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Chemiluminescent probe for detecting fibroblast activation protein, its synthesis method and application

A fibroblast, chemiluminescence technology, applied in chemical instruments and methods, chemiluminescence/bioluminescence, analysis by chemical reaction of materials, etc., to achieve the effect of expanding the scope of application and important application value

Active Publication Date: 2022-06-21
FUDAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the detection methods of FAPα mainly include RT-PCR, immunohistochemical method, Western bolt method, fluorescence method, etc., and there is a gap in the technology of chemiluminescence method for the determination of FAPα.

Method used

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  • Chemiluminescent probe for detecting fibroblast activation protein, its synthesis method and application
  • Chemiluminescent probe for detecting fibroblast activation protein, its synthesis method and application
  • Chemiluminescent probe for detecting fibroblast activation protein, its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Synthesis of the adamantane-dioxetane chemiluminescent probe CFCL for the detection of fibroblast activation protein (see the appendix for the synthesis route). figure 1 shown).

[0042] (1) Synthesis of compound 7, the specific steps are:

[0043] (1) Dissolve m-hydroxybenzaldehyde (25.6 g, 209.6 mmol, 1 equiv.) in 150 mL of 90 % acetic acid, after the temperature of the reaction solution drops to 0 °C, add tert-butyl hypochlorite (25.0 g, 230.6 mmol, 1.1 equiv.); the reaction was monitored by high performance liquid chromatography; after the reaction was complete, the product (referred to as compound 1) was obtained by filtration as a white solid 13.8 g (42.2 % crude product yield); MS (ESI-): m / z C 7 H 5 ClO 2 Theoretical value: 155.00, 156.99; visible [M-H]-154.88, 156.88;

[0044] (2) Compound 1 (content based on 100%, 10.8 g, 69.2 mmol, 1 equiv.) was dissolved in 100 mL of methanol, and tetrabutylammonium tribromide (1.7 g, 3.5 mmol, 0.05 equiv.)...

Embodiment 2

[0057] Example 2: Synthesis of adamantane-dioxetane chemiluminescent probe BFCL for detection of fibroblast activation protein. (See the synthetic route figure 2 shown), the specific steps are:

[0058] (1) Combine tert-butoxycarbonyl-glycine-proline-OH (1.1 g, 44.04 mmol, 1equiv.) and ethyl 2-ethoxy-1(2H)-quinolinecarboxylate (2.0 g, 8.08 mmol). , 2 equiv.) was dissolved in 20 mL of dichloromethane and a solution of p-aminobenzyl alcohol in dichloromethane (1.0 g, 8.08 mmol, 2 equiv.) was added dropwise. The reaction was monitored by high performance liquid chromatography. After the reaction, an appropriate amount of dichloromethane was added to dilute and washed with water. The organic phases were combined, and after the saturated sodium sulfate solid was dried, the solvent was removed by vacuum rotary evaporation, and purified by silica gel column chromatography. The obtained product (referred to as compound b1) was a white solid, totaling 1.24 g (82.7 % yield);

[005...

Embodiment 3

[0061] Example 3: CFCL or BFCL assay for fibroblast activation protein in vitro.

[0062] A series of FAPα solutions of different concentrations were prepared, and 100 μL of each concentration was placed in a small well of a black 96-well plate, and 100 μL of CFCL or BFCL chemiluminescence probe with a concentration of 40 μM was added to each well, which was obtained by Xenogen IVIS. ® The in vivo imager was photographed and quantitatively analyzed by the instrument's own software. like image 3 As shown, the response value increases with the increase of FAPα concentration, and there is a good linear relationship between the response value and FAPα concentration.

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Abstract

The invention belongs to the technical field of small molecule chemiluminescent probes, in particular to a chemiluminescent probe for detecting fibroblast activation protein (FAPα), a synthesis method and application thereof. The chemiluminescence probe of the present invention is a kind of adamantane-dioxetane chemiluminescence probe, including two kinds of CFCL and BFCL; In the presence of anhydrous inert solvents, it is prepared by reacting with a sensitive group of FAPα through high-performance liquid chromatography; the chemiluminescent probe can be used for the detection of FAPα in vivo and in vitro, including the determination of FAPα in cells, tissues or plasma. FAPα, for imaging of FAPα in animals. The chemiluminescent probe can also be used to evaluate and screen FAPα inhibitors. The invention obtains a chemiluminescent probe by improving the adamantane-dioxetane to realize the detection of FAPα, which is an important technological breakthrough and further expands its application range.

Description

technical field [0001] The invention belongs to the technical field of small molecule chemiluminescence probes, and in particular relates to a chemiluminescence probe for detecting fibroblast activation protein and a synthesis method and application thereof. Background technique [0002] Compared with fluorescence technology, chemiluminescence originates from chemical reactions, does not require external excitation light source, and has the unique advantage of not being interfered by light scattering and autofluorescence; specific reaction of the substance. Chemiluminescence systems, including luminol, oxalate peroxide, etc., have complex composition systems, weak applicability in physiological environments, and the participation of oxidative substances in the reaction, which are mostly limited in the application of in vivo optical analysis. Determination of hydrogen peroxide, reactive oxygen radicals and their inhibitors or enhancers. Therefore, it is of great scientific ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C09K11/07G01N21/76A61K49/00
CPCC07D405/12C09K11/07G01N21/76A61K49/0013
Inventor 傅安辰曹志娟王宏博毛彦佳孙茹
Owner FUDAN UNIV
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