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Fluorescence probe for targeting tumor cells and new vessels and preparation method thereof

A fluorescent probe, tumor cell technology, applied in the field of analytical chemistry, to achieve the effects of high selectivity and sensitivity, easy availability of raw materials, and low preparation cost

Active Publication Date: 2018-12-07
川北医学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no literature report on the application of triarylboron in the design of bioluminescent probes targeting integrin αvβ3 tumor cells

Method used

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  • Fluorescence probe for targeting tumor cells and new vessels and preparation method thereof
  • Fluorescence probe for targeting tumor cells and new vessels and preparation method thereof
  • Fluorescence probe for targeting tumor cells and new vessels and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of Example 1 TAB-3-cRGD

[0048]

[0049] (1) Preparation of compound 2:

[0050] Under the protection of nitrogen, 10 g (32 mmol) of compound 2 was dissolved in 60 mL of dry diethyl ether, cooled to -78°C, and 20 mL of 1.6M n-butyllithium n-hexane solution was added dropwise thereto. The reaction was warmed to room temperature and stirred for 20 min. Then, it was cooled to -78°C again, and 1.25 mL (10 mmol) of boron trifluoride ether was added. The reaction was continued at room temperature with stirring overnight. The solvent was spin-dried, and further purified by silica gel column chromatography to obtain 4.0 g of white solid with a yield of 71%.

[0051] (2) Preparation of compound 3:

[0052] Put 595mg (3.2mmol) tert-butylpiperazine N-formate, 560mg (1mmol) compound 2, 864mg (9mmol) sodium tert-butyl alkoxide, and 27mg (0.12mmol) palladium acetate into a three-necked flask, on the double row tube Pump three times, under the protection of nitrogen...

Embodiment 2

[0059] Embodiment 2: the detection of the absorption spectrum and fluorescence spectrum of TAB-3-cRGD fluorescent probe

[0060] Prepare a TAB-3-cRGD probe PBS solution with a concentration of 10 μM, add 3 mL to a 10mm*10mm two-way cuvette, put it into a spectrophotometer with a baseline adjusted, and test the data in the range of 500-300; then Pour the solution into a 10mm*10mm four-way cuvette, use 405nm as the excitation wavelength, and test the fluorescence spectrum in the range of 430-700nm (see figure 1 ). Depend on figure 1 It can be seen that the maximum absorption peak of TAB-3-cRGD is at 380nm, and the maximum emission peak is at 490nm.

Embodiment 3

[0061] Example 3: Imaging application of TAB-3-cRGD fluorescent probe in living cells

[0062] Mouse fibroblasts NIH / 3T3, venous endothelial cells HUVEC-1, and glioma U87 cells were cultured in a confocal culture medium (the volume ratio of DMEM medium and fetal bovine serum in the medium was 9:1). on the dish. Place them in an incubator at 37° C., 5% (volume fraction) CO2 and 20% (volume fraction) O2, and cultivate them for 24-48 hours. Remove the culture medium, wash it three times with PBS, then add serum-free DMEM culture solution, add the solution of the TAB-3-cRGD fluorescent probe of the present invention in each culture dish respectively, continue to cultivate in the incubator for 15min, PBS ( Phosphate buffered saline) to wash the cultured cells 6 times. Fluorescent imaging was performed using a confocal microscope. The imaging conditions are: the excitation wavelength is 405nm, and the collection range is: 500-550nm. Such as figure 2 is the imaging image of TAB...

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Abstract

The invention provides a fluorescence probe for targeting tumor cells and new vessels. The fluorescence probe can solve the problem of selective imaging for cancer cells of high-expression integrin alpha v beta3. According to the design of the molecular structure of the fluorescence probe provided by the invention, RGD is used as a recognition group for performing multi-site modification on triaryl fluorophore so as to construct a multivalent probe capable of combining with integrin alpha v beta 3. The probe is capable of selectively imaging the cancer cells of high-expression integrin alpha vbeta 3 at cellular level and is capable of realizing the targeting imaging of a tumor site in vivo. Meanwhile, the synthetic process of the fluorescence probe provided by the invention is simple andeasy, the raw materials are low-cost and easily acquired, the preparation cost is low and the fluorescence probe is easy for popularization.

Description

technical field [0001] The invention relates to a novel fluorescent probe for targeted imaging of cancer cells and new blood vessels and a preparation method thereof, belonging to the technical field of analytical chemistry. Background technique [0002] Currently, cancer is a major disease worldwide, causing more than 7 million deaths per year, and it is predicted that cancer will become a bigger problem in the next 20 years. The development of selective visualization imaging technology for cancer cells or tissues is helpful to explore the mechanism of cancer occurrence and development, realize early diagnosis and prognosis assessment, improve surgical resection rate, and improve survival rate. [0003] Molecular imaging and probes are two methods that can detect diseases earlier, determine the nature of diseases, monitor treatment effects objectively and non-invasively, and predict disease development, which are mainly aimed at molecular and cellular lesions. Among them, ...

Claims

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Application Information

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IPC IPC(8): C07K5/09C07K1/06C09K11/06G01N21/64
CPCG01N21/6428C09K11/06C07K5/0817C09K2211/1007C09K2211/1074Y02P20/55
Inventor 刘军张小明朱江
Owner 川北医学院
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