Tumor targeting poly-asparagine free radical compounds and synthesizing method and use

A polyasparagine, tumor-targeting technology, used in the fields of chemistry and medicine, can solve the problems of short retention time, poor imaging effect, and no tissue or organ selectivity or targeting.

Inactive Publication Date: 2008-09-10
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, the stable free radicals of these small molecules have fast metabolism in the body, short retention time, low utilization rate, no tissue or organ selectivity or targeting, especially poor imaging effect on tumors

Method used

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  • Tumor targeting poly-asparagine free radical compounds and synthesizing method and use
  • Tumor targeting poly-asparagine free radical compounds and synthesizing method and use
  • Tumor targeting poly-asparagine free radical compounds and synthesizing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Tumor-targeting Polyasparagine Free Radical Compounds Containing Sulfadiazine

[0074] a) Reaction of sulfadiazine with bromoacetyl chloride

[0075] Dissolve 2.5g of sulfonamide (SN) in 40mL of N,N-dimethylformamide (DMF), add 2mL of triethylamine and stir, cool in an ice-water bath, slowly add 1.3g of bromoacetyl chloride dropwise under stirring, 0-5°C React for 2 hours, stir at room temperature for 4 hours, pass dry air to drive away the residual reaction gas, and store the reaction solution at 0-5°C for later use;

[0076] b) 5-Carboxylic acid-1,1,3,3-tetramethylisozaindene nitroxide free radical active ester

[0077]4.7g of 5-carboxylic acid-1,1,3,3-tetramethylisozaindene nitric oxide radical (20mmol) was dissolved in 30mL DMF and 2mL triethylamine mixed solvent, cooled to 0°C, and 4.1g N, N'-dicyclohexylcarbodiimide (20mmol), stirred at 0°C for 30 minutes, then added 2.3g of N-hydroxysuccinimide (20mmol), stirred at 0°C for 1 hour, and stirred at room temperatur...

Embodiment 2

[0081] Tumor-targeting polyasparagine free radical compounds containing sulfadiazine.

[0082] a) Preparation of 4-benzyloxycarbonyl amido-N-isethsulfadiazine and reaction with phosgene:

[0083] Dissolve 2.94g of 4-amino-N-isethsulfadiazine in 10mL of N,N-dimethylformamide, add 5mL of pyridine, cool in an ice-water bath at 0-5°C, add dropwise 5mL containing 1.7g of benzyloxy The benzyl alcohol solution of carbonyl chloride was reacted at 0-5°C for 4 hours and at room temperature for 6 hours; an appropriate amount of ether was added to precipitate, filtered, and vacuum-dried. The resulting white solid was dissolved in 50 mL N,N-dimethylformamide, and 2 mL Stir with ethylamine, cool in an ice-water bath, slowly add 4.5 mL of phosgene toluene solution dropwise under stirring, wherein the molar concentration of phosgene is 2 mol / mL, react at 0-5°C for 1 hour, stir at room temperature for 2 hours, and drive off with dry air Residual phosgene, the reaction solution was stored at 0...

Embodiment 3

[0090] Porphyrin-containing tumor-targeting polyasparagine free radical compounds.

[0091] a) 5-(4-aminophenyl)-10,15,20-three (4-sulfonic acid phenyl) porphyrin reacts with bromoacetyl chloride:

[0092] 4.68g 5-(4-aminophenyl)-10,15,20-tris(4-sulfonic acid phenyl)porphyrin was dissolved in 30mL N,N-dimethylformamide, added 2mL triethylamine and stirred, Cool in an ice-water bath, slowly add 0.69 bromoacetyl chloride dropwise under stirring, react at 0-5°C for 2 hours, stir at room temperature for 4 hours, drive the residual reaction gas with dry air, and store the reaction solution at 0-5°C for later use;

[0093] b) Preparation of 5-5-amino-1,1,3,3-tetradeuteromethylisozaindene nitroxide free radical active ester

[0094] 2.29g of 5-amino-1,1,3,3-tetradeuteromethylisozaindene nitric oxide radical was dissolved in 30mL of anhydrous diethyl ether and 10mL of dichloromethane mixed solvent, and 1g of N,N'-dichloromethane was added Dissolve cyclohexylcarbodiimide in 20 mL of ...

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Abstract

The invention relates to a tumor targeting poly-asparagine radical compound and a synthetic method and uses thereof. The poly-asparagine radical compound consists of a carrier of poly-asparagine macromolecule and a side chain which has a tumor targeting group and a stable radical compound. The compound can be used for electron paramagnetic resonance imaging analysis and magnetic resonance imaging analysis of various tumors or cancer pathological changes in human bodies or other mammal bodies, X-ray CT and ultrasonic image medicinal imaging diagnosis.

Description

technical field [0001] The present invention relates to a class of tumor-targeting polyasparagine free radical compound and its synthesis method and application. Specifically, the polyasparagine macromolecule is used as a carrier, and the side chain contains a tumor-targeting group and a stable free radical compound and Their synthesis methods and uses. The invention belongs to the technical fields of medicine and chemistry. Background technique [0002] Free radicals are atoms or atomic group chemical substances with one or more unpaired electrons, which are prone to chemical reactions with other substances. Most free radicals are very short-lived, often measured in milliseconds or nanoseconds. Electron Paramagnetic (Spin) Resonance (EPR or ESR) is the most effective means to detect and analyze biological free radicals. In recent years, electron paramagnetic resonance imaging (EPR Imaging, EPRI), as a method for in vivo detection and multidimensional imaging analysis of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/34A61K49/12
Inventor 鄢国平刘艳吴江渝喻湘华李亮郭庆中杨隽杜飞鹏程智毓
Owner WUHAN INSTITUTE OF TECHNOLOGY
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