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Malononitrile derivative near-infrared hydrogen sulfide fluorescent probe as well as preparation method and application thereof

A fluorescent probe, malononitrile technology, applied in chemical instruments and methods, sulfonate ester preparation, fluorescence/phosphorescence, etc., can solve the problems of high detection limit, large background interference, slow response speed of hydrogen sulfide, etc., and achieve synthesis The effect of short route, high sensitivity and excellent selectivity

Pending Publication Date: 2019-07-12
XUZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the reported fluorescent probes respond to hydrogen sulfide only in the visible light region, and the background interference is relatively large. At the same time, the response speed to hydrogen sulfide is slow and the detection limit is high.

Method used

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  • Malononitrile derivative near-infrared hydrogen sulfide fluorescent probe as well as preparation method and application thereof
  • Malononitrile derivative near-infrared hydrogen sulfide fluorescent probe as well as preparation method and application thereof
  • Malononitrile derivative near-infrared hydrogen sulfide fluorescent probe as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1 Preparation of malononitrile derivatives near-infrared hydrogen sulfide fluorescent probe

[0044] (1) Preparation of formula II compound

[0045]

[0046]In a 50mL reaction flask, add malononitrile (1.90g, 28.76mmol), absolute ethanol (30mL) and piperidine (1.22g, 14.38mmol) successively, react for 5-10min, add isophorone (2.00g, 14.38mmol), at N 2 Under protection, the reaction was carried out at 65°C, monitored by TLC (petroleum ether: ethyl acetate = 5:1, V / V), until the reaction was completed. After 8 hours, the reaction was completed. The reaction solution was cooled to room temperature, poured into 80 mL of ice water, stirred, and a solid precipitated out, filtered with suction, dried, and recrystallized from n-hexane to obtain 1.8 g of an off-white solid, which was the pure product of the compound of formula II. was 66.6%.

[0047] (2) preparation of formula III compound

[0048]

[0049] In the 50mL reaction flask, add formula II compound...

Embodiment 2

[0060] Embodiment 2 optical performance detection method

[0061] (1) Solution preparation required for optical performance testing

[0062] Preparation of fluorescent mother nucleus storage solution: Use an analytical balance of 1 / 100,000 to weigh 3.2mg of fluorescent mother nucleus, pour it into a 10mL volumetric flask, dilute it with DMSO, and prepare it into a fluorescent mother nucleus with a concentration of 1.0mmol Store the solution and store it in the refrigerator at low temperature and away from light.

[0063] Preparation of the storage solution of the fluorescent probe: Weigh 5.5 mg of the fluorescent probe with an analytical balance of 1 / 100,000, pour it into a 10 mL volumetric flask, dilute it with DMSO, and prepare it into a fluorescent probe with a concentration of 1.0 mmol. Needle storage solution, and store it in the refrigerator at low temperature and avoid light.

[0064] Preparation of storage solutions for other interfering biological substances: L-cyst...

Embodiment 3

[0087] The cytotoxicity experiment (MTT method) of embodiment 3 probe SFP-CHO-P

[0088] In order to ensure that the probe SFP-CHO-P is used in tissue imaging and detection of tissue hydrogen sulfide, this application uses the MTT method to detect the toxicity of the probe in terms of cell (HT22). Firstly, prepare for the experiment, dilute the probe SFP-CHO-P into different concentrations, keep it for later use, and set 3 (or more) duplicate wells for each concentration. HT22 cells (provided by the Neurobiology Research Center of Xuzhou Medical University) were seeded in 96-well plates, with 50,000 cells per well, and the culture conditions were 5% CO 2 , 37°C. When the HT22 cells grew to a suitable density, the probes of different concentrations prepared in advance were added to the wells and incubated for 24 hours. After incubation, add 10 μL of MTT solution (concentration: 5 g / mL) to each well for incubation (4-5 h), when the incubation is over, remove the culture medium...

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Abstract

The invention discloses a malononitrile derivative near-infrared hydrogen sulfide fluorescent probe as well as a preparation method and application thereof. The probe has a structure represented by aformula I shown in the description. The preparation method comprises the following steps: firstly, mixing isophorone, malononitrile and piperidine, performing heating reflux under the protection of aninert gas, performing purification, mixing the obtained purified product, p-hydroxybenzaldehyde and piperidine, performing heating reflux under the protection of an inert gas, performing purification, mixing the obtained purified product, urotropine and trifluoroacetic acid, performing heating reflux under the protection of an inert gas, performing purification, finally mixing the obtained purified product, 2,4-dinitrobenzenesulfonyl chloride and triethylamine, performing a reaction under stirring at room temperature, and performing purification to obtain the fluorescent probe. The fluorescent probe provided by the invention has large Stokes shift (229 nm), a longer fluorescence emission wavelength (653 nm) and high sensitivity, can be used for specific detection of biological hydrogen sulfide, and has good biofilm permeability and low cytotoxicity; and the fluorescent probe has a simple synthetic route, a high yield and large practical values.

Description

technical field [0001] The invention relates to a hydrogen sulfide fluorescent probe, in particular to a malononitrile derivative near-infrared hydrogen sulfide fluorescent probe, a preparation method and application thereof, and belongs to the field of organic light-emitting materials. Background technique [0002] Hydrogen sulfide (H 2 S), the simplest biothiol, has been considered as a toxic substance polluting water and air for a long time, and is often studied as a toxic gas. The ingestion of different concentrations of hydrogen sulfide by the human body will cause different degrees of poisoning symptoms, which seriously endanger human health. However, with the continuous advancement and development of science, hydrogen sulfide is gradually found to be an important gas signal transmission medium in organisms, and it mainly exists in two forms in the body (1 / 3H 2 S,2 / 3NaHS), in a dynamic balance, maintaining the normal pH range of the body. Hydrogen sulfide has a syne...

Claims

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Application Information

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IPC IPC(8): C07C309/73C07C303/28C09K11/06G01N21/64
CPCC07C309/73C09K11/06C09K2211/1007C09K2211/1014C07C2601/16G01N21/6428
Inventor 刘毅郭安磊庞意鹏刘娇李鑫蕊徐婷
Owner XUZHOU MEDICAL UNIV
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