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A kind of enzymatic degradable polypeptide-based polyester ammonia and its preparation method and application

A technology based on polyester and enzyme degradation, applied in the field of biomedical materials, can solve the problems of slow degradation rate, long cycle, low drug loading rate of complexes, etc., achieve excellent biocompatibility, safe production process, and broaden the application Effect

Active Publication Date: 2021-05-04
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is to provide an enzymatically degradable polypeptide-based polyester ammonia and its preparation method and application, which overcomes the need for existing polyester ammonia materials to rely on arginine in biomedical aspects, and after modification It can only be used, the degradation rate of the formed complex is very slow, and the cycle is long, especially when it is used on chronic wounds, the material needs to be replaced regularly, the structure may be unstable when the drug is loaded, the drug loading rate is low, the drug will be released explosively, and cannot last for a long time Defects such as use

Method used

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  • A kind of enzymatic degradable polypeptide-based polyester ammonia and its preparation method and application
  • A kind of enzymatic degradable polypeptide-based polyester ammonia and its preparation method and application
  • A kind of enzymatic degradable polypeptide-based polyester ammonia and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 1. Preparation of Polypeptidyl Diamines

[0052] (1) Preparation of tripeptide:

[0053] Using standard FMOC solid-phase peptide synthesis (SPPS) technology, the material ratio involved in the reaction is as follows: 2-chlorotrityl chloride resin is 2g, 1.6mmol FMOC-Lys(Boc)-OH is 3.78g, 6.4mmol FMOC-Phe-OH was 2.48g, 6.4mmol FMOC-Leu-OH was 2.26g, 6.4mmol HBTU was 2.42g, 6.4mmol HOBt was 0.87g, 6.4mmol DIEA was 3ml, piperidine 5ml. Proceed as follows:

[0054] Add the resin to the peptide synthesis device, add dry DMF and soak for half an hour to make it fully swell, and finally discharge the solvent DMF.

[0055] Dissolve the amino acid with DMF, then transfer the solution to the peptide synthesis device containing the treated resin in the previous step, then add the catalyst DIEA, react at room temperature for 1.5h, make it fully fixed on the resin, and wash the resin with DMF .

[0056] Add the piperidine / DMF solution to the resin in the previous step to react f...

Embodiment 2

[0069] 1. Preparation of Polypeptidyl Diamines

[0070] (1) Preparation of tetrapeptide:

[0071] Using standard FMOC solid-phase peptide synthesis (SPPS) technology, the material ratio involved in the reaction is as follows: 2-chlorotrityl chloride resin is 2g, 1.6mmol FMOC-Lys(Boc)-OH is 3.78g, 6.4mmol FMOC-Phe-OH was 2.48g, 6.4mmol FMOC-Leu-OH was 2.26g, 6.4mmol HBTU was 2.42g, 6.4mmol HOBt was 0.87g, 6.4mmol DIEA was 3ml, piperidine 5ml. Proceed as follows:

[0072] Add the resin to the peptide synthesis device, add dry DMF and soak for half an hour to make it fully swell, and finally discharge the solvent DMF.

[0073] Dissolve the amino acid with DMF, then transfer the solution to the peptide synthesis device containing the treated resin in the previous step, then add the catalyst DIEA, react at room temperature for 1.5h, make it fully fixed on the resin, and wash the resin with DMF .

[0074] Add the piperidine / DMF solution to the resin in the previous step to react...

Embodiment 3

[0088] 1. Preparation of Polypeptidyl Diamines

[0089] (1) Preparation of tetrapeptide: The preparation method of tetrapeptide in Example 2 was used to prepare tetrapeptide.

[0090] (2) Preparation of ethanolamine protected by di-tert-butyl dicarbonate anhydride: Add ethanolamine (10.0ml, 165mmol) in anhydrous CH at -10°C 2 Cl 2 To the solution in (500 mL) was added triethylamine (24.5 mL, 250 mmol), followed by di-tert-butyl dicarbonate anhydride (36 g, 165 mmol). The solution was stirred at 25 °C for 20 h, then washed with saturated NHCl 4 The solution (100ml) was quenched. The aqueous layer was extracted with ethyl acetate (3 x 200ml). The combined organic layers were then washed with brine, MgSO 4 Drying and concentration under reduced pressure gave di-tert-butyl dicarbonate anhydride protected ethanolamine as a colorless oil.

[0091] (3) Reaction of tetrapeptide with phthalic anhydride and ethanolamine protected by di-tert-butyl dicarbonate anhydride: in the tetr...

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Abstract

The invention relates to an enzymatically degradable polypeptide-based polyester ammonia and its preparation method and application, comprising: (1) mixing a polypeptide, an acid anhydride, an alcohol amine small molecule protected by di-tert-butyl dicarbonate anhydride, an activator and a catalyst reaction to obtain polypeptide-based diamine; (2) p-nitrophenol, diacid chloride and catalyst mixed reaction to obtain p-dinitrobenzene active ester; (3) polypeptide-based diamine and p-dinitrobenzene active ester Solution polymerization to obtain enzymatically degradable polypeptide-based polyester ammonia, which is used in the field of wound antibacterial, bacterial biofilm inhibition or wound repair biomedicine. The production process is safe, non-toxic and low in cost.

Description

technical field [0001] The invention belongs to the technical field of biomedical materials, and in particular relates to an enzyme-degradable polypeptide-based polyester ammonia and its preparation method and application. Background technique [0002] Degradable polymers have attracted attention for their wide range of applications, especially in biomedical fields such as controlled drug release, gene transfer, and tissue engineering. Biodegradable aliphatic polyesters and polycarbonates have become the most important synthetic biomaterials due to their good biocompatibility and US Food and Drug Administration (FDA) approval for use in biomedical device administration. In practice, these classic biomedical polymers cannot meet the requirements of specific applications due to their shortcomings such as high hydrophobicity, uncontrollable degradation rate, and insufficient mechanical properties. [0003] Polyesteramides have been proposed as a new class of biomaterials with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/44C12P21/06A61K9/51A61K47/34A61L26/00
Inventor 吴德群李梦娜李发学王学利俞建勇
Owner DONGHUA UNIV
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