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18F-fluorine labeling pentapeptide complex and synthetic method thereof

A synthesis method and fluorine labeling technology, applied in the fields of medicine and chemistry, can solve the problems of short retention time, less research, low utilization rate, etc., and achieve the effects of good thermal stability, good water solubility and small dosage.

Inactive Publication Date: 2013-12-11
WUHAN INSTITUTE OF TECHNOLOGY
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Problems solved by technology

[0005] However, PET tracers currently used clinically, such as 18 F-FDG, 18 F-Al-NOTA, 18 F-FLT, etc., are all small molecular compounds, which are distributed in the human body according to the different metabolic needs of various parts in the body. They do not have tissue or organ selectivity or targeting, and especially have no specific effect on tumors. The imaging effect is poor, the metabolism in the body is fast, the retention time is short, and the utilization rate is low, and there is no tumor-targeted PET tracer in clinical application at home and abroad, and the tumor-targeted PET tracer and cancer There are few studies on metastatic lesions, so it is very important to develop tumor-targeted PET tracers with my country's independent intellectual property rights to improve the early clinical diagnosis of tumors in my country, the early identification of cancer metastatic lesions and the differential diagnosis of benign and malignant tumors. significance and far-reaching impact

Method used

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  • 18F-fluorine labeling pentapeptide complex and synthetic method thereof
  • 18F-fluorine labeling pentapeptide complex and synthetic method thereof
  • 18F-fluorine labeling pentapeptide complex and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 0.4g of 1,4,7-triazacyclonona-1,4,7-triacetic acid mono-N-hydroxysuccinimide active ester (1mmol) was added to the pentapeptide compound YIGSR (0.592g, 1mmol) and dissolved in 20mL N,N-dimethylformamide solution, electromagnetically stirred at room temperature for 6 hours. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent, and dried in vacuo to obtain 0.83 g of the ligand YIGSR-NOTA compound with a yield of 84%.

[0043] eluted with carbonate 18 F-fluoride solution (5.39GBq) was dissolved in 50 μL 0.4mol / mL K 2 CO 3 , neutralized with 5 μL glacial acetic acid, and added 1 μL 0.01mol / mL AlCl 3 ·6H 2 O was dissolved in 0.1mol / mL NaOAc solution (pH4), followed by adding 2μL of 0.01mol / mL ligand YIGSR-NOTA compound (0.01754g, 20nmol) dissolved in 0.1mol / mL NaOAc solution (pH4), at 105℃ Reaction 17min. Cool, with 1mL H 2 O dilutes the reaction mixture solution, separates and purifies with column chromatography, obtains 18 F-fluo...

Embodiment 2

[0045] 0.46g 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid mono-tert-butylene active ester (1mmol) was added to the pentapeptide compound YIGSR (0.592g, 1mmol) In a solution of 30 mL of dimethyl sulfoxide, electromagnetically stirred at room temperature for 4 hours. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent, and dried in vacuo to obtain 0.789 g of the ligand DOTA-YIGSR compound with a yield of 75%.

[0046] eluted with carbonate 18F - Fluoride solution (5.39GBq) was dissolved in 50 μL 0.4mol / mL K 2 CO 3 , neutralized with 5 μL glacial acetic acid, and added 1 μL 0.01mol / mL AlCl 3 ·6H 2 O was dissolved in a solution (pH4) of 0.1mol / mL NaOAc, followed by adding 2 μL of 0.01mol / mL ligand DOTA-YIGSR compound compound (0.01956g, 20nmol) was dissolved in a solution (pH4) of 0.1mol / mL NaOAc, in React at 105°C for 17 minutes. Cool, with 1mL H 2 O dilutes the reaction mixture solution, separates and purifies with column...

Embodiment 3

[0048] 0.486g of 1,4,7-triazacyclonona-1,4,7-triacetic acid-2-p-benzyl bromide (1mmol) was added to the pentapeptide compound YIGSR (0.592g, 1mmol) dissolved in 20mL N,N - To the solution of dimethylformamide, triethylamine (0.101 g, 1 mmol) was added, and electromagnetically stirred at room temperature for 12 hours. Filtration, the filtrate was evaporated under reduced pressure to remove the solvent, and dried in vacuo to obtain 0.89g ligand NOTA-C 6 h 4 CH 2 - YIGSR compound, yield 90%.

[0049] washed with salt 18 Dissolve F-fluoride solution (70.3MBq) in 50 μL of normal saline, neutralize with 5 μL of glacial acetic acid, add 2 μL of 0.01mol / mL AlCl 3 ·6H 2 O was dissolved in a 0.1mol / mL NaOAc solution (pH4), followed by the addition of 20 μL of the ligand NOTA-C 6 h 4 CH 2 -YIGSR compound (0.03932g, 2mmol / mL, 40nmol) was dissolved in 0.1mol / mL NaOAc solution (pH4), and reacted at 105°C for 15min. Cool, dilute the reaction mixture solution with 1mL PBS (pH7.4), se...

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Abstract

The invention relates to an 18F-fluorine labeling pentapeptide complex and a synthetic method thereof. The 18F-fluorine labeling pentapeptide complex has a chemical structural formula as shown in a formula 1, and a positron emission computed tomography tracer agent which has the advantages of good hydrophilicity and targeting on tumors can be prepared by utilizing the 18F-fluorine labeling pentapeptide complex. The method for synthesizing the 18F-fluorine labeling pentapeptide complex comprises the following steps of: (1) reacting a cyclic polyamine polycarboxylic compound with a pentapeptide compound, and connecting through a covalent bond to form a ligand; (2) reacting the ligand obtained from the step (1) with 18F-potassium fluoride and aluminum chloride to form the 18F-fluorine labeling pentapeptide complex. The 18F-fluorine labeling pentapeptide complex disclosed by the invention can be selectivity ingested and enriched by the tumors and achieves higher concentration in the tumors, thereby realizing the targeted imaging of the tumors and enhancing the contrast ratio and definition of the imaging.

Description

technical field [0001] The invention belongs to the technical fields of medicine and chemistry, and specifically relates to a class of 18 F-fluorine-labeled pentapeptide complex and its synthesis method Background technique [0002] Positron Emission Computed Tomography (PET) is currently the only clinical technology that uses anatomical morphology to perform functional, metabolic and receptor imaging. It is non-invasive and is currently used in the field of clinical nuclear medicine. One of the best means to diagnose and guide the treatment of tumors. As a new imaging technology, PET does not display the anatomical shape of the tissue like CT and MRI, but detects the abnormality of local tissue metabolism. Therefore, PET has been used to detect high-metabolism tissues or organs, such as the brain and heart. and diagnosis of malignant tumors. [0003] The imaging agent (tracer) used in PET is a compound similar to the endogenous metabolites of the human body, which can pa...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/13C07K1/107
Inventor 鄢国平鄢珈睿陈群二
Owner WUHAN INSTITUTE OF TECHNOLOGY
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