WO2018066914A1 - Tripeptide ayant des acides gras liés à celui-ci, et composition cosmétique anti-rides le comprenant - Google Patents

Tripeptide ayant des acides gras liés à celui-ci, et composition cosmétique anti-rides le comprenant Download PDF

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Publication number
WO2018066914A1
WO2018066914A1 PCT/KR2017/010913 KR2017010913W WO2018066914A1 WO 2018066914 A1 WO2018066914 A1 WO 2018066914A1 KR 2017010913 W KR2017010913 W KR 2017010913W WO 2018066914 A1 WO2018066914 A1 WO 2018066914A1
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WO
WIPO (PCT)
Prior art keywords
rgd
cosmetic composition
skin
compound
palmitoyl
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PCT/KR2017/010913
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English (en)
Korean (ko)
Inventor
박영준
문원강
박성준
송현남
이진서
박선경
이민섭
문성호
이승기
김종묵
김정윤
김주연
최치호
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㈜셀트리온
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Publication of WO2018066914A1 publication Critical patent/WO2018066914A1/fr

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    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
    • C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K19/00—Hybrid peptides, i.e. peptides covalently bound to nucleic acids, or non-covalently bound protein-protein complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0815—Tripeptides with the first amino acid being basic
    • C07K5/0817—Tripeptides with the first amino acid being basic the first amino acid being Arg

Definitions

  • the present invention relates to a tripeptide having a fatty acid bound thereto, and a cosmetic composition having an excellent skin wrinkle improvement effect.
  • Skin is an important organ that plays a variety of roles such as protecting the human body, barrier function, and excretory function.
  • skin cells are damaged by external environmental factors such as pollutants, ultraviolet rays, and stress, and cell turnover is not done properly, resulting in thinning of the epidermis, dermis and subcutaneous tissue, and deterioration of skin elasticity and wrinkles. Is formed.
  • Ultraviolet rays cause free radicals in the skin, resulting in increased damage and pigmentation of the skin cells, leading to a loss of direct function of the skin's major components, leading to skin aging.
  • Free radicals can be evaluated as a measure of antioxidant activity and anti-aging activity of free radicals as a cause of disease and aging in the human body.
  • the characteristics of skin aging include a decrease in elasticity, wrinkles, blemishes or freckles, and one of the causes is chain breakage of collagen and elastin, which are elastic fibers due to lipid peroxidation, abnormal crosslinking and chain breakage of hyaluronic acid. .
  • Lipid peroxidation is caused by oxidative stress, and in the process, free radicals, reactive oxygen species (ROS), are produced. This free radical production process has been reported to not only be a preliminary step of metabolic activation that is harmful to skin, but also cause skin cell and tissue damage.
  • proteolytic enzymes are induced by the active oxygen in relation to wrinkles may cause wrinkles by denaturing or destroying collagen or elastin, which gives elasticity to the skin.
  • collagen is the most abundant component of the matrix of the dermal layer of the skin, the control of biosynthesis and degradation of collagen is the key during skin aging process.
  • Collagen synthesis promoters are known compounds such as ascorbic acid (US Pat. No. 4,983,382), and retinoids (US Pat. No. 4,877,805) and their derivatives, and cosmetic compositions containing the same have been developed.
  • ascorbic acid is easily oxidized in the air and moisture, there is a stability problem, retinoids are unstable, and skin irritation problems have been reported in the skin application.
  • the peptide As a compound having a small skin irritation and having a skin wrinkle improvement effect, there is a peptide, the peptide is a major component of the protein, there is an advantage that can improve the skin wrinkles without side effects on the skin.
  • the RGD (Arg-Gly-Asp) sequence has been known as a cell recognition sequence since the late 1980s, and synthetic RGD peptides have been used since the early 1990s (Biochem. J. (1993) 296, 21- 24).
  • RGD-containing peptides affect integrin-mediated cell attachment and the function affects cell growth (Annu Rev Cell Dev Biol. (1996) 12). : 697-715.).
  • RGD is used as an ingredient for collagen activation and skin wrinkle improvement, but the tripeptide is hydrophilic and difficult to cross the skin barrier.
  • the present invention is to overcome the problems of the prior art as described above, in order to solve the difficulty of penetration of the RGD (arginine-glycine-aspartic acid) of the hydrophilic tripeptides into the skin barrier, by combining various hydrophobic fatty acids to the RGD -A number of derivatives having a lipophilic structure were prepared, and the present invention was completed by confirming that their skin wrinkle improvement efficacy is good.
  • RGD arginine-glycine-aspartic acid
  • the problem to be solved by the present invention is to provide a salt that is acceptable as a tripeptide or a cosmetic thereof to which a fatty acid of the formula [I] is bound.
  • Another problem to be solved of the present invention is to provide a cosmetic composition
  • a cosmetic composition comprising the tripeptide of the following [Formula I] or a salt acceptable as a cosmetic as an active ingredient and its use for improving wrinkles.
  • the present invention relates to a tripeptide combined with a fatty acid and a cosmetic composition having excellent skin anti-wrinkle effect.
  • the present invention provides a tripeptide to which a fatty acid is bound, an RGD to which a fatty acid is bound or a cosmetically acceptable salt thereof, more preferably palmitoyl-RGD or a cosmetically acceptable salt thereof.
  • the RGD is a tripeptide in which three amino acids of arginine, glycine, and aspartic acid are connected, and is known to have collagen synthesis efficacy and is used as a cosmetic raw material.
  • the RGD to which the fatty acid is bound is represented by the general formula of Formula (I).
  • n is an integer from 11 to 16.
  • palmitoyl-RGD is a compound represented by Formula (II) or Palm-Arg-Gly-Asp, wherein n is 15 in Formula (I).
  • the present invention also provides a tripeptide (RGD) to which the fatty acid of formula (I) is bound or a cosmetic composition comprising the same.
  • RGD tripeptide
  • the cosmetic composition is not only excellent skin anti-aging, wrinkle improvement, skin elasticity enhancement and skin penetration effect, but also provides a high effect in long-term storage stability and skin safety.
  • the amount of procollagen synthesis of the cells treated with the compound of Formula I may be 20% or more compared with the case where the compound of Formula III is treated at the same concentration.
  • the cosmetic composition of the present invention comprises 0.0001 to 2% by weight, preferably 0.01 to 0.05% by weight of the compound of formula (I) as an active ingredient based on the total weight of the cosmetic composition.
  • the present invention also provides a cosmetic composition for improving skin wrinkles comprising a tripeptide (RGD) to which the fatty acid of Formula (I) is bound or a salt thereof that is acceptable as a cosmetic.
  • a cosmetic composition for improving skin wrinkles comprising a tripeptide (RGD) to which the fatty acid of Formula (I) is bound or a salt thereof that is acceptable as a cosmetic.
  • the cosmetic composition of the present invention comprises 0.0001 to 2% by weight, preferably 0.01 to 0.05% by weight of the compound of formula (I) as an active ingredient based on the total weight of the cosmetic composition.
  • the cosmetic composition of the present invention is not particularly limited in its formulation, and may include a cosmetic composition combination commonly used in the art to which the invention pertains, depending on the formulation to be prepared.
  • the cosmetic composition of the present invention can be prepared in a formulation such as lotion, milky lotion, nourishing cream, pack, essence, essence, etc., according to the formulation to be prepared, emulsion, emulsifier, emulsion stabilizer, moisturizer, thickener, preservative, fragrance Can be selected and blended.
  • the present invention provides a method for preparing a compound of formula (I), comprising the following steps.
  • the palmitoyl-RGD of the present invention prepared according to the above method is not only stable but also shows an excellent effect on excellent skin anti-aging, wrinkle improvement, skin elasticity enhancement and skin penetration.
  • the tripeptide compound in combination with the fatty acid according to the present invention provides excellent skin anti-aging, wrinkle improvement, skin elasticity enhancement and skin penetration effect.
  • Figure 1 is a graph showing the results for the cytotoxicity test of fatty acid-bound RGD.
  • Figure 2 is a graph showing a comparison of the collagen synthesis effect of fatty acid-bound RGD.
  • Figure 3 is a graph comparing the skin transdermal absorption effect of the fatty acid-bound RGD.
  • 4 to 6 is a graph showing the effect of improving the wrinkles around the eyes of the composition containing palmitoyl-RGD.
  • the present invention provides a cosmetic composition for improving wrinkles comprising a tripeptide and a fatty acid is bound thereto.
  • the tripeptide to which the fatty acid is bound may be Palmitoyl-RGD.
  • N- (t-butoxycarbonyl) glycine N- (tert-Butoxycarbonyl) glycine, N-Boc-Gly-OH) (20 g, 114.17 mmol) with L-aspartic acid dibenzyl ester (L-aspartic acid dibenzyl ester) (55.43 g, 114.17 mmol) was dissolved in tetrahydrofuran (THF) (600 mL), then the temperature was lowered to 0 ° C. and 1-hydroxybenzotriazole hydrate (HOBt) (18.51) was added to the solution.
  • THF tetrahydrofuran
  • Human normal fibroblasts Human Dermal Fibroblast neonatal, Cascade Co., HDFn cells
  • Human Dermal Fibroblast neonatal, Cascade Co., HDFn cells were seeded in 24-micro well plates (5 ⁇ 10 4 cells / well) and incubated at 37 ° C., 5% carbon dioxide for 24 hours. . Discard the medium and wash with Phosphate Buffered Saline (PBS) and add 1% Penicillins / Streptomycin (P / S) to Dulbecco's Modified Eagle's Medium (DMEM). One medium was added and incubated for 24 hours.
  • PBS Phosphate Buffered Saline
  • P / S Penicillins / Streptomycin
  • DMEM Dulbecco's Modified Eagle's Medium
  • DMSO dimethyl sulfoside
  • Human normal fibroblasts were inoculated into 24-well microplates using Dulbo nasal eagle eggs supplemented with 10% fetal calf serum (5 ⁇ 10 4 cells / well), at 37 ° C., 5% CO 2 . Incubated for 24 hours. Serum was replaced with doubling nose fertilized eagle medium and incubated for 24 hours, and then each test compound was treated with an appropriate amount. After 48 hours of incubation, the cell culture solution was collected, and then the amount of procollagen was measured using a collagen measurement kit of Takara Corporation (Takara Shuzo Co., Ltd., Japan).
  • the cell culture fluids were collected into 96-well microplates uniformly coated with primary collagen antibodies, and antigen-antibody reactions occurred at 37 ° C. for 3 hours.
  • Cell cultures in the wells were removed and washed four times with phosphate buffered saline.
  • a color-causing substance was added and reacted at room temperature for 15 minutes, and then 1 N sulfuric acid solution was added to stop the reaction.
  • Absorbance at wavelength 450 nm was measured with a spectrophotometer.
  • a standard curve was prepared using the standard solution, and the absorbance obtained by the above method was substituted into the standard curve to calculate the amount of procollagen production of the cell culture solution to which each test compound was added.
  • the transdermal absorption experiment was conducted using the substance represented by Formula II, palmitoyl-RGD, and as a control, a comparison experiment was performed using RGD to which no fatty acid was bound.
  • RGD fatty acid
  • the transmittance was measured in a Franz diffusion cell.
  • RGD without fatty acid was used.
  • Human skin stored at ⁇ 20 ° C. was used to confirm skin permeability.
  • Transepidermal Water Loss (TEWL) confirmed that there was no skin damage to the skin (700 ⁇ m in thickness, -20 ° C. storage) to confirm the integrity of the structural skin before the test.
  • the detection amount was insignificant. It has a hydrophilic property that the RGD includes a basic amino acid R (arginine) and an acidic amino acid D (aspartic acid), and thus does not penetrate the stratum corneum, which contains a large amount of hydrophobic lipids, and thus is directly delivered to the skin cells. There is no problem.
  • stearoyl-RGD has excellent skin permeability, but is not suitable as a cosmetic because it is cytotoxic at a content that shows effective efficacy as shown in Table 1.
  • the hydrophobic fatty acid palmitoyl and RGD were conjugated, and skin permeability was improved by 15 times and procollagen synthesis efficiency was also improved.
  • palmitoyl-RGD raw material was dissolved in propanediol for each concentration to identify skin irritation.
  • palmitoyl-RGD was confirmed that there is no skin irritation up to a concentration of 0.05% by weight.
  • palmitoyl-RGD shows excellent stability to moisture and heat.
  • solubilized formulations were prepared as shown in Table 6 below.
  • Palmitoyl-RGD of addition I was solubilized, added and mixed, followed by mixing addition II.
  • Palmitoyl-RGD Concentration in Compositions Number of respondents Responsiveness 0.01 wt% 0 0.0 0.02 wt% 0 0.0 0.05 wt% 0 0.0
  • Palmitoyl-RGD Concentration in Compositions Number of respondents Responsiveness 0.01 wt% 0 0.0 0.02 wt% 0 0.0 0.05 wt% 0 0.0
  • the skin wrinkle improvement effect on the cosmetic composition including the palmitoyl-RGD was measured.
  • R2 and R3 values were evaluated as the main parameters of the wrinkles around the eyes, as measured by Visiometer SV600 (Courage-Khazaka electronic GmbH, Germany).
  • R2 corresponds to the largest of the difference between the five highest peaks and the lowest valleys for the five equally divided sections of the wrinkle profile
  • R3 defines the five equal segments along the X axis. It is the arithmetic average of the differences between the maximum and minimum values within each segment after dividing.
  • the R2 value decreased significantly after 4 weeks, after 8 weeks, and after 12 weeks of use (p ⁇ 0.05), and also after 8 weeks and after 12 weeks of use compared to the control. (p ⁇ 0.05).
  • the R3 values of the test product group were significantly decreased (p ⁇ 0.05) after 4 weeks, 8 weeks, and 12 weeks after use, and also significant after 8 weeks and 12 weeks after use. Difference (p ⁇ 0.05).
  • Ra means the average roughness (average roughness) of the wrinkle profile, the smaller the value can be seen that the wrinkles around the eyes is improved, the results of the measured Ra value is shown in the graph in FIG.
  • the Ra value of the test product group was significantly decreased after 12 weeks of use (p ⁇ 0.05) compared to before use, and also showed a significant difference (p ⁇ 0.05) after 4 weeks of use and 12 weeks after comparison with the control product. Confirmed.
  • Skin elasticity was measured before use, 4 weeks after use, 8 weeks after, and 12 weeks after the use of palmitoyl-RGD. Skin elasticity was measured once using the Cutometer CM 580 (CK Electronics, Koln, Germany) at the same site of both eyes, and R2 (skin remodeling force) was used as an evaluation data for skin elasticity. The value of R2 is the total elasticity, and the closer to 1, the more elastic the skin is. The result of the measured R2 value is graphically shown in FIG. 7.
  • the measured value of skin elasticity of the test product group was significantly increased after 4 weeks, 8 weeks, and 12 weeks after use (p ⁇ 0.05), and even after 4 weeks and 8 weeks of use compared to the control product. After 12 weeks, there was a significant difference (p ⁇ 0.05). Therefore, it was confirmed that the cosmetic composition including palmitoyl-RGD is effective in promoting skin elasticity.
  • the measured value of the dermal density of the test product group was significantly increased after 8 weeks and after 12 weeks of use (p ⁇ 0.05). p ⁇ 0.05). Therefore, it was confirmed that the cosmetic composition including palmitoyl-RGD is effective in improving skin dermal density.

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Abstract

La présente invention concerne un tripeptide ayant des acides gras liés à celui-ci et une composition cosmétique le comprenant et fournit un excellent anti-âge pour la peau, une réduction des rides, une amélioration de l'élasticité de la peau, et des effets de perméation de la peau.
PCT/KR2017/010913 2016-10-04 2017-09-29 Tripeptide ayant des acides gras liés à celui-ci, et composition cosmétique anti-rides le comprenant WO2018066914A1 (fr)

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KR1020160127375A KR101715599B1 (ko) 2016-10-04 2016-10-04 지방산이 결합된 트리펩타이드 및 이를 포함하는 주름 개선용 화장료 조성물
KR10-2016-0127375 2016-10-04

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KR101715599B1 (ko) * 2016-10-04 2017-03-13 (주)셀트리온 지방산이 결합된 트리펩타이드 및 이를 포함하는 주름 개선용 화장료 조성물
JP7273073B2 (ja) * 2018-07-06 2023-05-12 エニジェン カンパニー．，リミテッド． ペプチド複合体を有効成分として含有する微細ホコリ除去または吸着用化粧料組成物
CN112321674A (zh) * 2020-10-30 2021-02-05 润辉生物技术（威海）有限公司 一种类蛇毒三肽脂肪酸衍生物及其制备方法和应用

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KR20090133069A (ko) * 2009-04-14 2009-12-31 (주)케어젠 형질전환 성장인자의 활성을 가지는 펩타이드 및 그의 용도
KR20120107648A (ko) * 2011-03-22 2012-10-04 (주)셀인바이오 글리실프롤린 또는 글리실하이드록시프롤린과 팔미트산이 결합된 팔미토일 디펩타이드 및 그 제조방법
KR20130055505A (ko) * 2011-11-14 2013-05-28 (주)노바셀테크놀로지 콜라겐 합성능이 있는 신규 펩타이드 유도체 및 그의 용도
KR101715599B1 (ko) * 2016-10-04 2017-03-13 (주)셀트리온 지방산이 결합된 트리펩타이드 및 이를 포함하는 주름 개선용 화장료 조성물

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