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Isophorone fluorescence probe, and preparation method and application thereof

A technology of fluorescent probe and isophorone, which is applied in the preparation of carboxylic acid nitrile, fluorescence/phosphorescence, and preparation of organic compounds, can solve the problems of not being able to measure cells and large detection errors, and achieve good biomembrane communication. Permeability, avoidance of interference, and mild reaction conditions

Active Publication Date: 2016-04-27
XUZHOU MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Traditional detection of H 2 The methods of S include spectrophotometry and electrochemical method, but the detection errors of these two methods are relatively large, and they can only measure H in plasma or tissue homogenate. 2 S, cannot be used to measure H in cells or even in vivo 2 S

Method used

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  • Isophorone fluorescence probe, and preparation method and application thereof
  • Isophorone fluorescence probe, and preparation method and application thereof
  • Isophorone fluorescence probe, and preparation method and application thereof

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Experimental program
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Embodiment 1

[0032] Embodiment 1: the preparation of a kind of isophorone fluorescent probe comprises the following steps:

[0033] (1) Preparation of the compound of formula II: under the protection of inert gas, add isophorone (1.0mmol), malononitrile (1.0-4.0mmol), pyridine (0.1mmol-0.4mmol) into the reaction flask, and ethanol as the solvent , heated to reflux for 18-24h, cooled to room temperature after the reaction, the reaction solution was purified by silica gel column chromatography, the eluent was V petroleum ether: V ethyl acetate = 2-5:1, and the pure product of the compound of formula II was obtained;

[0034] (2) Preparation of the compound of formula III: under the protection of inert gas, the compound of formula II (1.0mmol), p-hydroxybenzaldehyde (1.0~4.0mmol) and pyridine (0.1~0.4mmol) are added in the reaction flask, ethanol is the solvent, Heating and reflux for 4-18 hours, after the reaction was completed, lowered to room temperature, concentrated, added deionized wate...

Embodiment 2

[0043] The water from the Kuihe River in Xuzhou City and the river flowing in the campus of Xuzhou Medical College were taken as representative water samples to further study the reliability of the probe molecules of the present invention for the detection of water samples. First filter the water samples to be tested, and add different concentrations of HS - solution (0, 1, 10, 60, 100 μM), add the fluorescent probe represented by formula I to make the final concentration 10 μM, and incubate at 37° C. for 1 h. Use a fluorescence spectrophotometer to detect the change in the response value of the reaction solution at 592nm, and the test results are as follows: Figure 7 shown. The fluorescence intensity response value of each sample is consistent with that of the standard sample. This result shows that the fluorescent probe molecule of the present invention can be used to quantitatively detect the concentration of hydrogen sulfide in the water environment.

Embodiment 3

[0044] Embodiment 3: Fluorescent probe molecule of the present invention detects hydrogen sulfide in food

[0045] Taking pork homogenate as a representative sample, the reliability of the probe molecule of the present invention for the detection of hydrogen sulfide in food was further studied. Take 9 parts of freshly purchased pork, each 3 parts as a group, put them in a constant temperature and humidity incubator to accelerate spoilage, take out 10 g of the required sample amount every 12 hours, homogenize and take the supernatant, add different concentrations of HS - solution (0, 1, 10, 60 μM), add the fluorescent probe shown in formula I to make the final concentration 10 μM, incubate at 37°C for 1h, and detect the response value change of the reaction solution at 592nm with a fluorescence spectrophotometer. Test results such as Figure 8 shown. The fluorescence intensity response value of each sample was basically the same as that of the standard sample, and the concent...

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Abstract

The invention discloses an isophorone fluorescence probe, and a preparation method and an application thereof. The structure of the fluorescence probe is represented by formula I. The preparation method comprises the following steps: adding isophorone, malononitrile and pyridine to a reaction bottle, carrying out heating refluxing under the protection of an inert gas for 18-24h, purifying, adding the above obtained pure product, p-hydroxybenzaldehyde and pyridine to the reaction bottle, carrying out heating refluxing under the protection of the inert gas for 4-18h, purifying, adding the obtained pure product, 2,4-dinitrofluorobenzene and triethylamine to the reaction bottle, stirring above materials for 8-36h, and purifying the obtained mixture to obtain the fluorescence probe. The fluorescence probe has large Stokes shift (182nm), long fluorescence emission wavelength (592nm), high sensitivity and good selectivity, can specifically detect hydrogen sulfide in organisms, environment and foods, has good biomembrane permeability and low cytotoxicity, and also has the advantages of simple synthesis route, high yield and very large practical values.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to an isophorone-based fluorescent probe and its preparation and application, and belongs to the field of organic light-emitting materials. Background technique [0002] Hydrogen sulfide (H 2 S) has always been considered to be just a poisonous gas with the smell of rotten eggs, but in recent years, it has been found that it is the third gas signal molecule that can play a physiological role in the living body after carbon monoxide and nitric oxide. A gaseous transmitter, it can quickly and freely pass through the cell membrane without any special carrier, affect a series of biological targets, and participate in the regulation of various functions of the body, such as neuroprotection, cell generation, angiogenesis, Anti-oxidative stress, etc. [0003] In the mid-1990s, it was discovered that the body can endogenously produce H 2 S gas, it is mainly produced in two ways in the body, one is ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C255/37C07C253/30G01N21/64
CPCC07C253/30C07C253/34C09K11/06G01N21/64C07C255/36C07C255/37
Inventor 刘毅丁燕黄捷房同勇尚言国刘莉张雨云郑显姚宏
Owner XUZHOU MEDICAL COLLEGE
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