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A near-infrared fluorescent probe for detecting hydrogen sulfide and its preparation method and application

A fluorescent probe and near-infrared technology, applied in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve problems such as damage, low sensitivity, and long response time, and achieve obvious phenomena, high sensitivity, and high selectivity Effect

Active Publication Date: 2022-02-11
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, these methods have certain disadvantages: low sensitivity, long response time, and great damage to organisms

Method used

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  • A near-infrared fluorescent probe for detecting hydrogen sulfide and its preparation method and application
  • A near-infrared fluorescent probe for detecting hydrogen sulfide and its preparation method and application
  • A near-infrared fluorescent probe for detecting hydrogen sulfide and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A near-infrared fluorescent probe HZ-NBD for detecting hydrogen sulfide has the following structural formula:

[0036]

[0037] Its preparation reaction formula is as follows:

[0038]

[0039] Specific steps are as follows:

[0040] 1) Weigh 0.691g (5mmol) of isophorone and 0.396g (6mmol) of malononitrile, dissolve in 10ml of absolute ethanol, reflux and stir for 6h under the protection of nitrogen, and remove the excess solvent by rotary evaporation to obtain a yellow solid, and then anhydrous Recrystallized from ethanol to obtain the target product 1 in light yellow crystals with a yield of 94%;

[0041] 2) 2.75mlPOCl 3 (30mmol) was slowly added dropwise to 3ml DMF, and then gradually added 6ml DMF in which 1.66g 3-N,N-diethylaminophenol (10mmol) was dissolved, heated to 75°C under reflux and stirred for 2h, cooled to room temperature and Pour into 60ml of ice water, with Na 2 CO 3 Adjust the pH to neutral, a large amount of brown-gray solids are formed, f...

Embodiment 2

[0056] A near-infrared fluorescent probe HZ-NBD for detecting hydrogen sulfide has the following structural formula:

[0057]

[0058] Its preparation reaction formula is as follows:

[0059]

[0060] Specific steps are as follows:

[0061] 1) Weigh 0.138g (1mmol) of isophorone and 0.079g (1.2mmol) of malononitrile, dissolve them in 5ml of absolute ethanol, and stir under reflux for 6h under nitrogen protection. The excess solvent was removed by rotary evaporation to obtain a yellow solid, which was then recrystallized from absolute ethanol to obtain the target product 1 in light yellow crystals with a yield of 94%;

[0062] 2) 4.12mlPOCl 3 (45mmol) was slowly added dropwise to 5.5ml DMF, then gradually added 8ml DMF in which 2.49g 3-N,N-diethylaminophenol (15mmol) was dissolved, heated to 73°C and stirred under reflux for 4h. Cool to room temperature after reaction finishes and pour into 60ml ice water, use Na 2 CO 3 Adjust the pH to neutral, a large amount of brow...

Embodiment 3

[0069] A near-infrared fluorescent probe HZ-NBD for detecting hydrogen sulfide has the following structural formula:

[0070]

[0071] Its preparation reaction formula is as follows:

[0072]

[0073] Specific steps are as follows:

[0074] 1) Weigh 0.414g (3mmol) of isophorone and 0.238g (3.6mmol) of malononitrile, dissolve them in 10ml of absolute ethanol, and stir under reflux for 6h under the protection of nitrogen. The excess solvent was removed by rotary evaporation to obtain a yellow solid, which was then recrystallized from absolute ethanol to obtain the target product 1 in light yellow crystals with a yield of 94%;

[0075] 2) 5.5mlPOCl was mixed under ice-bath stirring condition 3 (60mmol) was slowly added dropwise to 5ml DMF, then gradually added 10ml DMF in which 3.32g 3-N,N-diethylaminophenol (20mmol) was dissolved, heated to 70°C and stirred under reflux for 6h. Cool to room temperature after reaction finishes and pour into 100ml ice water, use Na 2 CO ...

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Abstract

The invention discloses a near-infrared fluorescent probe for detecting hydrogen sulfide and its preparation method and application. The structural formula of the probe is as follows: the preparation method is as follows: 1) react in ethanol with isophorone and malononitrile as raw materials , compound 1 was purified; 2) under ice-water bath conditions, POCl 3 and 3‑N, N‑diethylaminophenol were heated and stirred in DMF to reflux, and the pH was adjusted to neutral after the reaction, and compound 2 was purified; 3) Compound 1 and compound 2 were dissolved in ethanol for reaction, and purified to obtain HZ ‑1; 4) react HZ‑1 with NBD‑Cl to obtain HZ‑NBD. The fluorescent probe was applied to H in tetrahydrofuran-phosphate buffer. 2 The detection of S or the application of H in HepG2 cells and zebrafish 2 Detection of S. The fluorescent probe pair H 2 The recognition of S has good selectivity and high detection sensitivity, which can achieve the effect of naked eye recognition.

Description

technical field [0001] The invention relates to a near-infrared fluorescent probe for detecting hydrogen sulfide, a preparation method and application thereof, and belongs to the technical field of biological analysis and detection. Background technique [0002] Hydrogen sulfide (H 2 S) is a smell with a special smell, and its toxic pollution to the environment has been deeply studied. In addition, H 2 The content of S in the body is related to different physiological processes, such as H 2 S can participate in the change of hemoglobin, regulate various enzymes in the body, regulate nerve cells, relax vascular smooth muscle, protect gastric mucosa, and reduce pressure. However, in vivo H 2 S imbalance can lead to serious damage to the body, such as Alzheimer's disease, Down's syndrome, diabetes, liver cirrhosis, etc. [0003] At present, the existing detection methods include colorimetry, electrochemical analysis, chromatographic analysis and metal sulfide precipitation...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/12C09K11/06G01N21/64
CPCG01N21/6486C09K11/06C07D271/12C09K2211/1048C09K2211/1007
Inventor 赵红张晗江道勇贺祖茂杨买娥张娇谢伟楠
Owner SOUTHEAST UNIV