A kind of isophorone fluorescent probe and its preparation and application

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 short synthesis route

Active Publication Date: 2018-08-31
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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  • A kind of isophorone fluorescent probe and its preparation and application
  • A kind of isophorone fluorescent probe and its preparation and application
  • A kind of isophorone fluorescent probe and its preparation and application

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Effect test

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-based fluorescent probe and its preparation and application. The structure of the fluorescent probe is shown in formula I. First add isophorone, malononitrile, and pyridine into the reaction flask, heat and reflux for 18-24 hours under the protection of inert gas, and purify, then add the obtained pure product, p-hydroxybenzaldehyde, and pyridine into the reaction flask, Heating under reflux for 4-18 hours for purification, then adding the obtained pure product, 2,4-dinitrofluorobenzene and triethylamine into the reaction bottle, stirring for 8-36 hours, and obtaining the fluorescent probe after purification. The fluorescent probe of the present invention has large Stokes shift (182nm), longer fluorescence emission wavelength (592nm), high sensitivity, good selectivity, can specifically detect hydrogen sulfide in biology, environment and food, and also has good The biomembrane permeability and low cytotoxicity; the synthetic route is simple, the yield is high, and has great practical value.

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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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/37C09K11/06C07C253/30G01N21/64
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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