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Compound, preparation method of compound as well as fluorescent probe containing compound and application

A technology of fluorescent probes and compounds, which is applied in the field of organic small molecule probes, can solve the problems of short emission wavelength, complex operation, and long time consumption of probes, and achieve the effects of low post-processing difficulty, high reaction efficiency, and wide application range

Active Publication Date: 2019-05-28
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Therefore, fibroblast activation protein is expected to become a new effective target and play a huge role in the early detection and treatment of tumors. At present, although the drug research on FAPα inhibitors has led to the discovery of many FAPα-targeted inhibitors, including Candidate drugs in the second phase of clinical trials, but the current detection methods to determine whether FAPα is highly expressed in tissues are usually based on tissue sections, staining, and western blotting. The operation is more complicated and time-consuming
In the early days, there were not many related studies on rapid, simple and visual detection of FAPα. Some current reports on the detection of FAPα have short emission wavelengths of probes, and the application of in vivo imaging has certain limitations. In view of this, this application is proposed

Method used

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  • Compound, preparation method of compound as well as fluorescent probe containing compound and application
  • Compound, preparation method of compound as well as fluorescent probe containing compound and application
  • Compound, preparation method of compound as well as fluorescent probe containing compound and application

Examples

Experimental program
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Effect test

Embodiment 1

[0061] Compound I was prepared according to the following steps

[0062] (1) Dissolve 2g of cyclohexanone in a 1:1 solvent of DMF and dichloromethane, stir evenly, add 10g of phosphorus oxychloride at 0°C, heat at 50°C, reflux for 2h, pour the product solution into In cold water, stand still, suction filtration, obtain compound VII, the reaction formula of step (1) is as follows:

[0063]

[0064] (2) Mix compound VII obtained in step (1) with compound VI at a molar ratio of 1:3, disperse 100 mg of sodium acetate in acetic anhydride, and reflux at 70°C for 1 hour to obtain the crude product of compound 3, which is spin-dried with the solvent and silica gel Purified by column chromatography to obtain compound 3, the reaction formula of step (2) is as follows:

[0065]

[0066] Among them, R 3 for CH 3 ;

[0067] (3) Disperse compound V and compound IV obtained in step (2) in 30 ml of acetonitrile with a molar ratio of 1:5, add 138 mg of potassium carbonate, react at r...

Embodiment 2

[0075] Prepare fluorescent probes according to the same steps as in Example 1, wherein, R 3 =CH 2 CH 3 , R 2 = H, R 1 =CO 2 CC 3 h 9 , and the resulting product is denoted as FP2.

Embodiment 3

[0077] Fluorescent probes were prepared in the same manner as in Example 1, wherein R 3 =CH 3 , R 2 = Cl, R 1 =CO 2 CC 3 h 9 , and the resulting product is denoted as FP3.

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Abstract

The invention discloses a compound I. The compound I has a structure shown in a formula I (the formula I is shown in the description), wherein R1 is an acyl group, phenyl group or alkyl oxycarbonyl group containing 2-5 carbon atoms; R2 is a halogen atom or hydrogen atom; R3 is an alkyl group containing 1-18 carbon atoms. The invention also discloses a synthesizing method of the compound I, a fluorescent probe containing the compound I and application. The fluorescent probe provided by the invention has the advantages that the selectivity is excellent, the reaction is rapid, and fibroblast activating protein alpha can be simply, rapidly and visually detected.

Description

technical field [0001] The application relates to a fluorescent probe and its preparation method and application, belonging to the field of small organic molecule probes. Background technique [0002] Fibroblast activating protein α (FAPα) is a type II transmembrane glycoprotein with 760 amino acids, which belongs to the serine protease family and has dipeptidyl peptidase and collagenase activities. Studies have confirmed that FAPα is specifically expressed in the matrix of malignant epithelial tumors including breast cancer, skin melanoma, colon cancer, pancreatic cancer, lung cancer, and ovarian cancer, while normal human tissues except embryos, healing wounds, and physiologically reconstructed organs , generally not expressed. Studies have shown that FAPα is widely involved in the processes of growth, invasion, metastasis, angiogenesis, remodeling of extra-tumor matrix, and anti-tumor immunity in tumorigenesis and development. [0003] Therefore, fibroblast activation p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C09K11/06G01N21/64
Inventor 吴爱国邢洁龚秋雨邹瑞芬
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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