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Fluorescent probe of reversible sulfur dioxide/sulphurous acid (hydrogen) salt

A technology of sulfur dioxide and fluorescent probes, applied in the fields of fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of lack of detection, etc., and achieve the effect of easy-to-obtain raw materials, simple synthesis steps, and high yield

Inactive Publication Date: 2018-06-05
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the lack of detection of sulfur dioxide / sulfurous (bisulfite) salts in biological cells and living bodies, the present invention provides a method that can be used to selectively detect SO in cells and living bodies. 2 reversible fluorescent probe

Method used

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  • Fluorescent probe of reversible sulfur dioxide/sulphurous acid (hydrogen) salt
  • Fluorescent probe of reversible sulfur dioxide/sulphurous acid (hydrogen) salt
  • Fluorescent probe of reversible sulfur dioxide/sulphurous acid (hydrogen) salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 Preparation of Fluorescent Probes for Reversible Sulfur Dioxide / Sulfite (Hydrogen) Salt

[0042] (1) Synthesis of compound 9-ethyl-9H-carbazole (4):

[0043] ;

[0044] At room temperature, add 1.67 g carbazole (1) (10 mmol) and 240 mg sodium hydride (3) (6 mmol) into a flask filled with 6 mL DMF, stir for 1.5 hours, then add 5.4 g bromoethane dropwise (50 mmol) (2), stirred at room temperature for 2 hours, poured the reaction system into 150 mL of ice water, extracted with ethyl acetate, dried the ethyl acetate layer with anhydrous sodium sulfate, and removed the ethyl acetate under reduced pressure to obtain white The needle-like compound 9-ethyl-9H-carbazole (4), yield 87%. The product was directly carried out to the next reaction without further purification.

[0045] (2) Synthesis of compound 3-acetyl-9-ethyl-9H-carbazole (6):

[0046] ;

[0047] Weigh 975 mg of 9-ethyl-9H-carbazole (4) (5 mmol) into the reaction flask, add 4 mL of DCM, add 1.33 ...

Embodiment 2

[0051] Example 2 Different concentrations of SO 2 Absorption Spectrum Test and Fluorescence Test of

[0052] A dimethyl sulfoxide (DMSO) stock solution of the fluorescent probe CaP in Example 1 with a concentration of 1 mM was prepared for use.

[0053] Take an appropriate amount of fluorescent probe CaP for detecting sulfur dioxide according to the present invention in a 5 mL volumetric flask, and add an appropriate amount of acetonitrile to make the mother liquor concentration 1 mM; weigh a certain amount of sodium bisulfite and formaldehyde and dissolve them in ultrapure in water to make the stock solution concentration 100 mM. In the test solution, the concentration of the probe is 10 μM, and the concentration of sodium bisulfite is 0 μM, 1 μM, 2 μM, 5 μM, 8 μM, 10 μM, 12 μM, 15 μM, 18 μM, 20 μM, 25 μM , 30 μM, use HEPES buffer (HEPES, 10 mM, pH=7.4) to make up to volume, which contains acetonitrile with a volume fraction of 20%. Then carry out absorption spectrum test ...

Embodiment 3

[0054] Example 3 Detection of reversible performance of fluorescent probe CaP

[0055] Prepare 100 mM sodium bisulfite solution and 100 mM formaldehyde solution for later use.

[0056] Add 20 μL of the probe mother solution (1 mM) in Example 2 and 380 μL of acetonitrile into a 5 mL volumetric flask, make up to volume with HEPES buffer, shake well and perform fluorescence detection (λex = 270 nm, λem = 370 nm, 630 nm), to establish a curve of fluorescence intensity versus time; then add sodium bisulfite solution (final concentration: 30 µM) to the above system, shake well and perform fluorescence detection (λex = 270 nm, λem = 370 nm, 630 nm) to establish a curve of fluorescence intensity versus time; after the above solution was equilibrated, add formaldehyde solution (final concentration 300 µM) to establish a curve of fluorescence intensity versus time, the results are as follows image 3 shown. Depend on image 3 It can be found that in the presence of sulfite, the near-...

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Abstract

The invention provides a fluorescent probe of reversible sulfur dioxide / sulphurous acid (hydrogen) salt, with the chemical name of 7-diethylin-2-(9-ethyl-9H-carbazole-3) benzo iso-pyran oxonium ion. The fluorescent probe can detect sulfur dioxide / sulphurous acid (hydrogen) salt in a solution, cells, tissues or a living body, wherein the living body includes fish, mice, rat, guinea pig and rabbit;and reversibility is realized by formaldehyde. The fluorescent probe is simple in synthesis steps, easily available in material, high in yield and suitable for industrial application.

Description

technical field [0001] The invention relates to a fluorescent probe for rapid and reversible detection of sulfur dioxide, which belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Sulfur dioxide is one of the main pollutants in the atmosphere and an important symbol to measure whether the atmosphere is polluted. Sulfur dioxide generally enters the human body through the respiratory tract. Because it is easily soluble in water, many of them are blocked in the upper respiratory tract, and then form its derivatives such as sulfurous acid, sulfate, etc., which further stimulate the respiratory tract and cause a series of respiratory diseases. However, when it enters the blood The sulfur dioxide in the air can still reach the lungs through the blood circulation to stimulate the lungs. Sulfur dioxide entering the blood can destroy the activity of enzymes, thereby significantly affecting the metabolism of carbohydrates and proteins, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07D405/04C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/6486
Inventor 林伟英马燕燕赵玉萍
Owner UNIV OF JINAN
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