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2-[19F] fluoro-2-deoxy-glucose as well as preparation method and application thereof

A technology of glucose and glucosene, applied in the preparation of sugar derivatives, organic chemical methods, chemical instruments and methods, etc., can solve the problems of H-MRI signal-to-noise ratio, contrast and artifacts, and achieve good active targeting effect , good biological safety, and excellent imaging precision

Pending Publication Date: 2022-03-01
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the living body contains a large amount of water molecules (total mass accounts for 65% to 80%), 1 H-MRI suffers from issues with signal-to-noise ratio, contrast and artifacts

Method used

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  • 2-[19F] fluoro-2-deoxy-glucose as well as preparation method and application thereof
  • 2-[19F] fluoro-2-deoxy-glucose as well as preparation method and application thereof
  • 2-[19F] fluoro-2-deoxy-glucose as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1) prepare acetylated 2-[ 19 F] Fluoro-2-deoxy-glucose:

[0031]

[0032] Mix 6 g of commercial reagent 3,4,6-O-triacetyl-D-glucosene in 60 ml of mixed solution of nitromethane and water (5:1), and fluorinating agent (Selectfluor @ ) 10g room temperature reaction for 10h, spin dry, dissolve the solid with dichloromethane, extract with 5% sodium bicarbonate solution, collect the organic layer and spin dry, then add 50ml dichloromethane, 3.5ml pyridine, 2.5ml acetic anhydride and react at room temperature for 12h, then Add 40ml of saturated sodium bicarbonate solution for extraction twice, then collect the organic layer and spin dry the organic layer, separate and purify through the column to obtain the isomerically pure product. Among them: the column separation eluent ratio is ethyl acetate: n-hexane = 1:4.

[0033] 2) Preparation of 2-[ 19 F] Fluoro-2-deoxy-glucose:

[0034]

[0035] The acetylated 2-[ 19 F] Fluorine-2-deoxy-glucose 4g was reacted in 30wt% s...

Embodiment 2

[0037] put 2-[ 19 F] Fluoro-2-deoxy-glucose weighs a certain quality with D 2 The concentration of O is 0.5ml, 1, 2, 4, 8mM respectively, and then passed the 600MHZ test 19 F Fluor signal. image 3 2-[ 19 F]fluoro-2-deoxy-glucose 19 F fluorine signal ( 19 F-NMR) figure. Figure 4 For 2-[ 19 F]fluoro-2-deoxy-glucose 19 F fluorine signal ( 19 F-NMR) figure obtained 19 F Plot of signal-to-noise ratio of fluorine signal as a function of concentration.

Embodiment 3

[0039] put 2-[ 19 F] Fluoro-2-deoxy-glucose weighs a certain mass with H 2 The concentrations of O were 20, 40, 60, 80, 100, and 120 mM, respectively, and 2 ml were filled into chromatographic bottles, and then the imaging effect of fluorine signals in vitro was tested by 9.4T MRI. Figure 5 2-[ 19 F]Fluoro-2-deoxy-glucose in vitro imaging effect ( 19 F-MRI) figure. Figure 6 For 2-[ 19 F]Fluoro-2-deoxy-glucose in vitro imaging effect ( 19 F-MRI) signal-to-noise ratio versus concentration.

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Abstract

The invention discloses 2-[19F] fluoro-2-deoxy-glucose as well as a preparation method and application thereof, and relates to the field of magnetic resonance imaging, the 2-[19F] fluoro-2-deoxy-glucose is a product obtained on the basis that a hydroxyl group on the site 2 of glucose is substituted by fluorine-19, so that a nuclear magnetic signal is generated by utilizing a fluorine-19 atomic nucleus to carry out magnetic resonance imaging. The preparation method comprises the following steps: reacting 3, 4, 6-O-triacetyl-D-glucosene with a fluorinating agent in a mixed solution of nitromethane and water, then acetylating with pyridine and acetic anhydride, and finally deprotecting in a sodium methoxide methanol solution to obtain the probe. The probe is used for < 19 > F magnetic resonance imaging, has excellent imaging precision of MRI, has good biological safety as a glucose analogue, and has a good active targeting effect (transports protein through glucose) when applied to tumors.

Description

technical field [0001] The invention relates to the field of magnetic resonance imaging, in particular to a 19 F MRI Reagent 2-[ 19 F] Fluoro-2-deoxy-glucose and its preparation method and application. Background technique [0002] Magnetic resonance imaging (MRI) is widely used in the imaging diagnosis of soft tissue lesions because of its characteristics of no ionizing radiation, non-invasiveness, high-resolution tissue and tomography. An MRI scan can contain multiple levels of scan information and even full-body imaging. Combined with computer reconstruction technology, a three-dimensional image can be constructed, greatly improving the accuracy and precision of diagnosis. Among them, many patients need to inject MRI contrast agent to enhance the imaging effect, so as to achieve the purpose of accurate and rapid assessment of the disease. The current MRI is mainly for hydrogen nuclei ( 1 H) imaging, namely 1 H-MRI. However, because the living body contains a large a...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H5/02C07B59/00A61K49/10
CPCC07H1/00C07H5/02C07B59/005A61K49/10C07B2200/05
Inventor 高锦豪罗祥杰唐小雪李奥林泓域
Owner XIAMEN UNIV
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