Paramagnetic metal complex modified by aspartic acid-leucine copolymer and its preparation method and application

A technology of leucine copolymer and aspartic acid, applied in preparations for in vivo experiments, pharmaceutical formulations, drug delivery, etc., can solve the problems of low biodegradability, low liver targeting immunity, etc., and achieve Long imaging time, good water solubility, and the effect of improving the level of early diagnosis

Inactive Publication Date: 2017-01-11
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention aims to solve the technical problems of low biodegradability, low liver targeting and immunity in the prior art, and provides a kind of aspartic acid-leucine copolymer modified Paramagnetic metal complex and its preparation method and application

Method used

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  • Paramagnetic metal complex modified by aspartic acid-leucine copolymer and its preparation method and application
  • Paramagnetic metal complex modified by aspartic acid-leucine copolymer and its preparation method and application
  • Paramagnetic metal complex modified by aspartic acid-leucine copolymer and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0044] Preparation of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid gadolinium complex with aspartic acid-leucine copolymer modified by ethylenediamine

[0045] (1) Mix 20 grams of L-aspartic acid with 10 grams of L-leucine, add 10 grams of phosphoric acid solution with a mass fraction of 85% to the mixed mixture and stir evenly, under reduced pressure ( React at 24mmHg) for 5 hours, control the reaction temperature at 165°C, precipitate with deionized water, filter, wash, and dry under reduced pressure to obtain aspartic acid-leucine copolymer;

[0046] (2) Dissolve the aspartic acid-leucine copolymer synthesized in (1) in the N,N-dimethylformamide solution at room temperature, and add ethylenediamine and ethylenediamine dropwise under stirring. The mass ratio to the aspartic acid-leucine copolymer was 2.8:1, stirred at room temperature for 4 hours, ether precipitated, filtered, dialyzed, and lyophilized to obtain the aminated aspartic acid-leucine copolymer;

[0047] (3...

Embodiment 2

[0050] Preparation of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid gadolinium complex with aspartic acid-leucine copolymer modified by ethylenediamine

[0051] (1) Mix 2 g of L-aspartic acid with 20 g of L-leucine, add 8 g of phosphoric acid solution with a mass fraction of 85% to the mixed mixture and stir evenly, under reduced pressure ( React at 30mmHg) for 5 hours, control the reaction temperature at 165°C, precipitate with deionized water, filter, wash, and dry under reduced pressure to obtain an aspartic acid-leucine copolymer;

[0052] (2) Dissolve the aspartic acid-leucine copolymer synthesized in (1) in the N,N-dimethylformamide solution at room temperature, and add ethylenediamine and ethylenediamine dropwise under stirring. The mass ratio to the aspartic acid-leucine copolymer was 2.8:1, stirred at room temperature for 4 hours, ether precipitated, filtered, dialyzed, and lyophilized to obtain the aminated aspartic acid-leucine copolymer;

[0053] (3) Dissolve ...

Embodiment 3

[0056] Preparation of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid gadolinium complex with aspartic acid-leucine copolymer modified by ethylenediamine

[0057] (1) Mix 20 g of L-aspartic acid with 20 g of L-leucine, add 15 g of phosphoric acid solution with a mass fraction of 85% to the mixed mixture and stir evenly, under reduced pressure ( React at 200mmHg) for 5 hours, control the reaction temperature at 100°C, precipitate with deionized water, filter, wash, and dry under reduced pressure to obtain aspartic acid-leucine copolymer;

[0058] (2) Dissolve the aspartic acid-leucine copolymer synthesized in (1) in the N,N-dimethylformamide solution at room temperature, and add ethylenediamine and ethylenediamine dropwise under stirring. The mass ratio to the aspartic acid-leucine copolymer was 2.8:1, stirred at room temperature for 4 hours, ether precipitated, filtered, dialyzed, and lyophilized to obtain the aminated aspartic acid-leucine copolymer;

[0059] (3) Dissolve ...

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Abstract

The invention relates to a paramagnetic metal complex modified by an aspartic acid-leucine copolymer as well as a preparation method and an application of the paramagnetic metal complex, and is used for solving the technical problems of low biodegradability, low liver targeting property, immunity defects and the like of the existing liver-type macromolecular contrast agent. The paramagnetic metal complex is formed by taking the aspartic acid-leucine copolymer as a carrier, wherein annular 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid ligands are connected on side chains of the carrier. A magnetic resonance imaging contrast agent prepared from the paramagnetic metal complex provided by the invention has the characteristics of a corresponding polyamine multi-carboxy complex, so that the magnetic resonance imaging contrast agent is good in stability, water solubility and relaxation rate, and simultaneously has the targeting property to the liver so as to realize the targeted imaging to improve the imaging contrast ratio and the imaging definition. Thus, the magnetic resonance imaging contrast agent has a good effect for improving the early-stage diagnosis level of diseases of the liver organs.

Description

Technical field [0001] The invention relates to a magnetic resonance imaging contrast agent, in particular to a paramagnetic metal complex modified by aspartic acid-leucine copolymer, and a preparation method and application thereof. Background technique [0002] Compared with small-molecule contrast agents such as Dotarin, the liver-based macromolecular contrast agents have larger molecular size, slower penetrating capillary velocity, and lower molecular rotation rate, which can improve relaxation efficiency, reduce dosage and reduce toxicity. Moreover, with the special biochemical properties of polysaccharides, peptides, antibodies, vitamins and other molecules, the contrast agent can be enriched in the liver tissue, thereby achieving targeted imaging and improving imaging contrast and clarity. Most of the macromolecular contrast agents studied abroad are formed by introducing the small-molecule contrast agent Gd-DOTA into the polymer backbone or covalently coupling to a natur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/12A61K49/18
Inventor 李晓晶肖研薛蓉湛游洋齐晨丽裴奉奎
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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