Positron-nuclide-labeled dansyl amido diphenylethylene compound and synthesis method and application thereof

A technology based on dansylamide and methoxystilbene, which is applied in measuring devices, material analysis through optical means, instruments, etc., can solve the dual mode of PET without targeting cell apoptosis and targeting β-amyloid protein Imaging agents and other issues, to achieve the effect of easy automatic labeling, high radiochemical yield, and great application prospects

Active Publication Date: 2017-04-26
GUANGDONG HUIXUAN PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] To date, no optical and PET dual-modal imaging agents

Method used

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  • Positron-nuclide-labeled dansyl amido diphenylethylene compound and synthesis method and application thereof
  • Positron-nuclide-labeled dansyl amido diphenylethylene compound and synthesis method and application thereof
  • Positron-nuclide-labeled dansyl amido diphenylethylene compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Structural identification of precursor compounds and standard compounds

[0025] 1.1 Preparation of cells, animal sources and animal models

[0026] This study was approved by the Animal Experiment Ethics Committee of the First Affiliated Hospital of Sun Yat-Sen University (batch no.2012.001). S-180 fibrosarcoma cells and liver cancer cell lines were purchased from the Animal Laboratory Center of Sun Yat-sen University, Jurkat cells were purchased from the Chinese Academy of Sciences (Shanghai), and A549 cells were donated by the research group of Professor Zang Linquan from Guangzhou College of Pharmacy. Kunming mice: female, clean grade, weighing 18ˉ22g; nude mice: clean grade, four to five weeks old, purchased from the Animal Experiment Center of Sun Yat-sen University, license number SYXK (Guangdong) 2007-0081. All experimental mice were raised in the general animal laboratory of Zhongshan Medical College, 5 mice / cage, under constant temperature and humidity c...

Embodiment 211

[0040] Example 2 11 Radiosynthesis of C-DSB

[0041] Nuclear reaction by cyclotron 14 N(p,α) 11 C production 11 CO 2 , And then transferred to PET-CS-II-IT-I 11 C iodomethane synthesis module. 11 CO 2 It is trapped by a Loop ring (liquid nitrogen cooled to -160°C). Remove the liquid nitrogen cooling ring, pass in He gas (20mL / min) and release 11 CO 2 , By P 2 O 5 After the column is dried, it enters the reaction tube. Accessible 11 CO 2 With LiAlH 4 Reduction reaction occurs 11 CH 3 OH, and then react with HI to produce 11 CH 3 I. Under the action of He gas, 11 CH 3 I pass the high temperature Ag-triflate column to get 11 CH 3 -triflate( 11 C-CH 3 OTf). Before the experiment, 1 mg of the precursor 4-dansylamide-4'-hydroxystilbene (1) was dissolved in 0.2mL DMSO and 0.8mL acetone solution, 20μL 2.5M NaOH solution was added, and 0.3mL was charged into the reaction tube. 11 C-CH 3 OTf passes N 2 Carry it into the reaction tube until 11 CH 3 After I evaporated, continue to react at...

Embodiment 318

[0047] Example 3 18 Radiosynthesis of F-DFESB

[0048] Cyclotron passed 18 O(p,n) 18 F nuclear reaction produced 18 F - Ions, after being captured by QMA column, use K 222 Solution (K 2 CO 3 2.7mg dissolved in 0.1mL water, 12mg K 222 Dissolved in 0.9mL MeCN) Elution 18 F - To the reaction flask. Nitrogen gas (80 mL / min) was introduced, and the solvent was removed under heating at 116°C. Anhydrous acetonitrile (1.5 mL) was added, nitrogen gas was added and heated to 116°C, and water was removed again. Add the precursor 4-dansylamino-4'-methylsulfonyl triethoxy stilbene (3) solution (5 mg precursor dissolved in 1 mL acetonitrile) to the radioactive [K / K222] +18 F - In the reaction flask, heat to 100°C in a sealed reaction tube and keep it for 10 min. After cooling the reaction tube, add 10 mL of water to dilute and pass through the SEP PAK plus C18 column. 18 F-DFESB is adsorbed on the SEP PAK plus C18 cartridge, and the SEP PAK plus C18 cartridge is rinsed with 10 mL of water to ...

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Abstract

The invention relates to an optics and positron emission tomography (PET) dual-mode developer (formula 1) targeted to apoptotic cells and beta-amyloid protein, namely, a positron-nuclide-labeled 4-dansyl amido-4'-diphenylethylene compound. A synthesis method of the compound includes the steps that dansyl targeted to apoptotic cells and 1,2-diphenylvinyl-amino targeted to beta-amyloid protein are bound together, and then labeling is conducted. The compound is simple in radiosynthesis method, high in radiochemical yield and convenient to synthesize automatically, has broad application prospects and can be applied to anti-tumor therapy monitoring and differential diagnosis and scientific research on neurological and psychotic disorders like Alzheimer disease (AD). The formula 1 is defined in the description.

Description

[0001] 【Technical Field】 [0002] The present invention relates to an optical and PET dual-mode imaging agent for targeting apoptotic cells and targeting β amyloid: positron nuclide labeling 4-dansylamide-4'-stilbene-based compounds, and a synthesis method thereof And its application in the preparation of anti-tumor therapy monitoring and differential diagnosis and scientific research drugs for senile dementia (AD) and other neuropsychiatric diseases. [0003] 【Background technique】 [0004] Apoptosis is the orderly death of cells autonomously controlled by genes, and is a special form of death of eukaryotic cells. Apoptosis has important biological significance and can be seen in many physiological processes such as embryonic development, tissue differentiation, and immune regulation. Its abnormal regulation is associated with the occurrence of various malignant tumors, myocardial infarction, viral infectious diseases, and neurodegenerative diseases. Development is closely related ...

Claims

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Application Information

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IPC IPC(8): A61K51/04G01N21/84
Inventor 唐刚华
Owner GUANGDONG HUIXUAN PHARMA TECH
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