Fluorescent probe for detecting mercapto compounds as well as preparation method and using method of fluorescent probe

A sulfhydryl compound and fluorescent probe technology, applied in the field of bioengineering, can solve the problems of low signal-to-noise ratio, high response probes are rare, poor photostability, etc., and achieve high sulfhydryl detection sensitivity, excellent selectivity, and easy synthesis. Effect

Inactive Publication Date: 2012-08-15
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 fluorescence imaging of living cells; while acetyl halide derivatives are sulfhydryl derivatives, which can quickly react with sulfhydryl at room temperature and physiological pH, but the photostability is poor, especially when it is in solution, and it is easy to lose the fluorophore , so it is difficult to meet the requirements of biological detection and fluorescence imaging
So far, highly sensitive and high-response probes that can be truly used for the detection of sulfhydryl compounds are still relatively rare

Method used

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  • Fluorescent probe for detecting mercapto compounds as well as preparation method and using method of fluorescent probe
  • Fluorescent probe for detecting mercapto compounds as well as preparation method and using method of fluorescent probe
  • Fluorescent probe for detecting mercapto compounds as well as preparation method and using method of fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) Preparation of probe molecules

[0036] The reaction process is represented by the following reaction scheme:

[0037]

[0038] Step 1, preparation of formula II: Dissolve 0.2 g of hydroquinone in 50 mL of dichloromethane, then add 0.6 mL of triethylamine, add 0.6 g of dansyl chloride at 0°C, and then stir the reaction at room temperature After 10 hours, after the reaction was completed, the solvent was evaporated to dryness and separated with a silica gel column.

[0039] Step 2, preparation of formula I: Dissolve 0.6 g of compound of formula II in 50 mL of dichloromethane, add 1.5 mL of triethylamine, stir for 5 minutes, then add dropwise 0.9 g of 2,4- Dinitrobenzenesulfonyl chloride dichloromethane solution 10 mL, after the dropwise addition is complete, continue to stir at room temperature for 10 hours, remove the solvent under reduced pressure, separate and purify the crude product by silica gel column chromatography, and use petroleum ether: ethyl acetate ...

Embodiment 2

[0052] (1) Preparation of probe molecules

[0053] Reaction process is with embodiment 1:

[0054] Step 1, preparation of formula II: Dissolve 0.3 g of hydroquinone in 50 mL of dichloromethane, add 0.6 mL of triethylamine, add 0.9 g of dansyl chloride at 0°C, and then stir the reaction at room temperature for 12 hour, after the reaction was finished, the solvent was evaporated to dryness and separated with a silica gel column;

[0055] Step 2, preparation of formula I: Dissolve 0.9 g of compound of formula II in 50 mL of dichloromethane, add 1.5 mL of triethylamine, stir for 5 minutes, then add dropwise 1.4 g of 2,4- Dinitrobenzenesulfonyl chloride dichloromethane solution 10 mL, after the dropwise addition is complete, continue to stir at room temperature for 12 hours, remove the solvent under reduced pressure, separate and purify the crude product by silica gel column chromatography, and use petroleum ether: ethyl acetate = 4:1 is the eluent elution, and the pure product o...

Embodiment 3

[0065] (1) Preparation of probe molecules

[0066] Reaction process is with embodiment 1:

[0067] Preparation of Formula II: Dissolve 0.4 g of hydroquinone in 50 mL of dichloromethane, add 0.6 mL of triethylamine, add 1.2 g of dansyl chloride at 0°C, then stir and react at room temperature for 15 hours, and wait for After the reaction was completed, the solvent was evaporated to dryness and separated with a silica gel column;

[0068] Preparation of Formula I: Dissolve 1.2 g of the compound of Formula II in 50 mL of dichloromethane, add 1.5 mL of triethylamine, stir for 5 minutes, then add dropwise 1.8 g of 2,4-dinitro 10 mL of dichloromethane solution of benzenesulfonyl chloride, after the dropwise addition is complete, continue to stir at room temperature for 15 hours, remove the solvent under reduced pressure, separate and purify the crude product by silica gel column chromatography, and use petroleum ether: ethyl acetate = 4:1 For the eluent elution, the pure probe mole...

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Abstract

The invention discloses a fluorescent probe for detecting mercapto compounds as well as the preparation method and the using method of the fluorescent probe. The prior art difficultly meets the requirements for biological detection and fluorescent imaging. The fluorescent probe consists of two parts, wherein 2,4-dinitrobenzol sulfonyl is an identification group, and dansyl chloride derivative is an information report functional group; and when mercapto exists in a system, the mercapto can perform specific reaction with 2,4-dinitrobenzol sulfonyl, so that the fluorescence of the information report functional group is changed, and the specific detection of the mercapto group is realized. The probe is simple and convenient in molecular synthesis and good in stability, can be stored and used for a long term, has high mercapto detection sensitivity and excellent selectivity, does not act with other common interfering molecules, has long fluorescence emission wavelength (more than 500nm), can effectively avoid the interference from background fluorescence of which biological macromolecules are smaller than 500nm, and can be applied to detection of biological systems.

Description

technical field [0001] The invention belongs to the technical field of bioengineering, and in particular relates to a fluorescent probe for detecting sulfhydryl compounds, a preparation method and an application method thereof. Background technique [0002] Sulfhydryl groups are important components of many proteins and small molecules in living organisms, and they are the most reactive functional groups related to enzyme activity. A large number of biological phenomena are considered to depend on these thiol-containing thiols, such as redox reactions, methyl transfer reactions, carbon dioxide fixation reactions, and reactions involving coenzyme A. The content of certain sulfhydryl molecules in the body 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 detecti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/71C07C303/28C09K11/06G01N21/64
Inventor 韩益丰刘静
Owner ZHEJIANG SCI-TECH UNIV
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