Paramagnetic metal complex using aspartic acid-isoleucine copolymer as carrier, preparation method of paramagnetic metal complex and magnetic resonance imaging contrast agent

A technology of isoleucine copolymer and aspartic acid, which is applied in preparations for in vivo experiments and pharmaceutical formulations, can solve the problems of low contrast agent liver recognition, short imaging time, and low relaxation efficiency. Achieve good water solubility, long imaging time and high relaxation efficiency

Inactive Publication Date: 2016-02-24
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Claims
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Problems solved by technology

[0003] The purpose of the present invention is to solve the technical problems of low contrast agent liver recognition, short imaging time, and low relaxation efficiency in the prior art, and to provide an aspartic acid-isoleucine copolymer as a carrier Paramagnetic metal complex, preparation method and magnetic resonance imaging contrast agent

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  • Paramagnetic metal complex using aspartic acid-isoleucine copolymer as carrier, preparation method of paramagnetic metal complex and magnetic resonance imaging contrast agent
  • Paramagnetic metal complex using aspartic acid-isoleucine copolymer as carrier, preparation method of paramagnetic metal complex and magnetic resonance imaging contrast agent
  • Paramagnetic metal complex using aspartic acid-isoleucine copolymer as carrier, preparation method of paramagnetic metal complex and magnetic resonance imaging contrast agent

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[0040] The present invention also provides a method for preparing a paramagnetic metal complex with an aspartic acid-isoleucine copolymer as a carrier, comprising the following steps:

[0041] Step 1: preparing aspartic acid-isoleucine copolymer;

[0042] Step 2: reacting the aspartic acid-isoleucine copolymer obtained in step 1 with ethylenediamine to obtain an aminated aspartic acid-isoleucine copolymer;

[0043] Step 3: react the aminated aspartic acid-isoleucine copolymer obtained in step 2 with DOTA mono-N-hydroxyl sulfosuccinimide active ester to obtain aspartic acid-isoleucine 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid macromolecule ligand with copolymer as carrier;

[0044]Step 4: The 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid obtained in step 3 with aspartic acid-isoleucine copolymer as a carrier The molecular ligand reacts with the aqueous solution containing paramagnetic metal ions to obtain the paramagnetic metal complex with the aspar...

Embodiment 1

[0062] Preparation of Aspartic Acid-Isoleucine Copolymers Modified by Ethylenediamine 1,4,7,10-Tetraazacyclododecane-1,4,7,10-Gadolinium Tetraacetate Complexes

[0063] (1) Mix 20 grams of L-aspartic acid with 5 grams of L-isoleucine, add 8 grams of the mixed mixture into a phosphoric acid solution with a mass fraction of 85%, and stir evenly. (24mmHg) for 5 hours, the reaction temperature was controlled at 165°C, precipitated with deionized water, filtered, washed, and dried under reduced pressure to obtain an aspartic acid-isoleucine copolymer;

[0064] (2) Dissolve the aspartic acid-isoleucine copolymer synthesized in (1) in N,N-dimethylformamide solution at room temperature, and add ethylenediamine and ethylenediamine dropwise while stirring. The mass ratio of amine to aspartic acid-isoleucine copolymer was 2.8:1, stirred at room temperature for 4 hours, precipitated with ether, filtered, dialyzed, and freeze-dried to obtain aminated aspartic acid-isoleucine copolymer thi...

Embodiment 2

[0069] Preparation of Aspartic Acid-Isoleucine Copolymers Modified by Ethylenediamine 1,4,7,10-Tetraazacyclododecane-1,4,7,10-Gadolinium Tetraacetate Complexes

[0070] (1) Mix 20 grams of L-aspartic acid with 2 grams of L-isoleucine, add 8 grams of the mixed mixture into a phosphoric acid solution with a mass fraction of 85%, and stir evenly. (100mmHg) for 1 hour, the reaction temperature was controlled at 220°C, precipitated with deionized water, filtered, washed, and dried under reduced pressure to obtain an aspartic acid-isoleucine copolymer;

[0071] (2) with step (2) in embodiment 1;

[0072] (3) with step (3) in embodiment 1;

[0073] (4) Same as step (4) in Example 1.

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Abstract

The invention provides a paramagnetic metal complex using an aspartic acid-isoleucine copolymer as a carrier, a preparation method of the paramagnetic metal complex and a magnetic resonance imaging contrast agent, and belongs to the field of the magnetic resonance imaging contrast agent, in order to solve the technical problems of a contrast agent in the prior art which is relatively low in liver identification, short in imaging time and not high in relaxivity. The complex takes the aspartic acid-isoleucine copolymer as a carrier and is connected with a ring-shaped 1,4,7,10-tetraazacycl ododecane-1,4,7,10-tetraacetic acid ligand on a side chain of the carrier, and the structure of the complex is as shown in formula (I). The invention also provides a preparation method of the paramagnetic metal complex using the aspartic acid-isoleucine copolymer as a carrier. The invention also provides a magnetic resonance imaging contrast agent which is prepared from the paramagnetic metal complex using the aspartic acid-isoleucine copolymer as a carrier. The contrast agent disclosed by the invention has good selectivity for livers of human bodies or other mammals.

Description

technical field [0001] The invention belongs to the field of magnetic resonance imaging contrast agents, and in particular relates to a paramagnetic metal complex with aspartic acid-isoleucine copolymer as a carrier, a preparation method and a magnetic resonance imaging contrast agent. Background technique [0002] Magnetic resonance imaging contrast agent is an imaging-enhanced contrast agent that improves the imaging contrast between normal and diseased parts by changing the relaxation rate of water protons in local tissues in the body. About 50% of magnetic resonance imaging requires the use of magnetic resonance imaging contrast agent. At present, the clinical application of small molecule contrast agents has the disadvantages of short imaging time, low relaxation efficiency, long retention time in vivo, and inability to be excreted from the body. Linking small molecule contrast agents to macromolecular carriers can effectively improve the performance of contrast agents....

Claims

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Application Information

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IPC IPC(8): A61K49/12
Inventor 李晓晶湛游洋薛蓉祝云龙裴奉奎
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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