Fluorescent probe molecule for detecting diaphorase based on benzopyranidonitrile, preparation and application thereof

A technology of benzopyranonitrile and diaphorase, applied in fluorescence/phosphorescence, material analysis through optical means, material analysis, etc., can solve the problem of rare diaphorase and achieve good stability of physical and chemical properties , easy to synthesize, stable optical properties of fluorophores

Pending Publication Date: 2019-04-23
YUNNAN UNIV
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  • Abstract
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  • Claims
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  • Fluorescent probe molecule for detecting diaphorase based on benzopyranidonitrile, preparation and application thereof
  • Fluorescent probe molecule for detecting diaphorase based on benzopyranidonitrile, preparation and application thereof
  • Fluorescent probe molecule for detecting diaphorase based on benzopyranidonitrile, preparation and application thereof

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Embodiment 1

[0043] Embodiment 1: the synthesis of fluorescent probe molecule of the present invention

[0044] For specific synthetic routes, see figure 1 .

[0045] (1) Preparation of Compound 7: Dissolve 1-(2-hydroxyphenyl)ethanone (10.0g, 73.5mmol), sodium (8.00g, 0.34mmol) in 250mL ethyl acetate, react at room temperature for 8 hours, and react Suction filtration is performed after the end, the filter cake is washed twice with ethyl acetate, dissolved in deionized water, the pH of the solution is adjusted to neutrality with concentrated hydrochloric acid, extracted three times with ethyl acetate, the organic phase is retained, and dried with anhydrous sodium sulfate , the pale yellow solid obtained by distillation under reduced pressure after filtration was compound 7, and the yield was 60%.

[0046](2) Preparation of Compound 6: Dissolve Compound 7 (6.95 g, 38.9 mmol) in 70 mL of glacial acetic acid, slowly add 4.6 mL of concentrated sulfuric acid dropwise under stirring at room t...

Embodiment 2

[0053] Example 2: Selectivity of diaphorase detection fluorescent probe molecules based on benzopyranonitrile to diaphorase fluorescence detection

[0054] DMSO (dimethyl sulfoxide): PBS (0.01mol / L, pH=7.4) = 1:99 (v:v) solution was used to control the experimental conditions.

[0055] The fluorescent probe molecules of the present invention are dissolved in a solvent of DMSO:PBS=1:99 (v:v) and settled in a 100mL volumetric flask, and the concentration of the fluorescent probe molecules is prepared to be 5×10 -6 mol / L solution.

[0056] Divide the sample vials into 14 groups, add 3mL to each group of sample vials with a concentration of 5×10 -6 mol / L DMSO:PBS (0.01mol / L, pH=7.4)=1:99 (v:v) solution of the fluorescent probe molecule of the present invention, the first bottle of solution is used as a blank group, and the other 13 groups are respectively added with a concentration of 5 μL Ala, Arg, Cys, Gln, Glu, Gly, Hcy, His, Lys, Met, Thr, Val, DTD at 25 μg / μL. After the so...

Embodiment 3

[0058] Embodiment 3: Quantitative fluorescent detection of diaphorase by fluorescent probe molecule of the present invention

[0059] DMSO (dimethyl sulfoxide): PBS (0.01mol / L, pH=7.4) = 1:99 (v:v) solution was used to control the experimental conditions.

[0060] The fluorescent probe molecules of the present invention are dissolved in a solvent of DMSO:PBS=1:99 (v:v) and settled in a 100mL volumetric flask, and the concentration of the fluorescent probe molecules is prepared to be 5×10 -6 mol / L solution.

[0061] 2 mg of diaphorase (DTD) was dissolved in 800 μL of deionized water to prepare an aqueous solution of diaphorase with a concentration of 2.5 μg / μL.

[0062] Divide the sample vials into 21 groups, add 0 μL to 210 μL of diaphorase aqueous solution with a concentration of 2.5 μg / μL in each group of sample vials, and then use a concentration of 5×10 -6 DMSO:PBS (0.01mol / L, pH=7.4)=1:99 (v:v) solution of the fluorescent probe molecule of the present invention of mol / L...

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Abstract

The invention relates to a fluorescent probe molecule for detecting diaphorase based on benzopyranidonitrile, a preparation method and an application thereof. The molecular structure of the fluorescent probe is shown below. Further disclosed are a preparation method of the fluorescent probe molecule for detecting the diaphorase based on benzopyranidonitrile and the application of detecting the diaphorase in various substances, such as water samples and cells.

Description

technical field [0001] The invention belongs to organic functional materials for detecting trace substances, and relates to fluorescent probe molecules, preparation and application. Background technique [0002] Diaphorase (DTD) is a cytoplasmic flavoproteinase widely distributed in the body tissues of almost all animals. Current researches suggest that diaphorase has both positive and negative effects. The positive aspect is that it uses NADH (the reduced state of nicotinamide adenine dinucleotide, reduced coenzyme I) as an electron donor to reduce various quinones, stop quinone free radicals and prevent quinone free radicals from triggering the formation of superoxide anion O 2 - , preventing or reducing the production of free radicals and protecting cells from damage, this effect makes it considered a protective enzyme. On the other hand, negatively, it is overexpressed in many cancer tissues such as lung cancer, colon cancer, liver cancer and breast cancer, and its c...

Claims

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Application Information

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IPC IPC(8): C07D311/04C09K11/06G01N21/64
CPCC07D311/04C09K11/06C09K2211/1007C09K2211/1088G01N21/6428G01N21/643
Inventor 周莹曹洁陈秋玲何艳琪
Owner YUNNAN UNIV
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