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Fluorescence detection application of switching type mercaptan fluorescence labeling reagent as well as synthesis method thereof

A fluorescence detection and fluorescence labeling technology, which is applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of no solution, complex synthesis steps, high background interference rate, etc. The effects of high labeling yield and broad application prospects

Inactive Publication Date: 2018-09-04
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the number of maleimide-based fluorescent labeling reagents currently available is limited, and the fluorescence of the addition products of the existing fluorescent labeling reagents and thiols is not obvious, the background interference rate is high, and the synthesis steps are complicated, so its application is limited. However, the existing technology does not provide an effective and complete solution

Method used

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  • Fluorescence detection application of switching type mercaptan fluorescence labeling reagent as well as synthesis method thereof
  • Fluorescence detection application of switching type mercaptan fluorescence labeling reagent as well as synthesis method thereof
  • Fluorescence detection application of switching type mercaptan fluorescence labeling reagent as well as synthesis method thereof

Examples

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Effect test

Embodiment 1

[0031] The synthesis of the switch type thiol fluorescent labeling reagent of the present invention has 3 steps.

[0032] The specific synthesis process of switch type fluorescent labeling reagent is as follows figure 1 As shown, the operation steps are as follows:

[0033] 1. Preparation of Intermediate Ⅰ 9-((4-Acetylamino)-phenyl)-carbazole

[0034] Add 10g carbazole and 16.5g 4-bromoacetanilide to a 250mL three-necked flask, add 150mL dimethyl sulfoxide as a solvent, add 5g potassium carbonate, 2.5g cuprous iodide and 3mL di-tert-valeryl methane, and react in an oil bath at 130°C for 12h Overnight; after the reaction is over, the reaction solution is cooled to room temperature and 25°C and then suction filtered, and then the suction filtrate is poured into a 25wt% NaCl aqueous solution to precipitate a precipitate. The precipitated solid is recovered and dried to obtain Intermediate I9-((4-Acetylamino)- (Phenyl)-carbazole, the yield was 85 wt%.

[0035] 2. Preparation of intermedi...

Embodiment 2

[0044] In this example, the method described in Example 1 was used to synthesize the switch type thiol fluorescent labeling reagent of the present invention, and at the same time, the fluorescent properties of the switch type fluorescent labeling reagent were verified:

[0045] A 1μM N-(4-(carbazol-9-yl)-phenyl)-N-maleimide solution and a phenylethyl mercaptan standard solution of the same concentration were prepared with acetonitrile. Such as image 3 As shown, before the labeling reagent reacts with benzene ethyl mercaptan, the reagent has no fluorescence, and the fluorescence is significantly increased after the reaction. The best excitation and emission wavelengths of fluorescence are 290nm and 368nm, respectively. At the same time, using tryptophan standard solution as the reference solution, calculate the fluorescence quantum yield of N-(4-(carbazol-9-yl)-phenyl)-N-maleimide and its thiol derivative respectively Are 0.004 and 0.415.

Embodiment 3

[0047] In this example, the method described in Example 1 was used to synthesize the switch-type thiol fluorescent labeling reagent of the present invention, and the fluorescent labeling reagent was applied to the detection of sulfhydryl samples (grilled shrimp):

[0048] (1) Prepare a phosphate buffer solution with pH=7.4 and a concentration of 10mM; prepare a concentration of 1×10 separately -4 mol / L of the acetonitrile solution of the fluorescent labeling reagent of the present invention; the selected mercaptan standard contains five kinds, namely 2-methyl-1-propanethiol, 2-methyl-1-butanethiol, and furfuryl sulfide Alcohol, 2-methyl-3-furan mercaptan and benzene ethyl mercaptan, prepare five groups of different concentrations of mixed standard acetonitrile solution, the concentration of each group is 1μM, 10μM, 100μM, 1mM and 10mM.

[0049] (2) Add 50μL of phosphate buffer solution, 100μL of mercaptan standard solution and 50μL of acetonitrile solution of fluorescent labeling re...

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Abstract

The invention belongs to the technical field of fluorescence labeling and provides the fluorescence detection application of a switching type mercaptan fluorescence labeling reagent as well as a synthesis method thereof. According to the structure of the labeling agent, carbazole serves as a matrix ring and maleimide serves as a reaction group and an isotope labeled group, wherein the labeling reagent takes the carbazole as a fluorescence group and maleimide as a reaction activity group, and is used for performing fluorescence detection on the content of a sulfhydryl compound in a sample. Thesynthesis method is simple, convenient and easy to implement; the obtained switching type fluorescence labeling reagent is high in labeling reaction rate, avoids background interference and has high sensitivity; and the synthesis method is simple and convenient.

Description

Technical field [0001] The invention belongs to the technical application field of stable isotope labeling of organic small molecules, and specifically relates to a switch-type thiol fluorescent labeling reagent and a synthesis method and application thereof. Background technique [0002] High-performance liquid chromatography (HPLC for short) is widely used in research fields such as life analysis, environmental testing, and food evaluation due to its high sensitivity and high selectivity. However, currently available maleimide-based fluorescent labeling reagents are limited, and the existing fluorescent labeling reagents and thiol addition products have insignificant fluorescence, high background interference rate, complex synthesis steps, and certain restrictions on their applications. However, the existing technology does not provide an effective and complete solution. Summary of the invention [0003] The purpose of the present invention is to provide a switch type thiol flu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/02G01N21/64C07D403/10C09K11/06
CPCC07D403/10C09K11/06C09K2211/1007C09K2211/1029G01N21/643G01N30/02G01N2021/6439
Inventor 尤进茂于延新王博纪仲胤谭江坤庄建林李佳敏孙志伟
Owner QUFU NORMAL UNIV
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