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A magnetic resonance imaging contrast agent, its preparation method and application

A magnetic resonance imaging and contrast agent technology, applied in the application field of the product, to achieve excellent imaging contrast performance, long tumor targeting specificity, and good biocompatibility

Active Publication Date: 2022-02-11
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no report on the use of aptamers as targeting molecules for the targeted delivery of gadolinium-based complexes.

Method used

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  • A magnetic resonance imaging contrast agent, its preparation method and application
  • A magnetic resonance imaging contrast agent, its preparation method and application
  • A magnetic resonance imaging contrast agent, its preparation method and application

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preparation example Construction

[0040] Another aspect of the embodiments of the present invention also provides a method for preparing a magnetic resonance imaging contrast agent, which includes:

[0041] reacting at least α,ω-distacysamine polyethylene glycol with α-cyclodextrin to form pseudopolyrotaxanes;

[0042] At least reacting the pseudopolyrotaxane with Z-tyrosine, a Carter condensing agent, 1-hydroxybenzotriazole, and N,N-diisopropylethylamine to form a Z-tyrosine-terminated polyrotaxane alkyl;

[0043] At least reacting the Z-tyrosine-terminated polyrotaxane with propargylcarbonylimidazole to form a surface alkynyl-modified rapidly reductively cleavable polyrotaxane;

[0044] At least reacting the rapidly reductively cleavable polyrotaxane modified by the surface alkyne group with the lysine second-generation dendrimer whose terminal group is azide to form a cleavable polyrotaxane grafted by the lysine second-generation dendrimer ;

[0045] At least the cleavable polyrotaxane grafted with the s...

Embodiment 1

[0091] In this embodiment, a preparation method of an aptamer-targeted and rapidly reductively cleavable polyrotaxane as a carrier for MRI contrast agents comprises the following steps:

[0092] Step 1: Polyethylene glycol (Mw=4000) was refluxed with toluene and dried to remove water. Then, dry polyethylene glycol and N,N'-carbonyldiimidazole were added into the reaction flask at a molar ratio of 1:15, and the reaction flask was filled with dry nitrogen through three cycles of vacuuming and nitrogen filling. Mix in anhydrous tetrahydrofuran under the protection of nitrogen, and stir at room temperature for 18 hours to obtain active intermediate α, ω-biscarbonylimidazole polyethylene glycol, by-products and other impurities.

[0093] After the reaction in step 1, the solution was precipitated in ether, filtered by suction, redissolved in anhydrous tetrahydrofuran and reprecipitated in ether, repeated three times to remove unreacted reagents, collected the precipitate, and dried...

Embodiment 2

[0107] In this embodiment, a preparation method of an aptamer-targeted and rapidly reductively cleavable polyrotaxane as a carrier for MRI contrast agents comprises the following steps:

[0108] Step 1: This step is similar to Step 1 in Example 1, only the molar ratio of dry polyethylene glycol and N,N'-carbonyldiimidazole is adjusted to 1:20, and the stirring time at room temperature is adjusted to 24 hours.

[0109] Step 2: This step is completely similar to Step 2 in Example 1, except that the active intermediate PEG-CI and cystamine are dissolved in anhydrous THF at a molar ratio of 1:50. Under the protection of nitrogen, the tetrahydrofuran solution of PEG-CI was slowly added dropwise to the cystamine solution, and stirred at room temperature for 24 hours.

[0110] Step 3: This step is completely similar to Step 3 in Example 1, except that after 12 hours of reaction, the precipitate is collected by centrifugation. And, the obtained viscous suspension was stirred at room ...

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Abstract

The invention discloses a magnetic resonance imaging contrast agent, its preparation method and application. The preparation method comprises: reacting α,ω-dicystamine polyethylene glycol with α-cyclodextrin to form a pseudopolyrotaxane, and then capping with Z-tyrosine to obtain a Z-tyrosine-capped poly Rotaxane, and then reacted with propargylcarbonylimidazole to form surface alkyne-modified rapidly reductively cleavable polyrotaxane, and then reacted with azide-terminated lysine dendrimers to form lysine by click chemistry The cleavable polyrotaxane grafted by the second-generation dendrimer is then bonded with gadolinium chelate and loaded with gadolinium to form the cleavable polyrotaxane grafted by the second-generation dendrimer modified by gadolinium chelate. The magnetic resonance imaging contrast agent of the present invention has good biocompatibility, low toxicity, and high relaxation rate; the present invention also introduces the AS1411 aptamer as a targeting molecule to realize tumor cells and tumor cells overexpressing nucleolin in the cell membrane. Multivalent targeting of tumors is more conducive to in vivo tumor magnetic resonance imaging.

Description

technical field [0001] The invention relates to a contrast agent for magnetic resonance imaging and its preparation method, as well as the application of the magnetic resonance imaging contrast agent in the preparation of products with tumor detection function, belonging to the technical field of pharmaceutical preparation. Background technique [0002] With the development of science and technology, magnetic resonance imaging has become an effective means of clinical detection of diseases. Compared with other clinical imaging techniques, magnetic resonance imaging has many advantages in revealing anatomical structures, especially in detecting inflammatory tissues and solid tumors. In addition, magnetic resonance imaging also has no ionizing radiation damage, and multi-parameter imaging provides doctors with a large amount of diagnostic information and three-dimensional positioning capabilities. However, in order to further improve the sensitivity and accuracy of imaging, c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/18A61K49/08A61K49/12C08G83/00
CPCA61K49/085A61K49/128A61K49/1845C08G83/007
Inventor 裴仁军祖广月曹翼
Owner SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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