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Positron imaging agent <18>F-FPGalNAc as well as preparation method and application thereof

A positron imaging agent, 18f-fpgalnac technology, which is applied in the field of positron imaging agent 18F-FPGalNAc and its preparation, can solve the problems of developing false negatives in cancer, and achieves strong specificity, improved yield and imaging effect Good results

Active Publication Date: 2019-09-27
NANFANG HOSPITAL OF SOUTHERN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, 18 F-FDG is a non-tumor-specific tracer. In addition to the physiological uptake of normal tissues, some benign lesions, such as inflammation, active tuberculosis, sarcoidosis, inflammatory pseudotumor, and post-radiotherapy / surgery reactions, can manifest as 18 High intake of F-FDG leads to false positive results, while some malignant tumors, such as bronchoalveolar carcinoma, clear cell renal cell carcinoma, well-differentiated hepatocellular carcinoma, and some small and slow-growing cancers are false negative

Method used

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  • Positron imaging agent &lt;18&gt;F-FPGalNAc as well as preparation method and application thereof
  • Positron imaging agent &lt;18&gt;F-FPGalNAc as well as preparation method and application thereof
  • Positron imaging agent &lt;18&gt;F-FPGalNAc as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] A positron imaging agent 18 The preparation method of F-FPGalNAc comprises the following steps:

[0056] 1) Disperse 4-pentyn-1-ol (2.52g, 30mmol) in 80mL of dichloromethane, then add triethylamine (10.12g, 100mmol), 4-dimethylaminopyridine (0.16g, 1.32mmol) and p-toluenesulfonyl chloride (6.86g, 36mmol), reacted at room temperature for 14h, added ammonium chloride (5.35g, 0.1mol) to neutralize triethylamine, then extracted with ethyl acetate, and then subjected the extract to anhydrous sodium sulfate Remove water, vacuum distillation and column chromatography to obtain light yellow liquid Yield 83%; 1 H NMR (600MHz, CDCl 3 )δ7.80(d, J=8.3Hz, 2H), 7.35(d, J=8.1Hz, 2H), 4.15(t, J=6.1Hz, 2H), 2.44(d, J=13.4Hz, 3H) ,2.26(dt,J=6.9,2.6Hz,2H),1.86(m,2H),1.23(m,1H);

[0057] 2) Will (35.7mg, 0.15mmol) was dispersed in 1mL acetonitrile, then added 18 F ions (100mCi), reacted at 85°C for 10min to obtain Yield 40%;

[0058] 3) Will (1g, 4.6mmol) was dispersed in 40m...

Embodiment 2

[0071] A positron imaging agent 18 The preparation method of F-FPGalNAc comprises the following steps:

[0072] 1) Disperse 4-pentyn-1-ol (2.52g, 30mmol) in 100mL of dichloromethane, then add triethylamine (10.12g, 100mmol), 4-dimethylaminopyridine (0.16g, 1.32mmol) and p-toluenesulfonyl chloride (6.86g, 36mmol), react at room temperature for 10h, add ammonium chloride (5.35g, 0.1mol) to neutralize triethylamine, extract with ethyl acetate, and then remove the extract with anhydrous sodium sulfate Separated by water, vacuum distillation and column chromatography to obtain light yellow liquid Yield 74%; 1 H NMR (600MHz, CDCl3 )δ7.80(d, J=8.3Hz, 2H), 7.35(d, J=8.1Hz, 2H), 4.15(t, J=6.1Hz, 2H), 2.44(d, J=13.4Hz, 3H) ,2.26(dt,J=6.9,2.6Hz,2H),1.86(m,2H),1.23(m,1H);

[0073] 2) Will (35.7mg, 0.15mmol) was dispersed in 1mL acetonitrile, then added 18 F ions (100mCi), reacted at 80°C for 10min to obtain Yield 30%;

[0074] 3) Will (1g, 4.6mmol) was dispersed in 40mL of py...

Embodiment 3

[0079] A positron imaging agent 18 The preparation method of F-FPGalNAc comprises the following steps:

[0080] 1) Disperse 4-pentyn-1-ol (2.52g, 30mmol) in 100mL of dichloromethane, then add triethylamine (10.12g, 100mmol), 4-dimethylaminopyridine (0.16g, 1.32mmol) and p-toluenesulfonyl chloride (6.86g, 36mmol), react at room temperature for 20h, add ammonium chloride (5.35g, 0.1mol) to neutralize triethylamine, extract with ethyl acetate, and then remove the extract with anhydrous sodium sulfate Separated by water, vacuum distillation and column chromatography to obtain light yellow liquid Yield 81%; 1 H NMR (600MHz, CDCl 3 )δ7.80(d, J=8.3Hz, 2H), 7.35(d, J=8.1Hz, 2H), 4.15(t, J=6.1Hz, 2H), 2.44(d, J=13.4Hz, 3H) ,2.26(dt,J=6.9,2.6Hz,2H),1.86(m,2H),1.23(m,1H);

[0081] 2) Will (35.7mg, 0.15mmol) was dispersed in 1mL acetonitrile, then added 18 F ions (100mCi), reacted at 90°C for 10min to obtain Yield 35%;

[0082] 3) Will (1g, 4.6mmol) was dispersed in 20mL of ...

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Abstract

The invention discloses a positron imaging agent <18>F-FPGalNAc as well as a preparation method and an application thereof. The structural formula of the positron imaging agent is show in the description. The positron imaging agent <18>F-FPGalNAc contains an N-acetylgalactosamine group, binding affinity of the N-acetylgalactosamine group and an ASGPR (asialoglycoprotein receptor) is far higher than that of a galactose group and the ASGPR, and the positron imaging agent <18>F-FPGalNAc can specifically target tumors such as HepG2, A549, MDA-MB-231, MCF-7, HCT116 and the like with high ASGPR expression and has a good imaging effect.

Description

technical field [0001] The invention relates to a positron imaging agent 18 F-FPGalNAc and its preparation method and application. Background technique [0002] Malignant tumors can threaten human life and health, so early diagnosis and treatment are crucial. Anatomical imaging (ultrasound, CT, and MRI, etc.) can evaluate tumors from changes in anatomical forms such as size, shape, and density, and can provide accurate anatomical information of organs or tissues. It is currently the most commonly used clinical examination method. However, the formation of malignant tumors is a complicated process. Mutations of proto-oncogenes, tumor suppressor genes, and genes that directly or indirectly control cell proliferation occur first, followed by molecular changes and functional abnormalities, and finally morphological changes. . Therefore, only the diagnosis of tumors at the cellular and molecular levels is the real early diagnosis, while anatomical imaging cannot achieve molecu...

Claims

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Application Information

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IPC IPC(8): C07H19/056C07H1/00A61K51/04
CPCC07H19/056C07H1/00A61K51/0453C07B2200/05
Inventor 孙朋辉荀超超韩彦江胡孔珍黄顺王猛吴湖炳李贵平
Owner NANFANG HOSPITAL OF SOUTHERN MEDICAL UNIV
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