WO2015174601A1 - Peptide ayant une activité permettant d'améliorer les affections cutanées, et son utilisation - Google Patents
Peptide ayant une activité permettant d'améliorer les affections cutanées, et son utilisation Download PDFInfo
- Publication number
- WO2015174601A1 WO2015174601A1 PCT/KR2014/011276 KR2014011276W WO2015174601A1 WO 2015174601 A1 WO2015174601 A1 WO 2015174601A1 KR 2014011276 W KR2014011276 W KR 2014011276W WO 2015174601 A1 WO2015174601 A1 WO 2015174601A1
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- peptide
- skin
- seq
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
Definitions
- the present invention relates to peptides having skin condition improving activity and uses thereof.
- peptides having an amino acid sequence of SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3 or SEQ ID NO: 4 are effective for antioxidant activity.
- the present invention was completed by identifying that it has excellent physiological activity such as inhibiting skin cell death, increasing collagen production, and inhibiting inflammatory response.
- Another object of the present invention to provide a composition for improving skin conditions.
- the present invention provides a skin condition improvement comprising one amino acid sequence selected from the group consisting of SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3, and SEQ ID NO: 4 It provides a peptide having activity.
- SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3, or SEQ ID NO: 4 are effective for antioxidant activity. It has been shown that it has excellent physiological activity such as inhibiting skin cell death, increasing collagen production and suppressing inflammatory reaction.
- the peptide of the present invention comprises the amino acid sequence of SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3 or SEQ ID NO: 4.
- the peptide of the present invention is SEQ ID NO: 1 sequence, SEQ ID NO: It consists essentially of the amino acid sequence of the 2nd sequence, the 3rd sequence list, or the 4th sequence list.
- the peptide of SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3 or SEQ ID NO: 4 of the peptide exhibits antioxidant activity, inhibits death of skin cells, and inhibits collagen production. Increasing and suppressing inflammatory reactions result in wrinkle improvement, skin regeneration, skin elasticity improvement, skin aging inhibition, wound regeneration, skin regeneration, skin damage caused by UV light, and inflammatory skin disease and relief.
- the inhibitory activity of the peptides of the present invention is due to the inhibition of expression of inflammatory cytokines.
- peptide refers to a linear molecule formed by binding amino acid residues to each other by peptide bonds.
- Peptides of the present invention are known in the art for chemical synthesis methods, in particular solid phase synthesis techniques (Merrif ield, J. Amer. Chem. Soc. 85: 2149-54 (1963); Stewart, et al. , Solid Phase Peptide Synthesis, 2nd. Ed., Pierce Chem. Co .: Rockford, 111 (1984)) or liquid phase synthesis technology (US Pat. No. 5,516,891).
- the N- or C-terminus of the peptide is an acetyl group, fluorenyl methoxy carbonyl group, formyl group, palmitoyl group, myristyl group, stearyl group and polyethylene glycol (PEG) Protecting groups selected from the group consisting of may be combined.
- the term “stability” means not only “in vivo” stability but also storage stability (eg, phase is storage stability).
- the above protecting groups serve to protect the peptides of the present invention from the attack of protein cleavage enzymes in vivo.
- the present invention provides a peptide comprising one amino acid sequence selected from the group consisting of SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3, and SEQ ID NO: 4 It provides a composition for improving skin conditions comprising as an active ingredient.
- composition of the present invention includes a peptide consisting of the amino acid sequence of the above-described sequence list 1 sequence, sequence list 2 sequence, sequence list 3 sequence or sequence list 4 sequence of the present invention as an active ingredient, common content is The description is omitted to avoid excessive complexity of the present specification.
- the peptide consisting of the amino acid sequence of SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3 or SEQ ID NO: 4 of the present invention has an antioxidant effect, skin cells Inhibits death, increases collagen production and inhibits inflammation, which includes wrinkle improvement, skin regeneration, skin elasticity improvement, skin aging inhibition, wound regeneration, skin rejuvenation and inflammatory skin disease. It is very effective for improving skin condition.
- the composition of the present invention comprises (a) a cosmetically effective amount of the peptide of the present invention as described above; and (b) a cosmetically acceptable carrier. It is a cosmetic composition.
- cosmetic effective amount means an amount sufficient to achieve the efficacy or activity of the peptides described above.
- Cosmetic compositions of the present invention may be prepared in any formulation commonly prepared in the art, for example, solutions, suspensions, emulsions, paste gels, creams, lotions, powders, soaps, surfactant-containing cleansing It may be formulated as an oil, powder foundation, emulsion foundation, wax foundation and spray, but is not limited thereto. More specifically, it may be prepared in the form of a flexible lotion, nutrition lotion, nutrition cream massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder.
- the carrier components include animal oils, vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc or zinc oxide. Can be used.
- lactose When the formulation of the present invention is a powder or spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as the carrier component, especially in the case of spray It may additionally include propellants such as chlorofluorohydrocarbons, propane / butane or dimethyl ether.
- propellants such as chlorofluorohydrocarbons, propane / butane or dimethyl ether.
- a solvent, a solubilizer or an emulsifier is used as the carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 , Fatty acid esters of 3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.
- the carrier component is water, a liquid diluent such as ethanol or propylene glycol; Microcrystalline salose, aluminum metahydroxy bentonite, agar or tracant and the like can be used.
- the formulation of the present invention is a surfactant-containing cleansing agent
- Ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.
- the components included in the cosmetic composition of the present invention include components conventionally used in cosmetic compositions, in addition to the peptide and carrier components as active ingredients, and include, for example, conventional agents such as antioxidants, stabilizers, solubilizers, vitamins, pigments and flavorings. Adjuvants may be included.
- the present invention comprises the steps of administering to the subject a composition comprising a peptide consisting of a sequence Moktok 1st sequence, sequence 2nd sequence, sequence 3rd sequence or sequence 4th sequence as an active ingredient It provides a method for improving the skin condition comprising a.
- the method for improving skin condition of the present invention is carried out using the above-described composition, and the common contents between the two are omitted in order to avoid excessive complexity of the present specification.
- the peptide consisting of SEQ ID NO: 1, SEQ ID NO: 2, SEQ ID NO: 3 or SEQ ID NO: 4 of the present invention exhibits skin condition improving activity.
- the peptide of the present invention exhibits antioxidant activity, inhibits the death of skin cells, increases collagen production, and has anti-inflammatory activity.
- the peptide of the present invention is very effective for improving skin condition including wrinkle improvement, skin regeneration, skin elasticity improvement, skin aging inhibition, wound regeneration, skin regeneration, skin damage improvement by UV rays and inflammatory skin disease relief.
- the present invention provides a composition for improving skin condition comprising the peptide described above.
- La-Id is a graph confirming the inhibitory effect of ROS increase in skin cells by ultraviolet light after treatment of the peptide of the present invention.
- Figure 2a-2b is a result of confirming the inhibitory effect of cell death by ultraviolet light after treatment of the peptide of the present invention.
- Figure 3a-3d is the result of measuring the expression level of p-p53 in accordance with the peptide treatment of the present invention.
- Figures 4a-4d is the result of measuring the expression level of Bcl2 in accordance with the peptide treatment of the present invention.
- Figure 5a-5d is the result of measuring the expression level of pERK according to the peptide treatment of the present invention.
- Figure 6a-6b is the result of measuring the expression level of the inflammatory cytokine gene according to the peptide treatment of the present invention by RT-PCR.
- Figure 7a-7d is the result of measuring the expression level of C0X2 in accordance with the peptide treatment of the present invention.
- Figure 8a-8d is the result of measuring the expression level of TNF- ⁇ according to the peptide treatment of the present invention.
- 9A-9D show the results of measuring the expression level of MMP1 according to the peptide treatment of the present invention.
- Figure 10a-10b is the result of measuring the change in the amount of free radicals in the cell increased by ultraviolet light after the peptide treatment of the sequence 1, the second sequence of the present invention.
- 11 is a result of measuring the expression level of the pro- collagen gene according to the second sequence peptide treatment of the present invention.
- chloro trityl chloride resin CTL resin, Nova biochem Cat No. 01-64-0021
- MC methylene chloride
- DMF dimethylformamide
- 10 ml of dichloromethane solution was added to the reactor, 200 ⁇ l of Fmoc-Gly-0H (Bachem, Swiss) and 400 mmole of diisopropyl ethylamine (DIEA) were added thereto, stirred to dissolve well, and reacted with stirring for 1 hour.
- Cys-Gly-CTL resin was prepared by deprotection twice in the same manner as above with the deprotection solution. After washing thoroughly with DMF and MC and performing a Kaiser test once again, the following amino acid attachment experiments were performed. Fmoc-I le, Fmoc-Trp, Fmoc-Lys (Boc), Fmoc-Glu (OtBu), Fmoc-Ser (tBu), Fmoc-Ser (tBu) and Fmoc-Glu (OtBu) based on selected amino acid sequences The chain was added in order. The Fmoc-protector was reacted twice with a deprotection solution twice for 10 minutes and then washed well.
- Acetylation of acetic anhydride, DIEA, and HoBt was carried out for one hour, and the prepared peptidyl resin was washed three times with DMF, MC, and methanol, and then dried by flowing nitrogen air slowly.
- 30 ml of dry and fugitive solution [Tr if luroacet ic ac id) 81.5%, distilled water 5%, thioanisole 5% phenol 5%, EDT 2.5% and TIS 1] 30 ml
- the reaction was kept shaking at room temperature for 2 hours.
- the resin was filtered off and the resin was washed with a small amount of TFA solution and combined with the mother liquor.
- Molecular weight 1038.0 (theoretical value: 1038. 1) of the peptide 1 when measured using a molecular weight measuring instrument, a peptide
- the molecular weight 1146.3 (theoretical value: 1146.2) of the peptide 3 were obtained.
- Seed HaCaT human keratinocyte line
- the peptides of SEQ ID NOS: 1 to 4 were treated by concentration (1-10 ug / ml) and incubated in a 37 ° C. incubator for 30 minutes and then irradiated with UVBC25 mJ) at 37 ° C. Incubate for 48 hours in the incubator.
- the cells are treated with 10 ⁇ M concentration of DCFH-DA (sigma) and the cells are obtained after incubation in a 37 ° C. incubator for 30 minutes. Add 1 ml of PBS and centrifuge (6, 000 rpm, 3 minutes), and then add 600 ⁇ l of PBS again to perform FACS analysis.
- Anti-pp53 antibody (Santa Cruz Biotechnology, USA) to confirm the expression of apoptosis factor
- anti-pE antibody Sura Cruz Biotechnology, USA
- anti-Bcl2 antibody Sura Cruz Biotechnology
- PCR is performed using primers for pro-inflammatory factors (C0X2, TNF-alpha), cytolytic factor (MMP1) and PCR premix (Intron).
- Target-specific primer sequences used for PCR of inflammation inducing factor and cytolytic factor are as follows: C0X2 forward primer sequence, 5'-TTGGTCTACAAGACGCCACA-3 'and C0X2 reverse primer 5'-CGGTTAATACGGGGTTGTTG-3' (annealed) Temperature, 60 ° C); TNF-alpha forward primer sequence, 5'-CGTCAGCCGATTTGCTATCT— 3 'and TNF-alpha reverse primer, 5'-CGGACTCCGCAAAGTCTMG-3' (annealing temperature, 60 ° 0; ⁇ PI forward primer sequence, 5'-ATTCTACTGATATCGGGGCnTGA-3 'and MMP1 reverse primer, 5'-ATGTCCTTGGGGTATCCGTGTAG-3 '(annealing temperature, 60 ° C.) Load
- Example 5 the NIH3T3 (epidermal cells), collagen type la chain increased expression experiments 2X10 5 cells / NIH3T3C skin cell lines in cell density in 6-well plates in the wells) and seeded. After overnight incubation, the peptide of SEQ ID NO: 2 sequence is treated with 10 U g / ml and incubated in a 37 ° C. incubator for 24 hours. After the cultured cells are recovered, RNA is prepared by treating RNA extraction solution (Easy Blue, Intron), and cDNA synthesis is performed using RT premix (Intron). ⁇ PCR is performed using primers for the col lagen type 1 a chain and PCR premix (Intron).
- the target-specific primer sequences used for PCR of the extracellular constructs are as follows: Col lagen type 1 a chain forward primer sequence, 5'-CTCGAGGTGGACACCACCCT- 3 'and Col lagen type 1 a chain reverse primer sequence, 5'- CAGCTGGATGGCCACATCGG-3 '(annealing temperature, 60 ° C). 5 ⁇ of PCR products were loaded onto a 1% agarose gel and the bands were identified in Gel-Doc.
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Abstract
Cette invention concerne un peptide constitué de SEQ ID No : 1, SEQ ID No : 2, SEQ ID No : 3 ou SEQ ID No : 4, ayant une activité permettant d'améliorer les affections cutanées. Le peptide selon l'invention manifeste une activité antioxydante, inhibe la mort des cellules cutanées, accroît la production de collagène et a une activité d'inhibition de l'inflammation. Le peptide selon l'invention est très efficace pour l'amélioration de l'état de la peau comprenant la réduction des rides, la régénération de la peau, l'amélioration de l'élasticité de la peau, l'inhibition du vieillissement de la peau, la réparation des lésions, l'atténuation des dommages cutanés dus aux rayons ultraviolets, et l'atténuation des maladies inflammatoires de la peau. Une composition destinée à améliorer les affections cutanées, comprenant le peptide selon l'invention est en outre décrite.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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KR1020140057190A KR20150130616A (ko) | 2014-05-13 | 2014-05-13 | 피부상태 개선 활성을 갖는 펩타이드 및 이의 용도 |
KR10-2014-0057190 | 2014-05-13 |
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WO2015174601A1 true WO2015174601A1 (fr) | 2015-11-19 |
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PCT/KR2014/011276 WO2015174601A1 (fr) | 2014-05-13 | 2014-11-21 | Peptide ayant une activité permettant d'améliorer les affections cutanées, et son utilisation |
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KR20180019966A (ko) * | 2016-08-17 | 2018-02-27 | (주)진셀팜 | 항염증 활성을 가지는 펩타이드, 및 이의 용도 |
KR20180019967A (ko) * | 2016-08-17 | 2018-02-27 | (주)진셀팜 | 항염증 및 항균 활성을 가지는 펩타이드, 및 이의 용도 |
KR20180019969A (ko) * | 2016-08-17 | 2018-02-27 | (주)진셀팜 | 주름 개선 활성 및 피부 개선 효과를 가지는 펩타이드, 및 이의 용도 |
WO2018086732A1 (fr) * | 2016-11-10 | 2018-05-17 | Asc Regenity Ltd. | Formulations cosmétiques pour application topique contenant des molécules dérivées de l'érythropoïétine |
KR101900747B1 (ko) * | 2016-08-17 | 2018-09-20 | (주)진셀팜 | 항염증 펩타이드, 및 이의 용도 |
KR101900746B1 (ko) * | 2016-08-17 | 2018-11-05 | (주)진셀팜 | 피부 상태 개선 효과를 가지는 펩타이드, 및 이의 용도 |
EP3418291A4 (fr) * | 2016-02-18 | 2019-01-02 | Caregen Co., Ltd. | Peptide possédant une activité favorisant la croissance des cheveux et son utilisation |
US11103436B2 (en) | 2017-08-31 | 2021-08-31 | Caregen Co., Ltd. | Peptide exhibiting wrinkle-improving activity and uses thereof |
CN116284256A (zh) * | 2022-01-25 | 2023-06-23 | 上海中翊日化有限公司 | 一种六肽-9环肽及其应用 |
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KR101831888B1 (ko) * | 2016-04-15 | 2018-04-16 | (주)케어젠 | 항염증 활성을 갖는 펩타이드 및 이의 용도 |
KR101869783B1 (ko) * | 2016-08-17 | 2018-06-22 | (주)진셀팜 | 미백 활성이 우수한 펩타이드, 및 이의 용도 |
KR102042600B1 (ko) * | 2018-02-13 | 2019-11-08 | 전북대학교산학협력단 | 항산화 및 항염증 활성을 갖는 홍갯지렁이 유래 신규 펩타이드 및 이의 이용 |
KR102265430B1 (ko) * | 2019-08-20 | 2021-06-15 | 주식회사 케어젠 | 피부 상태 개선 활성을 갖는 펩타이드 및 이의 용도 |
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KR20180019967A (ko) * | 2016-08-17 | 2018-02-27 | (주)진셀팜 | 항염증 및 항균 활성을 가지는 펩타이드, 및 이의 용도 |
KR20180019969A (ko) * | 2016-08-17 | 2018-02-27 | (주)진셀팜 | 주름 개선 활성 및 피부 개선 효과를 가지는 펩타이드, 및 이의 용도 |
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KR101900746B1 (ko) * | 2016-08-17 | 2018-11-05 | (주)진셀팜 | 피부 상태 개선 효과를 가지는 펩타이드, 및 이의 용도 |
KR101955510B1 (ko) * | 2016-08-17 | 2019-03-11 | (주)진셀팜 | 주름 개선 활성 및 피부 개선 효과를 가지는 펩타이드, 및 이의 용도 |
JP2019533712A (ja) * | 2016-11-10 | 2019-11-21 | エーエスシー・リジェニティー・リミテッド | エリスロポエチン由来分子を含む局所適用のための美容用製剤 |
JP7167019B2 (ja) | 2016-11-10 | 2022-11-08 | エーエスシー・リジェニティー・リミテッド | エリスロポエチン由来分子を含む局所適用のための美容用製剤 |
CN110234311A (zh) * | 2016-11-10 | 2019-09-13 | Asc瑞珍尼特有限公司 | 含有***衍生的分子的用于局部应用的美容制剂 |
WO2018086732A1 (fr) * | 2016-11-10 | 2018-05-17 | Asc Regenity Ltd. | Formulations cosmétiques pour application topique contenant des molécules dérivées de l'érythropoïétine |
US10456346B2 (en) | 2016-11-10 | 2019-10-29 | Asc Regenity Ltd. | Cosmetic formulations for topical applications containing erythropoietin-derived molecules |
AU2017357374B2 (en) * | 2016-11-10 | 2023-05-18 | Asc Regenity Ltd. | Cosmetic formulations for topical applications containing erythropoietin-derived molecules |
US11197812B2 (en) | 2016-11-10 | 2021-12-14 | Asc Regenity Ltd. | Cosmetic formulations for topical applications containing erythropoietin-derived molecules |
CN110234311B (zh) * | 2016-11-10 | 2022-08-12 | Asc瑞珍尼特有限公司 | 含有***衍生的分子的用于局部应用的美容制剂 |
US11103436B2 (en) | 2017-08-31 | 2021-08-31 | Caregen Co., Ltd. | Peptide exhibiting wrinkle-improving activity and uses thereof |
EP3677590A4 (fr) * | 2017-08-31 | 2021-10-06 | Caregen Co., Ltd. | Peptide présentant une activité d'atténuation des rides et utilisations associées |
US11672749B2 (en) | 2017-08-31 | 2023-06-13 | Caregen Co., Ltd. | Peptide exhibiting wrinkle-improving activity and uses thereof |
EP4349359A3 (fr) * | 2017-08-31 | 2024-07-17 | Caregen Co., Ltd. | Peptide présentant une activité d'amélioration des rides et ses utilisations |
EP4349361A3 (fr) * | 2017-08-31 | 2024-07-17 | Caregen Co., Ltd. | Peptide présentant une activité d'amélioration des rides et ses utilisations |
EP4349360A3 (fr) * | 2017-08-31 | 2024-07-17 | Caregen Co., Ltd. | Peptide présentant une activité d'amélioration des rides et ses utilisations |
CN116284256A (zh) * | 2022-01-25 | 2023-06-23 | 上海中翊日化有限公司 | 一种六肽-9环肽及其应用 |
CN116284256B (zh) * | 2022-01-25 | 2024-02-06 | 上海中翊日化有限公司 | 一种六肽-9环肽及其应用 |
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