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A kind of simulated antimicrobial peptide copolymer and preparation method thereof

A technology of copolymers and antibacterial peptides is applied in the field of biomedical polymer antibacterial materials and achieves the effects of mild reaction conditions, easy availability of experimental raw materials and simple operation.

Inactive Publication Date: 2020-05-26
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is little research on the preparation of mimetic antimicrobial peptides by using amino polyhedral oligomeric silsesquioxanes to trigger the ring-opening polymerization of lysine N-carboxy-cyclic anhydride and valine N-carboxy-cyclic anhydride monomers. There are reports

Method used

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  • A kind of simulated antimicrobial peptide copolymer and preparation method thereof
  • A kind of simulated antimicrobial peptide copolymer and preparation method thereof
  • A kind of simulated antimicrobial peptide copolymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1) Preparation of polyhedral polysilsesquioxane-poly(lysine-co-valine) copolymer

[0020] Put 2.1g of L-lysine with benzyloxycarbonyl-protected amino groups and 30mL of dry tetrahydrofuran into a 100mL three-necked flask, stir and disperse at 50°C, dissolve 1.5g of triphosgene in 10mL of tetrahydrofuran, and slowly add the triphosgene solution into the system. Under the protection of nitrogen, react for 3h. After precipitating with 10 times the volume of n-hexane, suction filtration, and then recrystallizing the precipitate twice with ethyl acetate / n-hexane with a volume ratio of 1:1, and vacuum drying at room temperature for 24 hours to obtain a white powdery product. 1.85 g of lysine N-carboxy-cyclic anhydride was obtained, 80.67%.

[0021] Put 3g of valine and 40mL of dry tetrahydrofuran into a 100mL three-necked flask, stir and disperse at 50°C, dissolve 3.8g of triphosgene in 20mL of tetrahydrofuran, and slowly add the triphosgene solution. Under the protection ...

Embodiment 2

[0029] (1) Preparation of polyhedral polysilsesquioxane-poly(lysine-co-valine) copolymer

[0030] Put 2.1g of L-lysine with benzyloxycarbonyl-protected amino groups and 30mL of dry tetrahydrofuran into a 100mL three-necked flask, stir and disperse at 50°C, dissolve 1.5g of triphosgene in 10mL of tetrahydrofuran, and slowly add the triphosgene solution into the system. Under the protection of nitrogen, react for 3h. After precipitating with 10 times the volume of n-hexane, suction filtration, and then recrystallizing the precipitate twice with ethyl acetate / n-hexane with a volume ratio of 1:1, and vacuum drying at room temperature for 24 hours to obtain a white powdery product. 1.85 g of lysine N-carboxy-cyclic anhydride was obtained, 80.67%.

[0031]Put 3g of valine and 40mL of dry tetrahydrofuran into a 100mL three-necked flask, stir and disperse at 50°C, dissolve 3.8g of triphosgene in 20mL of tetrahydrofuran, and slowly add the triphosgene solution. Under the protection o...

Embodiment 3

[0039] (1) Preparation of polyhedral polysilsesquioxane-poly(lysine-co-valine) copolymer

[0040] Put 2.1g of L-lysine with benzyloxycarbonyl-protected amino groups and 30mL of dry tetrahydrofuran into a 100mL three-necked flask, stir and disperse at 50°C, dissolve 1.5g of triphosgene in 10mL of tetrahydrofuran, and slowly add the triphosgene solution into the system. Under the protection of nitrogen, react for 3h. After precipitating with 10 times the volume of n-hexane, suction filtration, and then recrystallizing the precipitate twice with ethyl acetate / n-hexane with a volume ratio of 1:1, and vacuum drying at room temperature for 24 hours to obtain a white powdery product. 1.85 g of lysine N-carboxy-cyclic anhydride was obtained, 80.67%.

[0041] Put 3g of valine and 40mL of dry tetrahydrofuran into a 100mL three-necked flask, stir and disperse at 50°C, dissolve 3.8g of triphosgene in 20mL of tetrahydrofuran, and slowly add the triphosgene solution. Under the protection ...

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Abstract

The invention provides a simulated antibacterial peptide copolymer and a preparation method thereof. The preparation method comprises the following steps: taking aminopolyhedral polysilsesquioxane as an initiating agent, initiating lysine N-carboxyl-intracyclic anhydride and valine N-carboxyl-intracyclic anhydride to perform ring-opening polymerization and obtaining a polyhedral polysilsesquioxane-poly(lysine-co-valine)-simulated antibacterial peptide copolymer through de-protection; performing ring-opening polymerization reaction for 56-72 hours through the N-carboxyl-intracyclic anhydrides at a room temperature and obtaining a polyhedral oligomeric silsesquioxane-poly(lysine-co-valine) random copolymer through de-protection treatment. The simulated antibacterial peptide copolymer synthesized by the method is simple and convenient to operate, mild in reaction conditions and easily-available in experimental raw materials; the minimal inhibitory concentrations of the simulated antibacterial peptide copolymer aureus as an antibacterial agent against escherichia coli and staphylococcus are 256 mug / mL and 32 mug / mL respectively, and the simulated antibacterial peptide copolymer can be applied to the field of biomedical materials.

Description

technical field [0001] The invention relates to a simulated antibacterial peptide copolymer and its preparation method, in particular to the preparation and application of a simulated antibacterial peptide random copolymer containing polyhedral oligomeric silsesquioxane and composed of lysine and valine, belonging to The field of biomedical polymer antibacterial materials. Background technique [0002] The hydrophobicity of natural antimicrobial peptides mostly comes from amino acid residues such as leucine, alanine, cysteine ​​and valine, while its positive charge comes from lysine and arginine residues. Different from the antibacterial mode of antibiotics, antimicrobial peptides have broad-spectrum antibacterial activity and are difficult to produce drug resistance. Synthetic mimetic antimicrobial peptides are synthetic polypeptides prepared by imitating the structure and function of natural antimicrobial peptides, which can have good antibacterial properties and cell sel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G77/455A01N55/10A01P1/00
CPCA01N55/00C08G77/455
Inventor 袁晓燕刘波姚添甜周培琼赵蕴慧任丽霞
Owner TIANJIN UNIV