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Bispyrene-modified peryleneimide derivative fluorescent probe and its synthesis method and application

A perylene imide and fluorescent probe technology, applied in the field of protein detection, can solve the problems of complex data collection and large consumption of array-type sensing samples, and achieve simple data collection, good fluorescence emission performance, and fast response speed Effect

Inactive Publication Date: 2018-08-24
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Array-type sensing has problems such as large sample consumption and complex data acquisition.
Therefore, it is very challenging and advantageous to develop a single type of fluorescent sensor that can effectively distinguish and recognize proteins.
[0004] At present, there are few reports on the differential detection of proteins based on fluorescent sensors based on the conformational regulation of perylene imide derivative aggregates

Method used

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  • Bispyrene-modified peryleneimide derivative fluorescent probe and its synthesis method and application
  • Bispyrene-modified peryleneimide derivative fluorescent probe and its synthesis method and application
  • Bispyrene-modified peryleneimide derivative fluorescent probe and its synthesis method and application

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preparation example Construction

[0043] The above-mentioned synthetic method based on bispyrene-modified peryleneimide derivative fluorescent probe comprises the following steps:

[0044] 1) Synthesis of pyrenesulfonyl derivatives

[0045] Under protective atmosphere protection and ice bath conditions with a flow rate of 0.5-0.8mL / s, add the chloroform solution of pyrenesulfonyl chloride dropwise to the chloroform solution of diaminooxyalkane at a rate of 5-8 s / drop Among them, the protective atmosphere adopts other inert gases such as nitrogen, argon or neon, and the molar ratio of pyrenesulfonyl chloride to diaminooxyalkane is 1:(5~10); after the dropwise addition, stir at room temperature for 2~8h, and The reaction liquid was washed with saturated brine for 6-7 times, then dried overnight with anhydrous sodium sulfate, washed with 1mol / L hydrochloric acid, and then neutralized with 3mol / L sodium hydroxide aqueous solution, so that the pH value was between 7-8 . Extract with chloroform, collect the extrac...

Embodiment 1

[0059] A bispyrene-modified peryleneimide derivative fluorescent probe with the following structural formula was synthesized:

[0060]

[0061] Its synthetic method comprises the following steps:

[0062] 1) Synthesis of pyrenesulfonyl derivatives

[0063] Under the conditions of nitrogen protection and ice-bath stirring at a flow rate of 0.6mL / s, 9.97mmol of 1,8-diamino-3,6-dioxoctane was added to a three-necked flask filled with 60mL of chloroform, and then 0.997mmol of pyrenesulfonyl chloride was dissolved in 50mL of chloroform and added dropwise to the above solution at a rate of 6 s / drop to obtain a mixed solution. In the mixed solution, pyrenesulfonyl chloride and 1,8-diamino-3,6-bis The molar ratio of oxyoctane is 1:10. After the dropwise addition, stir at room temperature for 2 hours. After stopping the reaction, wash the reaction solution with saturated brine for 6 to 7 times, then dry it with anhydrous sodium sulfate overnight, then wash it with 1mol / L hydrochlo...

Embodiment 2

[0070] A bispyrene-modified peryleneimide derivative fluorescent probe with the following structural formula was synthesized:

[0071]

[0072] Its synthetic method step is as follows:

[0073]In step 1 of the synthesis of pyrenesulfonyl derivatives in Example 1, the 1,8-diamino-3,6-dioxoctane used was replaced with 3,6,9-trioxaundecane with an equimolar mass - 1,11-diamine replacement, other steps are the same as the corresponding Example 1.

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Abstract

The invention discloses a di-pyrene modified perylene bisimide derivative fluorescent probe and a synthesis method and application thereof, and belongs to the technical field of protein detection. The preparation of the fluorescent probe comprises the following steps that in a protective atmosphere, 1-methyl-2-pyrrolidinone solution of a pyrene sulfonyl derivative is added into a 1-methyl-2-pyrrolidinone solution of perylene; then, anhydrous zinc acetate is added to obtain a mixed solution; next, the mixed solution is stirred; heating reflux is performed for 10 to 15h at 150 to 200 DEG C; after the reaction liquid obtained after the reflux is cooled to the room temperature, filtering is performed to obtain filter liquid; the filter liquid is subjected to acid washing; precipitates occur; suction filtration is performed; filter cake is obtained; the filter cake is washed and dried to obtain the di-pyrene modified perylene bisimide derivative fluorescent probe. The fluorescent probe provided by the invention has the advantages that the chemical stability is high; the response speed is high; the sensitivity is high; the discrimination performance is good; the sample consumption quantity is small; the data collection is simple, and the like. The instant and on-line detection of the protein can be realized. The fluorescent probe provided by the invention can be used for respectively realizing the distinguished detection of various proteins.

Description

【Technical field】 [0001] The invention belongs to the technical field of protein detection, and relates to a fluorescent probe for measuring protein in aqueous phase and its synthesis method and detection method, in particular to a bispyrene-modified perylene imide derivative fluorescent probe and its synthesis method and application. 【Background technique】 [0002] Protein is an important class of biological macromolecules, the material basis of life activities, and the basic material that constitutes all tissues in the body, accounting for about 18% of the human body. It has the functions of repairing tissues, maintaining normal metabolism of the body, and transporting various substances in the body And many other functions are closely related to various forms of life activities, and have a special status in living organisms. Therefore, the specific recognition and quantitative analysis of proteins will help promote the development of proteomics, drug diagnosis, and patho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/06C09K11/06G01N21/64
CPCC07D471/06C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029G01N21/6486
Inventor 丁立平卜雨范俊梅丁敏房喻
Owner SHAANXI NORMAL UNIV
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