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Porphyrin modified by diethylenetriamine pentaacetic acid gadolinium and preparation method and application thereof

A technology of diethylenetriaminepentaacetic acid and porphyrin, applied in the field of porphyrin, can solve the problem that the biocompatibility of porphyrin is not much improved, and achieve the effects of high enhancement effect, strong fluorescence effect and high relaxation effect.

Active Publication Date: 2010-08-18
INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, neither the introduction of carboxyl group nor the introduction of sulfonic acid group improved the biocompatibility of porphyrin much.

Method used

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  • Porphyrin modified by diethylenetriamine pentaacetic acid gadolinium and preparation method and application thereof
  • Porphyrin modified by diethylenetriamine pentaacetic acid gadolinium and preparation method and application thereof
  • Porphyrin modified by diethylenetriamine pentaacetic acid gadolinium and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] (1) 0.2g 5,10,15,20-tetra-[p-aminophenyl] porphyrin, 1.4g diethylenetriaminepentaacetic acid bicyclic anhydride, 1.0ml triethylamine dissolved in 15ml dimethyl In sulfoxide, under the catalysis of 4,4-dimethylaminopyridine, stir at room temperature for 12h. After the reaction is complete, add 30mL of water, let it stand, and precipitate the product. Suction filtration to obtain the crude product. Washing with dichloromethane for 3 times and ethanol for 3 times, drying and recrystallizing to obtain a porphyrin compound modified with diethylenetriaminepentaacetic acid;

[0044] (2) Weigh 0.6g of the porphyrin compound modified by diethylenetriaminepentaacetic acid and dissolve it in 50ml of water, add 0.54g of gadolinium chloride, adjust the pH to 7.0-8.0, stir electromagnetically for 12h, and pour the reaction solution into 30mL (CH 3 CH 2 OH: (CH 3 CH 2 ) 2 (0=1: 1) separate out product in the mixed solution, suction filtration, obtain the porphyrin modified by ga...

Embodiment 2

[0048] The preparation method of the porphyrin modified by gadolinium diethylene triamine pentaacetate comprises the steps:

[0049] (1) 0.5g 5-(4-aminophenyl)-10,15,20-phenylporphyrin, 1.2g diethylenetriaminepentaacetic acid bicyclic anhydride, 0.5ml triethylamine were dissolved in 20mL pyridine, Under the catalysis of 4,4-dimethylaminopyridine, it was stirred at room temperature for 36h. After the reaction is complete, add 30mL of H 2 O, precipitated product. Suction filtration to obtain the crude product. Washing with dichloromethane for 3 times, ethanol for 3 times, drying, and recrystallization to obtain a porphyrin compound modified with diethylenetriaminepentaacetic acid;

[0050] (2) Dissolve 0.3 g of the diethylenetriaminepentaacetic acid-modified porphyrin compound in 30 ml of water, add 0.29 g of gadolinium chloride, adjust the pH to 7.0-8.0, and stir electromagnetically for 20 h. 8mL of water was evaporated, and the reaction solution was poured into 30mL (CH3 C...

Embodiment 3

[0053] The preparation method of the porphyrin modified by gadolinium diethylene triamine pentaacetate comprises the steps:

[0054] (1) 0.5g 5,10-bis(4-aminophenyl)-15,20-diphenylporphyrin, 2.0g diethylenetriaminepentaacetic acid bicyclic anhydride, 2.0ml triethylamine are dissolved in N, In 30 mL of N-dimethylformamide, under the catalysis of 4,4-dimethylaminopyridine, stir at room temperature for 36 h. After the reaction is complete, add 30mL of H 2 0, the product is separated out, suction filtered, washed 3 times with 6ml methylene chloride, washed 3 times with 10ml ethanol, and recrystallized to obtain the porphyrin compound modified by diethylenetriaminepentaacetic acid;

[0055] (2) Weigh 0.6g of diethylenetriaminepentaacetic acid-modified porphyrin compound and dissolve it in 50ml of water, add 0.68g of gadolinium chloride, adjust the pH to 7.0-8.0, and react with electromagnetic stirring for 30h. 10mL of water was evaporated, and the reaction solution was poured int...

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Abstract

The invention discloses porphyrin modified by diethylenetriamine pentaacetic acid gadolinium and a preparation method and application thereof. The porphyrin modified by diethylenetriamine pentaacetic acid gadolinium has the following structure (I) shown in the specification of the invention. The porphyrin modified by diethylenetriamine pentaacetic acid gadolinium has favorable water solubility and higher biomagnetic effect. Through large quantity of grope by the inventor, the orphyrin modified by diethylenetriamine pentaacetic acid gadolinium has high enhancement in clinical MRI (Magnetic Resonance Imaging) and also stronger fluorescence quantum yield, strong fluorescent effect and wide application prospect and can be applied to the fields of nonlinear photoelectric materials, magnetic resonance imaging diagnosis, fluorescent molecular probes and the like. A preparation method of a porphyrin contrast agent modified by the diethylenetriamine pentaacetic acid gadolinium is concise and easy to operate.

Description

technical field [0001] The invention relates to a porphyrin, in particular to a porphyrin modified with gadolinium diethylene triamine pentaacetate, a preparation method and application thereof. Background technique [0002] Magnetic resonance imaging (MRI) technology has been widely used in the diagnosis of various diseases, especially for cardiovascular diseases and tumors. MRI contrast agent is a class of drugs that can enhance the contrast of magnetic resonance signals between normal tissue and diseased tissue, and display organ function and body fluid status. The paramagnetic metal complex Gd (diethylenetriaminepentaacetic acid) used as MRI contrast agent It has good biocompatibility with the human body and has been widely used clinically. It was later found that Gd-diethylenetriaminepentaacetic acid also has some shortcomings, such as too fast elimination and non-specific distribution in the body, so that the contrast of MRI images cannot be significantly improved. P...

Claims

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Application Information

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IPC IPC(8): C07F5/00C09K11/06A61K49/06G01N21/64
Inventor 刘天军王玉茂武莉吕丰
Owner INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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