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Pegylated polyethyleneimine macromolecular magnetic resonance imaging contrast agent and preparation method of contrast agent

A technology of polyethyleneimine and magnetic resonance imaging, which is applied in the field of medical imaging contrast agents, can solve the problems of complex structure of polyamidoamine dendrimers, complex synthesis methods of block copolymers, and short blood circulation time, etc. Vascular and tissue imaging quality, improved biocompatibility and blood circulation time, and good practical value

Active Publication Date: 2014-06-25
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, it has been reported to link polyamidoamine dendrimer with targeting peptide to load gadolinium ion chelate (Han et al., Peptide-conjugated polyamidoamine dendrimer as a nanoscale tumor-targeted T1magnetic resonance imaging contrast agent, Biomaterials, 32 (2011), 2989 -2998) to achieve tumor-targeted MR imaging, but due to the complex structure of polyamidoamine dendrimers, it is difficult to mass-produce and expensive, which limits its wide promotion and application
In addition, Shiraishi et al. loaded gadolinium ion chelating agent with polyethylene glycol polylysine block copolymer (Shiraishi et al, Polyion complex micelle MRI contrast agents from poly(ethylene glycol)-b-poly(l-lysine) block copolymers having Gd-DOTA; preparations and their control of T1-relaxivities and blood circulation characteristics, Journal of Controlled Release, 2010, 148, 160-167) are used for MR imaging, but the synthesis method of block copolymers is complicated and the blood circulation time shorter

Method used

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  • Pegylated polyethyleneimine macromolecular magnetic resonance imaging contrast agent and preparation method of contrast agent
  • Pegylated polyethyleneimine macromolecular magnetic resonance imaging contrast agent and preparation method of contrast agent
  • Pegylated polyethyleneimine macromolecular magnetic resonance imaging contrast agent and preparation method of contrast agent

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Experimental program
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Effect test

Embodiment 1

[0056] Such as figure 1 PEI-DTPA(GdIII)-mPEG was prepared as indicated.

[0057] 80 mg of PEI (branched, Mw=25,000, purchased from Sigma-Aldrich) was dissolved in 40 mL of water, and 6 mL of an aqueous solution containing 57.1 mg of cDTPAA (purchased from Sigma-Aldrich) was added dropwise under stirring. Stir the reaction at room temperature for 12 hours to obtain an aqueous solution of PEI-DTPA; dialyze the reaction solution, and finally freeze-dry the aqueous solution of the product to obtain PEI-DTPA (108 mg, white solid);

[0058]Weigh 68.6mg of prepared PEI-DTPA, dissolve in 15mL of water, then dissolve 160mg of mPEG-NHS (molecular weight 5000, purchased from Shanghai Xibao Biological Co., Ltd.) in 16mL of water, add dropwise to PEI under magnetic stirring -in an aqueous solution of DTPA, and stirred at room temperature for 15 hours, finally dialyzed the reaction solution, and lyophilized the aqueous solution of the product to obtain PEI-DTPA-mPEG (212mg, white solid); ...

Embodiment 2

[0065] Preparation of PEI-DTPA(Gd III)-mPEG.

[0066] The rest is as shown in Example 1. In the step A: 120 mg of polyethyleneimine (PEI) was dissolved in 60 mL of water, and 9 mL of an aqueous solution containing 85.7 mg of cDTPAA was added dropwise;

[0067] In the step B: 240 mg of mPEG-NHS was dissolved in 24 mL of water, and added dropwise to the aqueous solution of 102.9 mg of PEI-DTPA prepared in step A;

[0068] In the step C: add 15.8 mg of gadolinium trichloride to the aqueous solution of 171.5 mg of PEI-DTPA-mPEG prepared in step B, and stir and react at room temperature for 4 hours to obtain a PEI-DTPA(GdIII)-mPEG aqueous solution, Then add 90 μL of triethylamine and stir for 40 minutes, finally add 60 μL of acetic anhydride, stir for 24 hours, then perform dialysis and freeze-dry to obtain the macromolecular magnetic resonance imaging contrast agent PEI-DTPA (Gd III) of PEGylated polyethyleneimine -mPEG.

Embodiment 3

[0070] T measured by in vitro MR 1 Value to test the MR imaging effect of the material PEI-DTPA(GdIII)-mPEG synthesized in Example 1 and the clinical MR contrast agent gadopentetate meglumine.

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Abstract

The invention belongs to the field of medical imaging contrast agents, and provides a pegylated polyethyleneimine macromolecular magnetic resonance imaging contrast agent and a preparation method of the contrast agent. The preparation method comprises the following steps: first, modifying a gadolinium ion chelating agent DTPA (Diethylenetriamine Pentaacetic Acid) on the surface of PEI (Polyethyleneimine) to prepare PEI-DPTA; second, modifying a composite material by pegylation to prepare PEI-DTPA-mPEG; and finally, chelating gadolinium ions to prepare PEI-DTPA (Gd III)-mPEG, and acetylating residual amino groups on the surface of PEI. The pegylated polyethyleneimine macromolecular magnetic resonance imaging contrast agent obtained by the invention realizes in vivo MR (Magnetic Resonance) blood vessel and kidney imaging of a mouse as well as passive targeted MR imaging detection of tumor tissues. The contrast agent is wide in application prospect.

Description

Technical field: [0001] The invention belongs to the field of medical imaging contrast agents, in particular to a polymer magnetic resonance imaging contrast agent based on polyethylene glycolated polyethyleneimine and a preparation method thereof. Background technique: [0002] Magnetic resonance imaging (MR) uses magnetic resonance phenomena to obtain electromagnetic signals from the human body to reconstruct human body information. It is a type of tomography (Tang Xiaoying, Liu Zhiwen, Liu Weifeng, Wu Qiyao, Magnetic resonance imaging technology and equipment development strategy, Science Herald, 2008, 26(9), 90-92; Wang Jun, Liu Jia, Application and Development Prospect of Functional Magnetic Resonance Imaging, Modern Instruments, 2008, 01, 6-10). This imaging technology is non-invasive, and can obtain tissue tomographic images and three-dimensional volume images in any direction, so it is widely used in clinical disease monitoring. However, in order to achieve high sen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K49/12C08G81/00C08G73/04
Inventor 朱巍周盛源吴振凯陈雄生贾连顺
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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