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Fluorescent probe based on coumarin carbazone derivative and preparation method and application of fluorescent probe

A fluorescent probe, base coumarin technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of high detection limit, achieve low detection limit, high sensitivity, and wide potential application value Effect

Active Publication Date: 2019-04-19
XUCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, Chinese patent CN108276371A discloses a coumarin thiocarbazone derivative, but there is a high detection limit (the detection limit is 1.008×10 -7 mol / L)

Method used

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  • Fluorescent probe based on coumarin carbazone derivative and preparation method and application of fluorescent probe
  • Fluorescent probe based on coumarin carbazone derivative and preparation method and application of fluorescent probe
  • Fluorescent probe based on coumarin carbazone derivative and preparation method and application of fluorescent probe

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preparation example Construction

[0031] The present invention also provides the preparation method of the fluorescent probe based on the coumarin carbazone derivative described in the above technical scheme, comprising the following steps:

[0032] After mixing 7-diethylamino-3-acetylcoumarin and ethanol solution, adding carbazide to obtain a mixture;

[0033] The mixture is subjected to reflux reaction under normal pressure to obtain a solution;

[0034] After the solution is cooled, the fluorescent probe based on the coumarin carbazone derivative is obtained.

[0035] In the present invention, after mixing 7-diethylamino-3-acetyl coumarin and ethanol solution, carbazide is added to obtain the mixture. In the present invention, the molar ratio of 7-diethylamino-3-acetylcoumarin to carbazide is preferably 1:1.

[0036] In the present invention, the dosage ratio of the 7-diethylamino-3-acetylcoumarin to the ethanol solution is preferably 0.002-0.004mol:0.005-0.01L.

[0037] In the present invention, the eth...

Embodiment 1

[0048] Synthesis of Coumarin Carbazone Derivatives

[0049] Dissolve 0.259g of 7-diethylamino-3-acetylcoumarin carbazone in 10mL of absolute ethanol, then add 0.09g of carbazide, then add two drops of glacial acetic acid to catalyze, reflux and stir for 3h under normal pressure, and cool After reaching room temperature, a large amount of solids were precipitated, filtered under reduced pressure, and the filter residue was washed with absolute ethanol to obtain a yellow solid, which was the target product based on coumarin carbazone derivatives, and the yield of the target product was 75%.

[0050] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the coumarin carbazone derivative that makes, the result is as follows figure 1 As shown, the NMR data are as follows:

[0051] 1 H NMR (400MHz, d 6 -DMSO)δ:9.50(1H,s,NH),8.26(1H,s,NH),7.89(1H,s,Ar-H),7.48-7.51(1H,d,Ar-H),6.71-6.76 (1H,d,Ar-H),6.54(1H,s,Ar-H),4.11(s,2H,NH 2 ),3.43-3.4...

Embodiment 2

[0055] Determination of AIEE Properties of Coumarin Carbazone Derivatives

[0056] The coumarin carbazone derivatives prepared in the above-mentioned Example 1 were used as fluorescent probes in DMSO / HEPES buffer solutions (5×10 -3 mol / L, pH=7.4) to prepare a molar concentration of 1×10 -5 mol / L solution, adopt fluorescence spectrometer to carry out fluorescence spectrum analysis (excitation wavelength is 418nm) to it respectively, record the fluorescence intensity value at 505nm place, the fluorescence spectrum figure of gained is shown in image 3 , the inset represents the fluorescence change of the solution under a 365 nm UV lamp. pass image 3 It can be seen that as the proportion of the system buffer solution increases, the fluorescence emission intensity of the coumarin carbazone derivatives prepared in Example 1 of the present invention also increases, and the green fluorescence of the solution under the excitation of a 365nm ultraviolet lamp is simultaneously enhanc...

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Abstract

The invention provides a fluorescent probe based on a coumarin carbazone derivative and a preparation method and application of the fluorescent probe, and belongs to the field of organic synthesis. The fluorescent probe based on the coumarin carbazone derivative can form a stable complex with Cu2+, has good Cu2+ ion recognition performance, shows significant AIEE properties in a buffer solution of2-[4-(2-hydroxyethyl)-1-piperazinyl]ethanesulfonic acid (HEPES, 5*10<-3>mol / L, containing DMSO with the volume ratio of 0.5%) with the pH of 7.4 and shows high selective fluorescence recognition performance for Cu2+ ions. Through the addition of Cu2+, green fluorescence of a probe solution is almost completely quenched, the fluorescence attenuating effect is achieved, and naked-eye discriminationdetection can be achieved. More importantly, the fluorescent probe can also be used for fluorescence imaging detection of Cu2+ ions in cells, has the advantages of being quick, convenient to use, high in sensitivity, low in detection limit and high in selectivity, and has high potential application value. The structural formula of the coumarin carbazone derivative is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a fluorescent probe based on a coumarin carbazone derivative and a preparation method and application thereof. Background technique [0002] Cu 2+ It plays an important role in the biological systems of plants, animals and humans. More importantly, high concentrations of Cu 2 + Highly toxic to organisms such as many bacteria and viruses, while Cu 2+ Altered cellular homeostasis is associated with several severe neurodegenerative diseases such as Alzheimer's, Wilson's and Menkes' diseases. Therefore, there is an urgent need to develop effective probes for Cu in biological systems 2+ detection. [0003] In recent years, fluorescent molecular probe technology has become an important means of detecting metal ions due to its high sensitivity, simple operation, and low cost. Therefore, Cu 2+ Fluorescent probes have received extensive attention. However, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/6428G01N2021/6432
Inventor 许志红罗文峰王阳雷萌萌周起航
Owner XUCHANG UNIV
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