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Glucosamine derivative ligand compound and preparing method, tricarbonyl Tc-99m labeled complex and preparing method and application of tricarbonyl Tc-99m labeled complex

A ligand compound, glucosamine technology, applied in the field of clinical nuclear medicine, can solve problems such as limited use of cyclotrons, short half-life, etc., and achieve stable performance, easy preparation, and simple preparation effects

Active Publication Date: 2015-10-28
INST OF HIGH ENERGY PHYSICS CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 18 F-FDG has wide applications in nuclear medicine, but 18 The half-life of F is relatively short, and the use of a cyclotron is relatively expensive in the preparation process, and the use is still limited

Method used

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  • Glucosamine derivative ligand compound and preparing method, tricarbonyl Tc-99m labeled complex and preparing method and application of tricarbonyl Tc-99m labeled complex
  • Glucosamine derivative ligand compound and preparing method, tricarbonyl Tc-99m labeled complex and preparing method and application of tricarbonyl Tc-99m labeled complex
  • Glucosamine derivative ligand compound and preparing method, tricarbonyl Tc-99m labeled complex and preparing method and application of tricarbonyl Tc-99m labeled complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1 Preparation of glucosamine derived ligand compound (DAP-n-DG)

[0046] Such as figure 1 shown, including the following steps:

[0047] (1) Synthesis of tert-butyl 2-amino-2-cyanoacetate (II)

[0048] Add 11.98 g of tert-butyl 2-oximino-2-cyanoacetate (I) into 88 mL of deionized water, add 80 mL of saturated aqueous sodium bicarbonate solution prepared in advance, and react under stirring for about 40 min. The reaction bottle was placed in a 40°C oil bath, and a total of 33 g of sodium hydrosulfite was added in portions. The reaction is about 9h. Add 15g of sodium chloride, fully dissolve and cool to room temperature. The mixture was repeatedly extracted with dichloromethane (50 mL each time), the organic phase extract was dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain 2.10 g of brown oil (II), with a yield of 19%.

[0049] (2) Synthesis of 2.2-(N-tert-butoxycarbonylamino)-2-tert-butyl cyanoacetate (I...

Embodiment 2 3

[0077] Example 2 Preparation of Tricarbonyl Technetium-99m Labeled Complexes

[0078] Weigh 5.5 mg of sodium borohydride, 20 mg of sodium potassium tartrate, and 4 mg of sodium carbonate into penicillin vials, cover with a rubber stopper and then seal with an aluminum cap, extract air with an aspirating needle, and inject CO gas into it for 10-20 min. will be used from medical 99 Mo- 99m Sodium pertechnetate Na[ 99m TCO 4 ] Eluent 2mL (about 2mCi·mL -1 ), added into the reaction flask, shaken to dissolve, and then reacted for 30 minutes under the condition of heating in a metal bath at 75°C to obtain the tricarbonyl technetium-99m intermediate. Add 1mol·L -1 hydrochloric acid to adjust the pH to 7.

[0079] Dissolve 10mg DAP-2-DG in 0.5mL 0.5mol·L -1 In the pH7.0 phosphate buffer solution, add tricarbonyl technetium-99m intermediate solution. React at 95°C for 15 minutes. get 99m Tc(CO) 3 -DAP-2-DG.

[0080] Through thin layer chromatography and HPLC identification...

Embodiment 3 3

[0081] Example 3 Preparation of Tricarbonyl Technetium-99m Labeled Complexes

[0082] Weigh 5.5 mg of sodium borohydride, 20 mg of sodium potassium tartrate, and 4 mg of sodium carbonate into penicillin vials, cover with a rubber stopper and then seal with an aluminum cap, extract air with an aspirating needle, and inject CO gas into it for 10-20 min. will be used from medical 99 Mo- 99m Sodium pertechnetate Na[ 99m TCO 4 ] Eluent 2mL (about 2mCi·mL -1 ), added into the reaction flask, shaken to dissolve, and then reacted for 30 minutes under the condition of heating in a metal bath at 75°C to obtain the tricarbonyl technetium-99m intermediate. Add 1mol·L -1 hydrochloric acid to adjust the pH to 7.

[0083] Dissolve 2mg DAP-3-DG in 0.5mL 0.5mol·L -1 In pH7.0 phosphate buffer solution, add tricarbonyl technetium-99m intermediate solution. React at 95°C for 15 minutes. get 99m Tc(CO) 3 -DAP-3-DG.

[0084] Through thin layer chromatography and HPLC identification, it...

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Abstract

The invention provides a glucosamine derivative ligand compound and a preparing method thereof. The invention further provides a tricarbonyl Tc-99m labeled complex, wherein the tricarbonyl Tc-99m labeled complex is of the structure shown in the general formula (B). The invention further provides a preparing method and application of the tricarbonyl Tc-99m labeled complex. According to the glucosamine derivative ligand compound, 3-Aminoalanine is used for being coupled with glucosamine, the raw materials are easy to obtain, and the preparing method is easy and convenient to implement. The tricarbonyl Tc-99m labeled complex is formed by the glucosamine derivative ligand compound and the radioactive tc-carbonyl-99m, and is high in chemical stability, simple in preparation, high in chemical purity, good in biological property and capable of being used for preparing a novel tumor SPECT developer. The structure is shown in the specification.

Description

technical field [0001] The invention relates to the technical field of clinical nuclear medicine, in particular to a glucosamine-derived ligand compound and a preparation method thereof, as well as a tricarbonyl technetium-99m labeled complex obtained from the glucosamine-derived ligand compound, a preparation method and the use. Background technique [0002] Glucose is an important substance required for energy metabolism. After entering the blood circulation, it depends on the glucose transporter (glucose transporter, GLUT) to enter cells in the body. The energy metabolism of tumor cells is abnormal, and their glucose uptake is higher than that of normal cells. Therefore, the uptake of glucose and its analogs by tumor tissue can be used to prepare radioactive molecular probes for glucose metabolism, which can be used for non-invasive examination and evaluation of tumors in vivo. 18 F-deoxyglucose ( 18 F-FDG) is the hydroxyl group on the second carbon atom of glucose by ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H5/06C07H1/00C07F13/00A61K51/04A61K103/10
CPCY02P20/55
Inventor 杨文江刘宇张延华魏乐薛井泉汪建军
Owner INST OF HIGH ENERGY PHYSICS CHINESE ACADEMY OF SCI
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