A novel sulfhydryl fluorescent probe, its preparation method and its application

A fluorescent probe and sulfhydryl technology, applied in the field of preparation and new sulfhydryl fluorescent probes, can solve the problems of lack of selectivity, fixed-point labeling of proteins, and inability to respond well to the biological properties of polysaccharides, and achieve high fluorescence intensity and stability. good effect

Inactive Publication Date: 2016-01-20
CHINA PHARM UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although these traditional fluorescent reagents have a wide range of applications, there are still some defects. For example, there are few reports on the fluorescent labeling of polysaccharides. Most of the existing labeling methods lack selectivity and cannot well reflect the biological properties of polysaccharides. Existing fluorescent reagents cannot rationally label proteins. Some fluorescent reagents have weak fluorescent signals and unstable fluorescent signals, which cannot satisfy the research on the biological properties of biological macromolecules.

Method used

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  • A novel sulfhydryl fluorescent probe, its preparation method and its application
  • A novel sulfhydryl fluorescent probe, its preparation method and its application
  • A novel sulfhydryl fluorescent probe, its preparation method and its application

Examples

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Embodiment 1

[0046] The preparation of embodiment 12-(2-mercaptoethylamino) benzamide

[0047] 1) Dissolve 19ml of chloroacetaldehyde solution with a mass percentage of 40% in 40ml of aqueous solution, cool to 0°C in an ice bath to obtain diluted chloroacetaldehyde solution, add dropwise a sodium carbonate solution with a concentration of 2Mol / L, and adjust the pH to 3 ;

[0048] 2) Dissolve 9.9g of sodium hydrosulfide in 33ml of water to obtain an aqueous solution of sodium hydrosulfide, cool it to 0°C in an ice bath, and add it dropwise to the chloroacetaldehyde solution at a rate of 2-3 drops per second, and at the same time, at 200 rpm Stir the chloroacetaldehyde solution at a constant speed, and a white solid precipitates out in the solution. After the sodium hydrosulfide is added, filter it with suction and dry it in vacuum to obtain mercaptoaldehyde;

[0049] 3) Dissolve 434mg of mercaptoaldehyde in 120ml of methanol solution, stir until dissolved at room temperature, add 1.5g of 2-a...

Embodiment 2

[0052] The preparation of embodiment 22-(2-mercaptoethylamino) benzoylformic acid

[0053] 1) 28.5ml mass percentage is that 40% chloroacetaldehyde solution is dissolved in 60ml aqueous solution, is cooled to 0 ℃ in ice bath, obtains the diluted chloroacetaldehyde solution, drips the sodium carbonate solution that concentration is 2Mol / L, adjusts pH to be 3 or so;

[0054] 2) Dissolve 15g of sodium hydrosulfide in 50ml of water to obtain an aqueous solution of sodium hydrosulfide, cool it to 0°C in an ice bath, and add it dropwise to the chloroacetaldehyde solution at a rate of 2-3 drops per second, at the same time at a rate of 200 rpm Constantly stirring the chloroacetaldehyde solution, a white solid precipitates out in the solution, and after the sodium hydrosulfide is added, it is suction filtered and vacuum-dried to obtain mercaptoaldehyde;

[0055] 3) Dissolve 108 mg of mercaptoaldehyde in 50 ml of methanol solution, stir at room temperature until dissolved, add 304 mg ...

Embodiment 3

[0058] Example 3 Using the compound of the present invention to specifically label the non-reducing end of heparin

[0059] 1. Use 2-(2-mercaptoethylamino)benzamide to specifically label the non-reducing end of heparin

[0060] Add 500mg of enoxaparin into 3.6ml of water, stir to dissolve, and add 1.27mg of benzethonium chloride into 1.1ml of water, slowly drop the benzethonium chloride solution into the low molecular weight heparin sodium solution, and stir for 1h , washed with water 3 times, filtered, and dried under reduced pressure to obtain 240 mg of benzethon chloramine salt.

[0061] Take 100mg of benzethon chloramine salt and add 2ml of dichloromethane, stir to dissolve, add 110ul benzyl chloride, stir at room temperature for 24h, add sodium acetate-methanol solution after the reaction, stir for 30min, remove the supernatant, wash with methanol for 3 times, filtered, dried under reduced pressure, and freeze-dried to obtain low molecular weight heparin benzyl ester.

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Abstract

The invention belongs to the technical field of biological measurement and in particular relates to a novel sulfhydryl fluorescent probe as well as a preparation method and an application thereof. The novel sulfhydryl fluorescent probe has a structure shown in a formula 1 shown in the specification, wherein R=NH2 or COOH. The novel sulfhydryl fluorescent probe can be used for quantitative analysis or location tracing on polysaccharide, peptide, proteins and nucleic acid.

Description

technical field [0001] The invention belongs to the technical field of biological detection, and in particular relates to a novel sulfhydryl fluorescent probe, a preparation method and an application thereof. Background technique [0002] Fluorescent labeling technology refers to the use of some fluorescent substances to covalently bind or physically adsorb on a certain group of the molecule to be studied, and use its fluorescence characteristics to provide information about the research object. Fluorescent labeling technology originated in the 1940s by using fluorescently labeled antibodies to detect corresponding antigens. With the development of modern medicine and molecular biology, and the application of various advanced fluorescent detection technologies and instruments, fluorescent labeling as a non-radioactive label The technology has received a lot of attention and has achieved rapid development. It is widely used in the detection of intracellular and extracellular ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07C323/25C07C319/06G01N21/64G01N33/58
Inventor 陈依军王宗强史少波
Owner CHINA PHARM UNIV
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