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High-water-solubility nuclear magnetic resonance imaging contrast agent and preparation method thereof

A nuclear magnetic resonance imaging, water-soluble technology, applied in pharmaceutical formulations, preparations for in vivo tests, organic chemistry, etc., can solve problems such as unsatisfactory water-solubility and restricted application

Inactive Publication Date: 2012-11-14
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the complexes with long chain structures are not ideal in terms of water solubility, which restricts their further application.

Method used

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  • High-water-solubility nuclear magnetic resonance imaging contrast agent and preparation method thereof
  • High-water-solubility nuclear magnetic resonance imaging contrast agent and preparation method thereof
  • High-water-solubility nuclear magnetic resonance imaging contrast agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Preparation of tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7-triacetate hydrobromide. In a 250 ml schlenk bottle, 1,4,7,10-tetraazacyclododecane (4.2 g, cyclen, laboratory-made) and anhydrous sodium acetate (6.6 g) were dissolved in N,N-dimethyl acetamide (50 ml). Then, a solution of tert-butyl bromoacetate (13 ml) in N,N-dimethylacetamide (20 ml) was added at -20°C. After the addition, react at room temperature for 1-2 days to obtain the crude product. Pour it into deionized water (500 ml), add an appropriate amount of sodium bicarbonate, and adjust the pH of the solution to 8-9. During this period, a large amount of white solids were precipitated, and the filtrate was removed by filtration. Dissolve the white solid in dichloromethane, dry it with anhydrous magnesium sulfate, then concentrate to 20 ml, add 200 ml of anhydrous ether, a white solid precipitates out, filter and collect the product.

[0028] (2) Dissolve trimethylamine hydrochloride (1.9 g) i...

Embodiment 2

[0035] (2) Dissolve dimethylhexadecyl tertiary amine hydrochloride (3.1 g) in 20 ml deionized water, add epichlorohydrin under mechanical stirring, react at 25°C-55°C for 6 h, and it becomes viscous A solid was formed, filtered, drained, and recrystallized using an ethanol\ether system to obtain the pure product 3-chloro-2-hydroxypropylhexadecyldimethylammonium chloride.

[0036] (3) Replace 3-chloro-2-hydroxypropyltrimethylammonium chloride with 3-chloro-2-hydroxypropyl hexadecyldimethylammonium chloride; the rest are the same as in Example 1. The test results show that the longitudinal relaxation time has a good linear relationship with the concentration of gadolinium ions (such as figure 2 ), and finally calculate the longitudinal relaxation rate r 1 =3.7 mM -1 the s -1 .

Embodiment 3

[0038] (2) Dissolve dimethylbehenyl tertiary amine hydrochloride (7.8 g) in 80 ml deionized water, add epichlorohydrin under mechanical stirring, and react at 35 °C-55 °C for 24 h to obtain crude The product, after dehydration and drying, was recrystallized with ethanol\ether system to obtain the pure product 3-chloro-2-hydroxypropyl behenyldimethylammonium chloride.

[0039] (3) Replace 3-chloro-2-hydroxypropyltrimethylammonium chloride with 3-chloro-2-hydroxypropylbehenyldimethylammonium chloride; the rest are the same as in Example 1. The test results show that the longitudinal relaxation time has a good linear relationship with the concentration of gadolinium ions (such as image 3 ), and finally calculate the longitudinal relaxation rate r 1 =8.7 mM -1 the s -1 .

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Abstract

The invention relates to a high-water-solubility nuclear magnetic resonance imaging contrast agent and a preparation method of the high-water-solubility nuclear magnetic resonance imaging contrast agent. The high-water-solubility nuclear magnetic resonance imaging contrast agent is gadolinium (III) complex which is based on 1, 4, 7, 10-tetraazacyclododecane-1, 4, 7-triacetic acid (DO3A) and modified by quaternary ammonium salt side chain. The nuclear magnetic resonance imaging contrast agent prepared by the gadolinium (III) complex is good in water solubility, stability and relaxation rate, and the relaxation rate of the nuclear magnetic resonance imaging contrast agent can be controllably adjusted by controlling the length of the side chain.

Description

technical field [0001] The invention relates to a highly water-soluble nuclear magnetic resonance imaging contrast agent and a preparation method thereof. Background technique [0002] Magnetic resonance imaging (MRI) is a technology that uses the resonance of hydrogen nuclei of water molecules in a living body to generate signals, and obtains images through spatial encoding and reconstruction. As a non-invasive diagnostic method, MRI can not only provide an excellent 3D image of soft tissue, but also reveal the function and physiological state of the physiological process of the internal organs of the organism. Compared with other diagnostic methods, the sensitivity of MRI is low, and multiple accumulations are needed to overcome this shortcoming in the detection, but in medical MRI, it is impossible to carry out long-term accumulation tests. The use of MRI contrast agents (MRI contrast agents, MRI CAs) can change the relaxation rate of protons to improve the diagnosis of ...

Claims

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Application Information

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IPC IPC(8): A61K49/10C07D257/02
Inventor 胡爱国杨恒王伟陈莹莹
Owner EAST CHINA UNIV OF SCI & TECH
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