Positron emission tomography radiotracer for diseases associated with translocator protein overexpression, translocator protein-targeting ligand for fluorescence imaging diagnosis and photodynamic therapy, and preparation method therefor

A technology of radiotracer and translocator protein, which is applied in photodynamic therapy, radioactive carriers, and radioactive preparations in vivo, to achieve the effects of shortening diagnosis time, improving emission, and high signal-to-noise ratio

Pending Publication Date: 2020-11-17
SEOUL NAT UNIV R&DB FOUND
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  • Claims
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Problems solved by technology

This aromatic fluorine-18 labeling method efficiently provides in vivo images with high signal-to-noise ratio due to the strong carbon-fluorine (C(sp2)-F) bond, but aromatic nucleophilic fluorine-18 labeling is less reactive than For aliphatic fluorine-18 labeling, attempts have been made to develop various precursors and reaction methods in order to improve reactivity.

Method used

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  • Positron emission tomography radiotracer for diseases associated with translocator protein overexpression, translocator protein-targeting ligand for fluorescence imaging diagnosis and photodynamic therapy, and preparation method therefor
  • Positron emission tomography radiotracer for diseases associated with translocator protein overexpression, translocator protein-targeting ligand for fluorescence imaging diagnosis and photodynamic therapy, and preparation method therefor
  • Positron emission tomography radiotracer for diseases associated with translocator protein overexpression, translocator protein-targeting ligand for fluorescence imaging diagnosis and photodynamic therapy, and preparation method therefor

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preparation example Construction

[0038] In order to achieve the stated purpose, the preparation method of the fluorine-18 labeled PET imaging radiotracer targeting translocation protein overexpression of the present invention may comprise the following steps: the preparation step of fluorine-18 reaction solution, dissolving the The fluorine-18 water generated by the cyclotron is added to acetonitrile (CH3CN, acetonitrile) together with the phase transfer catalyst and heated to a temperature of 85°C to 95°C to prepare the generated fluorine-18 reaction solution; the precursor preparation step, let 2-(4-Aryltrimethyltin-6,8-dichloroimidazo[1,2-a]pyridin-3-yl)dipropylacetamide and (diacetoxy)iodoarene derivatives Perform the reaction to prepare iodonium salt precursor (precursor A type) or let 2-(4-bromoaryl-6,8-dichloroimidazo[1,2-a]pyridin-3-yl)dipropylethyl Amide reacts with bis(pinacolate) diboron to prepare boron ester precursor (precursor Btype); iodonium salt reaction solution preparation step, the iodoni...

specific Embodiment approach

[0059] Based on the principle that the inventor can properly define the concept of the relevant terms in order to explain his invention using the best method, it should be interpreted in accordance with the meaning and concept of the technical idea of ​​the present invention.

[0060] The present invention will be described in detail below. However, the present invention can be realized in various forms without being limited by one embodiment disclosed below. The main purpose of this embodiment is to fully disclose the present invention and fully explain the scope of the present invention to those with ordinary knowledge.

[0061] figure 1 A chemical formula showing a synthesis process of a fluorine-18-labeled radiotracer using an iodonium precursor and a boroester precursor in an example of the present invention.

[0062] figure 2 A graph showing the HPLC chromatogram of the isolation of pure fluorine-18 labeled radiotracer from a synthetic mixture that is one example of a...

preparation example 1

[0133] Preparation 1: 2-(6,8-dichloro-2-(4-(trimethylstannyl)phenyl)-imidazo[1,2-a]pyridin-3-yl)-N, Preparation of N-dipropylacetamide

[0134]

[0135] (Step 1): Preparation of 4-(4-bromophenyl)-4-oxo-N,N-dipropylbutanamide

[0136] 3-(4-Bromobenzoyl)propionic acid (2.0g, 7.8mmol) and 1,1'-carbonyldiimidazole (1.4g, 8.6mmol) were dissolved in tetrahydrofuran (THF, 50ml) and stirred for 30 minutes. After 30 minutes, N,N'-dipropylamine (1.2 mL, 8.6 mmol) and triethylamine (1.3 ml, 9.4 mmol) were added and stirred for 3 hours. After the solvent was removed by negative pressure, the residue was extracted with ethyl acetate after being poured into 0.1N aqueous hydrogen chloride solution. The extracted organic solvent is treated with sodium sulfate and filtered, and the remaining organic solvent is evaporated by negative pressure. The residue was purified by column chromatography to obtain the target compound.

[0137] 1H NMR (400MHz, CDCl3) δ0.86(t, J=7.4Hz, 3H, CH3), 0.95(...

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Abstract

The present invention obtains, by PET, images of neurogenic inflammation, cerebral apoplexy and tumors, which are associated with new translocator protein overexpression, through a fluorine-18-labeledtranslocator protein overexpression-targeting PET radiotracer, thereby diagnosing patients with various brain diseases and tumors, and providing a brain neurogenic inflammation and tumor imaging diagnosis to more patients in comparison to a conventional carbon-11-tracer because of the long half-life of fluorine-18.

Description

technical field [0001] The present invention relates to a fluorine-18 labeled positron emission tomography radiotracer for targeting translocation protein overexpression, a fluorescent ligand for fluorescence imaging and photodynamic therapy, and a preparation method thereof. More specifically, the present invention relates to A positron emission tomography radiotracer that uses iodonium salt or boronate precursor to prepare and label the selective / specific uptake of fluorine-18 in neuroinflammation and tumor models to the inflammatory field, and replaces fluorine-18 Fluorescent ligands for targeted fluorescence imaging and photodynamic therapy by overexpressing translocation proteins prepared by introducing fluorescent substances and their preparation methods. Background technique [0002] Microglial cells in the central nervous system help activate the nervous system and maintain a stable internal environment. One of its functions is to secrete neurotrophin or nitric oxide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K51/04A61K41/00A61P25/00A61P35/00
CPCA61P25/00A61P35/00A61K51/0455C07B59/00A61K49/0052A61K51/0453A61K41/0038A61K41/0057C07B59/002
Inventor 金相殷李炳喆李相熙N·狄诺拉V·拉昆塔纳A·A·洛佩多塔A·库特里格内利M·佛朗哥
Owner SEOUL NAT UNIV R&DB FOUND
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