Retinol-modified collagen, method for producing same, and external composition for skin containing same

A retinol and collagen technology, which is applied in the preparation method of peptides, medical preparations containing active ingredients, skin diseases, etc., can solve the problem of not being able to obtain satisfactory anti-aging effects on the skin, and achieve excellent anti-wrinkle effects , Excellent safety and excellent affinity

Active Publication Date: 2013-04-24
NARA INSTITUTE OF SCIENCE AND TECHNOLOGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, conventional collagen and collagen derivatives have the problem of not being able to obtain a satisfactory and excellent skin aging prevention effect

Method used

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  • Retinol-modified collagen, method for producing same, and external composition for skin containing same
  • Retinol-modified collagen, method for producing same, and external composition for skin containing same
  • Retinol-modified collagen, method for producing same, and external composition for skin containing same

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preparation example Construction

[0103] In the method for producing retinol-modified collagen of the present invention, the collagen, dicarboxylic acid and its anhydride, and retinol described above in the description of retinol-modified collagen are used.

[0104] In addition, the coupling of dicarboxylic acid or its anhydride to collagen can be carried out by a method known per se using the solvent, dehydration condensation agent, and condensation assistant as described above for synthesizing collagen.

[0105] The addition reaction to dicarboxylic acid-coupled collagen is usually carried out under the conditions of adding 1 to 2 equivalents of DIPEA to 1 mole of peptide units in DMF (dimethylformamide) or the like. Here, the reaction of binding retinol to dicarboxylic acid-coupled collagen was carried out using this condition, but it was found that almost no retinol was added. Surprisingly, it was found that when tertiary amines are used as solvents in the step of combining retinol with dicarboxylic acid g...

Embodiment

[0112] Next, examples are given to further describe the present invention in detail, and they are for the purpose of illustration, and the present invention is not limited thereto. In addition, unless otherwise stated, % represents mass %.

preparation example

[0114] Synthesis of Retinol-modified Collagen

[0115] (1) Synthesis reaction of poly(Pro-Hyp-Gly)

[0116] Dissolve Pro-Hyp-Gly (PHG) tripeptide (Peptide Research Institute Co., Ltd.) in 10mM phosphate buffer (pH7.4) and stir, add 1-hydroxybenzotriazole (HOBt) for stirring, and cool to below 5°C. Add 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, let it stand for 90 minutes (reaction), warm, add 10mM phosphate buffered saline (PBS; pH7.4, containing 0.15M NaCl) to stop the reaction. After dialysis, the reactant was freeze-dried to obtain spongy synthetic collagen.

[0117] (2) Evaluation of Poly(Pro-Hyp-Gly) Synthesis

[0118] The obtained synthetic collagen (poly-PHG) was subjected to gel permeation chromatography (GE ヘルスケアジャパン Co., Ltd., AKTA purifier system, column: Superdex 200HRGL, flow rate: 0.5ml / min, eluent: 10mM phosphate buffered saline ( PBS; pH 7.4, containing 0.15M NaCl)) for molecular weight determination. As a result, it was confirmed that ...

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Abstract

Disclosed is a compound which exhibits a higher effect of preventing wrinkle formation, a higher effect of improving wrinkles, a higher effect of making the skin beautiful, and a higher effect of improving skin quality than conventional retinol and retinol derivatives in a sustained manner. Further disclosed are a method for producing the same, and an external composition for the skin and a sheet-shaped cosmetic each containing the same as an active ingredient. More specifically disclosed are retinol-modified collagen in which a dicarboxylic acid is attached to at least one hydroxyl group of collagen and retinol is attached to a carboxyl group of at least one attached dicarboxylic acid, a method for producing the same, and an external composition for the skin and a sheet-shaped cosmetic each containing the same as an active ingredient.

Description

technical field [0001] The present invention relates to retinol-modified collagen which is suitable for skin and exhibits an excellent effect of preventing skin aging, and more specifically, to retinol-modified collagen, a method for producing the same, and a composition for external use on the skin and a sheet cosmetic containing the same The retinol-modified collagen has low toxicity to cells, does not cause itching, etc., has excellent safety, increases the expression of the hyaluronic acid synthase gene and increases the production of hyaluronic acid for a long time, and also improves the production of collagen. Synthetic, so that it can exert excellent wrinkle prevention effect, wrinkle improvement effect, skin beautification effect and skin quality improvement effect. Background technique [0002] As the skin ages, wrinkles increase in the skin. Among the wrinkles, there are wrinkles that penetrate thinly under the eyes and are at the level of the epidermis (epidermal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/78A61K8/65A61K8/67A61K31/07A61K38/00A61P17/00A61Q19/00C07C403/00C12N15/09
CPCC12N15/09A61K31/07A61K8/671A61Q1/02A61K8/67A61Q19/10C07C403/00A61Q1/00A61Q19/08A61Q5/12A61K38/39A61K8/65A61Q19/00A61Q1/12C07K1/1077A61Q5/02A61K38/00C07K14/78A61P17/00A61P43/00
Inventor 谷原正夫高市佳奈前田真理子三井司山本和司平野晶子
Owner NARA INSTITUTE OF SCIENCE AND TECHNOLOGY
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