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Synthesis and application of BODIPY dye-based hypochlorite fluorescent probe

A fluorescent probe and compound technology, applied in the synthesis and application of hypochlorous acid and fluorescent probes, can solve the problems of limited application, slow reaction process, poor selectivity, etc., and achieve shortened detection time, enhanced fluorescence intensity, and high sensitivity high effect

Inactive Publication Date: 2017-03-22
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But at the same time, some shortcomings of these probes have also been exposed, such as certain cytotoxicity, slow reaction process, poor selectivity, low fluorescence quantum yield, susceptible to interference by other ions, etc., these The disadvantages also greatly limit the application of these probes in vivo

Method used

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  • Synthesis and application of BODIPY dye-based hypochlorite fluorescent probe
  • Synthesis and application of BODIPY dye-based hypochlorite fluorescent probe
  • Synthesis and application of BODIPY dye-based hypochlorite fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the synthesis of intermediate compound 1

[0050]

[0051] As shown in the above process, add 80 mL of dry dichloromethane and 0.58 mL of benzoyl chloride to a 250 mL round-bottomed flask, protect with nitrogen gas, slowly add 1.1 mL of 2,4-dimethylpyrrole, dropwise After adding 5 drops of trifluoroacetic acid (TFA), the mixed solution was stirred at room temperature in the dark for 10 h. Then 1.08 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was added to the reaction, and stirring was continued for 1 h at room temperature in the dark. Afterwards, 10 mL of triethylamine was added dropwise to the reaction in an ice bath, and after stirring for 15 min, 10 mL of boron trifluoride ether (BF 3 ·Et 2 O), remove the ice bath, and continue to react at room temperature for 2 h. After the reaction is complete, wash with 100 mL of saturated NaHCO 3 The solution was quenched, washed with distilled water (3×50 mL) and then extracted with dichloromethane (3...

Embodiment 2

[0052] Embodiment 2: Synthesis of fluorescent probes based on BODIPY dyes

[0053] (1) Synthesis of compound 2.

[0054] Add 6 mL (78 mmol) of N,N-dimethylformamide (DMF) to a 250 mL round-bottomed flask, pass through nitrogen protection, and then add 15.0 mL (160 mmol) of phosphorus oxychloride in an ice-water bath, Stir for 10 min, remove the ice bath, return to room temperature and stir for 30 min. Then, weigh 316 mg (1 mmol) of compound 1 synthesized in Example 1 and dissolve it in 40 mL of dichloroethane (ClCH 2 CH 2 Cl), and injected into the flask, and continued to react at 40°C for 3 h. Then cooled to room temperature and slowly poured into saturated NaHCO in an ice-water bath 3 , add an appropriate amount of NaHCO 3 Continue stirring at room temperature for 1 h until the solution is slightly alkaline. After the reaction was complete, it was extracted with dichloromethane (3×50 mL), the organic phases were combined, and the solvent was spin-dried under reduced pr...

Embodiment 3

[0057] Example 3: Synthesis of fluorescent probes based on BODIPY dyes

[0058] (1) Synthesis of compound 2.

[0059] Add 15 mL (195 mmol) of N,N-dimethylformamide (DMF) to a 250 mL round-bottomed flask, pass through nitrogen protection, and then add 6.0 mL (64 mmol) of phosphorus oxychloride in an ice-water bath, Stir for 10 min, remove the ice bath, return to room temperature and stir for 30 min. Then, weigh 316 mg (1 mmol) of compound 1 synthesized in Example 1 and dissolve it in 60 mL of dichloroethane (ClCH 2 CH 2 Cl), and injected into the flask, and continued to react at 55°C for 6 h. Then cooled to room temperature and slowly poured into saturated NaHCO in an ice-water bath 3 , add an appropriate amount of NaHCO 3 Continue stirring at room temperature for 1 h until the solution is slightly alkaline. After the reaction was complete, it was extracted with dichloromethane (3×50 mL), the organic phases were combined, and the solvent was spin-dried under reduced press...

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Abstract

The invention belongs to the technical fields of preparation and application of compounds, and in particular, relates to synthesis and application of a BODIPY dye-based hypochlorite fluorescent probe; a BODIPY derivative is firstly synthesized as a fluorescent probe; the synthesis comprises the steps: utilizing N,N-dimethyl formamide and phosphorus oxychloride, then adding a compound 1, dissolving in dichloroethane, carrying out a reaction, adding NaHCO3 until the solution is weakly alkaline, and after completion of the reaction, purifying through column chromatography to obtain a compound 2; then dissolving diamino maleonitrile and the compound 2 in ethanol, adding a few drops of acetic acid, carrying out a stirring reaction at room temperature, and finally obtaining the purified product. The fluorescent probe is used for detection of hypochlorite ions in tap water, Yangtze River water and sodium hypochlorite disinfection liquids; the fluorescent probe is capable of rapid identification of ClO<->, the fluorescence intensity is increased rapidly and obviously with addition of the hypochlorite and can be stable within 10 s, and thus the detection time is greatly shortened.

Description

technical field [0001] The invention belongs to the technical field of compound preparation and application, and in particular relates to the synthesis and application of hypochlorous acid and fluorescent probes based on BODIPY dye. Background technique [0002] Hypochlorous acid (HOCl) is an important reactive oxygen species (ROS) in organisms. It is generally believed that the internal [0003] The source of hypochlorous acid is produced by H 2 o 2 and Cl - It is produced by peroxidation reaction catalyzed by peroxidase, especially in leukocytes. Hypochlorous acid can destroy invading bacteria and pathogens, so it is of great significance to the human immune system. However, excessive hypochlorous acid can also damage DNA and protein molecules, eventually leading to some diseases, such as cardiovascular disease, atherosclerosis, kidney disease, Osteoarthritis and cancer etc. In addition, HOCl and its conjugate base ClO - It is a common drinking water, swimming pool d...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C07F5/003C09K11/06C09K2211/1096G01N21/6428
Inventor 顾磊吴嘉聪夏晋晨李媛媛韩娟王赟倪良
Owner JIANGSU UNIV
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