Carbazole ratio-dependent pH fluorescence probe, and preparation method and application thereof

A fluorescent probe and ratiometric technology, applied in the field of fluorescent probes, can solve the problems of limited types of pH fluorescent probes and lack of attention in the development of pH fluorescent probes, so as to overcome the interference of photobleaching and cell autofluorescence, and strengthen ICT effect, high sensitivity, and selectivity

Inactive Publication Date: 2015-05-20
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Unfortunately, there is a lack of attention to the development of pH fluorescent probes for extremely

Method used

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  • Carbazole ratio-dependent pH fluorescence probe, and preparation method and application thereof
  • Carbazole ratio-dependent pH fluorescence probe, and preparation method and application thereof
  • Carbazole ratio-dependent pH fluorescence probe, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 2-(2-(9-ethyl-carbazole-3-)vinyl)-1,1-dimethyl-benzo[e]indole:

[0026]

[0027] Under the protection of inert gas, add 1.2g (5.38mmol) N-ethylcarbazole-3-carbaldehyde and 1.0g (5.00mmol) 1,1,2-trimethyl-1H-benzo [e] Indole, then add 20mL of absolute ethanol and stir to dissolve it, heat and reflux for 15h under the catalysis of 1mL piperidine, the color of the solution gradually changes from yellow to reddish brown, cool the reaction solution to room temperature, and then pour it into 200mL of distilled water , after extracting with dichloromethane solvent, remove the organic solvent, the crude product is separated by column chromatography (dichloromethane / methanol=100 / 1, V / V) to obtain orange solid 1.2g, yield 68%, m.p.:243-245 ℃. 1 H NMR (300MHz, DMSO-d 6 )δ(ppm):1.33-1.37(t,3H,-CH 3 ),1.68(s,6H,-CH 3 ),4.46-4.53(q,2H,-CH 2 -),7.25-7.30(m,1H,Ar-H),7.41-7.46(m,1H,-CH-),7.46-7.53(2H,Ar-H),7.59-7.70(m,3H,Ar- H),7.78-7.81(d,1H,Ar-H),7.94-8.04(m,3H,A...

Embodiment 2

[0029] The probe in Example 1 was stored in DMSO (dimethyl sulfoxide) to prepare a stock solution with a concentration of 1 mM. H 2 O / DMSO (V / V=4 / 1) system dilutes the probe to a final concentration of 10 μM, adjusts the pH value of the system with 1 mol / L of HCl, and records its ultraviolet absorption spectrum ( figure 1). With the decrease of the pH value, the absorption peak at the short wavelength decreases gradually, and the absorption peak at the long wavelength increases significantly, and there is an isosbestic point near 440nm. At the same time, the color of the solution changed from yellow to red ( figure 2 ).

Embodiment 3

[0031] with H 2 O / DMSO (V / V=4 / 1) system dilutes the probe to a final concentration of 10 μM, adjusts the pH value of the system with 1mol / L HCl, fixes the excitation wavelength at 440nm, and records its fluorescence emission spectrum ( image 3 ). As the pH value decreased, the fluorescence intensity at 523nm decreased gradually, while a new emission peak appeared at 605nm and was significantly enhanced, and an iso-emission point appeared near 562nm. Under UV light, the color of the solution changed from green to red ( Figure 4 ).

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Abstract

The invention discloses a carbazole ratio-dependent pH fluorescence probe, a preparation method of the probe and application of the probe to testing the change of extreme acidic pH in living cells and escherichia coli. The preparation method comprises the following steps: under the protection of inert gas, dissolving N-ethyl carbazole-3-formaldehyde (or a derivative thereof) and a 1,1-dialkyl-2-methyl-1H-benzo-indole-[e] derivative into absolute ethyl alcohol, performing a heating reflux reaction to prepare a crude product by taking piperidine as a catalyst; and concentrating the crude product, and performing silica gel column separation to obtain a pure product. The probe shows a ratio emission fluorescence characteristic under extreme acidic conditions and meanwhile has the advantages of high sensitivity and favorable selectivity for H+, large Strokes displacement and the like. Besides, the probe can penetrate a cytomembrane to mark a cell and is suitable for testing the change of extreme acidic pH in cells and escherichia coli.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a carbazole ratio emission pH fluorescent probe and a preparation method and application thereof. Background technique [0002] Intracellular pH plays an important role in the regulation of cell, enzyme and tissue functions. The pH values ​​within different prokaryotes as well as within different subcellular organelles of eukaryotic cells range from alkaline to strongly acidic. Abnormal pH can lead to cellular dysfunction, which in severe cases can lead to diseases such as inflammation, cancer and Alzheimer's disease. Therefore, sensitive and accurate real-time monitoring of intracellular pH can provide important information for studying the physiological and toxicological processes of cells at the molecular level. [0003] Among the many methods for detecting intracellular pH, fluorescence analysis has the characteristics of non-destructive, high sensitivity, fast response, high signal-t...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/86C12Q1/02G01N21/64C12R1/19
Inventor 樊丽李增波高首勤牛卫芬董川双少敏
Owner SHANXI UNIV
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