions, so that the concentration of the probe compound contained in each group of solutions is 10 micromolar, and the concentration of active oxygen species is 300 micromolar, so that the active oxygen The molar ratio of the species to the probe compound is 30:1; the excitation wavelength is 437 nm, and the fluorescence intensity is tested by a fluorescence photometer, as figure 2 As shown, the results show that the probe solution of the present invention ...

Embodiment 3

[0053] Embodiment 3, cell imaging experiment

[0054] 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 / liter of fluoride ion for 10 minutes, and then treated with 10 micromoles / liter of the fluorescent probe of the present invention Process for 30 minutes. Cells were excited with a light source with an excitation wavelength of 437 nm and imaged under a confocal microscope. Figure 4 It is an imaging diagram of MCF-7 cells cultured with the fluorescent probe of the present invention and hydrogen peroxide.

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Abstract

The invention relates to a reactive type hydrogen peroxide fluorescent probe compound and preparation and application thereof. The hydrogen peroxide fluorescent probe compound has the structure as shown in a formula I. The preparation method comprises the steps that 4-diethylaminosalicylaldehyde and 4-bromobenzyl bromide are dissolved in acetone, anhydrous potassium carbonate is taken as a catalyst, a refluxing reaction is conducted under the protection of nitrogen, and a product II is obtained; the product II and bis(pinacolato)diboron react under the protection of nitrogen by taking [1,1.-bis(diphenylphosphino)ferrocene]dichloropalladium as a catalyst, and a product III is obtained; the product III and malononitrile are subjected to stirring at room temperature by taking piperidine as a catalyst, and the final product probe I is obtained. The probe compound has good selectivity and sensitivity to hydrogen peroxide, is low in detection limit and free of toxicity to cells and can be applied to detection and imaging of hydrogen peroxide in the cells.

Description

technical field [0001] The invention relates to a hydrogen peroxide fluorescent probe compound and its preparation and application, belonging to the technical field of fluorescent probes. technical background [0002] Hydrogen peroxide is one of the active oxygen species in the human body, which is produced through the metabolism of oxygen and the catalysis of enzymes. Appropriate levels of hydrogen peroxide can promote the activation of immune cells, cell growth and proliferation, but excessive levels of hydrogen peroxide may cause many serious diseases, such as Alzheimer's disease, Parkinson's disease, heart and brain Vascular disease, and cancer to name a few. Therefore, it is of great significance to identify and monitor the content of hydrogen peroxide in cells in real time. [0003] At present, there are mainly electrochemical methods, elemental analysis mass spectrometry and other methods for the detection of hydrogen peroxide in organisms. The sample preparation pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
Inventor 吕正亮史孝民范春华
Owner UNIV OF JINAN
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