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Synthesis and application of near-infrared two-photon conversion type SO2 fluorescent probe

A fluorescent probe and two-photon technology, which is applied in the field of organic small molecule fluorescent probes, can solve the problems of environment and concentration effects, and achieve the effect of fast recognition speed and good specificity

Inactive Publication Date: 2018-09-14
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems that existing molecular fluorescent probes for detecting sulfur dioxide are easily affected by the environment and concentration, the present invention provides a two-photon conversion fluorescent probe for near-infrared detection of sulfur dioxide; the present invention also provides a preparation method for the above-mentioned fluorescent probes and use in the detection of sulfur dioxide / bisulfite (bi)sulfite in solutions, cells and organisms

Method used

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  • Synthesis and application of near-infrared two-photon conversion type SO2 fluorescent probe
  • Synthesis and application of near-infrared two-photon conversion type SO2 fluorescent probe
  • Synthesis and application of near-infrared two-photon conversion type SO2 fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 Synthesis of Fluorescent Probes

[0046] (1) Synthesis of compound 1

[0047] ;

[0048] In a 100 mL round bottom flask, add 4-diethylamino salicylaldehyde (1.93 g, 10 mmol) and cyclohexanone (1.20 g, 12 mmol) and mix, add 10 mL of concentrated sulfuric acid to it and heat at reflux at 90°C and stir After 5 h, cool to room temperature, place the reaction system at -5 °C, add an appropriate amount of perchloric acid dropwise and add 200 mL of water, a large amount of solid precipitates, filter under reduced pressure, wash the filter cake with ethanol 2-3 times, and dry in vacuo , to obtain compound 1. The crude product was recrystallized from ethanol to obtain pure product. Yield: 87%;

[0049] (2) Synthesis of compound 2

[0050] ;

[0051] In a 100 mL round bottom flask, add 30 mL of ethanol, 4-diethylamino salicylaldehyde (1.93 g, 10 mmol), ethyl acetoacetate (1.30 g, 10 mmol), and a small amount of piperidine ( 150 μL), heated to 85°C and refluxe...

Embodiment 2

[0058] Example 2 Fluorescence probes detect the fluorescence intensity of different concentrations of sodium bisulfite

[0059] The dimethyl sulfoxide mother solution of the fluorescent probe obtained in Example 1 with a concentration of 1 mM was prepared for use.

[0060] The final concentration of the probe was 10 μM, PBS solution (pH 7.4) containing 20% ​​acetonitrile solution was mixed with different concentrations of sodium bisulfite (1 μM, 2 μM, 3 μM, 4 μM, 5 μM, 6 μM, 7 μM, 8 μM, 9 μM, 10μM, 15μM, 20μM, 25μM, 30μM, 35μM, 40μM, 45μM, 50μM) are fully effective for fluorescence detection (λ ex =440 nm, λ em =530nm;λ ex =645 nm, λ em =835nm). The fluorescence intensity in each system was obtained, and the standard curve of fluorescence intensity and sodium bisulfite concentration was established, and the results were as follows: image 3 shown. Depend on image 3 It can be seen that as the concentration of sodium bisulfite increases, the fluorescence intensity at 530...

Embodiment 3

[0061] Example 3 Kinetic Test of Fluorescent Probe Recognition of Sulfur Dioxide

[0062] A dimethyl sulfoxide test mother solution of the fluorescent probe compound 4 obtained in Example 1 was prepared at a concentration of 1 mM for use.

[0063] Prepare the probe with a final concentration of 10 μM, PBS solution (pH 7.4) containing 20% ​​acetonitrile solution, fully react with sodium bisulfite (50 μM), and perform fluorescence detection every 3s (λ ex =440 nm, λ em =530nm;λ ex =645 nm, λ em =835 nm). The fluorescence intensity in each system was obtained, and the standard curve of fluorescence intensity and time was established, such as Figure 4 shown. Depend on Figure 4 It can be seen that with the increase of time, the fluorescence intensity at 530 nm gradually increases, and the fluorescence intensity at 835 nm gradually decreases, and the reaction reaches equilibrium within 12 s, indicating that the probe can quickly recognize sulfur dioxide.

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Abstract

The invention provides a near-infrared two-photon conversion type SO2 fluorescent probe. The SO2 fluorescent prob is shown in the description. Anionic groups of the fluorescent probe are preferably perchlorate ions. The ratio type fluorescent probe for detecting sulfur dioxide has the advantages of being extremely high in recognition speed, resistant to interference of various ions, amino acids and active oxygen and good in specificity, and at the same time, background and environmental interference is eliminated. The near-infrared two-photon conversion type SO2 fluorescent prob has a potential application value for detecting sulfur dioxide in environmental and biological systems.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting sulfur dioxide, which belongs to the field of small organic 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 has certain damage to t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82C09K11/06G01N21/64A61K49/00
CPCA61K49/0032C07D311/82C09K11/06C09K2211/1088G01N21/643G01N21/6486
Inventor 林伟英赵玉萍马燕燕
Owner UNIV OF JINAN
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