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Extremely-acidic carbazole pH fluorescent probe and preparing method and application thereof

A fluorescent probe and carbazole technology, applied in the field of fluorescent probes, can solve the problem of less fluorescent probes, and achieve the effects of low cost, simple synthesis steps, and reduced interference

Inactive Publication Date: 2016-11-09
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the pH fluorescent probes with excellent performance reported in the literature are suitable for the detection of pH values ​​under weak acid conditions (pH 4.0-5.5) and near-neutral conditions (pH 6.8-7.4), while the determination of pH in extremely acidic environments ( pH<4.0) There are very few reports on fluorescent probes

Method used

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  • Extremely-acidic carbazole pH fluorescent probe and preparing method and application thereof
  • Extremely-acidic carbazole pH fluorescent probe and preparing method and application thereof
  • Extremely-acidic carbazole pH fluorescent probe and preparing method and application thereof

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Embodiment 1

[0027] The preparation of embodiment 1 extremely acidic carbazole pH fluorescent probe

[0028] (1) Synthesis of 9-butylcarbazole

[0029] Add 8.35g (0.050mol) of carbazole and 60mL of dimethyl sulfoxide into a 100mL three-necked flask equipped with a magnetic stirring device, a thermometer and a reflux condenser. After stirring to dissolve, quickly add 3.0g (0.054mol) Potassium hydroxide, heated to 90°C, reacted under stirring until the solids were completely dissolved, continued to react for 30 minutes, cooled, installed a constant pressure dropping funnel, and slowly added 5.5mL (0.051mol) bromobutyl dropwise after the reaction solution cooled to below 38°C alkyl. Keep stirring at 90°C for 5h. After the reaction was completed, it was poured into double volume of ice water while it was still hot, and left to stand overnight, a white precipitate precipitated out. Filter with suction, wash the filter cake with water three times, remove inorganic matter and dimethyl sulfoxid...

Embodiment 2

[0037] Embodiment 2 Fluorescent probe BILE changes with the ultraviolet absorption spectrogram of pH

[0038] Add 20.0 μL fluorescent probe BILE stock solution to 2.0 mL system, adjust the pH value with HCl, and record its UV absorption spectrum ( figure 1 ). The UV absorption at 298nm and 391nm both decreased with the decrease of pH value.

Embodiment 3

[0039] Fluorescence titration diagram of embodiment 3 fluorescent probe BILE changing with pH

[0040]Add 20.0 μL of fluorescent probe BILE stock solution to 2.0 mL of water system, adjust the pH value of the system with HCl, and detect it on a fluorescence spectrophotometer. As the pH value decreases, the fluorescence intensity at 502 nm gradually weakens. Instrument parameters: the slit widths of the excitation wavelength and emission wavelength are 5.0nm and 5.0nm respectively, the voltage is 600V, and the maximum excitation wavelength of the fluorescent probe solution is: λ ex is 380nm and the maximum emission wavelength is λ em 502nm. Use the fluorescence intensity F at 502nm to plot the pH value, and use Sigmoidal to fit to obtain pK a =2.93; the best linear response range of BILE is pH2.63-3.28 through linear fitting, the regression equation is: F=2495.42×pH-6316.28, and the linear coefficient is R 2 = 0.9926. (See figure 2 , image 3 )

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Abstract

The invention discloses an extremely-acidic carbazole pH fluorescent probe and a preparing method and application thereof. The fluorescent probe is 3-(9-butyl carbazole-3-cyanovinyl) pyridine. The preparing method includes the steps that carbazole and bromobutane are dissolved in a DMSO / KOH mixed solution, stirring and heating are carried out, and 9-butyl carbazole is generated; DMF serves as a solvent, POCl3 and the 9-butyl carbazole are reacted, and 3-formyl-9-butyl carbazole is obtained; then the obtained 3-formyl-9-butyl carbazole and 3-pyridyl acetonitrile are mixed in methyl alcohol, potassium tert-butoxide is added, the mixture is drawn, filtered and dried, a yellow solid product is obtained, and the extremely-acidic carbazole pH fluorescent probe can be obtained. The probe has the advantages that the low pKa value is achieved, the high sensitivity, the high selectivity and the good stability for H+ are shown, the detection process is easy, convenient and rapid, and the detection result is accurate. In addition, according to the laser confocal scanning microscopical technology, the novel fluorescent probe can be used for detecting biological sample pH change at the extremely-acidic environment.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to an extremely acidic carbazole pH fluorescent probe and a preparation method thereof, and the probe is used to detect pH changes of biological samples in an extremely acidic environment. Background technique [0002] Intracellular pH plays an essential role in participating in cellular activities, such as: cell cycle regulation, cell growth and apoptosis, ion transport, enzyme activity, calcium regulation, muscle contraction, and multidrug resistance. [0003] Abnormal pH can lead to cell dysfunction and even severe cases can lead to diseases such as inflammation, cancer, Alzheimer's disease and so on. Therefore, sensitive and accurate real-time monitoring of the dynamic changes of pH can provide important information for studying the physiological and toxicological processes of cells at the molecular level. [0004] Compared with many pH detection methods such as microelectrode, NMR, and u...

Claims

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Application Information

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IPC IPC(8): C07D401/06C09K11/06G01N21/64
CPCC07D401/06C09K11/06C09K2211/1029G01N21/6428G01N21/6447G01N2021/6443
Inventor 钞建宾王会娟宋凯伦张永斌李志清
Owner SHANXI UNIV
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