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Manganese compound and preparation method and application thereof

A technology of manganese complexes and ligands, applied in the field of imaging agents for magnetic resonance imaging

Inactive Publication Date: 2012-05-23
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Magnetic resonance imaging contrast agent with tumor therapeutic effect has not been reported

Method used

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  • Manganese compound and preparation method and application thereof
  • Manganese compound and preparation method and application thereof
  • Manganese compound and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1 (best reaction condition example):

[0021] The ligand N-(2-propionyl ethyl)-N,N-bis(2-pyridylmethyl)amine and MnCl 2 Dissolve in an aqueous solution at a molar ratio of 1:1 and control at 30°C; add ammonium chloride (0.1 mol) as a catalyst, and the reaction time is 2 hours. The product was purified by silica gel column chromatography (developing solvent: tetrahydrofuran:petroleum ether=3:2), and concentrated to remove the solution to obtain a light yellow manganese complex: [LMnCl 2 ]. Yield, 63%. Molecular formula: C 17 h 21 Cl 2 MnN 3 o 2 Elemental analysis: measured value C, 48.34; H, 4.62; N, 9.58, Mn, 12.62. Calculated value C, 48.02; H, 4.98; N, 9.88, Mn, 12.92.IR(v cm -1 , KBr): 3057m (=CH), 2986m (-CH 2 -), 1730m(C=O), 1603s, 1571m, 1442s, 777s(pyridine).UV-vis((H 2 O / nm, vcm -1 ,ε)38461(8900).

Embodiment 2

[0023] The ligand N-(2-propionyl ethyl)-N,N-bis(2-pyridylmethyl)amine and MnCl 2 Dissolve in aqueous solution at a molar ratio of 2:1, controlled at 20°C; add ammonium chloride (0.1 mol) as a catalyst, and react for 1 hour. The product was purified by silica gel column chromatography (developing solvent: tetrahydrofuran:petroleum ether=3:2), and concentrated to remove the solution to obtain a light yellow manganese complex: [LMnCl 2 ]. Yield: 25%. Molecular formula: C 17 h 21 Cl 2 MnN 3 o 2 Elemental analysis: measured value C, 48.34; H, 4.62; N, 9.58, Mn, 12.62. Calculated value C, 48.02; H, 4.98; N, 9.88, Mn, 12.92.IR (v cm -1 , KBr): 3057m (=CH), 2986m (-CH 2 -), 1730m(C=O), 1603s, 1571m, 1442s, 777s(pyridine).UV-vis((H2 O / nm, vcm -1 ,ε)38461(8900).

Embodiment 3

[0025] The ligand N-(2-propionyl ethyl)-N,N-bis(2-pyridylmethyl)amine and MnCl 2 Dissolve in an aqueous solution at a molar ratio of 1:1, and control at 40°C; add ammonium chloride (0.1 mol) as a catalyst, and react for 1 hour. The product was purified by silica gel column chromatography (developing solvent: tetrahydrofuran:petroleum ether=3:2), and concentrated to remove the solution to obtain a light yellow manganese complex: [LMnCl 2 ]. Yield: 45%. Molecular formula: C 17 h 21 Cl 2 MnN 3 o 2 Elemental analysis: measured value C, 48.34; H, 4.62; N, 9.58, Mn, 12.62. Calculated value C, 48.02; H, 4.98; N, 9.88, Mn, 12.92.IR (v cm -1 , KBr): 3057m (=CH), 2986m (-CH 2 -), 1730m(C=O), 1603s, 1571m, 1442s, 777s(pyridine).UV-vis((H 2 O / nm, vcm -1 ,ε)38461(8900).

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Abstract

The invention discloses a manganese compound and a preparation method and application thereof, and relates to the technical field of magnetic resonance imaging (MRI). The manganese compound is dichloro-N-(2-propionic carbethoxy)-N,N-bis(2-picolyl) amine synthetic manganese, and the molecular formula is C17H21Cl2MnN3O2. The preparation method for the manganese compound comprises the following steps: dissolving ligand dichloro-N-(2-propionic carbethoxy)-N,N-bis(2-picolyl) amine and MnCl2 into aqueous solution in a molar ratio of 1 to 1, and controlling the temperature to be between 20 and 40 DEG C; and synthesizing ammonium chloride and a catalyst in a molar ratio of the ammonium chloride to the MnCl2 of 0.2 to 1, reacting the mixture at the temperature of 30 DEG C for 1 to 4 hours, purifying a product by using silica gel column chromatography, concentrating the product and removing the solution to obtain light yellow manganese compound. The manganese compound is applied in the aspect of magnetic resonance imaging in a liver cancer body; and compared with the blank aqueous solution without the manganese compound, the compound can remarkably improve the tumor diagnosis effect, has magnetic resonance imaging function and tumor targeting property, and can be used as a magnetic resonance imaging contrast agent for the tumor.

Description

technical field [0001] The invention relates to the technical field of magnetic resonance imaging (MRI), in particular to an imaging agent for magnetic resonance imaging and an application thereof. Background technique [0002] Magnetic resonance imaging (MRI) is a noninvasive and rapid imaging method for the detection of brain tumors and blood vessels. Magnetic resonance imaging has the advantages of safety, non-invasiveness, no ionizing radiation, no radiation damage, high time resolution and spatial resolution, and has become the main imaging technology for clinical diagnosis of vascular lesions and intracranial tumors. Since Gd-DTPA was used in clinical trials in 1983, in order to improve the sensitivity and targeting of imaging agents and reduce their toxicity, people have carried out a lot of research and development on MRI contrast agents (B.Jebasingh, V.Alexander.Inorg.Chem. , 2005, 44:9434-9443). Commonly used imaging agents are gadolinium diethylenetriaminepentaa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F13/00A61K31/555A61K49/06A61P35/00
Inventor 陈秋云
Owner JIANGSU UNIV
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