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Contrast medium of dual-sector targeted magnetic resonance imaging contrast and preparation thereof

An MRI and contrast agent technology, applied in the direction of MRI/MRI contrast agent, etc., can solve the problems of high injection dose and injection frequency, short stay time, etc.

Inactive Publication Date: 2011-07-27
WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantage of small molecular weight contrast agents is that they diffuse rapidly into the extracellular matrix and therefore remain in the blood circulation for a short time, which requires relatively high injection volumes and frequency of injections

Method used

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  • Contrast medium of dual-sector targeted magnetic resonance imaging contrast and preparation thereof
  • Contrast medium of dual-sector targeted magnetic resonance imaging contrast and preparation thereof
  • Contrast medium of dual-sector targeted magnetic resonance imaging contrast and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 1) Synthesis of sector-shaped parts containing small molecule ligands:

[0052] a: Weigh 0.1mol of ethylenediamine and dissolve it in 50ml of dichloromethane, add it to a 250ml there-necked flask, and slowly add dropwise 50ml of the dichloromethane solution that dissolves 0.1mol of di-tert-butyl dicarbonate (BOC anhydride) under stirring, The reaction was carried out at room temperature for 12 hours. Using dichloromethane:methanol=3:7 (V / V) as the eluent, the ethylenediamine protected at both ends was separated and removed by silica gel column chromatography, and the ethylenediamine product protected at one end was retained.

[0053] b: the above-mentioned product of 0.05mol was dissolved in 15ml of methanol, added to a 100ml there-necked flask, slowly dripped with 25ml of methanol solution dissolved with 0.4mol of methyl acrylate, stirred at room temperature for 12 hours, and the solvent methanol and excess were removed by rotary evaporation of methyl acrylate to give...

Embodiment 2

[0067] 1) Synthesis of sector-shaped moieties containing small molecule ligands

[0068] a: Synthesis of compounds containing 8 terminal ester groups. Same as 1) a, b, and c in Example 1, and repeat steps b and c until a compound containing 8 terminal ester groups is synthesized.

[0069] b: Take 10 mmol of the compound containing 8 terminal ester groups in 10 ml of water, add 0.1 mmol NaOH, react at 50 °C for 12 hours, dialyze with a dialysis membrane with a molecular weight of 500 for 24 hours, and freeze-dry to obtain a protective group containing 8 terminal carboxyl groups. Dendrimers.

[0070] c: Dissolve 1.0 mmol of the product obtained in step b in 10 ml of dichloromethane solvent, add 1.0 ml of 1M hydrochloric acid to the solution, and react at 35° C. for 12 hours (TLC tracks the reaction progress) to remove the BOC protecting group. After the reaction was completed, the reaction mixture was purified by column chromatography.

[0071] 2) Synthesis of sector part conta...

Embodiment 3

[0083] 1) Synthesis of sector-shaped parts containing small molecule ligands:

[0084] Same as Example 1.

[0085] 2) Synthesis of sector part containing targeting group:

[0086] Same as Example 1.

[0087] 3) Preparation of double sector compounds

[0088] Dissolve 0.8 mmol of the product obtained in 1) in 5 ml of DMSO, slowly add 0.8 mmol of adipoyl chloride dropwise with stirring, react at room temperature for 2 hours, and use a dialysis bag with a molecular weight cut-off of 500 to dialyze against deionized water for 12 hours. The dialyzed product was purified by column chromatography, and the adipoyl chloride product with only one end reacted was retained.

[0089] 0.6 mmol of the product was dissolved in 5 ml of DMSO, 2) 0.5 mmol of the product was slowly added dropwise with stirring, and the reaction was carried out at room temperature for 2 hours to obtain a double fan-shaped dendrimer. The reaction mixture was dialyzed against deionized water for 24 hours and lyo...

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Abstract

The invention discloses a contrast medium of dual-sector targeted magnetic resonance imaging and preparation thereof, wherein the contrast medium is prepared by the reaction of a dual-sector compound and a metal chloride. The metal chloride is GdCl3, FeCl3, FeCl2 or MnCl2; the dual-sector compound is as follows: two sector dendritic molecules are connected on a connecting group R; each sector dendritic molecule has 2<n> end groups, and n is a natural number; the end group of one sector dendritic molecule is a targeted group X, and the end group of the other sector dendritic molecule is a carboxyl group or a residue goup Y of a small molecular ligand; and the structure of the dual-sector compound is shown as in formula (1) or formula (2). The contrast medium has good targeting characteristic and high sensitivity to cancer cells.

Description

(1) Technical field [0001] The invention relates to a dual sector targeting nuclear magnetic resonance imaging contrast agent and a preparation method thereof (2) Background technology [0002] In 1973, Lauterbur applied Magnetic Resonance Imaging (MRI) technology to human diagnosis for the first time, which made this technology rapidly developed and widely used in biology, medicine and other fields. [0003] MRI signal intensity depends on tissue characteristic parameters and imaging time parameters. By choosing appropriate pulse sequence and time parameters or changing the MRI tissue characteristic parameters, the contrast of magnetic resonance images can be improved. MRI contrast agents can improve the imaging sensitivity of MRI and can overcome the limitations of common imaging sequences. By changing the proton relaxation time of the tissue and then changing the signal intensity generated by the proton, the contrast between normal tissue and diseased tissue is improved...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/06
Inventor 张伟禄周雪梅邰玉蕾晁国库樊洪斌熊静赵亚娟金雪华司朗诵
Owner WENZHOU UNIV
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