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Preparation method of high-selectivity hypochlorous acid fluorescent probe

A fluorescent probe and high-selectivity technology, applied in the field of fluorescent probes, can solve the problems of insufficient response, high background fluorescence, poor selectivity of hypochlorous acid, etc., and achieve the elimination of background fluorescence interference, sensitive detection effect, and good practical application. potential effect

Inactive Publication Date: 2020-09-22
JIANGSU UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] Many fluorescent probes have been reported for the detection of hypochlorous acid, but these fluorescent probes have different defects, such as complex synthesis steps, poor selectivity to hypochlorous acid, high background fluorescence, low water solubility and insufficient response wait quickly
Among them, the high background fluorescence of the probe is an important factor that leads to the reduction of the accuracy of the detection.

Method used

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  • Preparation method of high-selectivity hypochlorous acid fluorescent probe
  • Preparation method of high-selectivity hypochlorous acid fluorescent probe
  • Preparation method of high-selectivity hypochlorous acid fluorescent probe

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Embodiment 1

[0032] Synthesis of fluorescent probes;

[0033] Synthetic route such as figure 1 .

[0034] Synthesis of 7-dimethylaminocoumarin-3-acyl chloride: In a 100ml round bottom flask, add 7-dimethylaminocoumarin-3-carboxylic acid (1.2g, 5.15mmol), dropwise add 5ml of Water Thionyl Chloride. N 2 Stir at room temperature under protection for 4h. After suction filtration, the filter cake was washed with cold anhydrous ether to obtain a yellow solid compound 7-dimethylaminocoumarin-3-acyl chloride (0.75 g, yield 57.8%). It was directly used in the next reaction without purification.

[0035] Synthesis of fluorescent probe CMFP-HOCl: In a 100-ml round-bottomed flask, the compound 7-dimethylaminocoumarin-3-acid chloride (0.3 g, 1.2 mmol) was completely dissolved in 10 mL of anhydrous CH 2 Cl 22,4-Dinitrophenylhydrazine (0.15 g, 0.75 mmol) was added thereto, and then triethylamine (2 mL, 14.4 mmol) was added dropwise, and stirred at room temperature for 24 h. After the reaction sto...

Embodiment 2

[0038] Preparation of fluorescent probe and hypochlorous acid solution;

[0039] 1. Weigh an appropriate amount of fluorescent probe CMFP-HOCl and dissolve it in chromatographically pure N, N-dimethylformamide (DMF) to prepare a 1.0 mM fluorescent probe molecular stock solution;

[0040] 2. Weigh an appropriate amount of sodium hypochlorite and dilute it with distilled water to obtain a 10mM hypochlorous acid solution and dilute it step by step to obtain a 10-0.1mM hypochlorous acid solution;

[0041] 3. Weigh an appropriate amount of KH 2 PO 4 、Na 2 HPO 4 , NaCl, and KCl were fixed to volume with distilled water to obtain a phosphate buffered saline solution (PBS) with a concentration of 0.01M and pH=7.4;

[0042] 4. Use acetonitrile and the PBS obtained in step 3 to mix according to the volume ratio of acetonitrile:PBS=4:6, add a certain volume of the fluorescent probe stock solution in step 1 and the hypochlorous acid solution in step 2, and the obtained mixed The conc...

Embodiment 3

[0044] Fluorescent spectrometry of fluorescent probes in response to HOCl;

[0045] figure 2 (a) is the fluorescence emission spectrum of the fluorescent probe CMFP-HOCl (10 μM) in response to 0-55 μM hypochlorous acid. The excitation spectrum used in the experiment is 400nm, and the emission wavelength range is 420-600nm. Both the excitation and emission slit widths are 10 nm, and the fluorescence measurement instrument used is a Thermo Fisher Lumina fluorescence spectrophotometer. like figure 2 As shown, the fluorescent probe CMFP-HOCl itself only emits weak fluorescence. After adding hypochlorous acid, the solution emits obvious fluorescence emission at 473nm, and the fluorescence intensity increases with the increase of hypochlorous acid concentration. This is because hypochlorous acid can specifically cut off the hydrazide bond in the fluorescent probe molecule, releasing the fluorescence of the fluorescent group 7-dimethylaminocoumarin-3-carboxylic acid. figure 2...

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Abstract

The invention belongs to the field of fluorescent probes, and particularly relates to a preparation method and application of a high-selectivity hypochlorous acid fluorescent probe. The invention provides the preparation method for obtaining the fluorescent probe through a two-step reaction of 7-dimethylaminocoumarin-3-carboxylic acid and 2,4-dinitrophenylhydrazine. The high-selectivity hypochlorous acid fluorescent probe prepared by the method has low background fluorescence, and has good sensitivity and high selectivity on detection of hypochlorous acid; the probe can be used for detecting hypochlorous acid under a physiological pH condition; test paper prepared from the probe is successfully used for detecting hypochlorous acid in water; the probe has been successfully used for detecting hypochlorous acid in living cells of non-therapeutic purposes.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a preparation method of a highly selective hypochlorous acid fluorescent probe and its test paper detection application of hypochlorous acid in water and the application of fluorescent imaging detection of hypochlorous acid in living cells for non-treatment purposes . Background technique [0002] Hypochlorous acid is an important reactive oxygen species with strong oxidizing properties. It is widely used in production and life, and is often used as bleach and disinfectant. Endogenous hypochlorous acid in organisms is produced by hydrogen peroxide (H 2 o 2 ) and chloride ions (Cl - ) is produced under the catalysis conditions of myeloperoxidase (MPO). Hypochlorous acid plays an important role in the immune system due to its strong antimicrobial properties and is an important link in the biological defense process. In addition, hypochlorous acid also af...

Claims

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Application Information

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IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06G01N21/6428G01N21/643C09K2211/1088C09K2211/1007
Inventor 姜舒韩志湘许海王洋董良欢代晓婷
Owner JIANGSU UNIV
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