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Phenolic acid polypeptide conjugate as well as preparation method and application thereof

A technology of polypeptide coupling and phenolic acid, which is applied in the field of medicine, can solve the problems of reduced physiological activity, limited application range, and low safety, and achieve the effects of improved safety, reduced by-product formation, and increased yield

Active Publication Date: 2021-05-28
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the phenolic acid molecule contains both carboxyl and hydroxyl groups, it is easy to form intramolecular or intermolecular esterification of the phenolic acid under the conditions of the esterification reaction, resulting in many by-products and low yield.
The formed phenolic acid ester has a hydrophilic head and a hydrophobic tail similar to surfactants, which may destroy cell membranes through surfactant-like effects, and its safety is low, which limits its application range
In addition, since the phenolic hydroxyl group is the main group that exerts physiological activity in phenolic acid compounds, modification of the phenolic hydroxyl group may lead to a reduction or loss of physiological activity

Method used

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  • Phenolic acid polypeptide conjugate as well as preparation method and application thereof
  • Phenolic acid polypeptide conjugate as well as preparation method and application thereof
  • Phenolic acid polypeptide conjugate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] In this example, gallic acid-polypeptide conjugates were prepared by the following method, specifically including the following steps:

[0051] (1) Polypeptide solid-phase synthesis method using FMOC strategy, using amino acid protected by FMOC at the amino terminal as raw material, using Liberty Lite automatic microwave peptide synthesizer from CEM Company to synthesize, and the operation method was carried out according to the instrument manual.

[0052] Synthetic reagent selection:

[0053] (a) Carrier resin: 2-chlorotrityl chloride resin, degree of substitution: 0.5.

[0054] (b) Deprotection reagent: 20% piperidine in DMF.

[0055] (c) Coupling reagent: HOBT, acid-binding agent: DIEA are used in the condensation reaction.

[0056] (2) Connect the required amino acids in the polypeptide sequence from right to left. After the reaction is completed and the KLVFFAED polypeptide is synthesized, gallic acid, PyBOP, and DIEA are dissolved in DMF and coupled with the res...

Embodiment 2

[0060] In this example, gallic acid-polypeptide conjugates were prepared by the following method, specifically including the following steps:

[0061] (1) Polypeptide solid-phase synthesis method using FMOC strategy, using amino acid protected by FMOC at the amino terminal as raw material, using Liberty Lite automatic microwave peptide synthesizer from CEM Company to synthesize, and the operation method was carried out according to the instrument manual.

[0062] Synthetic reagent selection:

[0063] (a) Carrier resin: 2-chlorotrityl chloride resin, degree of substitution: 0.5.

[0064] (b) Deprotection reagent: 20% piperidine in DMF.

[0065] (c) Coupling reagent: HOBT, acid-binding agent: DIEA are used in the condensation reaction.

[0066] (2) Connect the required amino acids in the polypeptide sequence from right to left. After the reaction is completed and the KLVFFAED polypeptide is synthesized, gallic acid, DMAP, and DIEA are dissolved in DMF and coupled with the resi...

Embodiment 3

[0070] In this example, gallic acid-polypeptide conjugates were prepared by the following method, specifically including the following steps:

[0071] (1) Polypeptide solid-phase synthesis method using FMOC strategy, using amino acid protected by FMOC at the amino terminal as raw material, using Liberty Lite automatic microwave peptide synthesizer from CEM Company to synthesize, and the operation method was carried out according to the instrument manual.

[0072] Synthetic reagent selection:

[0073] (a) Carrier resin: 2-chlorotrityl chloride resin, degree of substitution: 0.5.

[0074] (b) Deprotection reagent: 20% piperidine in DMF.

[0075] (c) Coupling reagent: HOBt, acid binding agent: DIEA are used during the condensation reaction.

[0076] (2) Connect the required amino acids in the polypeptide sequence from right to left. After the reaction is completed and the KLVFFAED polypeptide is synthesized, gallic acid, PyBOP, and TEA are dissolved in DMF and coupled with the ...

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Abstract

The invention provides a phenolic acid polypeptide conjugate as well as a preparation method and application thereof. The phenolic acid polypeptide conjugate is formed by connecting phenolic acid and polypeptide through amido bonds, wherein the phenolic acid mainly comprises gallic acid, rosmarinic acid, ferulic acid, caffeic acid, protocatechuic acid, chlorogenic acid, sinapic acid and vanillic acid; and the amino acid sequence of the polypeptide is KLVFFAED. The preparation method comprises the following steps: (1) synthesizing KLVFFAED polypeptide by using a polypeptide solid-phase synthesis method; (2) under the protection of an inert atmosphere, dissolving a phenolic acid solution, a catalyst and an alkaline reagent into DMF to be coupled and reacted with the resin, and after reaction, cutting off the polypeptide from the resin by using a cutting reagent to obtain a phenolic acid polypeptide conjugate crude product; and (3) separating, purifying and freeze-drying to obtain the phenolic acid polypeptide conjugate. Compared with unmodified phenolic acid, the phenolic acid polypeptide conjugate has the advantages that fat solubility and stability can be improved, so that the phenolic acid polypeptide conjugate can be more easily taken by cells, a targeting effect can be realized, toxic and side effects on normal cells are reduced, and a drug treatment effect is efficiently played.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a phenolic acid polypeptide conjugate and a preparation method and application thereof. Background technique [0002] Phenolic acid compounds refer to organic acids containing several phenolic hydroxyl groups on the same benzene ring, and are widely found in plant seeds, roots, stems, and leaves in nature. Since the molecule contains one or more phenolic hydroxyl groups, it can react with oxidative free radicals to generate semiquinone free radicals, so it can exhibit antioxidant, anti-free radical, anti-inflammatory, antibacterial and antiviral effects, and neurological effects through different mechanisms. protection etc. However, due to the phenolic hydroxyl group and carboxyl group of phenolic acid compounds, the alkane chain in the molecule is relatively short, and it contains double bonds at the same time, so it has strong hydrophilicity, poor fat solubility,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/107C07K1/04C07K1/06A61K47/64A61K31/192A61P25/28
CPCC07K7/06A61K47/64A61K31/192A61P25/28
Inventor 丁杨张华清季艺周建平白凯文
Owner CHINA PHARM UNIV
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