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Sulfur dioxide derivative proportion fluorescence probe with half cyanine and flavonol as fluorophores and application thereof

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

Inactive Publication Date: 2017-03-22
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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  • Sulfur dioxide derivative proportion fluorescence probe with half cyanine and flavonol as fluorophores and application thereof
  • Sulfur dioxide derivative proportion fluorescence probe with half cyanine and flavonol as fluorophores and application thereof
  • Sulfur dioxide derivative proportion fluorescence probe with half cyanine and flavonol as fluorophores and application thereof

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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] The flavonol fluorophore was obtained through two-step reaction of o-hydroxyacetophenone and p-carboxybenzaldehyde, and then the aromatic aldehyde group was introduced through the construction of amide bonds, and then condensed with indole salt to obtain the 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...

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 proportion fluorescence probe with half cyanine and flavonol as fluorophores. The fluorescence probe is formed by connecting a flavonol fluorophore with a half cyanine fluorophore in a non-conjugated mode and is named as L-HF1, and the chemical structure formula of the fluorescence probe is shown as formula (I). The invention further discloses application of the fluorescence probe in detecting sulfur dioxide derivatives in liquid or cells. Experiments prove that the probe can act with the sulfur dioxide derivatives selectively, a testing system is changed from red to colorless so that tests can be recognized by naked eyes, fluorescence is changed from red to green, and the phenomena can be analyzed by an ultraviolet absorption spectrometry and a fluorescence spectrophotometer. Meanwhile, the fluorescence probe is disclosed by the invention can achieve high-sensitivity tests of the 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 Applications(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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