Magnetic resonance imaging probe based on hyaluronic acid-peptide dendrimer-gadolinium conjugate and preparation method thereof

A technology of dendrimer and hyaluronic acid, which is applied in the field of medical imaging, can solve the problems of expelling the size from the body and the difficulty of macromolecular synthesis, and achieves the effects of regular structure, small steric hindrance and high relaxation efficiency.

Active Publication Date: 2019-04-19
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, high algebraic peptide dendrimers are difficult to synthesize, and when used alone, they are easily excreted due to their small size

Method used

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  • Magnetic resonance imaging probe based on hyaluronic acid-peptide dendrimer-gadolinium conjugate and preparation method thereof
  • Magnetic resonance imaging probe based on hyaluronic acid-peptide dendrimer-gadolinium conjugate and preparation method thereof
  • Magnetic resonance imaging probe based on hyaluronic acid-peptide dendrimer-gadolinium conjugate and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0046] The magnetic resonance imaging probe based on the hyaluronic acid-peptide dendrimer-gadolinium conjugate has a structure in which multiple fan-shaped peptide dendrimers and gadolinium conjugates are connected to the hyaluronic acid sugar chain. The specific structure is as follows:

[0047]

[0048] Among them, A is a lysine fan-shaped peptide dendrimer with ethylenediamine as the core, R is connected to the terminal amino group of the peptide dendrimer,

[0049]

[0050] Conjugate I: n=1, A is a 1st generation lysine fan-shaped dendrimer.

[0051] Conjugate II: n=4, A is a 2-generation lysine fan-shaped dendrimer.

[0052] Conjugate III: n=6, A is a 3rd generation lysine fan-shaped dendrimer.

[0053] Conjugate IV: n=8, A is a 3-generation lysine fan-shaped dendrimer.

[0054] Conjugate V: n=16, A is a fan-shaped dendrimer of 4th generation lysine.

Embodiment 2

[0056] The preparation method of the magnetic resonance imaging probe based on the hyaluronic acid-peptide dendrimer-gadolinium conjugate, the peptide dendrimer-gadolinium conjugate and the alkynyl end are synthesized respectively Hyaluronic acid was oxidized, and then the final product Dendronized-HA-Gd was synthesized through a copper-catalyzed click reaction.

Embodiment 3

[0058] This embodiment is on the basis of embodiment 2:

[0059] The synthesis of the peptide dendrimer-gadolinium conjugate is as follows:

[0060] In the first step, the dendrimers protected by the Boc group were used as raw materials, and the dendrimers were dissolved in anhydrous CH under nitrogen-protected ice bath conditions. 2 Cl 2 In, TFA was added therein, after the reaction was finished, TFA was removed, the reaction product was dissolved in DMF, and under the ice bath condition of nitrogen protection, DIPEA, HOAt, HATU and DOTA were added to the system at the same time, and the intermediate product was obtained by reaction;

[0061] In the second step, the intermediate product was dissolved in anhydrous CH 2 Cl 2 In, TFA was added to it, after the reaction was finished, TFA was removed, the reaction product was dissolved in deionized water, and GdCl was added to it 3 ·6H 2 O, after the reaction is over, a peptide dendrimer-gadolinium conjugate is obtained.

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Abstract

The invention provides a magnetic resonance image probe based on hyaluronic acid-peptide dendrimer-gadolinium conjugates. The magnetic resonance image probe structurally comprises a plurality of fan-shaped peptide dendrimer and gadolinium conjugates connected onto a hyaluronic acid carbohydrate chain. Hyaluronic acid (HA) is selectively taken as a macromolecular skeleton chain segment, and an MRI contrast agent (Dendronized-HA-Gd) based on the hyaluronic acid-peptide dendrimer-gadolinium conjugates is constructed in combination with the advantages of HA and peptide dendrimer. The structural skeleton has a biodegradable capacity, and a degradable segment is constructed without introducing other sensitive bonds.

Description

technical field [0001] The invention belongs to the technical field of medical imaging, and relates to a polymer magnetic resonance imaging probe, in particular to a magnetic resonance imaging probe based on a hyaluronic acid-peptide dendrimer-gadolinium conjugate and a preparation method thereof. Background technique [0002] In the clinical diagnosis of magnetic resonance imaging, it usually takes several minutes or tens of minutes to complete the entire operation, while the current commercial gadolinium-based contrast agent circulates in the body for only ten minutes. During the imaging process, signal may appear The embarrassing situation that the contrast agent has been metabolized and excreted before the collection is completed limits its application in some more complex imaging. Therefore, at present, a lot of research work is focused on linking small-molecule gadolinium-based contrast agents to macromolecular carriers, such as dendrimers, liposomes, and macromolecula...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/14A61K49/12
CPCA61K49/085A61K49/126A61K49/14
Inventor 罗奎顾忠伟郭春花
Owner SICHUAN UNIV
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