A Proportional Fluorescent Probe of Sulfur Dioxide Derivatives Using Semi-Cyanine and Flavonol as Fluorophores and Its Application

A fluorescent probe, sulfur dioxide technology, used in fluorescence/phosphorescence, organic chemistry, luminescent materials, etc., can solve problems such as human health hazards and adverse reactions, and achieve good selectivity, specificity, and high sensitivity.

Inactive Publication Date: 2019-03-26
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if the content of sulfur dioxide derivatives in the body is too high, it will cause a series of adverse reactions and cause harm to human health.

Method used

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  • A Proportional Fluorescent Probe of Sulfur Dioxide Derivatives Using Semi-Cyanine and Flavonol as Fluorophores and Its Application
  • A Proportional Fluorescent Probe of Sulfur Dioxide Derivatives Using Semi-Cyanine and Flavonol as Fluorophores and Its Application
  • A Proportional Fluorescent Probe of Sulfur Dioxide Derivatives Using Semi-Cyanine and Flavonol as Fluorophores and Its Application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1 The preparation of the ratio fluorescent probe of sulfur dioxide derivatives using semi-chuancyanine and flavonol as fluorophores according to the present invention

[0024] O-hydroxyacetophenone and p-carboxybenzaldehyde undergo ring closure in two steps to obtain flavonol fluorophores, and then introduce aromatic aldehyde groups through the construction of amide bonds, and then condense with indole salts to obtain compound L-HF1.

[0025] Above-mentioned reaction process reaction formula is as follows:

[0026]

[0027] Compound 1 (1mmol), Compound 2 (1mmol), DMAP (0.1mmol) and EDC (1mmol) were added to 30mL of dichloromethane, and after reacting at room temperature for 8 hours, the organic phase was washed with brine, dried over anhydrous sodium sulfate, and pumped After filtration, the liquid phase was spin-dried, and silica gel column chromatography (dichloromethane: ethyl acetate = 1:1) gave compound 3 with a yield of 82% and a melting point of 238...

Embodiment 2

[0038] Using a microsyringe, quantitatively add various anions (F - , Cl - ,Br - , I - , HCO 3 - ,NO 3 - ,NO 2 - ,N 3 - ,AcO - ,H 2 PO 4 - ,ClO - ,ClO 3 - , SO 4 2- , HSO 4 - ,HS - ,SCN - ,S 2 o 3 2- , HSO 3 - and SO 3 2- ) and various amino acid molecules (glutamate, histidine, lysine, tryptophan, valine, arginine, sarcosine, aspartic acid, cysteine, homocysteine, glutathione) at a final concentration of 1 mM, after 5 minutes of action, the fluorescence spectrophotometry test was performed, and the probe It has good selectivity to sodium sulfite and sodium bisulfite, and the comparison before and after adding sodium sulfite and sodium bisulfite shows obvious changes in fluorescence emission. See figure 1 , 2, 3.

Embodiment 3

[0040] Intracellular fluorescence imaging test:

[0041] HeLa cells: at 37°C, HeLa cells were cultured for 1 hour in the cell culture solution added with 5 μM L-HF1; then cultured in the cell culture solution with different concentrations of sodium bisulfite for 0.5 hours. Fluorescence imaging showed that the probe L-HF1 could penetrate into the cells, and the intensity ratio of green fluorescence to red fluorescence gradually increased with the increase of sodium bisulfite concentration. See Figure 4 .

[0042] L-02 cells: at 37°C, L-02 cells were cultured for 1 hour in the cell culture solution added with 5 μM L-HF1, and then cultured in the cell culture solution with different concentrations of sodium bisulfite for 0.5 hours. Fluorescence imaging showed that the probe L-HF1 could penetrate into the cells, and the intensity ratio of green fluorescence to red fluorescence gradually increased with the increase of sodium bisulfite concentration. Add 5 μM probe L-HF1 to live...

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Abstract

The invention discloses a sulfur dioxide derivative ratio fluorescent probe using semi-chuancyanine and flavonol as fluorophores. Named as L-HF1, its chemical structural formula is as shown in formula (I). The invention also discloses the application of the fluorescent probe in detecting sulfur dioxide derivatives in liquid or cells. Experiments have confirmed that the probe of the present invention can selectively react with sulfur dioxide derivatives, so that the test system changes from red to colorless, making the detection visible to the naked eye, and the fluorescence changes from red to green. These phenomena can be detected by ultraviolet absorption and fluorescence. Spectrophotometer for analysis. At the same time, the fluorescent probe disclosed in the invention can realize high-sensitivity detection of trace sulfur dioxide derivatives, and has important application value.

Description

technical field [0001] The invention relates to a proportional fluorescent probe of sulfur dioxide derivatives with semi-chuancyanine and flavonol as fluorophores, in particular to a fluorescent probe capable of detecting endogenous sulfur dioxide derivatives of liver cancer cells and its application; it belongs to organic small molecule fluorescence Probe technology field. Background technique [0002] Flavonol is a fluorescent structure with ESIPT (excited state intramolecular proton transfer) phenomenon and high fluorescence quantum yield. It is a very important green fluorescent dye, which is used for luminescent materials, chemical sensors and labeling biomolecules after modification. . In recent years, the use of fluorescence changes to detect sulfur dioxide derivatives in living cells has been continuously developed. [0003] Cells can use cysteine ​​and other substrates and intracellular enzymes to produce sulfur dioxide derivatives - sulfite and bisulfite, which c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C09K11/06G01N21/64
CPCC07D405/12C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088G01N21/6428G01N21/6486
Inventor 赵宝祥苗俊英李东鹏王朝阳
Owner SHANDONG UNIV
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