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 i

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

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0043] Example 1 Preparation of near-infrared hydrogen sulfide fluorescent probes of malononitrile derivatives

[0044] (1) Preparation of compound of formula II

[0045]

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

[0047] (2) Preparation of compound of formula III

[0048]

[0049] In a 50mL reaction flask, add the compound of formula II (0.79g, 4.24mmol), absolute et...

Example Embodiment

[0060] Example 2 Optical performance detection method

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

[0062] Preparation of fluorescent mother nucleus storage solution: Weigh 3.2 mg fluorescent mother nucleus using a one-hundredthousandth analytical balance, pour it into a 10mL volumetric flask, dilute the volume with DMSO, and prepare it into a fluorescent mother nucleus with a concentration of 1.0 mmol Store the liquid and place it in the refrigerator at low temperature and avoid light.

[0063] Preparation of the fluorescent probe storage solution: Use a one-hundredthousandth analytical balance to weigh 5.5 mg of the fluorescent probe, pour it into a 10 mL volumetric flask, dilute the volume with DMSO, and prepare 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 other interfering biological substance storage solutions: mix L-cysteine...

Example Embodiment

[0087] Example 3 Cytotoxicity test of probe SFP-CHO-P (MTT method)

[0088] In order to ensure that the probe SFP-CHO-P is used for tissue imaging and tissue hydrogen sulfide detection, this application uses the MTT method to detect the cell (HT22) toxicity of the probe. First, prepare for the experiment. Dilute the probe SFP-CHO-P to different concentrations, save them for later use, and set 3 (or more) multiple wells for each concentration. Inoculate HT22 cells (provided by the Neurobiology Research Center of Xuzhou Medical University) in a 96-well plate with 50,000 cells in each well and culture conditions at 5% CO 2 , 37°C. When the HT22 cells grow to a suitable density, add probes of different concentrations prepared in advance to the wells and incubate for 24 hours. After incubation, add 10μL of MTT solution (concentration of 5g / mL) to each well for incubation (4-5h). When the incubation is over, remove the culture medium in the well, and then add 150μL of DMSO to each wel...

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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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