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A targeting compound for nuclide labeling and its preparation method and application

A compound and nuclide technology, applied in the field of medical imaging, can solve problems such as systematically raising, achieve the effect of short labeling time, increase target/non-target ratio, and speed up clearance

Active Publication Date: 2017-10-17
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The research on targeting molecular monomers and multimer probes can effectively enhance the affinity and binding force of molecular probes to tumor tissues. No one has systematically proposed or studied the concept of this targeting molecular multimer.

Method used

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  • A targeting compound for nuclide labeling and its preparation method and application
  • A targeting compound for nuclide labeling and its preparation method and application
  • A targeting compound for nuclide labeling and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1 - the synthesis of folic acid targeting monomer compound

[0057] The preparation method of folic acid targeting monomer compound, the reaction formula is as follows:

[0058]

[0059] 1)D 0 -FA 1 as an example

[0060] Dissolve folic acid in an appropriate amount of dimethyl sulfoxide, add a certain amount of N-hydroxysuccinimide (NHS) and dicyclohexylcarbodiimide (DCC), and filter after the reaction is complete in the dark. A certain amount of propargylamine (D 0 ) into the above-mentioned FA-NHS filtrate, add a small amount of N, N-diisopropylethylamine (DIPEA), after the reaction is complete, precipitate with ether, collect the precipitate and dry it to obtain D 0 -FA 1 .

[0061] 2) Preparation of azido HYNIC

[0062] Add 6-chloro-nicotine acid to an appropriate amount of 80% hydrazine hydrate, heat at high temperature to make it react completely, and concentrate to obtain a light yellow solid. Dissolve the solid in water, adjust the pH to b...

Embodiment 2

[0065] Embodiment 2——Synthesis of PEG-modified folic acid targeting monomer compound

[0066] The preparation method of the PEG-modified folic acid targeting monomer compound, the reaction formula is as follows:

[0067]

[0068] 1) FA-PEG-NH 2 Synthesis

[0069] Dissolve folic acid in an appropriate amount of dimethyl sulfoxide, add a certain amount of N-hydroxysuccinimide (NHS) and dicyclohexylcarbodiimide (DCC), and filter after the reaction is complete in the dark. Dissolve 2,2'-(ethylenedioxy)bis(ethylamine) in DMSO, add appropriate amount of DIPEA, dropwise add DMSO solution in which FA-NHS is dissolved, after the reaction is complete, precipitate with dichloromethane, collect the precipitate and dry it. FA-PEG-NH 2 .

[0070] 2) Synthesis of FA-PEG-COOH

[0071] Add excess succinic anhydride and catalytic amount of 4-dimethylaminopyridine to FA-PEG-NH 2 DMSO solution, stirred overnight at room temperature, filtered the reaction solution, precipitated with ether...

Embodiment 3

[0076] Example 3——Synthesis of folic acid-targeted polymer compound

[0077] The preparation method of folic acid targeting polymer compound, the reaction formula is as follows:

[0078]

[0079] 1) Molecular skeleton D n Synthesis:

[0080]

[0081] I)D 0.5 Synthesis

[0082] In an ice-water bath, 100 mL of methanol solution of methyl acrylate was added to a three-necked flask, and propargylamine (D) was added dropwise under nitrogen protection. 0 ) in methanol solution 50mL. After reacting in an ice bath for 1h, react at room temperature for 3d, and remove the solvent anhydrous methanol and excess methyl acrylate by rotary evaporation to obtain D 0.5 For the yellow liquid.

[0083] II) D 1 Synthesis

[0084] In an ice-water bath, the D 0.5 Soluble in methanol, slowly dropwise added to methanol solution containing ethylenediamine under the protection of nitrogen. After the dropwise addition, the reaction was continued in an ice bath for 1 h, and then stirred a...

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Abstract

The invention discloses a targeting compound for nuclide labeling and its preparation method and application. The general structural formula of the complex is as follows: or wherein R1 is a nuclide chelating group, R2 is a targeting group, and Dn It is a molecular skeleton formed by repeated Michael addition reaction and amidation reaction with propargylamine as the initial reactant, and its peripheral group is amino group, n represents different algebra and its value is an integer greater than or equal to 0, m=2n. The monomer and multimer formed by the targeting group and nuclide of the targeting compound used for nuclide labeling of the present invention have high targeting and affinity to tumor tissue, and high-quality imaging results can be obtained through instrument scanning , to effectively monitor tumor or inflammatory diseases.

Description

technical field [0001] The invention belongs to the technical field of medical imaging, and in particular relates to a targeting compound for nuclide labeling, a preparation method and application thereof. Background technique [0002] Malignant tumors have become a serious disease that threatens human health and life. Early detection, early diagnosis and early treatment are effective measures to treat and control tumors, but certain auxiliary diagnostic methods are needed. One of these involves molecular imaging diagnostics. Molecular imaging is known as the medical imaging of the 21st century and is one of the most promising frontier fields of medical science. However, the embodiment of its superiority requires imaging targeting compounds with good targeting and specificity in order to better diagnose and treat diseases. Nuclear medicine technology is a non-invasive technology that synthesizes highly specific tumor imaging agents, which will play an important role in the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00C07D475/04C09K11/06
Inventor 张现忠郭志德宋曼莉张蒲刘畅赵祚全吴晓伟
Owner XIAMEN UNIV
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