WO2017082690A1 - Peptide multifonctionnel à perméation cutanée présentant des activités de blanchiment, d'élasticité de la peau, d'atténuation des rides, et de cicatrisation - Google Patents

Peptide multifonctionnel à perméation cutanée présentant des activités de blanchiment, d'élasticité de la peau, d'atténuation des rides, et de cicatrisation Download PDF

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Publication number
WO2017082690A1
WO2017082690A1 PCT/KR2016/013031 KR2016013031W WO2017082690A1 WO 2017082690 A1 WO2017082690 A1 WO 2017082690A1 KR 2016013031 W KR2016013031 W KR 2016013031W WO 2017082690 A1 WO2017082690 A1 WO 2017082690A1
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WIPO (PCT)
Prior art keywords
skin
peptide
derivative
multifunctional
multifunctional peptide
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PCT/KR2016/013031
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English (en)
Korean (ko)
Inventor
최호일
김동석
송상용
양현
이정옥
고희주
송강
김민석
Original Assignee
주식회사 펩트론
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Priority claimed from KR1020160149947A external-priority patent/KR101746787B1/ko
Publication of WO2017082690A1 publication Critical patent/WO2017082690A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/08—Peptides 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • 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

Definitions

  • the present invention relates to a multifunctional peptide having a skin-permeating function-based whitening, elasticity and wrinkle improvement effect, and more particularly, a skin permeation function, inhibiting melanin production, promoting collagen production, and function of skin keratin stem cell proliferation. It relates to a method to utilize the multifunctional peptide having a functional cosmetics and pharmaceutical raw materials.
  • Skin is the organ with the largest surface area in the human body, and is a route for effective drug delivery when used properly.
  • stratum corneum which is composed of dead cells on the outermost side of the skin, the skin permeability of the foreign material is extremely low, which makes it difficult to deliver substances with high molecular weight and hydrophilicity.
  • studies on various skin penetration methods have been attempted, but the delivery of the drug through the properties of the chemical without physically damaging or irritating the skin It is considered to be almost impossible, and the situation is continuously developed due to various advantages that can be expected from the material that overcomes it.
  • Collagen in the skin is a structural protein produced by skin fibroblasts, and it is known that the decrease in production due to aging and the change in its structure are related to wrinkle formation of the skin.
  • Melanin in the skin acts to protect the skin from UV rays and free radicals in the body, but abnormal activation of melanocytes causes hyperpigmentation such as blemishes, freckles and blotch, resulting in aesthetic problems.
  • Skin keratin stem cells present in the basal epidermal layer of the skin are known to play an important role in skin regeneration by controlling the growth and differentiation of keratinocytes as well as the fibroblasts of the dermis.
  • the present invention was completed by discovering a multifunctional peptide material that not only has a skin permeation function, but also inhibits melanin synthesis and promotes collagen synthesis and proliferation of skin keratin stem cells.
  • one object of the present invention is to provide a skin permeable multifunctional peptide having a function of inhibiting melanin synthesis and collagen synthesis, and promoting the proliferation of skin keratin stem cells and dermal dermal fibroblasts in addition to skin permeation function.
  • Another object is to provide a cosmetic composition for skin whitening, skin elasticity enhancement, or wrinkle improvement comprising the skin permeable multifunctional peptide.
  • Another object of the present invention is to provide a skin permeable multifunctional temperide. It provides a pharmaceutical composition for skin whitening, skin elasticity enhancement or wrinkle improvement comprising.
  • Another object is for wound healing comprising the skin permeable multifunctional peptide It is to provide a pharmaceutical composition.
  • Another object of the present invention is to provide a composition for transdermal delivery of a physiologically active substance containing the skin permeable multifunctional peptide or a derivative thereof and the peptide and a bioactive substance.
  • Another object of the present invention is to provide a method for skin whitening, skin elasticity improvement, wrinkle improvement or wound healing, which comprises using the skin permeable multifunctional tempide or a derivative thereof.
  • Another object of the present invention is to provide a method for transdermal delivery of a physiologically active substance, using the skin permeable multifunctional peptide or derivatives thereof.
  • the present invention relates to a skin permeable multifunctional peptide having the amino acid sequence of SEQ ID NO: 1 or derivatives thereof.
  • the skin permeable multifunctional peptide according to the present invention has a property of effectively penetrating the skin, and when foreign substances are combined, it can be effectively transferred into the skin, and thus can be used as a tool for mass transfer, and excellent melanin synthesis. Inhibiting ability, collagen synthesis, exfoliation promoting effect of skin keratin stem cells and dermal fibroblasts, the peptide alone can be useful as cosmetics, medicines for skin whitening, skin elasticity improvement, wrinkle improvement or wound healing.
  • FIG. 1 is a graph quantitatively confirming the wound healing effect when using a skin permeable multifunctional peptide alone according to the present invention.
  • Figure 2 is a graph confirming the skin permeation effect in the case of simple mixing of the skin permeable multifunctional peptide and the permeation target 20mer peptide according to the present invention.
  • the present invention relates to a skin permeable multifunctional peptide having the amino acid sequence of SEQ ID NO: 1 or derivatives thereof.
  • the derivative specifically refers to a peptide having a sequence in which one or more amino acids of the amino acid sequence of SEQ ID NO: 1 are substituted with alanine (Ala).
  • Preferably means a peptide having an amino acid sequence selected from SEQ ID NOs: 2 to 8.
  • Synthesis of the peptides of the invention can be carried out, for example, using a device or using genetic engineering techniques. Automated peptide when synthesized using a device
  • Peptides are purified and analyzed by Japan. Final peptides are identified using a mass spectrometer (HP 1 100 Series LC / MSD, Hewlett-Packard, Roseville, USA).
  • a bacterium lacking protease such as BL21 ( ⁇ DE3) and BL21 (DE3) pLys after introducing the corresponding nucleotide sequence of a desired peptide into a protein expression vector (vector). Expression using IPTG
  • the skin permeable multifunctional peptide according to the present invention was identified using phage display technique and selected by verifying the efficacy of the identified peptide.
  • the skin epidermis is removed after a certain time and information about peptide sequence and appearance frequency is amplified by remaining phages remaining inside the skin except the epidermis. Can be secured.
  • the peptide having a skin permeation function 2) melanin synthesis inhibitory effect in mouse melanocytes, 3) human Collagen synthesis in fibroblasts, 4) Proliferation in human dermal keratinocytes 5) Wound healing effect due to the proliferation of human dermal dermal fibroblasts 6) Effectiveness of skin permeation effect of the target substance when mixed with the target substance Verification multifunctional peptide was selected.
  • the peptide according to the present invention has a skin permeability and thereby can transport or deliver a variety of active substances such as low molecular weight materials, and at the same time, by itself, multifunctional, particularly excellent skin whitening, skin elasticity increase, wound healing and wrinkle improvement effect. It is characterized by showing, the usefulness regarding a drug or cosmetics is large. Furthermore, in the case of transporting or delivering various active materials, the active materials may be transported or delivered by covalently bonding the active materials and the template according to the present invention, or by simply mixing the active materials with the peptides according to the present invention.
  • the method of covalently binding the active substance and the skin permeable multifunctional peptide according to the present invention can be appropriately prepared using known techniques.
  • the physiologically active substance is a substance that enhances or inhibits the function of a living body in living life, and means any substance including a drug that can exert a desired effect in a living body.
  • the bioactive substance may include, but is not limited to, peptides, polypeptides, polynucleotides, nanoparticles, DNA, RNA, small molecule compounds, and the like.
  • the present inventors confirmed the transdermal delivery by the skin permeable multifunctional peptide according to the present invention using as a physiologically active substance to deliver a random peptide of 20mer.
  • the skin-permeable multifunctional peptide of the present invention not only shows excellent skin permeability compared to the transmittance of the TAT protein known as PTD (Protein transduction domain), but also excellent melanin even when used alone. Biosynthesis inhibitory effect, collagen synthesis effect, keratin stem cell proliferation effect and dermal fibroblast proliferation effect.
  • PTD Protein transduction domain
  • the present invention provides a skin permeable multifunctional peptide It relates to a cosmetic composition for skin whitening, skin elasticity enhancement or wrinkle improvement comprising as an active ingredient.
  • the term “wrinkle” means a skin line caused by the decay of the skin, can be caused by the cause of the gene, the reduction of collagen and elastin in the dermis of the skin, the external environment.
  • wrinkle improvement refers to inhibiting or inhibiting wrinkles from being generated on the skin, or alleviating wrinkles already generated.
  • skin elasticity is represented by the elastic fibers composed of elastin (elastin) present in the dermal layer
  • elastin elastin
  • skin elasticity enhancement ' refers to the elastic fibers composed of elastin and collagen, which are collagen fibers The state of skin elasticity is maintained.
  • the cosmetic composition according to the present invention is a solution, an external ointment, a cream, a product, a nourishing cosmetic, a flexible cosmetic, a pack, a flexible water, an emulsion, a makeup base, an essence, a soap, a liquid detergent, a bath, a sunscreen cream, a sun oil suspension, an emulsion Liquids, pastes, gels, lotions, powders, soaps, surfactant-containing cleansing, oils, powder foundations, emulsion foundations, waxes
  • the cosmetic composition of the present invention may further include one or more cosmetically acceptable carriers formulated in general skin cosmetics, and as conventional components, for example, oil, water, surfactants, moisturizers, lower alcohols, Thickening crab, chelating agent, colorant, preservatives, fragrances and the like may be appropriately blended, but is not limited thereto.
  • cosmetically acceptable carriers formulated in general skin cosmetics, and as conventional components, for example, oil, water, surfactants, moisturizers, lower alcohols, Thickening crab, chelating agent, colorant, preservatives, fragrances and the like may be appropriately blended, but is not limited thereto.
  • the present invention relates to a pharmaceutical composition for skin whitening, wrinkle improvement, skin elasticity enhancement or wound healing, comprising the multifunctional skin penetration peptide.
  • the composition of the present invention may further comprise suitable carriers, excipients and diluents commonly used in the manufacture of pharmaceutical compositions.
  • the compositions of the present invention can be used in the form of oral dosage forms, external preparations, suppositories, and sterile injectable solutions, such as powders, granules, tablets, capsulants, suspensions, emulsions, syrups, aerosols, etc., respectively, according to conventional methods.
  • Carriers, excipients, and diluents that may be included in the composition include lactose, dextrose, sucrose, sorbbi, manny, xylly, erythris, malty, starch, acacia rubber, alginate, gelatin, calcium Phosphate, calcium silicate, cellulose, methyl cellulose, Microcrystalline cellulose, polyvinylpyridone, water, methylhydroxy benzoate,
  • the multifunctional skin permeable peptide which is an active ingredient, is preferably in the form of a transdermal preparation.
  • Preferred dosages of the pharmaceutical compositions of the present invention vary depending on the condition and weight of the patient, the extent of the disease, the form of the drug, the route of administration and the duration, and may be appropriately selected by those skilled in the art. Administration may be administered once a day or may be divided several times.
  • the cosmetic or pharmaceutical composition according to the present invention may further include at least one substance having a skin whitening, skin wrinkle improvement, skin elasticity enhancement or wound healing function.
  • the present invention is to provide a composition for transdermal delivery of the skin-permeable multifunctional peptide or derivatives thereof and the bioactive material containing the peptide and the bioactive material.
  • the skin permeable multifunctional peptide or derivatives thereof and the bioactive material in the transdermal delivery composition may be in a mixed form or in a complex form covalently linked to each other.
  • the present invention provides a skin whitening, skin elasticity enhancement, wrinkle improvement or wound healing method, using the skin permeable multifunctional peptide and a cosmetic or pharmaceutical composition comprising the same as an active ingredient, and the skin
  • the present invention relates to a method for transdermal delivery of an active substance comprising the use of a permeable multifunctional ramide and a cosmetic or pharmaceutical composition comprising the same as an active ingredient.
  • the form of the cosmetic or pharmaceutical composition, the administration and route and duration of application it may be appropriately selected by those skilled in the art.
  • Coupling reagent was used as HBTU (2- (lH-Benzotimzloe-1-yl) -1,1,3,3-tetramethyluronium hexafluorophate I HOBt (Hydroxybenzo triazloe) I NMM (N-methylmorpholine).
  • the fluorescent peptides for confirming skin permeability are 6-amino hexanoic acid as a linker at the N-terminal part of the peptide.
  • FITC fluorescein isothiocyanate
  • the resultant mixed solution contained an excess of diethyl ether solvent stored in storage.
  • the treatment produces a precipitate.
  • the precipitate obtained was centrifuged to completely precipitate, and excess trifluoroacetic acid, thianizol, ethanedithiol, and the like were firstly removed, and the same procedure was repeated twice to obtain a solid.
  • heptapeptides 2 to 9 are derivatives of heptapeptide 1 (SEQ ID NO: 1) according to the present invention.
  • FCDV-15 The excised pig skin (1.77 cm 2) Franz (Franz) cell proliferation (FCDV-15, Labfine,
  • isophosphate buffer (pH 7.4) equally 13 ⁇ in the receiver chamber.
  • the temperature of the receiver chamber is maintained at 37 ⁇ 0.5 ° C, and the magnetic bar is stirred at a speed of 600 rpm and the conditions are maintained until the end of the experiment.
  • Hepta peptides labeled with fluorescence (FITC) and derivatives thereof and TAT labeled with positive control fluorescence were applied to the pig skin surface in contact with the donor chamber and peptides and derivatives thereof were transferred to the receiver chamber after 20 hours.
  • Peptide quantification was spectrophotometer;: was used (Nanodrop2000 Thermoscientific USA). Table 1 shows the results of analyzing the permeability of heptapeptide, and Table 2 shows the results of performing alanine scanning as a method for verifying the effective sequence of heptapeptide.
  • the skin transmittance (%) between the derivatives of heptapeptide l (KLTTQMM) is fluorescent heptapeptide 1 Compared with (FITC-linker-KLTTQMM), fluorescent heptapeptide 2 was 3.06 times, fluorescent heptapeptide 3 was 1.69 times, fluorescent heptapeptide 4 was 0.95 times, fluorescent heptapeptide 5 was 1.98 times, and fluorescent heptapeptide 6 was 1.96 times, respectively.
  • the fluorescent heptapeptide 8 was 1.31 fold change.
  • tyrosinase inhibitory substances which are cosmetic materials for whitening
  • substances that induce melanin synthesis inhibition in skin cells also have a great potential for skin whitening.
  • whitening can be expected as an inhibitory effect on melanin biosynthesis of melanoma cells.
  • 6-well plates containing DMEM (Dulbecco's modified eagle medium, Gibco) medium were inoculated (IX 10 5 cells / well) and incubated at 37 ° C for 24 hours in a C0 2 incubator at 5% concentration. After 24 hours, the medium was removed from each well, and the medium containing Arbutin (Sigma Aldrich) as a positive control group, the medium containing 20 ppm heptapeptide as the experimental group,
  • heptapeptide was shown to inhibit melanin biosynthesis in melanoma cells not only as a negative control group but also as arbutin, a positive control group known to have an effect on whitening.
  • Example 4 Measurement of Collagen Synthesis of Human Dermal Fibroblasts
  • the amount of collagen synthesis of fibroblasts is an indicator of wrinkle formation in the skin. Wrinkles are known to occur due to decreased collagen synthesis and degradation of existing collagen. As a result, promoting collagen synthesis of fibroblasts can have an effect of inhibiting wrinkle formation and improving existing wrinkles.
  • Fibroblasts human dermal fibroblast (ATCC) are seeded in 96-well plates containing fibroblast basal medium (PCS-201-020; ATCC) medium (3 x 10 3 cells / well) and incubated in a C0 2 incubator at 5% concentration. Incubated at 37 ° C for 24 hours. After 24 hours, the medium was removed from each well, followed by a medium containing vitamin C as a positive control group and 20 ppm as an experimental group.
  • PCS-201-020 fibroblast basal medium
  • Heptapeptide-containing medium serum-free medium as negative control, and incubated for 48 hours. After 48 hours, cell culture medium was collected to prepare a sample. The amount of collagen in the sample was determined using a collagen measurement kit (Procollagen Type I C-peptide EIA kit; MK101; Takara, Kyoto, Japan). The amount of PICP) was measured. The experiment was performed according to the method described in the manual. The experimental results are shown in Table 5.
  • heptapeptide 1 increased the collagen synthesis of fibroblasts to the same degree as that of the positive control group.
  • Human skin keratinocytes were purchased from CellnTec (USA), and the growth factor Cnt-57 was added to 500 m of Cnt-BM medium according to the instructions, and used for culture.
  • Human skin keratinocytes were seeded in 96-well folate (5 ⁇ 10 3 cells / well) and incubated at 37 ° C. for 24 hours in a CO 2 incubator at 5% concentration. After 24 hours, the cells were treated at 100, 200, 400 ppm concentrations to confirm the cytotoxicity of the heptapeptide, and after 48 hours, the degree of cytotoxicity was confirmed by CCK-8 kit (CK04; Dojindo).
  • CK04 doxorubicin hydrochloride
  • heptapeptide was found to be cytotoxic at 100-200 ppm.
  • the heptapeptide according to the present invention was treated to human dermal fibroblasts at a concentration of 20 ppm, and the extent of wound healing was confirmed by quantifying the movement distance of cells after 48 hours. It was.
  • Human dermal fibroblasts were purchased from ATCC, and cultured media for fibroblasts were incubated at 37 ° C for 24 hours in a C0 2 incubator at 5% concentration. Human dermal fibroblasts were seeded in 6-well plates and incubated for 24 hours before heptapeptide treatment.
  • Vitamin C as a positive control was treated at the same concentration of 20ppm, the same time conditions, the results are shown in Table 7 and FIG.
  • Heptapeptide 1 (KLTTQMM) has its own effects on wound healing : it is associated with vitamin C, a positive control group known to have a wound healing effect.
  • Heptapeptide 1 (KLTTQMM: SEQ ID NO: 1) and derivatives thereof, including the drug according to the present invention, heptapeptide 9 (GLTTQMM: SEQ ID NO: 9)
  • heptapeptide 1 SEQ ID NO: 1
  • the removed dorsal dorsal skin (1.77 cm 2 ) of the Balb / c mouse was fixed between the donor chamber and the receiver chamber of a Franz diffusion cell (FCDV-15, Labfme, Korea) and isotonic phosphate in the receiver chamber. 13 mL of layer solution (H 7.4) were provided in the same manner. And the temperature of the receiver chamber was maintained at 37 ⁇ 0.5 ° C, the magnetic bar was stirred at a speed of 600 rpm and the conditions were maintained until the end of the experiment.

Abstract

La présente invention concerne un peptide multifonctionnel et son utilisation, ledit peptide multifonctionnel présentant des effets de blanchiment, d'élasticité, et d'atténuation des rides basés sur une fonction de perméation cutanée, et plus particulièrement, une méthode permettant d'utiliser, comme matière première dans des cosmétiques et des médicaments fonctionnels, un peptide multifonctionnel présentant des effets de perméation cutanée, d'inhibition de la production de mélanine, de promotion de la production de collagène, et de promotion de la prolifération des cellules souches kératiniques. Ledit peptide multifonctionnel à perméation cutanée, selon la présente invention, a comme caractéristique de traverser facilement la peau et est exceptionnellement efficace pour inhiber la synthèse de la mélanine et promouvoir la synthèse du collagène et la prolifération des cellules souches kératiniques, rendant ainsi le peptide utile, même indépendamment, en tant que produits cosmétiques ou médicaments pour le blanchiment de la peau, l'amélioration de l'élasticité de la peau, l'atténuation des rides ou la cicatrisation des plaies.
PCT/KR2016/013031 2015-11-12 2016-11-11 Peptide multifonctionnel à perméation cutanée présentant des activités de blanchiment, d'élasticité de la peau, d'atténuation des rides, et de cicatrisation WO2017082690A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2015-0159196 2015-11-12
KR20150159196 2015-11-12
KR1020160149947A KR101746787B1 (ko) 2015-11-12 2016-11-11 미백, 피부 탄력, 주름 개선 및 상처치유 활성을 갖는 다기능성 피부투과 펩타이드
KR10-2016-0149947 2016-11-11

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WO2017082690A1 true WO2017082690A1 (fr) 2017-05-18

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WO2023073718A1 (fr) * 2021-10-31 2023-05-04 Gigi Cosmetic Laboratories Ltd Compositions cosmétiques destinées à être utilisées pour le soin de la peau
CN117106022A (zh) * 2023-10-25 2023-11-24 深圳市维琪科技股份有限公司 七肽化合物及其组合物和用途

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WO2023073718A1 (fr) * 2021-10-31 2023-05-04 Gigi Cosmetic Laboratories Ltd Compositions cosmétiques destinées à être utilisées pour le soin de la peau
CN117106022A (zh) * 2023-10-25 2023-11-24 深圳市维琪科技股份有限公司 七肽化合物及其组合物和用途
CN117106022B (zh) * 2023-10-25 2024-01-23 深圳市维琪科技股份有限公司 七肽化合物及其组合物和用途

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