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Acetylated hyaluronate oligopeptide and preparation and application methods therefor

The technology of hyaluronan and uronic acid oligopeptide is applied in the field of functional cosmetics, which can solve the problems of hyaluronic acid and oligopeptide being easily inactivated by enzymatic hydrolysis, unstable structure of polypeptide substances, and short activity time. Achieve the effect of promoting penetration of the skin barrier, enhancing moisturizing, wrinkle-removing and anti-aging effects, and being less susceptible to environmental influences

Active Publication Date: 2020-01-21
润辉生物技术(威海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, hyaluronidase and protease in the human body can hydrolyze hyaluronic acid and oligopeptides, so hyaluronic acid and oligopeptides that are absorbed through skin penetration and on the skin surface are easily deactivated by enzymolysis. Stable and susceptible to denaturation and inactivation due to adverse external environmental factors, resulting in a short active time, so it is necessary to select appropriate dosage forms and protective agents according to the characteristics of the ingredients to improve stability and prolong their efficacy

Method used

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  • Acetylated hyaluronate oligopeptide and preparation and application methods therefor
  • Acetylated hyaluronate oligopeptide and preparation and application methods therefor
  • Acetylated hyaluronate oligopeptide and preparation and application methods therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of hyaluronan-TBA:

[0038] (1) 300g molecular weight is that the hyaluronan of 50kDa is dissolved in 10L deionized water, then passes through 732 (H + ) type cation exchange column to remove the Na + Convert to H + , to obtain an eluent containing hyaluronan;

[0039] (2) Add 200g of TBAOH to the eluent containing hyaluronan in step (1), stir for 2 hours, and neutralize to obtain a hyaluronan-TBA reaction solution;

[0040] (3) ultrafiltration, washing, and concentration of the hyaluronan-TBA reaction solution obtained in step (2) through an ultrafiltration membrane (molecular weight cut-off 500D), to remove excess TBAOH, to obtain a hyaluronan-TBA product;

[0041] (4) Freeze-drying the hyaluronan-TBA product obtained in step (3) to obtain a hyaluronan-TBA solid powder.

Embodiment 2

[0043] Preparation of Fmoc-Ser-Ile-Lys-Val-Ala-Val-COOH crude peptide:

[0044] (1) Resin swelling: Take 25g of CTC resin with a substitution degree of 1.2mmol / g, add 200ml DCM to swell the resin for 0.5h, drain the solvent, wash the resin twice with DMF, and drain the solvent;

[0045] (2) Preparation of Fmoc-Val-CTC resin: a) Mix Fmoc-Val-OH, DIEA and the CTC resin swollen in step (1) according to the ratio of molar mass ratio of 3:6:1, at 25°C Reaction under conditions for 2 hours to obtain Fmoc-Val-CTC resin; b) Add the mixed solution of MeOH, DMF and DIEA to the resin, react at 30°C for 30 minutes, seal the resin, and wash the resin twice with DMF, Drain the solvent to obtain the blocked Fmoc-Val-CTC resin;

[0046] (3) Removal of Fmoc protecting group: add volume fraction 20% PIP-DMF solution to the blocked Fmoc-Val-CTC resin obtained in step (2), and carry out de-Fmoc protection twice under the condition of 10~30°C : After the first de-Fmoc protection and the second d...

Embodiment 3

[0052] Preparation of Fmoc-Ile-Lys-Val-Ala-Val-COOH crude peptide:

[0053] (1) Resin swelling: Take 25g of CTC resin with a substitution degree of 1.2mmol / g, add 200ml DCM to swell the resin for 0.5h, drain the solvent, wash the resin twice with DMF, and drain the solvent;

[0054] (2) Preparation of Fmoc-Val-CTC resin: a) Mix Fmoc-Val-OH, DIEA and resin according to the molar mass ratio of 3:6:1, react at 25°C for 2h to obtain Fmoc-Val- Val-CTC resin; b) Add the mixed solution of MeOH, DMF and DIEA to the resin, react at 10-30°C for 30 minutes, seal the resin, wash the resin twice with DMF, and drain the solvent to obtain the seal After Fmoc-Val-CTC resin;

[0055] (3) Removal of Fmoc protecting group: add volume fraction 20% PIP-DMF solution to the blocked Fmoc-Val-CTC resin obtained in step (2), and carry out de-Fmoc protection twice under the condition of 10~30°C : After the first de-Fmoc protection and the second de-Fmoc protection, wash the resin with DMF until the pH...

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Abstract

The invention relates to an acetylated hyaluronate oligopeptide and preparation and application methods therefor. The acetylated hyaluronate oligopeptide is used for solving the technical problems inthe prior art that acetyl hyaluronic acid and oligopeptide substances are instable in structure and the acetyl hyaluronic acid and oligopeptides in functional type cosmetics are required to be added separately, are prone to enzymolysis, are poor in chemical stability and short in acting time and are prone to deactivation caused by environmental influence. The invention provides the preparation method for the acetylated hyaluronate oligopeptide capable of reducing wrinkles and resisting senescence. The method comprises the following steps: connecting the acetyl hyaluronic acid and the oligopeptide in a covalent bond form: performing connecting through producing an amido bond by subjecting epsilon-NH2 of a Lys side chain of an oligopeptide sequence and -COOH of the acetyl hyaluronic acid toan amide condensation reaction, thereby producing the acetylated hyaluronate oligopeptide. The invention simultaneously provides the application method for the acetylated hyaluronate oligopeptide. Theacetylated hyaluronate oligopeptide and the preparation and application methods therefor are extensively applied to the technical fields of functional type cosmetic technologies and reshaping facialbeautifying products.

Description

technical field [0001] The invention belongs to the technical field of functional cosmetics, in particular to a hyaluronan oligopeptide and its preparation and application method. Background technique [0002] The development of functional cosmetics has become the theme of today's cosmetics industry. The added bioactive ingredients play an important role in regulating the growth and metabolism of cells, such as polypeptides and polysaccharides, which can effectively deal with skin damage and promote skin repair. . Peptides have special biological activities, which play an important role in regulating the growth, development and metabolism of the body. Their special physiological activities play an important role in the regulation of skin aging and care, and are widely used in beauty and skin care products. Cosmetic peptides are mainly small molecular oligopeptides composed of two to ten amino acids, which can promote cell growth, differentiation, reconstruction and repair, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K5/083C07K1/04C07K1/06C07K1/113C07K1/36C07K1/34C07K1/18A61K8/73A61K8/64A61Q19/00A61Q19/08C08B37/08
CPCC07K7/06C07K5/0806A61K8/735A61K8/64A61Q19/00A61Q19/08C08B37/0072A61K2800/57A61K2800/91Y02P20/55
Inventor 姬胜利殷金岗
Owner 润辉生物技术(威海)有限公司
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