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Ratiometric fluorescent probe of targeting mitochondria for sulfur dioxide

A sulfur dioxide, fluorescent probe technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve problems such as lack, and achieve the effects of low preparation cost, readily available raw materials, and simple and easy synthesis process

Inactive Publication Date: 2018-11-30
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the lack of fluorescent probes for sulfur dioxide targeting mitochondria in the prior art, the present invention provides a ratiometric fluorescent probe for detecting sulfur dioxide targeting mitochondria; Use in detection of sulfur dioxide / sulfite (hydrogen) in solution

Method used

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  • Ratiometric fluorescent probe of targeting mitochondria for sulfur dioxide
  • Ratiometric fluorescent probe of targeting mitochondria for sulfur dioxide
  • Ratiometric fluorescent probe of targeting mitochondria for sulfur dioxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Synthesis of Fluorescent Probes

[0035] (1) 7-diethylaminocoumarin (1 mmol) and p-piperazine acetophenone (1 mmol) in 1-hydroxybenzotriazole (0.5 mmol), 1-(3-dimethylaminopropyl) In the presence of -3-ethylcarbodiimide (3 mmol), N,N-diisopropylethylamine (0.1mL) and N,N-dimethylformamide (5mL), add to a 25 mL one-necked flask , stirred at room temperature for 5 hours. Use water-dichloromethane to extract, and obtain compound 4 after spin-drying the solvent:

[0036] ;

[0037] (2) 4-Diethylaminosalicylaldehyde (0.6mmol) and 3-(4-(4-acetylphenyl)piperazine-1-carbonyl)-7-diethylaminobenzene obtained in step (1) Pyrone was heated and reacted in the presence of concentrated sulfuric acid (5mL), stirred at 90°C for 2.5h, poured the resulting solution into ice water, added 4mL of perchloric acid, precipitated a solid, suction filtered, dried to obtain a solid, and then dichloro Methane:methanol=28.5:1 (v:v) was purified by column chromatography, and the purpl...

Embodiment 2

[0039] Example 2 Fluorescent Spectrum Test of Fluorescent Probes to Detect Different Concentrations of Sulfur Dioxide

[0040] Prepare different concentrations of sodium bisulfite buffer solutions (concentrations are 0, 1, 2, 5, 5.0, 10, 15, 20, 25, 30, 35, 40, 45, 50 μM), which contain the fluorescent Probe 10 μM, ethanol 5%wt, pH 7.4; fluorescence detection (λ ex =400 nm), record the fluorescence intensity at 483nm and 635nm, such as image 3 shown. Detect the fluorescence intensity of different concentrations of sodium bisulfite buffer solution (concentrations are 0-200μM) in the same way, and analyze I 483nm / I 635nm The linear relationship between the fluorescence intensity at and the concentration of sulfur dioxide, such as Figure 4 Shown: As the concentration of sodium bisulfite increases, the absorption peak at 483 nm gradually increases, and the absorption peak at 635 nm gradually decreases. When the concentration of sodium bisulfite reaches 100 μM, the absorptio...

Embodiment 3

[0041] Example 3 Selectivity of Fluorescent Probes

[0042] Various ions, amino acids and reactive oxygen species / reactive nitrogen solutions with a concentration of 100 mM were prepared as backup.

[0043] The solution of sodium sulfite and different interfering substances and the probe was prepared into a buffer solution (ethanol 5%wt, pH 7.4), the final concentration of interfering substances was 20 μM, the final concentration of probe was 10 μM, and the fluorescence detection was performed after shaking well (λ ex = 400 nm), to establish the fluorescence intensity ratio I 483nm / I635nm Histogram with each interfering substance, such as Figure 5 Shown: The interfering substances added in No. 1-10 are: blank, KI, CaCl 2 , FeSO 4 , Cys, NaClO, MgCl 2 , NaBr, ZnCl 2 、CuSO 4 、NiSO 4 , GSH, H 2 o 2 , SnCl 2 , TBHP, DBTP, NaCl, NaF, CoCl 2 , Fe 2 (SO 4 ) 3 、Na 2 S, probe. Depend on Figure 5 It can be seen that the fluorescent probe has a low fluorescence respon...

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Abstract

The invention provides a ratiometric fluorescent probe targeting mitochondria for detecting sulfur dioxide / sulfite (hydrosulphite). The ratiometric fluorescent probe has a structural formula as shownin the specification. The ratiometric fluorescent probe for detecting the sulfur dioxide provided by the invention has high recognition sensitivity, eliminates the interference of background, environment and concentration at the same time, is resistant to interference of various ions, amino acids and active oxygen, and has good specificity and potential application value for detecting the sulfur dioxide in environmental and biological systems. The probe provided by the invention has the advantages of simple and practicable synthetic process, cheap and easily-available raw materials, low preparation cost and easy popularization.

Description

technical field [0001] The invention relates to a fluorescent probe for rapid detection of sulfur dioxide, which belongs to the field of small organic molecule fluorescent probes. Background technique [0002] Mitochondria are the membrane-bound powerhouses of eukaryotic cells that use oxygen to generate biochemical energy in the form of adenosine triphosphate (ATP). In addition, mitochondria are involved in other biological processes such as signal transduction, cell differentiation, cell death, and maintenance of cell cycle control and cell growth. Thus, mitochondrial metabolism has been implicated in a large number of diseases, including atherosclerosis, Alzheimer's disease, Parkinson's disease, neuronal death in ischemic and hemorrhagic stroke, acute and chronic degenerative cardiac cell death and cancer. For example, recent research has shown that mitochondrial metabolism is a potential target in cancer therapy. [0003] SO 2 It is one of the main pollutants in the a...

Claims

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Application Information

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IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1059C09K2211/1088G01N21/6428
Inventor 林伟英宋文辉董宝利孔秀琪王超张楠
Owner UNIV OF JINAN
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