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Fluorescent probe for specifically responding to hypochlorous acid based on BODIPY dye and preparation and application

A fluorescent probe, hypochlorous acid technology, applied in the field of fluorescent probes, can solve the problems of short fluorescence emission wavelength, low selectivity, lack of imaging applications, etc., and achieve the effects of simple synthesis method, obvious detection signal, and convenient operation.

Active Publication Date: 2021-10-22
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the reported fluorescent probes have achieved ‒ detection, but there are still some problems, such as low selectivity (some ClO ‒ Probes may also be sensitive to H 2 o 2 and ONOO ‒ produce a response), the fluorescence emission wavelength is short (in the ultraviolet-visible region) and the imaging application in vivo is scarce, so the construction of ClO ‒ The study of novel long-wavelength fluorescent probes with high selectivity and the realization of cell and in vivo imaging is still imminent

Method used

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  • Fluorescent probe for specifically responding to hypochlorous acid based on BODIPY dye and preparation and application
  • Fluorescent probe for specifically responding to hypochlorous acid based on BODIPY dye and preparation and application
  • Fluorescent probe for specifically responding to hypochlorous acid based on BODIPY dye and preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The preparation steps of the probe are as follows:

[0042] (1) Preparation of compound 1

[0043]

[0044] N 2Under protection, dissolve p-hydroxybenzyl alcohol in 1,2-dichloroethane, add diisopropylethylamine in an ice-water bath, and add N,N-dimethylaminothioformyl chloride in a ratio of 1:1 equivalent , heated at 50°C for 24h, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0045] (2) Preparation of Compound 2

[0046]

[0047] The compound 1 prepared in step (1) was dissolved in dichloromethane, phosphorus tribromide was added in a ratio of 1:1.2 equivalent, stirred at room temperature for 1-2 hours, quenched with water, extracted with dichloromethane, and separated by column chromatography to obtain Compound 2;

[0048] (3) Preparation of compound 3

[0049]

[0050] N 2 Under the protection of the ice-water bath, sodium hydride is added to the tetrahydrofuran solvent and mixed to obtain a mixed solvent...

Embodiment 2

[0060] The preparation steps of the probe are as follows:

[0061] (1) Preparation of compound 1

[0062] N 2 Under protection, dissolve p-hydroxybenzyl alcohol in 1,2-dichloroethane, add diisopropylethylamine in an ice-water bath, and add N,N-dimethylaminothioformyl chloride at an equivalent ratio of 1:2 , heated at 50°C for 24h, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0063] (2) Preparation of Compound 2

[0064] The compound 1 prepared in step (1) was dissolved in dichloromethane, phosphorus tribromide was added in a ratio of 1:1 equivalent, stirred at room temperature for 1~2h, quenched with water, extracted with dichloromethane, and separated by column chromatography to obtain Compound 2;

[0065] (3) Preparation of compound 3

[0066] N 2 Under the protection of the ice-water bath, sodium hydride is added to the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and acetonyl p-toluenesulfonate oxime e...

Embodiment 3

[0072] The preparation steps of the probe are as follows:

[0073] (1) Preparation of compound 1

[0074] N 2 Under protection, dissolve p-hydroxybenzyl alcohol in 1,2-dichloroethane, add N,N-dimethylaminothioformyl chloride at an equivalent ratio of 1:1.5, and add diisopropylethylamine in an ice-water bath , heated at 50°C for 24h, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0075] (2) Preparation of Compound 2

[0076] The compound 1 prepared in step (1) was dissolved in dichloromethane, phosphorus tribromide was added according to the ratio of 1:2 equivalent, stirred at room temperature for 1-2h after adding alkali, quenched with water, extracted with dichloromethane, column layer Analysis and separation obtained compound 2;

[0077] (3) Preparation of compound 3

[0078] N 2 Under the protection of the ice-water bath, sodium hydride is added to the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and acet...

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Abstract

The invention provides a fluorescent probe for specifically responding to hypochlorous acid based on BODIPY dye and preparation and application thereof. The structural formula of the probe is shown in the specification. According to the probe, the BODIPY dye is selected as a fluorophore, and an N, N-dimethylamino thioformate group is selected as a recognition group. The detection mechanism is that the N, N-dimethylamino thioformate group is oxidized and removed by hypochlorous acid to cause electron transfer, and phenate is further subjected to a self-elimination reaction to release the fluorophore so as to cause the change of a fluorescence signal. The probe is used for detecting ClO <-> and is not interfered by other active nitrogen and active oxygen substances, the operation process is simple, convenient, rapid and sensitive, and the detection limit is 1.8 nM. More importantly, the probe can detect ClO <-> in cells and living bodies, and has a good application prospect in the field of biological monitoring.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a fluorescent probe based on BODIPY dye that specifically responds to hypochlorous acid, its preparation and application. Background technique [0002] Hypochlorous acid (HClO), as an important weakly acidic biological reactive oxygen species (ROS), is produced in organisms by H 2 o 2 and Cl － It is produced under the catalysis of myeloperoxidase (MPO). A certain concentration of HClO / ClO in the organism － It plays an important role in maintaining the normal physiological function of cells, cell signal transduction, maintaining homeostasis and immune defense system. However, excess HClO / ClO － It can lead to apoptosis and tissue damage, further increasing the risk of diseases such as Alzheimer's disease, neurodegenerative diseases, diabetes, cardiovascular disease, rheumatoid arthritis and cancer. Therefore, rapid and sensitive detection methods are essential for identifyin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06A61K49/00G01N21/64
CPCC07F5/022C09K11/06G01N21/6428G01N21/6456A61K49/0021C09K2211/1029C09K2211/1055Y02P20/55
Inventor 张健赵伟利范冠文鲁小艳苏慧慧王楠楠陶远芳秦淑春
Owner HENAN UNIVERSITY
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