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Magnetic resonance contrast agent as well as preparation method and application thereof

A magnetic resonance contrast agent and reaction technology, which is applied in the fields of nuclear magnetic resonance/magnetic resonance imaging contrast agents, chemical instruments and methods, and pharmaceutical formulations, and can solve problems such as huge side effects

Active Publication Date: 2021-09-10
GUANGZHOU PINGLAN MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In summary, the potential huge side effects of gadolinium-based magnetic resonance contrast agents, clinical Gd 3+ The safety of contrast agent NSF and brain deposition has become an urgent problem to be solved clinically

Method used

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  • Magnetic resonance contrast agent as well as preparation method and application thereof
  • Magnetic resonance contrast agent as well as preparation method and application thereof
  • Magnetic resonance contrast agent as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] To prepare trans-cyclohexyldiamine-dimethylphosphonic acid-diacetic acid ligand, the synthetic route is as follows:

[0067]

[0068] The specific preparation method of the ligand is as follows:

[0069] (1) Preparation of compound 1

[0070] With 100mL of anhydrous tetrahydrofuran (THF) as solvent, add cyclohexanediamine (10g, 98%, 85.8mmol), diethyl phosphite (24.2g, 98%, 171.6mmol), paraformaldehyde (total amount 8.31g , 96%, 266mmol, first add about one-fifth), heat to 95 ° C, reflux, add the remaining amount of paraformaldehyde in 4 times, and reflux for 4 hours;

[0071] After the reaction was completed, the solvent was removed by rotary evaporation under reduced pressure, and about 100 mL of dichloromethane and water were added to the raffinate for extraction. Wash once with water and saturated brine (about 50mL each time), and wash the organic phase with anhydrous Na 2 SO 4 After drying, filtering, and rotary evaporation under reduced pressure to remove d...

Embodiment 2

[0092] To prepare a paramagnetic metal manganese complex magnetic resonance contrast agent, the steps are as follows:

[0093] The compound (7.19g, 17.2mmol) obtained in (4) in Example 1 was added to 60mL of pure water, manganese chloride tetrahydrate (3.33g, 16.8mmol) was added under stirring, and the pH was adjusted to 7.3 with solid sodium hydroxide ~7.4, the resulting solution was freeze-dried to a solid of 11.68 g.

[0094] MS(ESI):[M+H] - Calculated value: 470.0, measured value: 469.9; [M+3H] + Calculated value: 472.0, measured value: 472.0.

Embodiment 3

[0096] The paramagnetic metal manganese complex magnetic resonance contrast agent (code name: KBR0826) that embodiment 2 obtains carries out following performance test:

[0097] 1. Determination of relaxation efficiency

[0098] Measurement method of relaxation efficiency: configure gradient concentration contrast agent solution (0.054, 0.109, 0.224, 0.451, 0.906mM, in Hepes buffer, pH = 7.4), use Numei PQ001 NMR contrast agent relaxation rate tester (0.5±0.08 T, the main frequency of the instrument: 21.3MHz; 32°C) The T of samples with different concentrations of contrast agents was obtained by testing 1 , T 2 Relaxation time, in terms of relaxation rate R i (R i =1 / T i , i=1, 2) and contrast agent concentration for linear fitting, the slope is the relaxation efficiency (relaxivity, r i ,i=1,2). Relaxation efficiency reflects the ability of magnetic resonance contrast agents to change the relaxation time of water molecules, and is an important parameter to measure the q...

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Abstract

The invention provides a magnetic resonance contrast agent as well as a preparation method and application thereof, and relates to the field of magnetic resonance contrast agents. The magnetic resonance contrast agent disclosed by the invention is prepared from a compound with structural characteristics of a formula I shown in the description. The magnetic resonance contrast agent disclosed by the invention can also be a compound with structural characteristics shown as a formula II or pharmaceutically acceptable salt thereof, M1 is a +2 ion of paramagnetic metal Mn, Fe, Eu or Dy, or a +3 ion of Mn, Fe, Eu or Dy; M2 is Na < + >, K < + > or meglumine cation; when M1 is a +2 valence ion, a is equal to 2; and when M1 is a + 3 valence ion, a is equal to 3. The magnetic resonance contrast agent has the characteristics of good water solubility, high relaxation efficiency, low toxic and side effects and the like.

Description

technical field [0001] The invention relates to the field of nuclear magnetic resonance contrast agents, in particular to a magnetic resonance contrast agent and a preparation method and application thereof. Background technique [0002] Magnetic Resonance Imaging (MRI) is the application of nuclear magnetic resonance technology in the medical field. Compared with other medical imaging methods, it has the advantages of high soft tissue contrast, multi-parameter and multi-sequence imaging, and no ionizing radiation damage. At present, nearly 50% of clinical magnetic resonance enhancement scans use the rare earth metal gadolinium (Gd 3+ ) magnetic resonance contrast agent. For the human body, gadolinium is an exogenous metal. Free Gd 3+ It is highly toxic, distributed in the bones and liver in the body, and can rapidly cause liver necrosis. Since 1988 Magen Microscope ( Bayer) FDA approval, gadolinium-based contrast agents (Gadolinium-based contrast agents, GBCA) clinic...

Claims

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Application Information

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IPC IPC(8): C07F9/38A61K49/10
CPCC07F9/3808A61K49/106Y02P20/55A61K49/103C07F9/3873C07F13/005C07F15/025
Inventor 朱江钟磊陈柯宇聂宇亭张俊丽夏倩沈成义雷军张小明宓庆宁
Owner GUANGZHOU PINGLAN MEDICAL TECH CO LTD
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