Caffeoyl-alpha-neoendorphin peptide derivative and use thereof as an anti-itch and anti-atopic material

A technology of peptide derivatives and compositions, applied in the field of caffeoyl endorphin derivatives, can solve the problems of easy oxidative deterioration and the like

Inactive Publication Date: 2013-04-03
BIO FD&C CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned caffeic acid is also a very poorly soluble substance, so there is a limit when it is applied to the skin, and there is a problem that it is easily oxidized and deteriorated even after dissolving a small amount in water.

Method used

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  • Caffeoyl-alpha-neoendorphin peptide derivative and use thereof as an anti-itch and anti-atopic material
  • Caffeoyl-alpha-neoendorphin peptide derivative and use thereof as an anti-itch and anti-atopic material
  • Caffeoyl-alpha-neoendorphin peptide derivative and use thereof as an anti-itch and anti-atopic material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Embodiment 1: Caffeoyl (R 1 , R 2 and R 5 is hydrogen, and R 3 for R 4 Preparation of hydroxy)-neoendorphin derivatives

[0102] 1.1: NH 2 Synthesis of protected peptide resins

[0103] In general, peptides are synthesized using 9-fluorenylmethoxycarbonyl (Fmoc) as an amino acid protecting group using the usual solid phase peptide synthesis (SPPS), and N-hydroxybenzotri Azole (N-hydroxybenzotriazole, HOBt) and N, N'-dicyclohexylcarbodiimide (N, N'-dicyclohexylcarbodiimide, DCC) as active agents to extend amino acid residues [References: Wang C.Chan, Perter D. White, 'Fmoc solid phase peptide synthesis', Oxford].

[0104] 1.2: Synthesis of caffeoyl-α-neoendorphin derivatives

[0105] To the NH synthesized by the above method 2 Protected peptide (-20% piperidine / NMP solution was added to the resin to remove the Fmoc bound to the amino group, and N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone, NMP) and dichloromethane (dichloromethane, DCM) after washing, at room...

experiment example 1

[0109] Experimental Example 1: Physical Stability Test of Caffeoyl-α-Neoendorphin Derivatives During Variable Temperature Treatment

[0110] In the case of cosmetics, considering the characteristics of products that are easily exposed to various external environments, physical stability under severe variable temperature conditions is an essential condition. The caffeoyl-α-neoendorphin derivative prepared in Example 1 has improved oxidation stability compared with caffeic acid in an aqueous solution state, and in order to confirm this improved physical stability After a certain period of storage under variable temperature conditions, a test to measure the degree of decomposition is carried out.

[0111] First, an aqueous solution of caffeoyl-α-neoendorphin derivatives at a concentration of 10,000ppm was subjected to variable temperature treatment conditions repeated in units of 8 hours at low temperature (4°C), normal temperature (20°C) and high temperature (40°C). , at interv...

experiment example 2

[0114] Experimental Example 2: Peptidase Stability Test of Caffeoyl-α-Neoendorphin Derivatives

[0115] In the caffeoyl-α-neoendorphin derivatives prepared in Example 1, the main component for improving atopic dermatitis is the caffeic acid part, which plays an anti-allergic effect. At the same time, as the peptide part α-Neoendorphins effectively relieve pruritus in atopic dermatitis. However, α-neoendorphin, the precursor substance of the peptide part, is a structure of amino acids, and when it acts on the skin, it is very fragile to the action of proteolysis or peptidase. Therefore, it is used as a cosmetic When used as a raw material, there are certain limitations in its biological stability.

[0116] The caffeoyl peptide derivative of the present invention greatly improves its biological stability through the synthesis with caffeic acid, and in order to confirm the improved stability to peptidase hydrolase through the synthesis with caffeic acid, under the temperature co...

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Abstract

Provided is a caffeoyl-alpha-eoendrophin peptide derivative, and use thereof as an anti-itching agent and an anti-atopic agent. More specifically, provided is a caffeoyl endorphin peptide derivative, which is applicable in a cosmetic material for anti-inflammatory use, such as for an atopic dermatitis treatment, and the like. The caffeoyl endorphin peptide derivative is safe for skin, has resistance to degradation by peptidases, and the like, and also has an excellent stability with respect to temperature change, and the like.

Description

technical field [0001] The present invention relates to caffeoyl-α-neoendorphin derivatives and their use as anti-itch and anti-specific materials. In particular, the present invention relates to being safe for the skin and at the same time, being resistant to decomposition by peptidases etc. when applied to the skin, and having high stability against temperature changes, so that it can be used for anti-inflammatory applications such as allergy treatment Caffeoyl endorphin derivatives in cosmetic materials and their uses. Background technique [0002] Skin is a very important tissue that is in direct contact with the external environment to protect the human body and has biochemical and physical functions. On the surface of human skin, the sebum film formed by the natural mixture of sebum secreted from sebaceous glands and water secreted by sweat glands covers the stratum corneum, so it can maintain a smooth and moist state. However, if the water content in the skin decrea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K7/08A61K8/64A61K38/08A61K38/10A61Q19/00A61P17/00A61P17/04A61P17/18
CPCC07K14/665A61K8/64A61Q19/00C07K7/06C07K7/08A61K38/08C07K14/675A61K38/10A61K38/33A61P17/00A61P17/04A61P17/18A61P29/00
Inventor 丁大现牟相炫李政勋金守净徐孝铉林昌日成知燕郑爱珍
Owner BIO FD&C CO LTD
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