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Amino acid-glucose derivative 99m TC compound and its prepn process

A technology of glucose derivatives, 99mtco-, applied in the field of amino acid-glucose derivative complexes and their preparation, can solve the problems of affecting the biological activity of glucose, weak coordination ability of bifunctional linkers, large molecular volume of bifunctional linkers, etc. question

Inactive Publication Date: 2012-09-05
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although new types of 99m A lot of work has been done on the Tc-labeled glucose derivative tumor imaging agent, and many valuable research results have been obtained, but there are also some general problems and defects: ①The molecular volume of the bifunctional linker connected with glucose is too large Big, 99m The biochemical properties and charge properties of the group formed by the coordination between Tc and the bifunctional linker change the properties of the sugar group connected to it, which affects the biological activity of glucose, resulting in the label being unable to be detected by the glucose transporter (GLUTs). ) recognized and transported into tumor cells or unable to be acted by hexokinase; ② bifunctional linker and 99m Tc coordination ability is not strong;③ 99m Tc-labeled glucose derivatives have poor stability in vivo and in vitro, etc.

Method used

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  • Amino acid-glucose derivative 99m TC compound and its prepn process
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  • Amino acid-glucose derivative 99m TC compound and its prepn process

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Experimental program
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Effect test

Embodiment 1

[0054] 99m The preparation method of the amino acid-glucose derivative complex (L7) of Tc label, its step is as follows:

[0055] 1. Synthesis of cysteine ​​methyl ester-linked glucose derivative (L7)

[0056] (1) Synthetic route:

[0057]

[0058] (2) Synthesis method:

[0059] a. Synthesis of compound 1 (cysteine ​​methyl ester hydrochloride)

[0060] 26ml (300mmol) of thionyl chloride was added dropwise to methanol in an ice-salt bath (-15°C), the mixture was stirred for 20min, 12.1g (100mmol) of L-cysteine ​​was added, and stirred at room temperature for 24h. Rotary evaporation was performed, and the obtained solid was washed several times with ethyl acetate to obtain cysteine ​​methyl ester hydrochloride with a product yield of 82.9%.

[0061] h 1 -NMR (DMSO-d 6 , 500MHZ): δ(ppm)3.29-3.33(m, 2H), 3.36-3.42(m, 2H), 3.76(s, 3H), 4.35-4.37(m, 1H).

[0062] b. Synthesis of Compound L7

[0063] Add 13.5g (100mmol) of cysteine ​​methyl ester hydrochloride to a round-...

Embodiment 2

[0093] Example 2: Synthesis of cysteine-linked glucose derivatives (L8)

[0094] (1) The structure of the compound:

[0095]

[0096] (2) Synthesis method:

[0097] Add 1.2g (10mmol) cysteine ​​and 1.9g (10mmol) D-glucose into a mixed solution of ethylene glycol dimethyl ether and water (volume ratio 8 / 2), heat and reflux for 3h, a white solid appears, After cooling, filter under reduced pressure, wash the precipitate with ethanol and ether, recrystallize from ethanol, and the product L8 is a white powder.

[0098] Yield 67.7%

[0099] Product melting point: 163.3~165.8℃

[0100] Elemental analysis results: measured values: N 5.11, C 37.42 and H 6.10%;

[0101] Theoretical: N 4.94, C 38.16 and H 6.05%

[0102] Mass spectrometry MS (ESI): found value: 284.0 (M+H) + , 306.0 (M+Na) + ;

[0103] Theoretical value: 284.0 (M+H) + , 306.0 (M+Na) + ;

[0104] h 1 -NMR (DMSO-d 6 , 500MHz): δ(ppm) 2.87(m, 1H), 3.02(m, 1H), 3.20(m, 1H), 3.36-3.38(m, 2H), 3.44-3.48(m, 1H),...

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Abstract

The present invention relates to one kind of 99mTc marked amino acid-glucose derivative complex, which has kernel of [99mTcO]3+ and ligand as shown below is L7 or L8. The complex has relatively high tumor ingestion, long detention time of the marker in tumor, and high targeting / non-targeting ratio.

Description

technical field [0001] The invention relates to an amino acid-glucose derivative complex and a preparation method thereof, in particular to an amino acid-glucose derivative complex 99m Tc complex and its preparation method. Background technique [0002] Glucose is the main energy source of the human body, and the normal work of the brain and heart is inseparable from the metabolism of glucose. 18 F-FDG(2-deoxy-2-[ 18 F]fluoro-D-glucose) is an extremely important PET radiopharmaceutical in medical diagnostics, eg in cardiology and neurology. Furthermore, since glucose metabolism is significantly increased in many types of tumors, 18 F-FDG is often used in the diagnosis and evaluation of tumors. As we all know, 18 F-FDG is an excellent radioactive molecular probe for PET clinical glucose metabolism imaging diagnosis, but its clinical application is greatly limited due to its high price and high application conditions. In recent years, based on the excessive metabolism of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F13/00A61K51/04A61K103/10
Inventor 刘锰朱霖刘亚静
Owner BEIJING NORMAL UNIVERSITY
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