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Degradable dendritic macromolecule magnetic resonance contrast agent and preparation method thereof

A magnetic resonance contrast agent and macromolecular technology, which is used in medical preparations, pharmaceutical preparations, and preparations for in vivo experiments with inactive ingredients, etc., can solve the problems of difficult molecular weight control, low contrast efficiency, and wide distribution, and achieve Simple operation, good imaging effect, and the effect of improving the level of diagnosis

Active Publication Date: 2013-04-24
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of linear polymer contrast agent has disadvantages such as difficult molecular weight control, wide distribution, and low imaging efficiency, which limit its clinical application (Hisata; Kobayasbi; Martin; W. Brecbbiel, Dwndrimer-based Macrom olecular MRI Contrast Agents :Characteristics and Application. Molecular Imaging2003, 2, 1-10.)

Method used

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  • Degradable dendritic macromolecule magnetic resonance contrast agent and preparation method thereof
  • Degradable dendritic macromolecule magnetic resonance contrast agent and preparation method thereof
  • Degradable dendritic macromolecule magnetic resonance contrast agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Synthesis of the first generation dendrimer contrast agent

[0040] The synthesis process contains three steps: (1) activation of DTPA; (2) synthesis of dendrimer ligand; (3) synthesis of dendrimer contrast agent.

[0041] (1) Activation of DTPA

[0042] NHS (2.108g) and DCC (3.78g) were dissolved in 40mL and 60mL of acetonitrile, respectively, and added dropwise to DTPA (12.005g) in acetonitrile in an ice bath. Reaction at room temperature for 8h. DCC was removed by filtration, acetonitrile was removed by rotary evaporation, and the product was dissolved in 30 mL dimethyl sulfoxide (DMSO) to obtain a DTPA-NHS solution.

[0043] (2) Synthesis of dendrimer ligands

[0044]

[0045] Tris(2-aminoethyl)amine (0.2g, 1.37mmol) shown in formula II and MAEA (2g, 10.94mmol) shown in formula III were reacted in an oil bath at 50°C for 48 hours to obtain the first generation poly Ester dendrimer G1.

[0046]

[0047] The first generation polyester dendrimer G 1...

Embodiment 2

[0053] Example 2 Synthesis of Second Generation Dendrimer Contrast Agent

[0054] (1) Activation of DTPA

[0055] NHS (2.108g) and DCC (3.78g) were dissolved in 40mL and 60mL of acetonitrile, respectively, and added dropwise to DTPA (12.005g) in acetonitrile in an ice bath. Reaction at room temperature for 8h. DCC was removed by filtration, acetonitrile was removed by rotary evaporation, and the product was dissolved in 30 mL DMSO to obtain a DTPA-NHS solution.

[0056] (2) Synthesis of dendrimer ligands

[0057] Dissolve the first generation polyester dendrimer G1 (1.5100g, 1.2mmol), cysteamine (0.6376g, 8.28mmol) and MAEA (9.14g, 49.68mmol) in 7mL DMSO, react at room temperature for 24h, 50℃ The oil bath reaction was carried out for 48 hours to obtain the second generation polyester dendrimer G2.

[0058]

[0059] Dissolve the second-generation polyester dendrimer G2 (0.3082g, 0.07653mmol) and cysteamine (0.0849g, 1.102mmol) in 2mL DMSO, react at room temperature for ...

Embodiment 3

[0064] Example 3 Synthesis of the third generation dendrimer contrast agent

[0065] (1) Activation of DTPA

[0066] NHS (2.108g) and DCC (3.78g) were dissolved in 40mL and 60mL of acetonitrile, respectively, and added dropwise to DTPA (12.005g) in acetonitrile in an ice bath. Reaction at room temperature for 8h. DCC was removed by filtration, acetonitrile was removed by rotary evaporation, and the product was dissolved in 30 mL DMSO to obtain a DTPA-NHS solution.

[0067] (2) Synthesis of dendrimer ligands

[0068] The second generation polyester dendrimer G2 (1.0755g, 0.2725mmol), cysteamine (0.2882g, 3.7605mmol) and MAEA (2.4221g, 13.1618mmol) were dissolved in 5mL DMSO and reacted at room temperature for 24h, 50 ℃ oil bath for 48 hours to obtain the third generation polyester dendrimer G3.

[0069]

[0070] Dissolve the third-generation polyester dendrimer G3 (0.4g, 0.0292mmol) and cysteamine (0.0648g, 0.841mmol) in 2mL DMSO, react at room temperature for 1.5h, and ...

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Abstract

The invention discloses a degradable dendritic macromolecule magnetic resonance contrast agent and a preparation method thereof. The degradable dendritic macromolecule magnetic resonance contrast agent is characterized in that a degradable dendritic macromolecule is used as a skeleton and micromolecular gadolinium chelates are connected to the degradable dendritic macromolecule so that the degradable dendritic macromolecule magnetic resonance contrast agent is formed. The degradable dendritic macromolecule magnetic resonance contrast agent has a relaxation rate of 17.4mM<-1>.s<-1> obviously higher than a relaxation rate of the common contrast agent, has a better MRI contrast effect, can be enriched in tumor tissue by enhanced permeation and retention effects of the degradable dendritic macromolecule magnetic resonance contrast agent, and improves MRI sensitivity and an early diagnosis level of cancers. The degradable dendritic macromolecule magnetic resonance contrast agent can be hydrolyzed by internal esterase catalysis and then is gradually discharged out of a human body so that the toxicity accumulation of gadolinium in a human body is avoided. The preparation method has simple processes, can be controlled easily and is suitable for industrial large-scale production.

Description

technical field [0001] The invention relates to the field of magnetic resonance contrast agents, in particular to a degradable dendrimer magnetic resonance contrast agent and a preparation method thereof. Background technique [0002] Magnetic resonance imaging (MRI), as an important medical imaging technology, has been widely used in the imaging diagnosis of various tissues and organs of the human body. Through the use of contrast agent-assisted imaging, it has high resolution for detecting tissue necrosis, ischemia, various malignant lesions and tumors, and has a series of characteristics such as non-toxic, non-radiation damage and high sensitivity. [0003] The metal chelating agent is connected to the macromolecular skeleton to increase its circulation time and relaxation rate in the body, and can actively or passively target cancer tissue through the hyperpermeability and retention (EPR) effect, which can improve the contrast effect of the contrast agent ( Kopecek, J.;...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K49/12A61K47/48
Inventor 唐建斌申有青李亭亭隋梅花
Owner ZHEJIANG UNIV
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