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Fluorine-containing potential dual-function probe based on chitosan structure and preparation method thereof

A chitosan, dual-function technology is applied in the field of novel fluorine-containing magnetic resonance imaging contrast agents and their preparation, which can solve the problems of fluctuation and inability to form MR images, and achieve the effect of good water solubility

Inactive Publication Date: 2013-09-25
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the early application of MRI, it is generally believed that the MRI scan can be completed without using a contrast agent (Contrast Agent). Forming clear MR images is difficult to meet clinical requirements, which requires further improvement of the contrast of MRI, that is, the use of contrast agents

Method used

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  • Fluorine-containing potential dual-function probe based on chitosan structure and preparation method thereof
  • Fluorine-containing potential dual-function probe based on chitosan structure and preparation method thereof
  • Fluorine-containing potential dual-function probe based on chitosan structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0027] Example 1: the fluorine-containing magnetic resonance contrast agent (CF 3 -CS 11 -Gd-DTPA-2)

[0028]

[0029] Where x, y, z=3,4,5,6,7,8,9,10.

[0030] Under the protection of nitrogen, 140.2 mg (average molecular weight about 2337, 0.06 mmol) of chitosan oligosaccharide with a degree of polymerization of 11 chained with diethylenetriaminepentaacetic acid (DTPA) and 66.0 mg of 4-dimethylaminopyridine (0.54 mmol) into a 50ml dry round bottom flask, and 1mL of dry dimethylformamide was added to form a suspension, then 113.4mg (0.54mmol) of trifluoroacetic anhydride was added dropwise, stirred at 25°C for 24h after the addition was completed, and 3mL of water was added to quench quench the reaction and add GdCl 3 ·6H 2 O (22.3mg, 0.06mmol) continued stirring at 25°C for 6h. After the reaction was completed, it was concentrated and dehydrated in vacuo, 30 mL of acetone was added, allowed to stand for 1 hour, and filtered to obtain 148.4 mg of the target product, wi...

example 2

[0032] Example 2: the fluorine-containing magnetic resonance contrast agent (CF 3 -CS 11 -Mn-DTPA-2)

[0033]

[0034] Where x, y, z=3,4,5,6,7,8,9,10.

[0035] Under the protection of nitrogen, 140.2mg (average molecular weight about 2337, 0.06mmol) of chitosan oligosaccharides with a degree of polymerization of 11 chained with diethylenetriaminepentaacetic acid (DTPA) and 54.6mg (0.54mmol) of triethylamine were added Put it into a 50ml dry round bottom flask, add 1mL of dry acetonitrile to form a suspension, then add 113.4mg (0.54mmol) of trifluoroacetic anhydride dropwise, stir at 25°C for 24h after adding, add 3mL of water to quench the reaction, and add MnCl 2 4H 2 O (47.6mg, 0.24mmol) continued to stir at 25°C for 6h. After the reaction was completed, it was concentrated and dehydrated in vacuo, 30 mL of acetone was added, and after standing for 1 h, it was filtered to obtain 130.2 mg of the target product, with a yield of 66.4%.

[0036] The in vitro relaxation rat...

example 3

[0037] Example 3: the fluorine-containing magnetic resonance contrast agent (CF 3 -CS 11 -Mn-EDTA-2)

[0038]

[0039] Where x, y, z=3,4,5,6,7,8,9,10.

[0040] Under the protection of nitrogen, 134.2 mg (average molecular weight about 2236, 0.06 mmol) of chitosan oligosaccharides (average molecular weight about 2236, 0.06 mmol) and 54.6 mg (0.54 mmol) of triethylamine were added to the In a 50ml dry round bottom flask, add 1mL dry dimethylacetamide to form a suspension, then add 113.4mg (0.54mmol) trifluoroacetic anhydride dropwise, stir at 25°C for 24h after adding, add 3mL water to quench the reaction, and Add MnCl 2 4H 2 O (11.9mg, 0.06mmol) continued stirring at 25°C for 6h. After the reaction was completed, it was concentrated and dehydrated in vacuo, and 30 mL of absolute ethanol was added. After standing for 1 h, it was filtered to obtain 123.7 mg of the target product, with a yield of 64.1%.

[0041] The in vitro relaxation rate of this product is 8.5L·mmol -...

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Abstract

The invention discloses a fluorine-containing potential dual-function probe based on a chitosan structure and a preparation method thereof and relates to the fields of magnetic resonance imaging and fluorine chemistry. The preparation method comprises the following steps of: adding oligomeric or polymeric chitosan chained with a diethylenetriamine pentaacetic acid (DTPA) or ethylenediaminetetraacetic acid (EDTA) structure and an organic base into a dry organic solvent, slowly adding trifluoroacetic anhydride, performing complete reaction at room temperature, then adding distilled water and a metal inorganic salt into a system, continuously reacting at the room temperature till the reaction is complete, performing vacuum concentration and dehydration, adding acetone or anhydrous ethanol, standing, and then filtering to get a target product, namely a fluorine-containing magnetic resonance contrast medium based on the chitosan structure. The fluorine-containing magnetic resonance contrast medium based on the chitosan structure, disclosed by the invention, has good water solubility, the relaxivity is 10-14L.mmol<-1>.s<-1>, which is 1-3 times of that of an existing common MRI (magnetic resonance imaging) contrast medium, namely magnevist (Gd-DTPA (gadopentetate dimeglumine)); and the fluorine-containing magnetic resonance contrast medium simultaneously has a potential 19F probe function due to the containing of a plurality of trifluoromethyl groups.

Description

technical field [0001] The invention relates to the fields of magnetic resonance imaging and fluorine chemistry, and in particular discloses a chitosan-based 19 A novel fluorine-containing magnetic resonance imaging contrast agent with F probe function and a preparation method thereof. Background technique [0002] Magnetic Resonance Imaging (MRI) is a medical imaging technology that uses different magnetic resonance signals generated by different tissues of the body under the influence of an external magnetic field for imaging. MRI has no ionizing radiation, can realize multi-nuclear and multi-parameter imaging, can scan in any orientation without changing the body position, has high spatial resolution and contrast without bone artifacts, and can reflect the water proton surrounding environment of the examined tissue With the advantages of obtaining relevant physiological and biochemical information, it has become one of the most effective clinical diagnostic methods. In ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K51/06A61K49/12C08B37/08A61K101/02
Inventor 朱卫华华明清张岐黄燕
Owner JIANGSU UNIV
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