Preparation method of metal coordination supermolecular nanogel

A metal coordination, nanogel technology, applied in the supramolecular field, can solve the problems of poor targeting of anti-tumor drugs, complex composition of natural porphyrin compounds, and high toxicity and side effects

Inactive Publication Date: 2014-11-19
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, natural porphyrin compounds have complex components and poor penetrability, which cannot meet clinical needs. It is necessary to modify their structure or synthesize new porphyrin molecules in order to obtain better photosensitive drugs.
After the porphyrin compounds are bonded to biomolecules or traditional anti-tumor drug molecules, the compounds show good pharmacological activity, which provides a new idea for solving the problems of poor targeting and high toxicity of anti-tumor drugs

Method used

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  • Preparation method of metal coordination supermolecular nanogel

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preparation example Construction

[0014] The invention provides a kind of preparation method of metal coordination supramolecular nanogel, comprising the following steps:

[0015] (1) Grafting histidine onto natural polysaccharides through EDC / DMAP condensation reaction to prepare histidine-modified natural polysaccharides;

[0016] (2) Preparation of metal-coordinated supramolecular nanogels through metal-coordination between metalloporphyrins and histidine.

[0017] In the present invention, the hydrophilic polymer is natural polysaccharide, preferably dextran, chitosan, hyaluronic acid. More preferred is dextran.

[0018] The number average molecular weight of the hydrophilic polymer is preferably 500-50000, more preferably 6000-40000, most preferably 6000-10000.

[0019] In the present invention, the said histidine is a type of small molecular monomer containing an imidazole ring, preferably histidine, BOC-protected histidine.

[0020] In the present invention, the metal is a metal that can coordinate w...

Embodiment example 1

[0026] Implementation Case 1 Preparation of Tetraphenylporphyrin

[0027] Measure 7.14mL (71.4mmol) of p-benzaldehyde into a three-necked flask, add 300mL of propionic acid as a solvent, and slowly drop 5mL (71.4mmol) of pyrrole into the reaction flask during the process of reflux, and continue to reflux after the addition After 30 minutes, the reaction was stopped. After cooling, filter with a Buchner funnel. The filter cake was washed with methanol until the filtrate was colorless, then washed with hot water until the filtrate was neutral, and then dried in a vacuum oven to obtain a crude product. Pure tetraphenylporphyrin was obtained by recrystallization three times with dichloromethane and ethanol. The obtained tetraphenylporphyrin was analyzed by nuclear magnetic resonance, infrared spectrum and ultraviolet spectrum, which proved that the tetraphenylporphyrin was successfully synthesized.

Embodiment example 2

[0028] Implementation Case 2 Preparation of Zinc Tetraphenylporphyrin

[0029] Take by weighing 1g (1.63mmol) tetraphenylporphyrin and put it into a three-necked flask, add 60mL of chloroform as a solvent, and in the process of reflux, add 1.43g (6.52mmol) zinc acetate dihydrate, after reflux reaction for 1h, After the reaction was stopped, after cooling to room temperature, the reaction solution was washed three times with water, and after washing, the organic phase was spin-dried to remove the solvent to obtain zinc tetraphenylporphyrin as a solid. The obtained tetraphenylporphyrin was analyzed by infrared spectrum and ultraviolet spectrum, which proved that tetraphenylporphyrin was successfully synthesized.

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Abstract

The invention provides a preparation method of metal coordination supermolecular nanogel. The metal coordination supermolecular nanogel is composed of natural polysaccharide, histidine and metalloporphyrin. The preparation method of the metal coordination supermolecular nanogel comprises the following steps: (1) grafting the histidine to the natural polysaccharide by use of an EDC/DMAP condensation reaction, thereby preparing the histidine-modified natural polysaccharide; and (2) preparing the metal coordination supermolecular nanogel under the metal coordination action of the metalloporphyrin and the histidine. The preparation method is simple and convenient in steps. The nanogel prepared by the method has tumor intracellular pH sensitivity, and excellent biocompatibility and biodegradability, can be taken as a carrier material for drug delivery and controlled release, and meanwhile, is capable of realizing tumor treatment by virtue of combined chemical treatment and photodynamic therapy.

Description

technical field [0001] The invention belongs to the technical field of supramolecules, and in particular relates to a method for preparing metal-coordinated supramolecular nanogels. Background technique [0002] Drug controlled release is to combine the drug with the drug carrier, and release the drug at an appropriate concentration and speed through diffusion, penetration, etc. in the body, so as to fully exert the efficacy of the drug. An ideal drug carrier should have the following characteristics: good biocompatibility, biodegradability, narrow molecular weight distribution and high drug loading capacity, high molecular polymers such as polyester and polyamino acid are non-toxic and biocompatible It has become the main material of the drug controlled release carrier due to its advantages of good quality and biodegradability. Malignant tumors have the characteristics of invasiveness, rapid growth, easy metastasis, and easy recurrence, which often make it impossible to ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/09C08J3/075C08B37/02C08B37/08A61K47/36A61K9/06
Inventor 陈莉姚雪梅陈笑非张喆
Owner NORTHEAST NORMAL UNIVERSITY
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