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A kind of polyethylene glycol-polyamide-amine-hydrophobic molecule linear-dendritic polymer and its preparation method

A technology of polyethylene glycol and polyamide, which is applied in the field of polyethylene glycol-polyamide-amine-hydrophobic molecular linear-dendrimer polymer and its preparation, can solve the problems of high price, low yield, limitation and the like, Achieving the effect of simple method, high yield and good biocompatibility

Active Publication Date: 2015-10-07
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the Fmoc-Lys(Fmoc)-OH used in the process of preparing dendritic polylysine in this method is expensive, and the deprotection conditions are not easy to control, and the yield is often low, which limits its application.

Method used

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  • A kind of polyethylene glycol-polyamide-amine-hydrophobic molecule linear-dendritic polymer and its preparation method
  • A kind of polyethylene glycol-polyamide-amine-hydrophobic molecule linear-dendritic polymer and its preparation method
  • A kind of polyethylene glycol-polyamide-amine-hydrophobic molecule linear-dendritic polymer and its preparation method

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preparation example Construction

[0078] The present invention also provides a preparation method of polyethylene glycol-polyamide-amine-hydrophobic molecule linear-dendritic polymer, comprising the following steps:

[0079] A) Mixing aminated aminated polyethylene glycol monomethyl ether having a structure of formula a or aminated aminated polyethylene glycol having a structure of formula b with methyl acrylate for addition reaction to obtain the first addition product ; Mix the first addition product with ethylenediamine, and perform ammonolysis reaction to obtain the 1.0th generation polymer of polyethylene glycol-polyamide-amine;

[0080] Mix the polyethylene glycol-polyamide-amine 1.0th generation polymer with methyl acrylate for an addition reaction to obtain a second addition product; mix the second addition product with ethylenediamine for ammonia Decomposition reaction, obtain polyethylene glycol-polyamide-amine 2.0th generation polymer;

[0081] Mix the polyethylene glycol-polyamide-amine 2.0th gene...

Embodiment 1

[0159] Take 10.0g (0.116mol) of methyl acrylate and dissolve it in 50mL of methanol, add it into the reaction flask, and stir in an ice bath. Then weigh 4.7g (0.0023mol) of aminated polyethylene glycol monomethyl ether with a number-average molecular weight of 2000, dissolve it in 50mL of methanol, and slowly add it dropwise into the reaction bottle for about half an hour. Seal the reaction bottle and move it to a 30°C oil bath to stir for 48 hours. The obtained product was spin-dried by a rotary evaporator, then dissolved in 20 mL of methanol, and settled in 100 mL of anhydrous ether. The solid obtained after suction filtration was evacuated by a vacuum oil pump for 8 hours. Finally, a white solid was obtained, which was the first addition product. Named MPEG2000D0.5, yield: 90.2%.

[0160] Take 10.0g (0.167mol) of ethylenediamine and dissolve it in 50mL of methanol, add it to the reaction bottle, and stir in an ice bath. Then weigh 3.3g (0.00167mol) of MPEG2000D0.5, dissol...

Embodiment 2

[0162] Take 10.0g (0.116mol) of methyl acrylate and dissolve it in 50mL of methanol, add it into the reaction flask, and stir in an ice bath. Then weigh 11.6g (0.0023mol) of aminated polyethylene glycol monomethyl ether with a number average molecular weight of 5000, dissolve it in 50mL of methanol, and slowly add it dropwise into the reaction flask for about half an hour. Seal the reaction bottle and move it to a 30°C oil bath to stir for 48 hours. The obtained product was spin-dried by a rotary evaporator, then dissolved in 20 mL of methanol, and settled in 100 mL of anhydrous ether. The solid obtained after suction filtration was evacuated by a vacuum oil pump for 8 hours. Finally, a white solid was obtained, which was the first addition product. Named MPEG5000D0.5, yield: 91.2%.

[0163] Take 10.0g (0.167mol) of ethylenediamine (large excess) and dissolve it in 50mL of methanol, add it to the reaction flask, and stir in an ice bath. Then weigh 8.3g (0.00167mol) of MPEG50...

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Abstract

The invention provides a polyethylene glycol-polyamide-amine-hydrophobic molecular linear-dendritic polymer with a structure of formula I, formula II, formula III, formula IV, formula V or formula VI. The preparation method of the polyethylene glycol-polyamide-amine-hydrophobic molecular linear-dendritic polymer comprises the following steps of: repeatedly carrying out Michael addition reaction on amination polyethylene glycol as a core and methyl acrylate and carrying out ammonolysis reaction on the amination polyethylene glycol and ethanediamine to obtain a polyethylene glycol-polyamide-amine polymer with different algebraic numbers and different primary amine numbers at the tail end; and carrying out the reaction of amino group and acyl chloride to obtain the polyethylene glycol-polyamide-amine-hydrophobic molecular linear-dendritic polymer. The prepared amphipathic macromolecule can be assembled into a nano particle in water and packaged with a drug. The method for preparing the polymer provided by the invention is simple and higher in yield. Moreover, the polyethylene glycol has good biocompatibility and can be used for prolonging the circulating time of the nano particle in the blood, so that the polymer provided by the invention has good application prospect as a nano drug carrier.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a polyethylene glycol-polyamide-amine-hydrophobic molecule linear-dendritic polymer and a preparation method thereof. Background technique [0002] With the development of nanotechnology, a variety of nanomaterials, such as polymer materials and inorganic materials, have been used in drug delivery systems. These nanoparticles can effectively transport a variety of different drugs, protect the drugs from being degraded in advance, and reduce the toxic and side effects of the drugs. Site enrichment for passive targeting. [0003] Although many types of nanoparticles have been developed as drug carriers, only a few types of materials have been approved by the FDA because of the potential toxicity and structural ambiguity of the carrier materials. Among them, the linear-dendritic polymer as a drug carrier has a well-defined structure, and the low-generation den...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00C08G65/48A61K47/34
Inventor 肖春生张羽李明强宋万通庄秀丽陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI