A kind of N-aryl-substituted carbazole fluorescent probe capable of specifically labeling cell membrane and preparation method thereof

A fluorescent probe and cell membrane technology, applied in the field of fluorescent probes, can solve the problems of poor specificity and low contrast of fluorescence imaging, and achieve the effects of reducing self-absorption, realizing fluorescence imaging, and achieving contrast

Active Publication Date: 2021-07-13
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the deficiencies or defects in the above-mentioned prior art, the purpose of the present invention is to provide an N-aryl substituted carbazole fluorescent probe capable of specifically labeling cell membranes and its preparation method, which can effectively solve the problem of traditional fluorescent probes. Poor specificity when labeling cell membranes and low contrast in fluorescence imaging

Method used

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  • A kind of N-aryl-substituted carbazole fluorescent probe capable of specifically labeling cell membrane and preparation method thereof
  • A kind of N-aryl-substituted carbazole fluorescent probe capable of specifically labeling cell membrane and preparation method thereof
  • A kind of N-aryl-substituted carbazole fluorescent probe capable of specifically labeling cell membrane and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0030] The synthesis of N-aryl substituted carbazole fluorescent probe CZDPPy capable of specifically labeling cell membranes comprises the following steps:

[0031] Step (1): Add 9-(4-bromophenyl)-3,6-di-tert-butylcarbazole (1.04g, 2.4mmol), 4-(4-pyridyl)phenylboronic acid to the dry reactor (398mg, 2.0mmol), Pd(PPh 3 ) 4 (116 mg, 0.1 mmol), Na 2 CO 3 (636mg, 6.0mmol), toluene (20mL), ethanol (6mL), water (2mL), react at 110°C for 24 hours under nitrogen protection. Cool to room temperature, add 20mL ethyl acetate to dilute, wash with saturated sodium chloride solution, anhydrous Na 2 SO 4 dry. After collecting the organic phase, the solvent was removed under reduced pressure, and the residue was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate=2 / 1, v / v), and vacuum-dried to obtain the N-aryl substituted carbazole precursor ( 814 mg, yield 80%);

[0032] Step (2): Add N-aryl-substituted carbazole precursor (200 mg, 0.4 mmol), m...

experiment example 1

[0041] Experimental example 1: fluorescent probe CZDPPy in DMSO / H 2 Aggregation-induced Luminescence in O System

[0042] Prepare DMSO / H with a concentration of 10 μM and water volume percentages of 10%, 30%, 50%, 60%, 70%, 80% and 90% of CZDPPy 2 O solution, then test the fluorescence emission spectrum of each solution and compare the change of fluorescence intensity at the maximum emission wavelength, the test results are as follows: image 3 shown. Among them, the instruments used for spectral characterization are: HITACHI U-2910 ultraviolet-visible spectrophotometer (scanning range 250-1100 nm), Horiba Fluoromax-4 fluorescence spectrometer.

[0043] Depend on image 3 It can be seen that the fluorescent probe CZDPPy has a strong intramolecular charge transfer effect and a large Stokes shift. 2 In the mixed solvent of O, the maximum fluorescence emission wavelength reaches the red light region of 580nm, which effectively reduces the self-absorption of fluorescent dyes a...

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Abstract

The invention discloses an N-aryl substituted carbazole fluorescent probe capable of specifically marking cell membranes and a preparation method thereof, belonging to the technical field of fluorescent probes. The N-aryl substituted carbazole capable of specifically marking cell membranes Azole fluorescent probes have a strong intramolecular charge transfer effect, a large Stokes shift, and exhibit obvious aggregation-induced luminescence, which overcomes the fluorescence quenching effect caused by aggregation of traditional fluorescent probes in cells. Cell membranes can be specifically labeled in human cervical cancer cells, enabling high-contrast fluorescence imaging. It can effectively solve the problems of poor specificity and low contrast of fluorescence imaging when traditional fluorescent probes label cell membranes.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to an N-aryl substituted carbazole fluorescent probe capable of specifically labeling cell membranes and a preparation method thereof. Background technique [0002] Fluorescent bioimaging is considered as a non-invasive assay for biological visualization due to its fast response, excellent temporal resolution, excellent sensitivity, in situ processability, ease of operation, and good reproducibility tool. [0003] As an important organelle with a phospholipid bilayer structure, the cell membrane is a two-dimensional protective boundary between living cells and their surroundings. Spit and selective permeation of substances play an important role. Due to the basic aqueous environment and complex intracellular environment in cells or organisms, traditional fluorescent probes have poor specificity when labeling cell membranes and low contrast in fluorescence imaging. Ther...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/10C09K11/06G01N21/64
CPCC07D401/10C09K11/06C09K2211/1029G01N21/6428G01N21/6458G01N2021/6439
Inventor 陈茂李成明
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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