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Preparation method and application of BODIPY (boron-dipyrromethene) and Cys (cysteine) fluorescent probe

A technology of fluorescent probe, fluoroboropyrrole, which is applied in the field of fluorescent probe to achieve the effect of rapid response and good selectivity

Inactive Publication Date: 2017-02-22
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there is no fluoroboropyrrole-based fluorescent molecular probe for the direct and rapid detection of Cys

Method used

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  • Preparation method and application of BODIPY (boron-dipyrromethene) and Cys (cysteine) fluorescent probe
  • Preparation method and application of BODIPY (boron-dipyrromethene) and Cys (cysteine) fluorescent probe
  • Preparation method and application of BODIPY (boron-dipyrromethene) and Cys (cysteine) fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of fluorescent probes

[0027] Synthetic route such as figure 1 shown.

[0028] Synthesis of Compound 2: In a 100mL round bottom flask, 4-hydroxybenzaldehyde (2.0mmol, 0.36g) and 2,4-dimethylpyrrole (4.4mmol, 0.42g) were added successively, and then 30mL of dichloromethane was added as a solvent. Magnetic stirring at room temperature, under N 2 In a protected environment, 1 drop of trifluoroacetic acid was added dropwise as a catalyst. After continuing stirring for about 6 h, dichlorodicyanobenzoquinone (2.0 mmol, 0.46 g) dissolved in 5 mL of dichloromethane was added dropwise to the reaction solution, and stirring was continued for about 0.5 h. Then, 0.4 mL of triethylamine and 0.4 mL of boron trifluoride ether were sequentially added to the reaction solution. The reaction is complete when yellow-green fluorescence is produced. The solvent was removed by a rotary evaporator, dichloromethane / hexane 1:1 (volume ratio) was used as eluent, and column chroma...

Embodiment 2

[0031] Solution preparation of fluorescent probe interacting with Cys

[0032] A certain amount of fluorescent probe was dissolved in EtOH to obtain a concentration of 1.0 × 10 -4 mol L -1 Probe stock solution. After dissolving a certain amount of Cys in water, transfer it to a 500mL volumetric flask, add water to the mark, and obtain a concentration of 1.0×10 -2 mol L -1 Cys. will be 1.0×10 -2 mol L -1 The Cys solution was gradually diluted with water to obtain 1.0 x 10 -3 -1.0×10 -8 mol L -1 Cys aqueous solution. Add 1.0mL of the probe stock solution and 1.0mL of the Cys aqueous solution into a 10mL volumetric flask, and dilute to the volume with buffer solution to obtain a concentration of 1.0×10 -5 mol L -1 fluorescent probe and 1.0 x 10 -3 -1.0×10 - 8 mol L -1 Cys mixed with the solution to be tested.

Embodiment 3

[0034] Measurement of Fluorescent Spectrum of Fluorescent Probe Interaction with Cys

[0035] A buffer solution with a pH value of 7.4 was used as a solvent to measure the fluorescence spectrum of the interaction between the fluorescent probe and Cys, and the results were as follows: figure 2 . The concentration of the fluorescent probe is 10 μM, the concentration of Cys is 0, 0.2, 0.8, 2, 5, 10, 15, 20, 25, 30 μM, the excitation wavelength is fixed at 480 nm, the emission wavelength range is 500-600 nm, and the slit width It is 5.0nm / 5.0nm. From image 3 It can be seen that before adding Cys, the fluorescent probe has a weak fluorescence emission peak at 517nm. With the addition of Cys, the emission peak at 517nm is greatly enhanced, and with the increase of Cys concentration, the fluorescence intensity of the probe is continuously enhanced. When 30 μM Cys is added, the fluorescence intensity is enhanced to 23 without Cys. times. This is because the aldehyde group of th...

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Abstract

The invention discloses a preparation method and an application of a boron-dipyrromethene (BODIPY) based fluorescent probe for determining cysteine (Cys). The structural formula of the probe is shown in the specification. The preparation method of the BODIPY derivative based Cys fluorescent probe with a simple structure is provided, and the BODIPY derivative based Cys fluorescent probe is used for directly measuring Cys concentration. In the system, the fluorescent probe shows good selectivity and is not interfered with other biological thiols (Hcy and GSH) and other 19 amino acids. The probe shows quite high sensitivity to Cys, and the fluorescence intensity is enhanced by 23 times when 3 equivalents of Cys are added. When the pH is between 6.0 and 8.0, determination of Cys by the fluorescent probe is not affected by pH. The fluorescence probe and Cys act quickly, and the response time is within 6 minutes. In addition, the probe can also be used in cell imaging to detect intracellular Cys.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a preparation method and application of a fluborazole-based Cys fluorescent probe. Background technique [0002] Cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH) are collectively referred to as biothiols, and they play an important role in life activities (Z.A.Wood, E.Schroder, J.R.Harris and L.B. Poole, Trends. Biochem. Sci., 2003, 28, 32-40.). Changes in the concentration of these thiols in organisms are closely related to the normality of certain life processes (Y. Murata, T. Shimamura and J. Hamuro, Int. Immunol., 2002, 14, 201-212.). Studies have shown that excessive Cys concentration is a major cause of cardiovascular disease and Alzheimer's disease, and Cys concentration in plasma has a great relationship with birth defects and Alzheimer's disease (S.E.Vollset, H.Refsum, L M.Irgens, B.M.Emblem, A.Tverdal, H.K.Gjessing, A.L.B.Monsen, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1029C09K2211/1055G01N21/6486
Inventor 李春艳付雅俊
Owner XIANGTAN UNIV
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