WO2023229102A1 - Nouveau peptide de blanchiment et composition cosmétique le contenant - Google Patents

Nouveau peptide de blanchiment et composition cosmétique le contenant Download PDF

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Publication number
WO2023229102A1
WO2023229102A1 PCT/KR2022/012595 KR2022012595W WO2023229102A1 WO 2023229102 A1 WO2023229102 A1 WO 2023229102A1 KR 2022012595 W KR2022012595 W KR 2022012595W WO 2023229102 A1 WO2023229102 A1 WO 2023229102A1
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Prior art keywords
whitening
skin
peptide
bicelphin
cosmetic composition
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PCT/KR2022/012595
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English (en)
Korean (ko)
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장상호
박준호
이선희
Original Assignee
주식회사 바이오셀트란
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Priority claimed from KR1020220064697A external-priority patent/KR102717793B1/ko
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Publication of WO2023229102A1 publication Critical patent/WO2023229102A1/fr

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/02Preparations for care of the skin for chemically bleaching or whitening the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • A61K2800/522Antioxidants; Radical scavengers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74Biological properties of particular ingredients
    • A61K2800/78Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782Enzyme inhibitors; Enzyme antagonists

Definitions

  • the present invention relates to a novel whitening peptide and a composition containing the same, and more specifically, to a cosmetic composition that exhibits an excellent skin whitening effect by combining a novel PTD (STeP) with a peptide known to have whitening efficacy.
  • STeP novel PTD
  • the skin surrounds the entire body and mainly plays the role of protecting the human body from various external irritants.
  • interest in healthy and beautiful skin increases in modern society, efforts to improve and maintain it are necessary.
  • skin whitening functionality is needed for white and clean skin.
  • Skin whitening can be expressed as improving dullness or brightening the skin, and it is known that the difference in a person's skin color depending on race or body part is determined by hemoglobin in the blood or melanin at the border of the epidermis and dermis.
  • the biosynthesis of melanin uses tyrosine, a type of amino acid, as a precursor, followed by DOPA, DOPA quinone, and indole-5,6-dihydroquinone, and then indole.
  • -It is biosynthesized from melanin, a polymer of 5,6-dihydroquinone.
  • Melanin is produced within melanocytes and moves to the boundary between the epidermis and dermis in the form of granules called melanosomes and is deposited there. Melanin is not only the direct cause of dark skin, but also has negative effects on skin beauty, such as promoting the formation of blemishes and freckles.
  • PTD Protein transduction domain
  • the present invention is a novel whitening peptide that exhibits an excellent skin whitening effect by combining a novel PTD (STeP) with an existing whitening peptide, and is highly purified, non-toxic, safe, and has superior skin whitening effects compared to existing whitening peptides, and a cosmetic product containing the same.
  • STeP novel PTD
  • the present invention seeks to provide a composition.
  • the present invention provides a cosmetic composition for skin whitening, characterized in that it contains a peptide having the amino acid sequence of SEQ ID NO: 1.
  • the skin whitening may preferably result from one or more selected from the group consisting of inhibition of tyrosinase activity, inhibition of DOPA oxidation activity, and inhibition of total melanin production in cells.
  • novel whitening peptide of the present invention and the cosmetic composition containing it can be obtained in high purity, are non-toxic and safe, and have excellent skin whitening functionality such as inhibition of tyrosinase, inhibition of DOPA oxidation activity, and inhibition of melanin production related to skin whitening. It can demonstrate much better whitening efficacy than existing whitening peptides. In addition, when actually applied to cosmetics, it can demonstrate excellent skin functionality together with other types of functional substances.
  • Figure 1 shows the results of an in-house analysis of the purity of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 2 shows the results of a consignment analysis of the purity of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 3 shows the results of an endotoxin quantitative test for the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 4 shows the cell viability test results (self-evaluation) of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 5 shows the results of a tyrosinase activity inhibition test (self-evaluation) of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 6 shows the results of an L-DOPA oxidation activity inhibition test (self-evaluation) of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 7 shows the results of a test (self-evaluation) measuring the total amount of melanin produced in cells of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 8 shows the cell viability test results (consignment evaluation) of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 9 shows the results of a tyrosinase activity inhibition test (commissioned evaluation) of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 10 shows the results of an L-DOPA oxidation activity inhibition test (commissioned evaluation) of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 11 shows the results of a test (consignment evaluation) measuring the total amount of melanin produced in cells of the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 12 shows the results of a comparative test for tyrosinase activity inhibition between the whitening peptide Bicelphin-oligopeptide68 of the present invention and the existing whitening peptide oligopeptide68.
  • Figure 13 shows the results of a comparative test on the inhibition of L-DOPA oxidation activity between the whitening peptide Bicelphin-oligopeptide68 of the present invention and the existing whitening peptide oligopeptide68.
  • Figure 14 shows the results of a comparative test measuring the total amount of melanin produced in cells between the whitening peptide Bicelphin-oligopeptide68 of the present invention and the existing whitening peptide oligopeptide68.
  • Figure 15 is a result graph showing changes in skin wrinkle parameters of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 16 is an optical photograph and a 3D photograph showing changes in skin wrinkles in a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 17 is a result graph showing changes in skin brightness and color parameters of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 18 is a graph showing the change in skin melanin index of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 19 is a result graph showing changes in skin transparency parameters of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 20 is a graph showing the change in skin gloss of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 21 is a photo showing the change in skin gloss of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 22 is a result graph showing changes in skin tone and tone uniformity of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 23 is a photograph showing the change in skin tone uniformity of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 24 is a graph showing the change in skin density of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 25 is a photograph showing the change in skin density of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 26 shows the results of a questionnaire evaluation on the efficacy of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • Figure 27 shows the results of a questionnaire evaluation regarding the usability of a cosmetic composition containing the whitening peptide Bicelphin-oligopeptide68 of the present invention.
  • the present invention provides a cosmetic composition for skin whitening, characterized in that it contains a peptide having the amino acid sequence of SEQ ID NO: 1.
  • the peptide having the amino acid sequence of SEQ ID NO: 1 is listed in the International Cosmetic Ingredient Dictionary (ICID) as "Bicelphin-BWP1", and its INCI (International Nomenclature Cosmetic Ingredient) name is "Oligopeptide-68 Oligopeptide-133". It was registered as.
  • an existing whitening peptide by combining Bicelphin, a novel PTD (STeP), with oligopeptide68, known as an existing whitening peptide, it inhibits tyrosinase better than existing whitening peptides. , it was able to demonstrate excellent skin whitening efficacy through inhibition of DOPA oxidation activity and inhibition of total melanin production within cells.
  • the skin whitening may result from one or more selected from the group consisting of inhibition of tyrosinase activity, inhibition of DOPA oxidation activity, and inhibition of total melanin production within cells.
  • the peptide having the amino acid sequence of SEQ ID NO: 1 may preferably be included in an amount of 0.0001 to 0.001% by weight, more preferably 0.0005% by weight, based on the total weight of the cosmetic composition. may be included.
  • the cosmetic composition of the present invention is not limited to a specific form (formulation) and includes all formulations, such as lotion, gel, water-soluble liquid, cream, essence, oil-in-water (O/W) type, and water-in-oil type.
  • W/O type emulsion basic cosmetic formulation consisting of ointment, oil-in-water and water-in-oil makeup base, foundation, skin cover, lipstick, lip gloss, face powder, two-way cake, eye shadow, cheek color, and eyebrow pencils It is better to use any one selected from color cosmetic formulations consisting of.
  • the cosmetic composition of the present invention may contain auxiliaries common in the cosmetic field such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic activators, preservatives, antioxidants, solvents, fragrances, fillers, blocking agents, pigments, odorants and dyes. It may be possible.
  • the novel Bicelphin-oligopeptide68 peptide of the present invention can be obtained in high purity and has no possibility of skin toxicity.
  • the novel Bicelphin-oligopeptide68 peptide of the present invention can be used as a functional material that exhibits various effects related to skin whitening when applied and manufactured as an actual cosmetic composition.
  • a new whitening peptide was developed by combining a new PTD (STeP) with an existing whitening peptide.
  • the synthesis and purification method of skin-permeable whitening peptide was solid phase peptide synthesis (SPPS, Solid Phase Peptide Synthesis).
  • SPPS Solid Phase Peptide Synthesis
  • Peptides by chemical synthesis are composed of C-Terminal to N-Terminal, and chemical synthesis includes the classic liquid phase method and solid phase method.
  • the peptide of the present invention was synthesized using a solid phase method.
  • the peptide developed through this was PTD-oligopeptide68 (hereinafter referred to as Bicelphin-oligopeptide68), and detailed information was shown in Table 1 below.
  • Liquid chromatography was used to analyze purity.
  • Liquid chromatography is characterized by separating the components of a mixture using a mobile phase (liquid) and a stationary phase (column). The purpose of the experiment is mainly to measure the size of the reaction of chemical substances over time using a detector. It is a method of quantifying substances.
  • the experiment was conducted using water and acetonitrile (ACN) as polar solvents and C18, a reversed-phase hydrophilic column, as the solvent for the sample and mobile phase whose purity is to be determined.
  • the solvent was prepared by adding 0.1% of trifluoroacetic acid to water and acetonitrile (ACN) for acid stability and used after removing air bubbles. Samples were prepared by filtering and injecting each into vials. To stabilize the device before the separation process, wash the pump 2-3 times with 100% acetonitrile, install a C18 column, and flow acetonitrile until the pressure and temperature are stabilized. Once the pressure was stabilized, the program was set and the purity of the protein was determined by measuring the size of the peak over time under the UV detection wavelength (214 nm, 280 nm).
  • the purity of the whitening peptide by HPLC was analyzed through in-house and consignment analysis, and as shown in Table 2 and Figures 1 and 2 (Bicelphin-BWP1 was analyzed, but the test sample name is written as BWP-1 for convenience), the result was 99.82. It has a high purity of 99.16%, which is considered to be equal or higher than the purity of other protein and peptide raw materials currently distributed in the cosmetic raw material market.
  • B16F10 cells were inoculated into a 24 -well plate at a concentration of 1.5 After incubation, 10ul Ez-cytox was added to each well, incubated for 1 hour, and absorbance was measured at 450 nm.
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) was confirmed to have no cytotoxicity compared to the solvent control group at a concentration of 50 uM or less.
  • Tyrosinase is an enzyme involved in the most important initial rate-determining step in the melanin biosynthesis pathway in the human body, and inhibition of the activity of this enzyme results in inhibition of melanin production.
  • This test is a method to evaluate the effect of the test sample on inhibiting tyrosinase activity by reacting the test sample, purified tyrosinase, and the substrate tyrosine in vitro.
  • the sample was dissolved in ethanol or an appropriate solvent, diluted to set a concentration range in which inhibition of tyrosinase activity can be confirmed, and treated to achieve at least 5 concentrations.
  • 220 ⁇ L of 0.1 M phosphate buffer (pH 6.5), 20 ⁇ L of sample solution, and 20 ⁇ L of mushroom tyrosinase solution (1,500 U/mL to 2,000 U/mL) (or human tyrosinase) were added to the test tube in that order.
  • 40 ⁇ L of 1.5-2 mM tyrosine solution was added and reacted at 37°C for 10-15 minutes, and then the absorbance was measured at 490 nm.
  • the blank sample solution was corrected using the solvent in which the sample was dissolved instead of the sample solution, and the results were compared using arbutin as a positive control.
  • the inhibition rate of tyrosinase activity was confirmed using Equation 1 below.
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) significantly reduced tyrosinase activity to 8.57-29.33% compared to the solvent control group at a concentration of 6.25-50 uM.
  • L-DOPA L-3,4-dihydroxyphenylalanine
  • the sample was dissolved in ethanol or an appropriate solvent, diluted to set a concentration range that can confirm the inhibition of tyrosinase activity for the DOPA oxidation reaction, and treated to achieve at least 5 concentrations.
  • 170 ⁇ L of 0.1 M phosphate buffer (pH 7.0), 10 ⁇ L of sample solution, and 10 ⁇ L of mushroom tyrosinase solution (1,500 U/mL ⁇ 2,000 U/mL) (or human tyrosinase) were added to the test tube in that order.
  • 10 ⁇ L of 8 mM L-DOPA solution was added, reacted at 37°C for 30 minutes, and absorbance was measured at 475 nm.
  • the blank sample solution was corrected using a solvent in which the sample was dissolved instead of the sample solution, and arbutin was used as a positive control and the results were compared and measured.
  • the inhibition rate of L-DOPA oxidation reaction was confirmed using Equation 2 below.
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) significantly reduced the L-DOPA oxidation activity to 5.88-21.46% compared to the solvent control group at a concentration of 6.25-50 uM.
  • cells were cultured, the amount of melanin inside the cells or the total amount of melanin inside and outside the cells was quantified and compared with a blank sample solution.
  • B16F10 melanoma cells Mouse melanoma cells (B16F10 melanoma cells) were selected and used based on efficacy test data from the Ministry of Food and Drug Safety's "Guidelines for the evaluation of effectiveness of functional cosmetics that help whiten the skin.” B16F10 cells were inoculated on the bottom of a culture dish, then DMEM mixed medium containing 1% Antibiotic-Antimycotic and 10% FBS was added and cultured in an incubator at 37°C and 5% CO 2 .
  • B16F10 cells were inoculated into a 6-well plate at a concentration of 1 ⁇ 10 5 cells/well and cultured for 24 hours under cell culture conditions. The medium was removed, the cells were washed with PBS, and then new medium without phenol red containing test substances diluted at each concentration and 100 nM ⁇ -MHS was added and cultured for 72 hours, and then the medium was removed. . Cells were washed with PBS, lysed at 60°C by adding 1M NaOH to each well, centrifuged, and the absorbance of the supernatant was measured at 490 nm.
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) significantly reduced the total melanin production by 29.72-50.18% compared to the solvent control group at a concentration of 6.25-50 uM.
  • B16F10 melanoma cells were inoculated into a 24 -well plate at a concentration of 1.5 After 72 hours of incubation, changes in cell shape due to test substance treatment at each concentration were observed under a microscope. MTT solution was added to each well to a final treatment concentration of 0.05% and cultured for 4 hours. After removing the culture medium, 1,000 ⁇ L of DMSO was added and shaken for more than 1 hour, and the absorbance was measured at 540 nm (Microplatereader; Epoch2, BioTek, USA).
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) of the present invention had no cytotoxicity and no cell shape or change compared to the solvent control group at a concentration of 50 uM or less (Mean ⁇ SD, p ⁇ 0.05).
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) of the present invention significantly reduced tyrosinase activity to 13.19-25.86% compared to the solvent control group at a concentration of 6.25-50 uM (Mean ⁇ SD, p ⁇ 0.05).
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) of the present invention significantly reduced L-DOPA oxidation activity by 7.61-16.23% compared to the solvent control group at a concentration of 6.25-50 uM (Mean ⁇ SD, p ⁇ 0.05).
  • B16F10 melanoma cells were inoculated into a 6-well plate at a concentration of 1 ⁇ 10 5 cells/well and cultured for 24 hours under cell culture conditions. The medium in each well was removed, the cells were washed with PBS, and then new cell culture medium without Phenol red containing diluted test substances of each concentration and 100 nM ⁇ -MSH was added and cultured for 72 hours. The cultured cells were used to measure the amount of intracellular melanin, and the cell culture medium was used to measure the amount of extracellular melanin. The total amount of melanin produced by the cells was calculated by adding the amount of melanin inside and outside the cells.
  • the cultured cells were washed with PBS, dissolved at 60°C by adding 1M NaOH to each well, and the absorbance of the lysed solution was measured at 400 nm.
  • the cells were The culture medium was transferred to a 1.5 ml tube, centrifuged, and the supernatant was transferred to a 96-well plate and absorbance was measured at 400 nm.
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) of the present invention significantly reduced the total melanin production of cells by 25.12-48.24% compared to the control group treated alone with ⁇ -MSH at a concentration of 6.25-50 uM ( Mean ⁇ SD, p ⁇ 0.05).
  • Bicelphin-oligopeptide68 a novel whitening peptide developed in the present invention by combining a novel PTD (STeP) with an existing whitening peptide, inhibits tyrosinase activity, L -It was found to be a substance with a whitening effect due to its excellent efficacy in inhibiting DOPA oxidation activity and total melanin production in cells.
  • STeP novel PTD
  • L -It was found to be a substance with a whitening effect due to its excellent efficacy in inhibiting DOPA oxidation activity and total melanin production in cells.
  • Bicelphin-oligopeptide68 Boicelphin-BWP1
  • a novel whitening peptide developed in Example 1 combining a novel PTD (STeP) with an existing whitening peptide
  • STeP novel PTD
  • BWP1 existing whitening peptide oligopepetide68
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) of the present invention shows a concentration-dependent decreasing trend compared to the solvent control group at a concentration of 6.25 to 50 uM, but in particular, the existing It was found to have a greater effect on whitening by showing superior tyrosinase inhibition efficacy (8.57-29.33%) than the whitening peptide BWP1 (0-15.76%).
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) of the present invention shows a concentration-dependent decreasing trend compared to the solvent control group at a concentration of 6.25 to 50 uM, but in particular, the existing It was found to have a greater effect on whitening as it showed superior DOPA oxidation activity inhibition efficacy (5.88-21.46%) than the whitening peptide BWP1 (2.62-19.82%).
  • Bicelphin-oligopeptide68 (Bicelphin-BWP1) of the present invention shows a concentration-dependent decreasing trend compared to the solvent control group, but in particular, , it was found to have a greater effect on whitening by showing superior melanin production inhibition efficacy (29.72-50.18%) than the existing whitening peptide, BWP1 (16.28-38.42%).
  • the new whitening peptide developed in the present invention by combining the existing whitening peptide with the new PTD (STeP) is a material that can be applied as a material with a much more effective whitening effect than the existing whitening peptide.
  • an ampoule-type cosmetic product was prepared as an example of a cosmetic composition containing the novel whitening peptide developed in Example 1, and the detailed composition was shown in Table 4.
  • Bicelphin-oligopeptide68 0.0005 Peptide A (Has the amino acid sequence of SEQ ID NO: 2) 0.0005 Peptide B (Binding of a peptide with the amino acid sequence of SEQ ID NO. 3 and tranexamic acid) 0.0005 Peptide C (Has the amino acid sequence of SEQ ID NO: 4) 0.0005 Peptide D (Has the amino acid sequence of SEQ ID NO: 5) 0.0005 glycerin 7.65 Butylene glycol 9.95 1,2-hexanediol 0.097 Propanediol 1.2 Sodium Hyaluronate 0.04 Purified water to 100
  • the skin irritation safety evaluation was conducted by DermaPro Co., Ltd., and the method and results were as follows.
  • Test subjects and number 30 women (34.50 ⁇ 7.22 years old) who met the selection and exclusion criteria.
  • PCPC Personal Care Products Council
  • Mean Example 2 0 - - - - - - - - - 0.0
  • Example 2 of the present invention was stable as a material in the hypoallergenic category in terms of primary irritation of human skin.
  • Test subjects and number 21 female subjects aged 38 to 60 years (average 49.76 ⁇ 5.36 years).
  • novel whitening peptide developed in the present invention can be used as a functional material that exhibits various effects related to skin whitening in actual cosmetic compositions.

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Abstract

La présente invention se rapporte à une composition cosmétique qui présente un effet considérable de blanchiment de la peau par liaison d'un nouveau PTD (STeP) à un peptide présentant un effet connu de blanchiment de la peau. La composition cosmétique peut être obtenue à une pureté élevée, n'est pas toxique et est donc sûre, et présente une fonctionnalité considérable de blanchiment de la peau, telle que l'inhibition de la tyrosinase, l'inhibition de l'activité d'oxydation de la DOPA, et l'inhibition de la production de mélanine, qui sont associées au blanchiment de la peau, et peut ainsi présenter un effet de blanchiment de la peau bien supérieur à celui des peptides de blanchiment de la peau classiques. De plus, la composition cosmétique peut présenter une fonctionnalité cutanée considérable conjointement avec d'autres types de matériaux fonctionnels lorsqu'elle est réellement appliquée à des produits cosmétiques.
PCT/KR2022/012595 2022-05-26 2022-08-23 Nouveau peptide de blanchiment et composition cosmétique le contenant WO2023229102A1 (fr)

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KR10-2022-0064697 2022-05-26
KR1020220064697A KR102717793B1 (ko) 2022-05-26 신규한 미백 펩타이드 및 이를 함유하는 화장료 조성물

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117801070A (zh) * 2024-03-01 2024-04-02 中国农业大学 一种美白祛斑消水肿青稞酒糟肽及其制备方法和应用
CN118005729A (zh) * 2024-02-27 2024-05-10 中国农业大学 一种具有酪氨酸酶抑制活性的多肽及其应用

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KR101095841B1 (ko) * 2009-02-19 2011-12-21 주식회사 나이벡 표적 선택적 세포/조직 투과기능 활성을 가지는 펩타이드 및 그 용도
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CN118005729A (zh) * 2024-02-27 2024-05-10 中国农业大学 一种具有酪氨酸酶抑制活性的多肽及其应用
CN117801070A (zh) * 2024-03-01 2024-04-02 中国农业大学 一种美白祛斑消水肿青稞酒糟肽及其制备方法和应用
CN117801070B (zh) * 2024-03-01 2024-06-07 中国农业大学 一种美白祛斑消水肿青稞酒糟肽及其制备方法和应用

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