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A kind of benzoxadiazole pH fluorescent probe, preparation method and application

A technology of benzoxadiazoles and fluorescent probes, applied in the field of applied biology, can solve the problems of long synthesis time and inconvenient synthesis, and achieve the effects of short time consumption, low toxicity and good selectivity

Active Publication Date: 2021-06-25
HUNAN UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Document CN107488446A discloses a colorimetric ratio-type acid-base fluorescent probe and its preparation method and application, but this preparation method needs to be carried out under a protective atmosphere, the synthesis is relatively inconvenient, and the synthesis time is long, and only the reflux reaction time requires 4-6 hours

Method used

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  • A kind of benzoxadiazole pH fluorescent probe, preparation method and application
  • A kind of benzoxadiazole pH fluorescent probe, preparation method and application
  • A kind of benzoxadiazole pH fluorescent probe, preparation method and application

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Embodiment 1

[0034] The synthesis of fluorescent probes includes the following experimental steps:

[0035] (1) Dissolve 4-chloro-7-nitrobenzofurazan (200mg, 1mmol), 1-[(2-pyridyl)methyl]piperazine (177mg, 1mmol) and triethylamine (0.5mL) In 5mL of anhydrous dichloromethane, the reaction mixture was stirred at room temperature for 1 hour, and the synthetic reaction equation of the fluorescent probe was as follows: figure 1 shown;

[0036] (2) The reaction solution was rotary evaporated, and the filtrate was purified by column, wherein the volume ratio of petroleum ether and ethyl acetate was 4:1 to obtain a yellow solid (296 mg, yield 87%).

[0037] The nuclear magnetic resonance H spectrum of gained fluorescent probe is: 1 H NMR (500MHz, CDCl 3 )δ (ppm): 8.45 (d, J = 8.5, 1H,), 7.39-7.37 (m, 3H), 7.34-7.32 (m, 1H), 6.31 (d, J = 9, 1H), 4.15 (t ,J=5,4H), 3.63(s,1H), 2.73(t,J=55Hz,4H); image 3 shown.

Embodiment 2

[0039] The experimental procedure of embodiment 2 is identical with the experimental procedure of embodiment 1, but in step (1) with 4-chloro-7-nitrobenzofurazan and 1-[(2-pyridyl) methyl] piperazine The mol ratio is changed to 2:1.

[0040] It was found through testing that the structure of the final product of Example 2 was consistent with that of Example 1, and the synthesis method of the probe of the present invention is not limited to the method described in the example.

Embodiment 3

[0042] The experimental procedure of embodiment 3 is identical with the experimental procedure of embodiment 1, but in step (1) with 4-chloro-7-nitrobenzofurazan and 1-[(2-pyridyl) methyl] piperazine The molar ratio was changed to 1:2.

[0043] It was found through testing that the structure of the final product of Example 3 was consistent with that of Example 1, and the synthesis method of the probe of the present invention is not limited to the method described in the example.

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Abstract

The invention discloses a benzoxadiazole-based pH fluorescent probe, a preparation method and an application thereof. The structural formula of the fluorescent probe is: the following preparation steps are also included, wherein 4-chloro-7-nitrobenzofurazan , 1‑[(2‑pyridyl) methyl] piperazine and triethylamine are dissolved in an organic solvent, and post-reaction treatment obtains a fluorescent probe; the 4‑chloro‑7‑nitrobenzofurazan and 1‑ The molar ratio of [(2-pyridyl)methyl]piperazine is 1:1; the volume ratio of the triethylamine to the organic solvent is 1:10; the fluorescent probe is used to detect the dynamic change of the pH value. The invention not only has simple synthesis and short time consumption, but also can detect the dynamic change of pH more conveniently and effectively by using the colorimetric and fluorescence-enhanced dual-channel probe technology.

Description

technical field [0001] The invention relates to the field of applied biology, in particular to a benzoxadiazole pH fluorescent probe, a preparation method and an application. Background technique [0002] In cells, the pH is generally between 6.8-7.4. When the pH in cells tends to be acidic, it often causes more diseases, such as inflammation, tumor, cystic fibrosis, etc. Therefore, monitoring the dynamic changes of intracellular pH (4.5-6.0) plays an important role in understanding and treating related diseases. Compared with pH measurement methods such as microelectrodes, NMR, and absorption spectroscopy, fluorescence spectroscopy detection technology has unique advantages for detecting pH changes in temporal and spatial distributions. In addition, the fluorescent probe method has the advantages of high selectivity and sensitivity, non-destructive analysis and easy operation of the detection system, and has a wide range of applications in the fields of environment, chemis...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12C09K11/06G01N21/64
CPCC07D413/12C09K11/06C09K2211/1029C09K2211/1044C09K2211/1048G01N21/6428
Inventor 申有名张春香张向阳丁祥周诗彪靳俊玲黄小兵
Owner HUNAN UNIV OF ARTS & SCI
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