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Amphiphilic polymer and preparing method thereof

A technology of amphiphilic polymers and polymers, applied in pharmaceutical formulations, medical preparations with non-active ingredients, etc., can solve problems such as lack of pH responsiveness, and achieve good application prospects

Active Publication Date: 2013-12-25
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, when some existing amphiphilic polymers are used as drug carriers, they are not pH-responsive, or have both pH-responsiveness and biocompatibility, which limits their application.

Method used

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  • Amphiphilic polymer and preparing method thereof
  • Amphiphilic polymer and preparing method thereof
  • Amphiphilic polymer and preparing method thereof

Examples

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preparation example Construction

[0072]The present invention also provides a method for preparing an amphiphilic polymer, comprising: combining an azide-functionalized polymer having a structure of formula (II) with polyethylene glycol monomethyl ether having a structure of formula (III) Paragraph-poly(γ-propynyl-L-glutamate), cuprous bromide, and pentamethyldivinyltriamine are mixed and reacted in an organic solvent to obtain an amphiphilic compound with the structure of formula (I) Polymer; Concrete reaction process is as follows:

[0073]

[0074] The organic solvent is preferably nitrogen, nitrogen dimethylformamide.

[0075] In formula (I) and formula (III), m is the degree of polymerization, preferably, 45≤m≤245, more preferably, 80≤m≤200; n and o are the degree of polymerization, preferably, 10≤n+ o≤200, more preferably, 50≤n+o≤100.

[0076] In formula (II) and formula (I), R is preferably:

[0077]

[0078] Wherein, k is the degree of polymerization, preferably 5≤k≤50, more preferably 10≤k≤30...

Embodiment 1

[0107] Mix 30 mL of propynyl alcohol with 20 g of L-glutamic acid, add 8 mL of concentrated sulfuric acid dropwise to the reaction system at 0°C, and complete the dropwise addition within 20 minutes, then stir the reaction overnight at room temperature. After the reaction, the reaction solution was poured into the sodium bicarbonate solution to obtain a white precipitate, which was recrystallized in water and filtered to obtain the product γ-propynyl-L-glutamate.

Embodiment 2

[0109] Mix 7.4 g of γ-propynyl-L-glutamate obtained in Example 1 with 3.96 g of triphosgene in 100 mL of dry tetrahydrofuran to obtain a suspension. Stir the reaction until the solution is clear, that is, the reaction is complete; after the reaction, settle the reaction system with 400mL of n-hexane, freeze it in a -20°C refrigerator overnight to obtain a layered solution, and then remove the upper layer of the layered solution Clear liquid, dissolve the yellow oily liquid in the lower layer in 100mL ethyl acetate, wash twice with 50mL ice water, then wash twice with 50mL cold 0.5wt% sodium bicarbonate aqueous solution, separate several layers, wash with anhydrous magnesium sulfate After drying overnight, the magnesium sulfate was removed by filtration, and the solution was spin-dried to obtain the product γ-propynyl-L-glutamic acid N-carboxyl internal anhydride.

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Abstract

The invention provides an amphiphilic polymer which has the structure shown in the formula (I), and the structure comprises a hydrophilic chain section and a hydrophobic chain section. An even and stable nano-micelle can be formed in the water solution and can be used for conveying hydrophobic medicines, meanwhile, the structure comprises a Schiff base structure, therefore, the amphiphilic polymer has the pH responsiveness, the amphiphilic polymer serving as a medicine carrier can have the intelligent responsiveness to the acid environment of the tumor locations, and the amphiphilic polymer has good application prospects in carrier pharmacology field. R is selected from .

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an amphiphilic polymer and a preparation method thereof. Background technique [0002] Amphiphilic polymers are polymers that have both hydrophilic and hydrophobic blocks. When the concentration of the amphiphilic polymer in water exceeds a certain value, its hydrophobic ends will automatically gather together to form a micelle particle with a hydrophobic interior and a hydrophilic exterior. This concentration is the critical micelle concentration, or CMC for short. The formed micelles have an important property, that is, solubilization, which can increase the solubility of oil-soluble drugs in water, so the micelles become an important carrier for the delivery of oil-soluble drugs. [0003] Compared with other carriers, micelles have many advantages: it can increase the bioavailability of drugs, reduce toxic side effects; prolong the circulation time of drugs in the b...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08G63/91C08G69/48A61K47/34
Inventor 肖春生张羽庄秀丽陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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