Carbazole reaction type fluorine ion fluorescent probe based on aryl alkene nitrile as well as preparation method and application of carbazole reaction type fluorine ion fluorescent probe

A technology of fluorescent probes and fluoride ions, applied in the field of detection, can solve the problems of difficulty in fluoride ion detection, low sensitivity, limitations, etc.

Pending Publication Date: 2022-08-09
贵州仁威生物科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Due to the small atomic radius and high electronegativity of fluorine, it is easy to form hydrogen bonds with the hydrogen bond donors in the water environment, which brings great difficulties to the detection of fluorine ions.
For example, the probe in the patent CN11103

Method used

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  • Carbazole reaction type fluorine ion fluorescent probe based on aryl alkene nitrile as well as preparation method and application of carbazole reaction type fluorine ion fluorescent probe
  • Carbazole reaction type fluorine ion fluorescent probe based on aryl alkene nitrile as well as preparation method and application of carbazole reaction type fluorine ion fluorescent probe
  • Carbazole reaction type fluorine ion fluorescent probe based on aryl alkene nitrile as well as preparation method and application of carbazole reaction type fluorine ion fluorescent probe

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Effect test

Embodiment 1

[0035] A method for preparing a carbazole-type reactive fluoride ion fluorescent probe based on acrylonitrile, comprising the following steps:

[0036] (a) Preparation of 2-methoxy-9-propyl-9H-carbazole

[0037] In a 100 mL round bottom flask, 2-methoxy-9H-carbazole (5.91 g, 30 mmol) and sodium hydroxide (4.2 g, 105 mmol) were added and dissolved in DMSO (60 mL), and iodopropane ( 10.2 g, 60 mmol). After all the raw materials were added, a condenser tube and an Ar balloon were placed above the round-bottomed flask, and the temperature was raised to 65 °C for 12 h after vacuuming for three times. After the reaction was completed, it was cooled to room temperature, diluted with 60 mL of water, extracted with dichloromethane (60 mL×3), the organic phases were combined and washed with saturated NaCl solution (100 mL×2), then anhydrous sodium sulfate was added and left to stand for 15 min, and the mixture was rotated under reduced pressure. The crude product was obtained by dryin...

Embodiment 2

[0047] A method for preparing a carbazole-based reactive fluoride ion fluorescent probe based on acrylonitrile, comprising the following steps:

[0048] (a) Preparation of 2-methoxy-9-propyl-9H-carbazole

[0049] In a 100 mL round bottom flask, 2-methoxy-9H-carbazole (4.93 g, 25 mmol) and sodium hydroxide (4.0 g, 100 mmol) were added and dissolved in DMSO (50 mL), and iodopropane ( 10.6 g, 62.5 mmol). After all the raw materials were added, a condenser tube and an Ar balloon were placed above the round-bottomed flask, and the temperature was raised to 65 °C for 14 h after vacuuming for three times. After the reaction was completed, it was cooled to room temperature, diluted with 50 mL of water, extracted with dichloromethane (50 mL × 3), the organic phases were combined and washed with saturated NaCl solution (100 mL × 2), then anhydrous sodium sulfate was added and allowed to stand for 15 min, and then rotated under reduced pressure. The crude product was obtained by drying...

Embodiment 3

[0059] A method for preparing a carbazole-type reactive fluoride ion fluorescent probe based on acrylonitrile, comprising the following steps:

[0060] (a) Preparation of 2-methoxy-9-propyl-9H-carbazole

[0061] In a 100 mL round bottom flask, 2-methoxy-9H-carbazole (5.91 g, 30 mmol) and potassium hydroxide (8.4 g, 150 mmol) were added and dissolved in DMSO (60 mL), and iodopropane ( 15.3 g, 90 mmol). After all the raw materials were added, a condenser tube and an Ar balloon were placed above the round-bottomed flask, and the temperature was raised to 60 °C for 16 h after vacuuming for three times. After the reaction was completed, it was cooled to room temperature, diluted with 60 mL of water, extracted with dichloromethane (60 mL × 3), the organic phases were combined and washed with saturated NaCl solution (100 mL × 2), anhydrous sodium sulfate was added and allowed to stand for 15 min, and the mixture was rotated under reduced pressure. The crude product was obtained by ...

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Abstract

The invention relates to the technical field of detection, in particular to a carbazole reactive fluorine ion fluorescent probe based on aryl alkene nitrile as well as a preparation method and application of the carbazole reactive fluorine ion fluorescent probe. According to the invention, carbazole is used as a fluorophore, a silicon-oxygen bond is used as a recognition group, 2-methyl cyanoacetate is introduced through a Knoevenagel condensation reaction, and a compound 3-(2-((tert-butyldimethylsilyl) oxy)-9-propyl-9H-carbazole-3-yl)-2-methyl cyanoacrylate is synthesized. Fluorine ions induce Si-O bond breakage through Lewis acid-base reaction to form O-attacking ortho-aryl allylazonitrile groups to generate intramolecular cyclization, so that the conjugate area of the probe is greatly increased, the quantum yield is improved, the fluorescence intensity is remarkably changed to detect the fluorine ions, the cell membrane permeability of probe molecules is enhanced by introducing ester groups, and the fluorescence intensity of the probe molecules is remarkably changed. A relatively good imaging effect is achieved on fluorine ions in cells.

Description

technical field [0001] The invention relates to the technical field of detection, in particular to a carbazole-based reactive fluoride ion fluorescent probe based on arylene nitrile, and a preparation method and application thereof. Background technique [0002] Fluorine is an essential element for the human body and one of the main components of human bones and teeth. It plays an important role in the formation of bone tissue and enamel, and participates in the metabolic process by activating or inhibiting the activity of various enzymes. Excessive intake of fluoride is detrimental to human health. Insufficient fluoride intake can lead to dental caries, osteodystrophy, long bone growth arrest and other major bone diseases, and microcytic anemia; excessive fluoride intake can lead to dental fluorosis, skeletal fluorosis, damage to brain function, and cause reproductive failure. System function impairment. my country is one of the countries with the most widespread endemic ...

Claims

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Application Information

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IPC IPC(8): C07F7/18C09K11/06G01N21/64
CPCC07F7/1804C07F7/188C09K11/06G01N21/6428G01N21/643G01N21/6456C09K2211/1029Y02P20/55
Inventor 刘晟溥邹英乐意鄢龙家刘力马婷婷
Owner 贵州仁威生物科技有限责任公司
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