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High-generation dendritic polylysine and preparation method thereof

A polylysine and dendritic technology, applied in the field of high-generation dendritic polylysine and its preparation, can solve the problem of low purity, poor drug loading and slow-release ability, and small internal space of molecules in high-generation dendritic polymers and other problems, to achieve the effect of excellent water solubility, wide application range and low manufacturing cost

Inactive Publication Date: 2019-07-19
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to its structural characteristics, the synthesis of low-generation dendritic polymers is relatively easy, and the purity of high-generation dendritic polymers is relatively low, making it difficult to synthesize.
The third or fourth generation polymers of dendritic polylysine products currently on the market, due to their small molecular weight, lead to small internal space in the molecule, and poor drug loading and sustained release capabilities.

Method used

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  • High-generation dendritic polylysine and preparation method thereof
  • High-generation dendritic polylysine and preparation method thereof
  • High-generation dendritic polylysine and preparation method thereof

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preparation example Construction

[0044]

[0045] The preparation method of high-generation dendritic polylysine, it comprises the steps:

[0046] (1), react the lysine monomer containing diamino protection, N,N'-dicyclohexylcarbodiimide (DCC) and N-hydroxysuccinimide (HoSu) in an organic solvent to obtain lysine Amino acid activated ester monomer, its structural formula is:

[0047]

[0048] Wherein, the protecting group of diamino in the lysine monomer containing diamino protection is the same, Z represents the first amino protecting group, and Z' represents the second amino protecting group;

[0049] (2), react the lysine activated ester monomer of step (1) and the hydrophobic molecule containing amino group in organic solvent, obtain the n generation dendritic polylysine, its structural formula is:

[0050]

[0051] Wherein, n is an integer selected from 1-19, A represents a hydrophobic group, Z represents a first amino protecting group, and Z' represents a second amino protecting group;

[0052]...

Embodiment 1

[0076] The preparation method of the fifth generation dendritic polylysine containing benzyloxycarbonyl protection of the present embodiment comprises the following steps:

[0077] (1) 2.07g (0.005mol) of lysine containing two benzyloxycarbonyl groups (structure shown below), 1.03g of N,N'-dicyclohexylcarbodiimide and 0.69g of N-hydroxysuccinimide The amine was dissolved in 50ml of tetrahydrofuran, and reacted at 25°C for 10 hours to obtain the first lysine activated ester monomer;

[0078]

[0079] (2) After mixing 0.915g of benzhydrylamine and the reaction solution of the first lysine activated ester monomer, react at 25°C for 16h to obtain the first generation dendritic polylysine containing benzyloxycarbonyl protection;

[0080] (3) the dendritic polylysine containing benzyloxycarbonyl protection of the first generation in step (2) is dissolved in the acetic acid solution (as deprotecting agent) containing 30wt% hydrobromic acid (HBr) in 50ml, at 25 After reacting at ℃...

Embodiment 2

[0093] The preparation method of the fifth generation dendritic polylysine containing N-fluorenyl methaneoxycarbonyl protection comprises the following steps:

[0094] (1) Add 2.95g (0.005mol) of lysine containing two N-fluorenyl methaneoxycarbonyl groups (the structure is shown below), 1.03g of N,N'-dicyclohexylcarbodiimide and 0.69g of N-hydroxy Succinimide was dissolved in 50ml of THF, and reacted at 25°C for 8h to obtain the first lysine activated ester monomer;

[0095]

[0096] (2) After mixing 0.915g of diphenylmethylamine and the first lysine activated ester monomer reaction solution, react at 25°C for 16h to obtain the first generation dendrimer containing N-fluorenyl moxycarbonyl protection. Lysine;

[0097] (3) the dendritic polylysine that the first generation contains N-fluorenmoxycarbonyl protection in step (2) is dissolved in the dichloromethane solution that is 50% piperidine by volume fraction in 50ml (as deprotecting agent ), reacted at 25°C for 3 hours,...

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Abstract

The invention provides high-generation dendritic polylysine and a preparation method thereof. According to the invention, amino-containing organic hydrophobic small molecules are taken as starting points and react with a double-protection lysine activated ester monomer to generate first-generation dendritic polylysine, second-generation dendritic polylysine and high-generation dendritic polylysine; and due to the hyperbranched spherical structure of the high-generation dendritic polylysine, a large cavity can be formed in molecules, a large number of modifiable groups such as high phenylalanine exist on the surface in a dense mode, the performance of the material is greatly changed, and a multifunctional medical polymer material can be rapidly synthesized. Compared with linear polylysine,the high-generation dendritic polylysine disclosed by the invention has the characteristics of being excellent in water solubility, incapable of being decomposed in water, capable of being developed into a carrier and the like, so that the application range is wide; in addition, the biological compatibility is good, and the hemolytic rate is lower than 10%; and the synthesis method of the high-generation dendritic polylysine disclosed by the invention is simple and low in manufacturing cost.

Description

technical field [0001] The invention belongs to the technical field of medical polymer materials, and in particular relates to a high-generation dendritic polylysine and a preparation method thereof. Background technique [0002] Dendritic polymers were first invented and successfully synthesized by American chemist Dr. Tomalia DA in the early 1980s. Dendrimers are large, dendritic molecules that are widely used in chemistry and biology. Dendrimers play an important role in research because of their three-dimensional regular structure, high degree of branching and nanoscale monodispersity. Among them, polypeptide dendrimers, as a member of dendrimers, have other characteristics in addition to the general characteristics of dendrimers, such as: good biocompatibility, protease hydrolysis and biodegradability, good water solubility and strong resistance to hydrolytic enzymes. These characteristics make it widely used in the field of biomedicine. However, due to the structur...

Claims

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Application Information

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IPC IPC(8): C08G83/00C08G69/10
CPCC08G69/10C08G83/003
Inventor 周春才钱宇盛
Owner TONGJI UNIV
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