Coumarin fluorescent probe as well as preparation method and application thereof

A fluorescent probe, coumarin-based technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems that are not suitable for real-time and on-site detection, complex sample pretreatment, and high detection cost, and achieve reaction The effect of short time, low detection limit and high detection sensitivity

Active Publication Date: 2020-10-16
NANTONG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the sensitivity of these methods is relatively high, they all have the disadvantages of high detection cost, complicated sample pretreatment, time-consuming, and are not suitable for real-time and on-site detection.

Method used

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

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Effect test

preparation example Construction

[0036] The preparation method of above-mentioned coumarin fluorescent probe is as follows:

[0037] 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 to adjust the pH of the system to 2-5. Ethyl acetate Extraction, ethanol recrystallization obtains such as formula (Ⅰ ’ ) the first intermediate product of the structure shown in );

[0038]

[0039] 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);

[0040]

[0041] S3. Dissolve the second intermediate product and triethylamine in dichloromethane solvent, then slowly add dropwise the dichloromethane solution of 2,4-dinitrobenzenesulfonyl chloride, react at 0...

Embodiment 1

[0061] Embodiment 1: Preparation of coumarin fluorescent probe L

[0062] 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%.

[0063] Synthesis of the second intermediate product: Put 0.69 g (3.67 mmol) of 7-hydroxycoumarin aldehyd...

Embodiment 2

[0066] Embodiment 2: Selective detection of GSH by coumarin fluorescent probe L:

[0067] Configure the coumarin-based fluorescent probe dimethyl sulfoxide standard solution with a molar concentration of 1.0mmol / L; in the system of PBS buffer solution, add the coumarin-based fluorescent probe dimethyl sulfoxide standard solution and molar Amino acid solution with a concentration of 10mmol / L; 16 minutes after stirring evenly, detect the change of the fluorescence emission spectrum of the solution;

[0068] The amino acids in the amino acid solution are: Cys, GSH, Hcy, Gly, Ala, Val, Leu, Ile, Pro, Phe, Tyr, Trp, Ser, Thr, Met, Asn, Gln, Asp, Glu, Lys, Arg, His, Vc;

[0069] Such as Figure 4 As shown, when no amino acid is added, the fluorescent probe L solution has almost no emission peak at 510nm. After adding GSH, the solution has a strong emission peak at 510nm. When other amino acids are added, except Cys and Hcy Amino acids containing sulfhydryl groups have not very st...

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Abstract

The invention belongs to the field of fluorescent molecular probes, and relates to a coumarin fluorescent probe as well as a preparation method and application thereof. The preparation method comprises the following steps: 7-hydroxycoumarin is used as a raw material to synthesize an intermediate 7-hydroxy-8-coumarin aldehyde, then the intermediate 7-hydroxy-8-coumarin aldehyde is used as a raw material to synthesize a second intermediate 8-(benzo[d]thiazole-2-yl)-7-hydroxy-2H-benzopyran-2-one, and 8-(benzo[d]thiazole-2-yl)-7-hydroxy-2H-benzopyran-2-one and 2,4-dinitrobenzenesulfonyl chloride carry out a substitution reaction to obtain the coumarin fluorescent probe. The coumarin fluorescent probe has specific selectivity on amino acids containing sulfydryl (-SH), such as GSH (glutathione),basically has no change with other common amino acid fluorescent signals, and is high in sensitivity and low in detection limit.

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 glutathione and its preparation method and application . Background technique [0002] Glutathione (GSH), cysteine ​​(Cys), and homocysteine ​​(Hcy) are amino acids containing a sulfhydryl group (-SH), which participate in various signal transduction processes such as redox reactions in cells. It plays a very important role in both physiological and pathological processes. Among them, GSH is the most abundant intracellular thiol and plays a crucial role in maintaining biological homeostasis by acting as an essential endogenous redox regulator. Abnormal levels of cellular glutathione may contribute to various diseases such as liver damage, cancer, Alzheimer's disease and cardiovascular disease. Therefore, effective detection o...

Claims

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Application Information

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IPC IPC(8): C07D417/04C09K11/06G01N21/64
CPCC07D417/04C09K11/06G01N21/6428C09K2211/1037C09K2211/1088G01N2021/6443
Inventor 汤艳峰王纯孙同明王敏敏王金王淼崔会会程冉沈璐婕徐润生
Owner NANTONG UNIVERSITY
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