Tumour positive electron developer S-(18 fluro-n-alkyl)-L-methionine and its preparation method

A technology of positron imaging agent and methionine, which is applied in the direction of pharmaceutical formulations, in vivo radioactive preparations, preparations for in vivo experiments, etc. It can solve the problems of application limitations, difficulty in distinguishing inflammation and tumor lesions, and low radiochemical yield.

Inactive Publication Date: 2003-04-16
NAN FANG HOSPITAL
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0002] 2- 18 F-2-deoxy-D-glucose (FDG) has been widely used in positron emission tomography (PET) imaging studies of tumors, cardiovascular diseases, and neuropsychiatric diseases, but it is difficult to distinguish between inflammation and tumor lesions in the differential diagnosis of tumors , and some amino acid PET imaging agents can make up for the deficiency of FDG
Currently, there are various 18 F labeled amino acids (such as L- 18 F-fluorophenylalanine, L-2- 18 F-fluorotyrosine and L-α-methyl- 18 F-fluorotyrosine, etc.) have been successfully developed and have shown good imaging effects, but the synthesis is difficult, the radiochemical yield is low, and its application is limited

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  • Tumour positive electron developer S-(18 fluro-n-alkyl)-L-methionine and its preparation method
  • Tumour positive electron developer S-(18 fluro-n-alkyl)-L-methionine and its preparation method

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Embodiment 1

[0019] Embodiment 1, S-(2- 18 Preparation of F-fluoroethyl)-L-methionine (FEMET).

[0020] 1. Standard S-(2- 19 F-fluoroethyl)-L-methionine ( 19 FEMET) preparation.

[0021] 60 mg (0.4 mmol) of L-homocysteine ​​thiolactone was dissolved in 320 μL (0.8 mmol) of 10% (mass volume ratio concentration) sodium hydroxide solution, 23 mL of DMSO was added, and the solution was heated to 80° C. Under stirring, 0.050 g (0.4 mmol) of 1-fluoro-2-bromoethane was added, and the reaction was heated and stirred at 90° C. for 2 h. Cool and pour over 2 g of crushed ice. After the crushed ice was dissolved, the pH value was adjusted to 7.5, and a precipitate was obtained. Filter, wash with water, and dry to obtain the crude product. Recrystallized with 60% acetic acid to obtain 0.023 g (0.14 mmol) of light yellow solid with a yield of about 35%. 1 H NMR (CDCl 3 )δ: 4.6(t, 2H), 4.2(t, 2H), 3.4(m, 1H), 2.8(t, 2H), 2.0(m, 2H). MS (EI) m / z: 167 (M + ).

[0022] 2. S-(2- 18 Preparation of...

Embodiment 2

[0028] Example 2, FEMET distribution experiment in animal model.

[0029] 1. Production of sarcoma-bearing mouse model.

[0030]S180 fibrosarcoma cells were cultured in mice for about a week, and the ascites containing sarcoma cells was extracted from the abdominal cavity of the mice with a syringe, and diluted with normal saline to a suspension of about 10 7 0.2 mL of cancer cells were inoculated subcutaneously in the left armpit of 17-25 g Kunming mice, and were raised under normal conditions for about 7 days. The tumor diameter ≥ 1.5 cm was selected.

[0031] 2. Production of mouse inflammation model.

[0032] Kunming mice weighing more than 20 g were taken, and 0.2 mL of turpentine oil was injected intramuscularly into the right hind limb to cause infection. After 4 to 7 days, the mice showed redness, swelling and movement disorders at the injection site, and those with abscess were selected.

[0033] 3. Distribution experiments in animals. Divide 20 mice into 5 groups ...

Embodiment 3

[0041] Example 3, PET imaging experiment of FEMET model mice.

[0042] 1. PET imaging of model mice. Before the examination, the model mice were fasted for 4-6 hours. After diluting the above-prepared FEMET with normal saline, inject about 1.8MBq / mouse of FEMET injection rapidly through the tail vein of the model mice. At 60 min and 120 min after injection, the emission scan and transmission scan were performed respectively, and the cross-sectional, coronal and sagittal plane images were obtained through computer reconstruction. and with 18 F-FDG PET imaging was compared.

[0043] 2. PET imaging results of model mice

[0044] The PET images of tumor model mice and inflammation model mice are shown in figure 1 . At 60 minutes after administration, fibrosarcoma (top picture) could highly uptake FDG and FEMET, and abscess tissue (bottom left picture) could also highly uptake FDG, but abscess tissue (bottom right picture) hardly took up FEMET. At 120 minutes after administr...

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Abstract

A position developer for tumor is prepared by the two-step synthesis which can easily realize autosynthesis. It is specific amino acid metabolism PET developer for distinguishing tumor from inflammation.

Description

technical field [0001] The invention relates to a positron emission tomography (PET) imaging agent and a preparation method thereof, in particular to S-( 18 F-fluoro-n-alkyl)-L-methionine and its preparation method. Background technique [0002] 2- 18 F-2-deoxy-D-glucose (FDG) has been widely used in positron emission tomography (PET) imaging studies of tumors, cardiovascular diseases, and neuropsychiatric diseases, but it is difficult to distinguish between inflammation and tumor lesions in the differential diagnosis of tumors , and some amino acid PET imaging agents can make up for the lack of FDG. [ 11 C-methyl]-L-methionine (MET) is a tumor PET imaging agent that is widely used after FDG, and has a high uptake in tumor tissues. It has been used in brain tumors, head and neck tumors, lung cancer, breast cancer, It is better than FDG in the differential diagnosis of brain tumors in the differential diagnosis and curative effect evaluation of lymphoma and melanoma, but ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K51/00
Inventor 唐刚华
Owner NAN FANG HOSPITAL
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