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A cyanine-based visible organic molecular fluorescent probe and its preparation method

A fluorescent probe and organic molecule technology, applied in the field of fluorescence spectrum detection and analysis, can solve the problems of specificity and sensitivity to be improved, long reaction time, etc., and achieve the effects of good probe stability, short action time and simple operation

Inactive Publication Date: 2020-09-11
NORTH CHINA ELECTRIC POWER UNIV (BAODING)
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Literature Dan Yang, Hua-Li Wang, Zhen-Ning Sun, Nga-Wai Chung, and Jian-Gang Shen, Journal of the American Chemical Society, 2006, 128, 6004-6005. Reported based on dichlorofluorescein (DCF) fluorescence The fluorescent probe HKGreen-1 established by the group is used to detect peroxynitrite anion. The probe produces green fluorescence after reacting with peroxynitrite anion for 15 minutes, but it also has a certain response to hydroxyl radicals. The reaction Longer time, specificity and sensitivity need to be improved

Method used

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  • A cyanine-based visible organic molecular fluorescent probe and its preparation method
  • A cyanine-based visible organic molecular fluorescent probe and its preparation method
  • A cyanine-based visible organic molecular fluorescent probe and its preparation method

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Embodiment 1

[0046] 1. Preparation of organic molecular fluorescent probes, the structural formula is as follows:

[0047]

[0048] (1) In a 50mL round bottom flask, 0.147mol phosphorus oxychloride (POCl 3 ) was added dropwise to 0.518mol of N,N-dimethylformamide (DMF, C 3 h 7 NO), keep the temperature below 5°C, remove the ice bath, and stir the mixture at room temperature for 1 hour; add 0.051mol bromoacetic acid, and heat the mixture at 70°C for 24 hours. After the reaction, add ice water to terminate the reaction and extract and remove the DMF dissolved in water, add a large amount of sodium carbonate until the pH=8, add absolute ethanol to filter out the inorganic salt, evaporate the obtained organic filtrate on a rotary evaporator until the solvent is completely removed, With 10mL, 50% H 2 SO 4 Neutralize the pale yellow residue with 200 mL CH 3 Cl extraction 3 times with MgSO 4 After drying and removing the solvent, triformylmethane is obtained, namely compound II;

[0049...

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Abstract

The invention belongs to the technical field of fluorescence spectrum detection and analysis, and particularly relates to a visual organic molecular fluorescence probe on the basis of cyanine and a method for preparing the visual organic molecular fluorescence probe. The visual organic molecular fluorescence probe comprises a cyanine fluorophore and benzothiazole groups. The method includes stepsof (1), dropwise adding phosphoryl chloride into N, N'-dimethylformamide to obtain mixtures, then adding the mixtures into bromoacetic acid and carrying out reaction to obtain products II; (2), carrying out reaction on 2, 3, 3'-trimethyl indole and ethyl iodide to obtain products III; (3), dropwise adding piperidine into the products II and the products III and carrying out reaction to obtain products IV; (4), carrying out reaction on the products IV and aminothiophenol at the room temperature to obtain the visual organic molecular fluorescence probe. The visual organic molecular fluorescenceprobe and the method have the advantages that obvious color change of the visual organic molecular fluorescence probe can be seen in natural light or ultraviolet lamps, linear relations between the fluorescence intensity and peroxynitrite negative ions are established, and accordingly the peroxynitrite negative ions can be qualitatively and quantitatively detected; the visual organic molecular fluorescence probe is good in selectivity and high in sensitivity, detection methods are easy to implement, and obvious effects can be realized.

Description

technical field [0001] The invention belongs to the technical field of fluorescence spectrum detection and analysis, in particular to a cyanine-based visible organic molecular fluorescent probe and a preparation method thereof. Background technique [0002] Reactive oxygen free radicals play an important physiological role in biological aging and disease, as well as normal immune metabolism and cell signal transduction. Due to the strong reactivity of active oxygen, they can chemically react with many different compounds, and qualitative or quantitative analysis can be carried out according to the degree of change of these reaction products or reactants. But until now, the determination of active oxygen species other than hydrogen peroxide is still an international problem, and thus, they have attracted much attention from the fields of chemistry, biology, and medicine. Peroxynitrite anion (ONOO - ) is NO·and O2· - It is a product of the mutual reaction, and it is a poten...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14C09K11/06G01N21/64
CPCC07D417/14C09K11/06C09K2211/1029C09K2211/1037G01N21/6428G01N2021/6432
Inventor 王素华侯田鑫余欢张奎岳季刘国强
Owner NORTH CHINA ELECTRIC POWER UNIV (BAODING)
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