Fluorescent probe for detecting biologic thiol and preparation method and usage method thereof

A fluorescent probe and sulfhydryl technology, applied in the field of bioengineering, can solve problems such as low signal-to-noise ratio, rare probes, poor photostability, etc., and achieve the effect of single recognition, excellent selectivity, and high sulfhydryl detection sensitivity

Inactive Publication Date: 2012-07-04
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the developed aryl halides, dansylaziridines, pyrenes, etc. have good selectivity and sensitivity, and the detection limit for sulfhydryl groups is generally around nanomolar (nmol), but these probes themselves have Strong fluorescence, which will cause low signal-to-noise ratio when used in live cell imaging; benzofuransulfonyl halide probes, although their autofluorescence is weak, need to react with sulfhydryl groups under alkaline and high temperature conditions, and cannot Applied to fluoresc...

Method used

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  • Fluorescent probe for detecting biologic thiol and preparation method and usage method thereof
  • Fluorescent probe for detecting biologic thiol and preparation method and usage method thereof
  • Fluorescent probe for detecting biologic thiol and preparation method and usage method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Preparation of probe molecules

[0040] The reaction process is represented by the following reaction scheme:

[0041]

[0042] 1) Preparation of formula II: under the protection of argon, add 0.6 g of m-hydroxybenzaldehyde and 1 g of 2,4-dimethylpyrrole into 150 mL of dichloromethane, stir to dissolve, and then add 0.5 mL of three Fluoroacetic acid was stirred and reacted at room temperature for 10 hours. After the reaction was completed, the solvent was evaporated to dryness and separated with a silica gel column.

[0043] 2) Preparation of formula III: under the protection of argon, 1.2 g of the compound of formula II was dissolved in 100 mL of dichloromethane, and 1.3 g of 2,3-dichloro-5,6 -Dicyano-p-benzoquinone (DDQ) in dichloromethane solution 100 mL, continue to stir the reaction for 4 hours, cool the system in an ice bath, then quickly drop 10 mL triethylamine and 15 mL trifluoride into the reaction system Boron ether solution, continue to stir for 3 h...

Embodiment 2

[0059] (1) Preparation of probe molecules

[0060] Reaction process is with embodiment 1:

[0061] 1) Preparation of formula II: under the protection of argon, add 0.9 g of m-hydroxybenzaldehyde and 1.5 g of 2,4-dimethylpyrrole into 150 mL of dichloromethane, stir to dissolve, and then add 0.5 mL of Tris Fluoroacetic acid was stirred and reacted at room temperature for 12 hours. After the reaction was completed, the solvent was evaporated to dryness and separated with a silica gel column.

[0062] 2) Preparation of formula III: under the protection of argon, 1.8 g of the compound of formula II was dissolved in 100 mL of dichloromethane, and 2.0 g of 2,3-dichloro-5,6 -Dicyano-p-benzoquinone (DDQ) dichloromethane solution 100 mL, continue to stir the reaction for 5 hours, cool the system in an ice bath, then quickly drop 10 mL triethylamine and 23 mL trifluoride into the reaction system Boron ether solution, continue to stir for 3 hours, remove the solvent under reduced pressu...

Embodiment 3

[0078] (1) Preparation of probe molecules

[0079] Reaction process is with embodiment 1.

[0080] 1) Preparation of formula II: under the protection of argon, add 1.2 g of m-hydroxybenzaldehyde and 2 g of 2,4-dimethylpyrrole into 150 mL of dichloromethane, stir to dissolve, and then add 0.5 mL of Tris Fluoroacetic acid was stirred and reacted at room temperature for 15 hours. After the reaction was completed, the solvent was evaporated to dryness and separated with a silica gel column.

[0081] 2) Preparation of formula III: under the protection of argon, 2.4 g of the compound of formula II was dissolved in 100 mL of dichloromethane, and 2.6 g of 2,3-dichloro-5,6 -Dicyano-p-benzoquinone (DDQ) dichloromethane solution 100 mL, continue to stir the reaction for 6 hours, cool the system in an ice bath, then quickly drop 10 mL triethylamine and 30 mL trifluoride into the reaction system Boron ether solution, continue to stir for 4 hours, remove the solvent under reduced pressure...

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Abstract

The invention discloses a fluorescent probe for detecting a biologic thiol and a preparation method and a usage method thereof. The fluorescent probe for detecting the biologic thiol consists of two parts: namely, a 2, 4-bi-nitrobenzene sulfonyl group which is a recognizing group and a boron difluoride-dipyrryl methane (BODIPY) derivative which is an information reporting functional group. The molecule of the probe can simply and quickly enter a living cell, generates a specificity reaction with the thiol in the cell, and causes to obviously enhance fluorescence intensity, so that the fluorescent probe further can be used for the fluorescence detection and the imaging of the active thiol in the living cell. The fluorescent probe has good stability, can be stored and used for a long time, is applicable to various environments in which the living cell grows, and has higher detection sensitivity for the thiol, strong anti-interference capability, excellent selectivity and no action on other common biologic interfering molecules. The fluorescent probe can simply enter the living cell and a living tissue; the single recognition of the thiol in a biologic system can be achieved effectively; and therefore, the fluorescent probe can be used for the fluorescence imaging of the living cell.

Description

technical field [0001] The invention belongs to the technical field of bioengineering, and in particular relates to a fluorescent probe for detecting biological sulfhydryl groups, a preparation method and a use method thereof. Background technique [0002] Sulfhydryl is the group with the highest chemical activity in cells, an important component of many proteins and small molecules in organisms, and plays an important role in the antioxidant system of cells. The content of sulfhydryl molecules is directly related to various diseases, such as cancer, Parkinson's disease, cardiovascular disease, etc. Therefore, it is of great significance to develop a rapid, sensitive and simple method for detecting thiols in biochemistry and clinical chemistry. Traditional detection methods include mass spectrometry, high performance liquid chromatography, electrochemical methods, and fluorescence methods. Due to its high sensitivity and wide dynamic response range, more importantly, fluore...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64A61K49/00
Inventor 韩益丰刘静
Owner ZHEJIANG SCI-TECH UNIV
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