Coumarin fluorescent probe and preparation method and application thereof

A fluorescent probe and coumarin-based technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as damaging biomolecules, affecting cell processes, and apoptosis

Active Publication Date: 2020-10-30
NANTONG UNIVERSITY
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  • Abstract
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Problems solved by technology

However, due to its strong oxidizing and nitrifying abilities, high levels of ONOO - May damage many biomolecules, including lipids, DNA, proteins and enzymes, which may further affect cellular processes and even cause cell necrosis and apoptosis, eventually leading to the emergence of various diseases, such as cardiovascular diseases and injuries, autoimmunity and Inflammatory disease, Alzheimer's disease, even cancer

Method used

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  • Coumarin fluorescent probe and preparation method and application thereof
  • Coumarin fluorescent probe and preparation method and application thereof
  • Coumarin fluorescent probe and preparation method and application thereof

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preparation example Construction

[0031] The preparation method of above-mentioned coumarin fluorescent probe is as follows:

[0032] S1. Dissolve 7-hydroxycoumarin and hexamethylenetetramine in acetic acid solvent and react at a temperature of 70-100°C. After the reaction, cool down to below 70°C and add hydrochloric acid to adjust the pH value of the system to 2-5. , extracted with ethyl acetate, and recrystallized from ethanol to obtain the formula (I ’ ) the first intermediate product of the structure shown;

[0033]

[0034] S2. Dissolve the first intermediate product, 2-aminothiophenol and sodium metabisulfite in N,N-dimethylformamide solvent, react at a temperature of 110-120°C, add water to precipitate a solid after the reaction, and filter to obtain The second intermediate product of the structure shown in formula (II);

[0035]

[0036] S3. Dissolving the second intermediate product, pinacol 4-bromomethylbenzene borate and potassium carbonate in acetonitrile solvent, reacting at 70-90°C, conc...

Embodiment 1

[0055] Embodiment 1: Preparation of coumarin fluorescent probe L

[0056] Synthesis of the first intermediate product: put 10g (61.6mmol) of 7-hydroxycoumarin (compound 1) and 4.8g (33.88mmol) of hexamethylenetetramine into a 100mL round bottom flask, add 30mL acetic acid Dissolve, heat to 90°C, stir and react for 8 hours to stop the reaction; cool down to 70°C, add 50mL of 1mol / L hydrochloric acid solution and stir to adjust the pH value to 2-5; add ice water, add ethyl acetate solvent extraction, extract Add 30 mL each time for three times, then dry the organic phase with anhydrous sodium sulfate, filter under reduced pressure, remove the solvent ethyl acetate by rotary evaporation of the filtrate under reduced pressure, and obtain a yellow solid; then recrystallize the yellow solid with absolute ethanol to obtain 1.8 g of the second An intermediate product, yield 18%.

[0057] Synthesis of the second intermediate product: Put 0.69 g (3.67 mmol) of 7-hydroxycoumarin aldehyd...

Embodiment 2

[0060] Embodiment 2: coumarin fluorescent probe L to ONOO - selective detection of

[0061] Configure a coumarin-based fluorescent probe dimethyl sulfoxide standard solution with a molar concentration of 1.0 mmol / L;

[0062] In a mixed buffer solvent of DMSO and PBS (v:v=80:20), add the coumarin fluorescent probe dimethyl sulfoxide standard solution and the analyte solution with a molar concentration of 10mmol / L and 0.7 mmol / L ONOO - solution; after stirring evenly, wait for 15 minutes to detect the change of the fluorescence emission spectrum of the solution;

[0063] Among them, the analytes include: Al 3+ , Ca 2+ 、Cu 2+ , Fe 2+ , Fe 3+ , Hg 2+ , Mg 2+ , Pb 2+ , Zn 2+ , Cys, GSH, Hcy, HNO 3 , NO, t Bnoo · 、H 2 o 2 , OH, ClO - ;

[0064] Such as Figure 4 As shown, when not adding any analyte, the fluorescent probe L solution has almost no emission peak at 500nm, when adding ONOO - Finally, the fluorescent probe solution showed a strong emission peak at 50...

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Abstract

The invention belongs to the field of fluorescent molecular probes, and discloses a coumarin fluorescent probe and a preparation method and application thereof. The preparation method comprises the following steps: synthesizing an intermediate 7-hydroxy-8-coumarin aldehyde by taking 7-hydroxycoumarin as a raw material, and synthesizing a second intermediate product 8-(benzo[d]thiazolyl-2-yl)-7-hydroxy-2H-benzopyran-2-one by taking the intermediate 7-hydroxy-8-coumarin aldehyde as a raw material, and performing substitution reaction on the second intermediate product 8-(benzo[d]thiazolyl-2-yl)-7-hydroxy-2H-benzopyran-2-one and 2, 4-dinitrobenzenesulfonyl chloride to synthesize the coumarin fluorescent probe. The fluorescent probe disclosed by the invention has specific selectivity on ONOO<-> and can be applied to in-vitro fluorescence detection of peroxynitrite.

Description

technical field [0001] The invention belongs to the field of fluorescent molecular probes, and relates to a coumarin-based fluorescent probe and its preparation method and application, in particular to a coumarin-based fluorescent probe for detecting peroxynitrite (ONOO-) Preparation method and application. Background technique [0002] Peroxynitrite (ONOO - ) is one of the most important endogenous reactive oxygen species (ROS) in living systems and plays a crucial role in various physiological and pathological processes such as signal transduction and antibacterial activity. However, due to its strong oxidizing and nitrifying abilities, high levels of ONOO - May damage many biomolecules, including lipids, DNA, proteins and enzymes, which may further affect cellular processes and even cause cell necrosis and apoptosis, eventually leading to the emergence of various diseases, such as cardiovascular diseases and injuries, autoimmunity and Inflammatory diseases, Alzheimer's...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06G01N21/6428C09K2211/1088C09K2211/1037C09K2211/1096G01N2021/6417
Inventor 汤艳峰王纯孙同明王敏敏王金王淼崔会会沈璐婕陈迁浴
Owner NANTONG UNIVERSITY
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