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Branched antibacterial polyamino acid and its preparation method and application

A polyamino acid, polylysine technology, applied in the field of medicine, can solve the problems of limitation, increase in charge density, hinder the development of antibacterial peptides or polymers, etc., and achieve the effect of improving antibacterial activity, good antibacterial activity, and avoiding toxic effects.

Active Publication Date: 2021-12-21
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, traditional linear antimicrobial peptides are limited by their structure, and their charge density is difficult to increase significantly with the increase of the number of charges, which has become a major problem hindering the development of antimicrobial peptides or polymers.

Method used

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  • Branched antibacterial polyamino acid and its preparation method and application
  • Branched antibacterial polyamino acid and its preparation method and application
  • Branched antibacterial polyamino acid and its preparation method and application

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preparation example Construction

[0036] The present invention also provides a method of branching an antibacterial polyamino acid, comprising a liquid phase synthesis method (an amino acid N-carboxy-cycloic anhydride (NCA) open loop polymerization method), solid phase synthesis method. The branched antibacterial polyamino acid synthesized by liquid phase synthesis (N-carboxy-cycloal acid anhydride open loop polymerization), has simple operation, high yield, low production cost, no spinning phenomenon, easy to obtain polymer polyamino acid Multiple advantages, but the synthesized polymer molecular weight distribution is relatively wide. The sequence and molecular weight of the polypeptide can be accurately controlled by solid phase synthesis method, but the synthesis time is long, high cost, and the sequence of direct synthesis is short. Therefore, although the antibacterial polyamino acid synthesized by two methods, it has the characteristics of avoiding toxic effects, less susceptible to hemolysis, high safety, ...

Embodiment 1

[0056] Example 1 Liquid phase synthesis method of star PLL antibacterial polyamino acid (PEI-G-PLL) (an amino acid N-carboxy-cycloal acid anhydride open loop poly)

[0057] 1. Synthesis of Star Poly L-lysine (PLL)

[0058] (1) Synthesis of amino acid N-carboxy-cycloalic anhydride (NCA)

[0059] Weigh ε-benzyloxycarbonyl-L-ε-benzoxycarbonyl-L-lysine, activated carbon, and triam (BTC) add anhydrous acetate (EA) to heat reflux, filtration, and obtain filtrate containing NCA crude product, the reaction route is as follows:

[0060]

[0061] The filtrate was frozen to -18 ° C or lower, and the saturated sodium hydrogencarbonate solution of 4 ° C was carried out with a saturated sodium hydrogen sodium hydrogen carbonate solution, respectively, and the residual hydrochloric acid and three light gas were removed. Finally, the product passes through crystallization and recrystallization processes in a compound of ethyl acetate-petroleum ether to obtain high purity NCA.

[0062] (2) Synth...

Embodiment 2

[0071] Example 2 Solid phase synthesis method of star PLL antibacterial polyamino acid

[0072] 1, synthesis of star PLL

[0073] (1) Synthesis of dendritic PLL kernel

[0074] DMF solution containing 20% ​​piperidine is removed from the FMOC protective group of Rink Amide-Mbha Resin resin, added to N, N'-bisflyfluorene methoxycarbonyl-lysine (Fmoc-Lys (FMOC) -OH) The coupling reaction is carried out by DMF as a solvent, 1-hydroxybenzene triazole (HOBT), and N, N'-diisopropyl carbon diimide (DIC) for condensants, and then with DMF containing 20% ​​piperidine The solution was removed from the FMOC protecting group to give a generation of dendritic L-lysine. Then by repeated coupling and deprotection process, a second-generation dendrim-shaped PLL having four amino groups and a three-generation dendrimal PLL having 8 amino groups is obtained as the core of the star PLL, and the joint route is as follows:

[0075]

[0076] Synthesis and Characterization of (2) of the star-PLL

[0077...

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Abstract

The invention provides a branched antibacterial polyamino acid. The branched antibacterial polyamino acid is a star-shaped branched polymer and a brush-shaped branched polymer, which is composed of an inner core and a branched chain; the inner core contains 4-15 A branched polymer of amino groups, wherein the branched chain is coupled to the inner core through a peptide bond; the branched chain is a hydrophilic polymer block, and the degree of polymerization of the hydrophilic polymer block is 5-20, and The monomers of the purely hydrophilic polymer block do not include hydrophobic monomers. The branched antibacterial polyamino acid has good antibacterial activity, and is less prone to hemolysis and has good biological safety.

Description

Technical field [0001] The present invention belongs to the field of medicine, and in particular, the present invention relates to a branched antibacterial polyamino acid and the preparation method thereof and applications. Background technique [0002] The emergence of antibiotics is one of the greatest discovery in human medicine history. Since I have been discovered, I saved the lives of countless people. However, in recent years, antibiotics have led to a large number of drug-resistant or even fatal pathogens, such as methylene-resistant Western Golden Staphylococcus aureus and anti-vibrant resistance copper pseudoma. These "super bacteria" with super-resistance to antibiotics have been widely spread around the world. Faced with this huge health crisis, antibacterial peptides (such as defensin, human antimicrobial peptide ll-37 and frogs, etc.) bring hope in killing these drug-resistant pathogens. Antibacterial peptide is also known as antimicrobial peptide or host defense pe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/10C09D177/04C09D187/00C09D5/14A61K31/785A61P31/04
CPCC08G69/10C09D177/04C09D187/005C09D5/14A61K31/785A61P31/04
Inventor 陆超吴传斌
Owner SUN YAT SEN UNIV
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