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Similar EDTA ligand containing O-phenolic hydroxyl, as well as non-gadolinium magnetic resonance contrast agent and preparation method thereof

A technology of dihydroxyphenyl and dibenzyloxy, which is applied in the field of EDTA-like ligands containing ortho-diphenolic hydroxyl groups and non-gadolinium magnetic resonance contrast agents and their preparation, and can solve problems such as low theoretical prediction values

Inactive Publication Date: 2016-12-07
川北医学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Clinically used small molecule gadolinium-based contrast agents (MW=500 or so) are too fast in the solution due to their turnover rate (τ R :~0.1ns, 25℃), the relaxation efficiency is usually 2.5-5.0mmol -1 the s -1 , much lower than the theoretical prediction value (~100.0mmol -1 the s -1 ,0.5T,25℃)

Method used

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  • Similar EDTA ligand containing O-phenolic hydroxyl, as well as non-gadolinium magnetic resonance contrast agent and preparation method thereof
  • Similar EDTA ligand containing O-phenolic hydroxyl, as well as non-gadolinium magnetic resonance contrast agent and preparation method thereof
  • Similar EDTA ligand containing O-phenolic hydroxyl, as well as non-gadolinium magnetic resonance contrast agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 EDTA-like ligand (L) containing o-diphenolic hydroxyl group: 2,2', 2", 2"'-((3-(3,4-dihydroxyphenyl)propane-1,2 diyl ) Preparation of diaminetetraacetic acid

[0068] The chemical reaction formula is:

[0069]

[0070] According to the above chemical reaction formula, the preparation method adopted in this embodiment is as follows:

[0071] (1) Preparation of compound 2, [(N-tert-butoxycarbonyl)-amino]]-3-[(3,4-dihydroxy)-phenyl]propionic acid methyl ester:

[0072]Add thionyl chloride (15mL, 95.68mmol) into 100mL of methanol solution of L-Dopa (14.5g, 73.6mmol) under ice-bath conditions, and react at room temperature for 24 hours under stirring. After the reaction is completed, the reaction solution is depressurized The solvent methanol in the reaction liquid was distilled off to obtain the product; the obtained product was dissolved with 100 mL of saturated sodium bicarbonate and the pH of the product solution was 7 to 8, and then di-tert-butyl dicarbon...

Embodiment 2

[0090] Example 2 Preparation of Paramagnetic Metal Complex Magnetic Resonance Contrast Agent (MnL)

[0091] The chemical reaction formula is:

[0092]

[0093] According to above-mentioned chemical reaction formula, the preparation method that present embodiment takes is as follows:

[0094] Compound 7 (0.1 g, 0.24 mmol) prepared in Example 1 was dissolved in Hepes buffer (pH=7.36, 5 mL) to obtain a compound 7 solution, and MnCl 2 4H 2 O (0.057g, 0.28mmol) was dissolved in Hepes buffer (pH=7.36, 5mL) to give MnCl 2 solution; under nitrogen protection and stirring, compound 7 solution and MnCl 2 The solution was added to the reaction vessel, stirred and reacted at room temperature under nitrogen protection for 10 minutes, and after the reaction was completed, the resulting reaction solution was filtered through a Sephdex G-25 gel column to remove Mn that did not participate in the reaction. 2+ , to obtain the Hepes solution of the Mn complex contrast agent (MnL) of the s...

Embodiment 3

[0103] Example 3 Fe coordination self-assembled metal cluster collective [Fe(MnL) 3 ] Preparation of magnetic resonance contrast agent

[0104] The chemical reaction formula is:

[0105]

[0106] According to above-mentioned chemical reaction formula, the preparation method that embodiment takes is as follows:

[0107] Compound 7 (0.1 g, 0.24 mmol) prepared in Example 1 was dissolved in Hepes buffer (pH=7.36, 5 mL) to obtain a compound 7 solution, and MnCl 2 4H 2 O (0.057g, 0.28mmol) was dissolved in Hepes buffer (pH=7.36, 5mL) to give MnCl 2 solution, the FeCl 3 (0.013g, 0.08mmol) was dissolved in Hepes buffer (pH=6.0, 2.0mL) to give FeCl 3 solution; under nitrogen protection and stirring, compound 7 solution and MnCl 2 The solution was added to the reaction vessel, and the reaction was stirred at room temperature for 10 min under the protection of nitrogen; then FeCl was added 3 Solution, under the protection of nitrogen, stirred and reacted at room temperature for...

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Abstract

The invention discloses a similar EDTA ligand namely 2,2',2'',2'''-((3-(3,4-dihydroxyphenyl) propane-1,2diyl) ethylene diamine tetraacetic containing O-phenolic hydroxyl, a non-gadolinium paramagnetic metal coordination compound namely a magnetic resonance contrast agent based on the ligand, a non-gadolinium metal agglomeration body namely a magnetic resonance contrast agent, a preparation method of the similar EDTA ligand, a preparation method of the non-gadolinium paramagnetic metal coordination compound namely the magnetic resonance contrast agent, and a preparation method of the non-gadolinium metal agglomeration body namely the magnetic resonance contrast agent. The 2,2',2'',2'''-((3-(3,4-dihydroxyphenyl) propane-1,2diyl) ethylene diamine tetraacetic is prepared for the first time, and the ligand combines the advantages of two structures of the O-phenolic hydroxyl and the EDTA, so that the non-gadolinium magnetic resonance contrast agent based on the ligand has high relaxation efficiency, good water solubility and good structure stability. Compared with a Gd type contrast agent used clinically, the non-gadolinium magnetic resonance contrast agent based on the ligand has the advantages that an order metal agglomeration body namely the contrast agent is self-assembled through coordination, the MRI imaging effects are better, more details can be displayed, and accurate analysis basis is provided for diagnosing multiple diseases.

Description

technical field [0001] The invention belongs to the technical field of molecular imaging biomedical materials, and relates to a contrast agent and a preparation method thereof, in particular to an EDTA-like ligand containing an o-diphenolic hydroxyl group and a non-gadolinium magnetic resonance contrast agent and a preparation method thereof. Background technique [0002] Magnetic Resonance Imaging (MRI, Magnetic Resonance Imaging) is a non-invasive diagnostic technique with the characteristics of high spatial resolution and high soft tissue contrast; And high-contrast imaging, which has the characteristics of both structural imaging and functional imaging. Structural imaging can display tangible solid lesions, and functional imaging can accurately determine the functional responses of the brain, heart, and liver. Compared with X-ray perspective technology (X-Ray, CT (Computed Tomohtaphy)) and radiographic technology (SPECT (Single Photo Emission Computed Tomography), PET (P...

Claims

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Application Information

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IPC IPC(8): C07C229/16C07C227/18C07C229/76C07F19/00C07F13/00C07F15/02A61K49/10
CPCA61K49/106C07C229/16C07C229/76C07F13/005C07F15/025
Inventor 陈钏朱江柳妍妍吴昌强王冰聂宇亭李云鹤张春燕黄渝程陈天武沈成义张小明
Owner 川北医学院
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