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Star-shaped cationic polymer containing dendriform polylysine element and preparation method thereof

A technology of cationic polymers and polylysine units, which is applied in the field of biomedical engineering materials to achieve high reaction efficiency, low raw material consumption, and low toxicity of metabolites

Active Publication Date: 2012-07-25
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the synthesis of star-shaped cyclodextrin-grafted dendritic polylysine and its application have not been reported by click chemistry

Method used

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  • Star-shaped cationic polymer containing dendriform polylysine element and preparation method thereof
  • Star-shaped cationic polymer containing dendriform polylysine element and preparation method thereof
  • Star-shaped cationic polymer containing dendriform polylysine element and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] a. Weigh triphenylphosphine and dissolve it in anhydrous N, N-dimethylformamide (DMF), then add iodine element at room temperature at 25°C, raise the temperature to 55°C; then add dry β-cyclopaste Fine (β-CD), N 2 Reaction under atmosphere for 48 hours; after the reaction, anhydrous N,N-dimethylformamide was removed by distillation under reduced pressure, and sodium methoxide solution was added under ice-water bath conditions; the resulting product was precipitated 7 times in methanol, and then vacuum-dried to obtain seven (6-iodo-6-deoxy)-β-cyclodextrin [β-CD-(I) 7 ]; the molar ratio of the β-cyclodextrin, triphenylphosphine and iodine simple substance is 1: 1.2: 1.4; the anhydrous N, N-dimethylformamide is added with 20 grams of dry Beta-cyclodextrin meter; the molar number of sodium methylate in the sodium methylate solution is 1.5 times of the dry beta-cyclodextrin molar number;

[0056] b. Dissolve the hepta(6-iodo-6-deoxy)-β-cyclodextrin and sodium azide obtaine...

Embodiment 2

[0058] a. Weigh triphenylphosphine and dissolve it in anhydrous N,N-dimethylformamide (DMF), then add iodine element at room temperature at 35°C, and raise the temperature to 70°C; then add dry β-cyclopaste Fine (β-CD), N 2 Reaction under atmosphere for 24 hours; after the reaction, anhydrous N, N-dimethylformamide was distilled off under reduced pressure, and sodium methoxide solution was added under ice-water bath conditions; the resulting product was precipitated 4 times in methanol, and then vacuum-dried to obtain seven (6-iodo-6-deoxy)-β-cyclodextrin [β-CD-(I) 7 ]; the molar ratio of the β-cyclodextrin, triphenylphosphine and iodine simple substance is 1: 1.5: 1.6; the anhydrous N, N-dimethylformamide is added 5 grams of dry Beta-cyclodextrin meter; the molar number of sodium methylate in the sodium methylate solution is 2.0 times of the dry beta-cyclodextrin molar number;

[0059] b. Dissolve the hepta(6-iodo-6-deoxy)-β-cyclodextrin and sodium azide obtained in step a ...

Embodiment 3

[0061] a. Weigh triphenylphosphine and dissolve it in anhydrous N,N-dimethylformamide (DMF), then add iodine element at room temperature at 5°C, and raise the temperature to 60°C; then add dry β-cyclopaste Fine (β-CD), N 2 Reaction under atmosphere for 32 hours; after the reaction, anhydrous N,N-dimethylformamide was removed by distillation under reduced pressure, and sodium methoxide solution was added under ice-water bath conditions; the resulting product was precipitated in methanol for 6 times, and then dried in vacuum to obtain seven (6-iodo-6-deoxy)-β-cyclodextrin [β-CD-(I) 7 ]; the molar ratio of the β-cyclodextrin, triphenylphosphine and iodine simple substance is 1: 1.3: 1.5; the anhydrous N, N-dimethylformamide is added with 15 grams of dry Beta-cyclodextrin meter; the molar number of sodium methylate in the sodium methylate solution is 1.8 times of the dry beta-cyclodextrin molar number;

[0062] b. Dissolve the hepta(6-iodo-6-deoxy)-β-cyclodextrin and sodium azid...

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Abstract

The invention discloses a star-shaped cationic polymer containing dendriform polylysine element, and a preparation method and application thereof. The method comprises the following steps: carrying out substitution reaction to introduce an azido group onto the C6 site of beta-cyclodextrin; carrying out coupling reaction on propargylamine and N,N'-di-tert-butoxycarbonyl-L-lysine, and carrying out repeated condensation and deprotection reactions to synthesize the alkynyl-containing dendriform polylysine; and coupling the two products by a click chemical process to obtain the star-shaped cationic polymer beta-CD-PLLD containing dendriform polylysine element. The polymer has the advantages of regular and easily controlled structure, single molecular weight distribution, favorable biocompatibility, biodegradability and the like, and is prospected to be widely used in the field of gene therapy.

Description

technical field [0001] The invention belongs to the field of biomedical engineering materials, in particular to a star-shaped cationic polymer containing dendritic polylysine units, a preparation method thereof, and its potential application as a biomedical material. Background technique [0002] Gene therapy is currently an effective method for the treatment of cancer and innate immune system diseases. The key to the implementation of this technology is to select the appropriate gene carrier and gene introduction method, so that the gene can be expressed in cells safely, efficiently, controllably and stably. Viral vectors are limited in clinical application due to their high risk, immune response, and incapability of large-scale production. Therefore, liposomes and other cationic polymers with high transfection efficiency are increasingly valued. [0003] Dendrimers are a class of monodisperse polymer materials with three-dimensional regular structure, highly branched and ...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08B37/16C08G83/00C12N15/87A61K47/40A61K47/34
Inventor 马栋曹凯迪张黎明陈弟虎
Owner SUN YAT SEN UNIV
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