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Selenium-containing fluorine-boron dye fluorescent probe and application thereof in ClO<-> detection

A fluorescent probe, fluorine and boron technology, applied in the field of fluorescent probes, can solve the problems of limited application prospects, inability to use hypochlorous acid for real-time detection, interference, etc.

Active Publication Date: 2014-02-12
ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above probes have good selectivity for hypochlorous acid, they are all single-wavelength fluorescence-enhanced probes, which are strongly disturbed by the external environment; and they are not reversible, so they cannot be used for real-time detection of hypochlorous acid. Its application prospects are greatly limited

Method used

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  • Selenium-containing fluorine-boron dye fluorescent probe and application thereof in ClO&lt;-&gt; detection
  • Selenium-containing fluorine-boron dye fluorescent probe and application thereof in ClO&lt;-&gt; detection
  • Selenium-containing fluorine-boron dye fluorescent probe and application thereof in ClO&lt;-&gt; detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Synthesis of p-methoxybenzaldehyde:

[0064] Add 1.26g of magnesium powder into a 250mL three-necked bottle, N 2 For protection, add 40mL THF, add a few grains of iodine (about 0.5g) to initiate the reaction, add p-bromobenzaldehyde 10g / 50mL THF dropwise, and continue to reflux to fully react after the addition. Then, under reflux, 19.5g p-methoxydiphenylselenium (Organic Syntheses Coll. 1988, 6,533) / 50mL THF was added dropwise, and the stirring was continued for 20 hours. The solvent was evaporated to dryness, dissolved in dichloromethane, and filtered. The solvent was evaporated to dryness and purified by column fractionation.

[0065] 1 H NMR (400MHz, CDCl 3 ,ppm):3.84(s,3H,OCH 3 ), 6.93(d,2H,Ar-H, J=8.0),7.3(d,2H,Ar-H,J=8.0),7.57(d,2H,Ar-H,J=8.0),7.65(d ,2H,Ar-H, J=8.0),9.88(s,1H,CHO). 13 C NMR (100MHz, CDCl 3 ,ppm):55.34,115.58,117.35,128.92,130.01,134.09,138.01,144.35,160.62,191.33. 77 Se NMR (95MHz, CDCl 3 ,ppm): 419.14.HRMS(TOF LD+)calcd.for C 14 h 1...

Embodiment 2

[0067] Synthesis of Probe A:

[0068] Such as figure 2 As shown, the structure of the probe compound used in this example is represented by code A.

[0069] Add 0.5 g of p-methoxybenzaldehyde and 0.35 g of 2,4-dimethylpyrrole into 60 mL of dichloromethane, drop a few drops (about 1 mL) of trifluoroacetic acid as a catalyst, and stir at room temperature until the reaction of the raw materials is complete. Add 0.39 g of 2,3-dichloro-5,6-dicyano-p-quinone (DDQ), continue stirring for 10-30 minutes, add 3 g of boron trifluoride ether, 1.5 g of triethylamine, and stir at room temperature for 10 After one hour, the solvent was evaporated to dryness, column separation and purification, and the solvent was evaporated to dryness to obtain an orange solid powder.

[0070] 1 H NMR (400MHz, CDCl 3 ,ppm):1.42(s,6H,CH 3 ),2.54(s,6H,CH 3 ),3.83(s,3H,OCH 3 ),5.97(s,2H,CH),6.9(d,2H,J=8.0,Ar-H),7.1(d,2H,J=8.0,Ar-H),7.39(d,2H,J=8.0 ,Ar-H),7.54(d,2H,J=8.0,Ar-H). 13 C NMR (100MHz, CDCl ...

Embodiment 3

[0072] Synthesis of Probe B:

[0073] Such as figure 2 As shown, the structure of the probe compound used in this embodiment is represented by code B, and the raw material BODIPY is represented by code C.

[0074] Raw material C (J.Phys.Chem.A 1998,102,10211) 0.65g, p-methoxybenzaldehyde 1.2g, piperidine 1mL, toluene 20mL, under nitrogen protection, react at 100-165°C overnight. The solvent was evaporated to dryness, purified by column separation, and the solvent was evaporated to give a blue solid powder.

[0075] 1 H NMR (400MHz, CDCl 3 ,ppm):1.42(s,6H,CH 3 ),3.84(s,6H,OCH 3 ),6.6(s,2H,CH),6.9(d,4H,J=7.2,Ar-H),7.15(d,2H,J=13,CH=CH),7.29-7.31(m,6H,Ar -H),7.44(d,4H,J=6.8,Ar-H),7.47-7.49(m,3H,Ar-H),7.54(d,4H,J=7.2,Ar-H),7.66(d ,2H,J=13,CH=CH). 13 C NMR (100MHz, CDCl 3 ,ppm):14.59,55.36,115.32,117.85,119.08,119.38,128.07,128.44,128.86,129.00,129.09,130.61,133.49,134.82,135.16,135.45,136.94,138.83,142.11,152.48,160.08. 77 SeNMR (95MHz, CDCl 3 ,ppm):406.48.HRMS (TOF LD...

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Abstract

The invention discloses synthesis of a selenium-containing fluorine-boron dye fluorescent probe and application of the selenium-containing fluorine-boron dye fluorescent probe in ClO<-> detection, relates to a fluorescent probe of which the fluorescence intensity or a wavelength is changed under the existence of ClO<-> and is recovered under the existence of reducing substances and aims to realize reversible or rate detection of the ClO<->. The invention provides a reversible fluorescent probe for selectively detecting the ClO<-> in cells. According to the fluorescent probe, a fluorine-boron dye (BODIPY) is used as a fluorescent parent, and an organic selenide structure is introduced to the dye parent to form a probe system; selenium is used as an active center generating reaction with the ClO<->, so that the ClO<-> can be selectively detected; due to the characteristic that an organic selenium oxide formed by organic selenide oxidization is easily reduced into the organic selenide through reducing micromolecules such as cysteine, reduced glutathione and metallothionein in a biological system, reversibility of probe molecules is achieved.

Description

technical field [0001] The present invention relates to a class for detecting ClO - Fluorescent probes, specifically, in ClO - Fluorescent probes that change in fluorescence intensity or wavelength in the presence of reducing substances such as cysteine, reduced glutathione, metallothionein, etc., and return to their original state in fluorescence intensity or wavelength. Background technique [0002] Reactive oxygen species (Reactive Oxygen Species, ROS), compared with ordinary oxygen molecules, they have a higher redox activity. Reactive oxygen species are necessary for biological and pathological processes. During infection and inflammation, phagocytic leukocytes, including neutrophils, monocytes, and macrophages, will produce reactive oxygen species to kill germs and pathogens. Therefore, active oxygen is of great significance to the human body. Hypochlorous acid is a highly active ROS. Unlike other reactive oxygen species and reactive nitrogen species (RNS), hypochl...

Claims

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Application Information

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IPC IPC(8): C09K11/06G01N21/64A61K49/00C12Q1/02
Inventor 韩克利王炳帅李鹏于法标孙小飞
Owner ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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