WO2017183942A2 - Peptide efficace pour augmenter la génération de collagène et composition le comprenant - Google Patents

Peptide efficace pour augmenter la génération de collagène et composition le comprenant Download PDF

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Publication number
WO2017183942A2
WO2017183942A2 PCT/KR2017/004288 KR2017004288W WO2017183942A2 WO 2017183942 A2 WO2017183942 A2 WO 2017183942A2 KR 2017004288 W KR2017004288 W KR 2017004288W WO 2017183942 A2 WO2017183942 A2 WO 2017183942A2
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WIPO (PCT)
Prior art keywords
peptide
composition
aging
less
skin
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Ceased
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PCT/KR2017/004288
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English (en)
Korean (ko)
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WO2017183942A3 (fr
Inventor
김상재
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GemVax and Kael Co Ltd
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GemVax and Kael Co Ltd
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Publication of WO2017183942A2 publication Critical patent/WO2017183942A2/fr
Publication of WO2017183942A3 publication Critical patent/WO2017183942A3/fr
Anticipated expiration legal-status Critical
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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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/18—Peptides; Protein hydrolysates
    • 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
    • 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

Definitions

  • the present specification relates to a functional peptide having a collagen production increasing effect and a composition comprising the same, and more particularly, to a functional peptide having a collagen production increasing effect and effective in improving skin wrinkles and preventing skin aging by lowering collagen production. It relates to a peptide composition.
  • Retinol and retinoids are known to be effective in various fields such as psoriasis, aging, cancer, and acne.
  • this retinoid is known to prevent collagen loss by stimulating collagen formation by inhibiting collagenase-1 (MMP-1) when applied to the skin to prevent and restore endogenous and photoaging.
  • MMP-1 collagenase-1
  • TGF- ⁇ Transforming growth factor
  • betulinic acid wild yam extract
  • wild yam extract Korean Patent Publication No. 2009-0055079
  • the above-described skin improvement active ingredients may cause local skin irritation reactions such as erythema, itching, psoriasis, and scaling when applied to the skin, and their stability has not been verified when applied to a living body.
  • Patent Document 1 KR 2009-0055079 A
  • the present inventors have developed a peptide having novel activity and found that it has collagen synthesis efficacy and completed the present invention.
  • One aspect of the present invention is a peptide having at least 80% sequence homology with a peptide consisting of any one of the amino acid sequences represented by SEQ ID NO: 1 to 3, a peptide that is a fragment of the peptide sequence, the peptide sequence or a peptide thereof Provided are peptides or salts thereof that exhibit collagen synthesis activity selected from the group consisting of:
  • Another aspect of the present invention provides an anti-wrinkle and anti-aging composition
  • an anti-wrinkle and anti-aging composition comprising the peptide or a salt thereof as an active ingredient.
  • the present invention has a sequence homology of at least 80% to a peptide consisting of any one of the amino acid sequences represented by SEQ ID NO: 1 to 3, a peptide that is a fragment of the peptide sequence, the peptide sequence or a peptide sequence thereof
  • anti-wrinkle and anti-aging methods comprising applying to a subject in need thereof at least one selected from the group consisting of peptides, and salts thereof.
  • the present invention provides a peptide consisting of any one of amino acid sequences represented by SEQ ID NOs: 1 to 3, peptides which are fragments of the peptide sequences, peptides which are peptides, or fragments thereof, for use in wrinkle improvement and anti-aging. At least one selected from the group consisting of peptides having at least 80% sequence homology with the sequences, and salts thereof.
  • the present invention provides a peptide comprising any one of amino acid sequences represented by SEQ ID NOs: 1 to 3 as an active ingredient for wrinkle improvement and anti-aging, a peptide which is a fragment of the peptide sequence, the peptide sequence or a fragment thereof
  • One or more non-therapeutic cosmetic uses selected from the group consisting of peptides having at least 80% sequence homology with peptide sequences, and salts thereof.
  • the present invention provides a peptide comprising any one of amino acid sequences represented by SEQ ID NOs: 1 to 3 for use in the preparation of a composition for improving wrinkles and preventing aging, a peptide which is a fragment of the peptide sequence, the peptide
  • One or more uses selected from the group consisting of peptides having at least 80% sequence homology with peptide sequences that are sequences or fragments thereof, and salts thereof.
  • the composition may be characterized in that the cosmetic composition for wrinkle improvement and anti-aging.
  • the cosmetic composition may be characterized in that it consists of any one formulation selected from the group consisting of skin, lotion, cream, foundation, essence, gel, pack, foam cleansing, soap and skin ointment. have.
  • the composition may be characterized in that the pharmaceutical composition for wrinkle improvement and anti-aging.
  • the composition may be characterized in that the composition for wrinkle improvement and anti-aging health functional food.
  • Peptides having the sequence of SEQ ID NO according to the present invention have collagen synthesis efficacy, it is expected to provide a wrinkle improvement and anti-aging composition comprising a peptide having collagen synthesis activity.
  • Wrinkle improvement and anti-aging effects according to the present invention refers to the effect of preventing or aging skin by inhibiting or improving the production of skin wrinkles through increased collagen production by the composition according to the present invention.
  • Figure 1 is a human skin fibroblast CCD-986SK cell line, a control (no treatment), a control group treated with TGF- ⁇ 20ng / ml positive control group, peptide according to the invention (CP-54, CP-55 CP-56) each divided into 50 ⁇ M treated group collagen synthesis (collagen synthesis) measured by comparing the results compared to the control (100%) based on the relative graph (%).
  • a peptide having novel activity of collagen synthesis consisting of the sequences of SEQ ID NOs: 1 to 3 is disclosed.
  • the peptides disclosed herein are at least 80%, at least 85%, at least 90%, at least 95%, at least 96%, at least 97%, at least 98%, 99% with each of the peptides selected from SEQ ID NOs: 1-3 It may include a peptide having the above sequence homology.
  • the peptides disclosed herein may include any one peptide selected from 1 to 3 and at least one amino acid, at least two amino acids, at least three amino acids, at least four amino acids, at least five amino acids, at least six amino acids or Seven or more amino acids may comprise a modified peptide.
  • amino acid changes belong to the property that allows the physicochemical properties of the peptide to be altered.
  • amino acid changes can be made, such as improving the thermal stability of the peptide, altering substrate specificity, changing the optimal pH, and the like.
  • Any one peptide selected from SEQ ID NOs: 1 to 3 according to an aspect of the present invention has the advantage of low intracellular toxicity and high in vivo stability.
  • the peptides set forth in SEQ ID NOS: 1 to 3 are shown in Table 1 below.
  • the "name” in Table 1 below is to distinguish peptides.
  • the present invention provides a nucleotide sequence encoding the peptide.
  • composition comprising a peptide comprising any one amino acid sequence selected from SEQ ID NO: 1 to 3 as an active ingredient.
  • composition according to one aspect of the present invention can be applied to all animals including humans, dogs, chickens, pigs, cows, sheep, guinea pigs or monkeys.
  • the external preparation composition for skin is not particularly limited in its formulation, and it is a softening longevity, astringent longevity, nourishing longevity, eye cream, nutrition cream, massage cream, cleansing cream, cleansing foam, cleansing water, powder, Formulations such as essences, packs, and the like.
  • the cosmetic composition according to an aspect of the present invention may be prepared in various forms according to a conventional cosmetic preparation method.
  • the cosmetic composition may be prepared in the form of a cosmetic product containing the peptide, lotion, cream, lotion, etc., which may be diluted with conventional cleansing liquid, astringent liquid, and moisturizing liquid.
  • the cosmetic composition may include conventional adjuvants such as stabilizers, solubilizers, vitamins, pigments, and flavorings commonly used in the field of cosmetic compositions.
  • the cosmetic composition comprising any one of the novel active peptides selected from SEQ ID NOs: 1 to 3 according to an aspect of the present invention may prepare a cosmetic composition by a known cosmetic composition preparation method, and is not limited to general skin cosmetics. Applicable to quasi-drugs and external medicines. These formulations may be prepared in any of the formulations commonly prepared, for example in the form of skins, lotions, creams, foundations, essences, gels, packs, foam cleansing, body oils, lipsticks, mascaras, makeup bases or soaps. It may be prepared as, but is not limited thereto.
  • any one new active peptide selected from SEQ ID NOs: 1 to 3 according to an aspect of the present invention, in addition to any one new active peptide selected from SEQ ID NOs: 1 to 3 other components of the formulation of the cosmetic, According to the purpose of use, those skilled in the art can mix and select the enemy without difficulty.
  • the cosmetic composition of the present invention may be used daily and may also be used for an indefinite period of time.
  • the amount, frequency of use and duration of use may be adjusted according to the age, skin condition or skin type of the user, and the concentration of the peptide.
  • compositions herein can be administered in any manner as desired, for example by oral, rectal, intravenous, arterial, muscular, subcutaneous, intradermal, endometrial or intraventricular injection.
  • Formulations for oral administration of a composition according to one aspect of the invention may be tablets, pills, soft or hard capsules, granules, powders, solutions or emulsions, and formulations for parenteral administration may be injections, drops, lotions, ointments. , Gels, creams, suspensions, emulsions, suppositories, patches or sprays, but is not limited thereto.
  • compositions herein may be used in the form of their pharmaceutically acceptable salts, and may be used alone or in combination with other pharmaceutically active compounds as well as in a suitable collection.
  • the salt is not particularly limited as long as it is pharmaceutically acceptable.
  • hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrofluoric acid, hydrobromic acid, formic acid acetic acid, tartaric acid, lactic acid, citric acid, fumaric acid, maleic acid, succinic acid, methanesulfonic acid , Benzene sulfonic acid, toluene sulfonic acid, naphthalene sulfonic acid and the like can be used.
  • the concentration of the peptide or salt thereof in the pharmaceutical composition according to one aspect of the present invention may be 1 to 100 ⁇ M.
  • the concentration is at least 1 ⁇ M, at least 3 ⁇ M, at least 5 ⁇ M, at least 7 ⁇ M, at least 10 ⁇ M, at least 15 ⁇ M, at least 20 ⁇ M, at least 25 ⁇ M, at least 30 ⁇ M, at least 35 ⁇ M, at least 40 ⁇ M, at least 50 ⁇ M, at least 60 ⁇ M, at least 70 ⁇ M, 80 ⁇ M or more, 85 ⁇ M or more, 90 ⁇ M or more, or 95 ⁇ M or more.
  • the concentration is 100 ⁇ M or less, 95 ⁇ M or less, 90 ⁇ M or less, 85 ⁇ M or less, 80 ⁇ M or less, 75 ⁇ M or less, 70 ⁇ M or less, 60 ⁇ M or less, 50 ⁇ M or less, 40 ⁇ M or less, 30 ⁇ M or less, 25 ⁇ M or less, 20 ⁇ M or less, 15 ⁇ M or less, 10 ⁇ M Or less, 7 ⁇ M or less, 5 ⁇ M or less, or 2 ⁇ M or less.
  • the concentration may preferably be 20 to 80 ⁇ M, more preferably 50 ⁇ M.
  • the dosage of the peptide or salt thereof according to one aspect of the present invention may be 0.1 ⁇ g / kg to 10 mg / kg.
  • the dosage is at least 0.1 ⁇ g / kg, at least 0.5 ⁇ g / kg, at least 1 ⁇ g / kg, at least 5 ⁇ g / kg, at least 10 ⁇ g / kg, at least 30 ⁇ g / kg, at least 50 ⁇ g / kg, at least 70 ⁇ g / kg , 100 ⁇ g / kg or more, 300 ⁇ g / kg or more, 500 ⁇ g / kg or more, 700 ⁇ g / kg or more, 900 ⁇ g / kg or more, 1 mg / kg or more, 2 mg / kg or more, 3 mg / kg or more, 4 mg / kg or more, 5 mg / kg or more , At least 6 mg / kg, at least 7 mg / kg, at least 8 mg / kg, at least 9 mg / kg, at least 9.5 mg
  • the dosage is 10 mg / kg or less, 9 mg / kg or less, 8 mg / kg or less, 7 mg / kg or less, 6 mg / kg or less, 5 mg / kg or less, 4 mg / kg or less, 3 mg / kg or less, 2 mg / kg or less, 1mg / kg or less, 900 ⁇ g / kg or less, 700 ⁇ g / kg or less, 500 ⁇ g / kg or less, 300 ⁇ g / kg or less, 100 ⁇ g / kg or less, 90 ⁇ g / kg or less, 70 ⁇ g / kg or less, 50 ⁇ g / kg or less, 30 ⁇ g / kg or less, 10 ⁇ g / kg or less, 7 ⁇ g / kg or less, 5 ⁇ g / kg or less, 3 ⁇ g / kg or less, 1 ⁇ g / kg or less, 0.9 ⁇ g / kg or less, 0.7 ⁇ g / kg or less, 0.5 ⁇ g / kg or less, 0.3 ⁇ g / kg or less,
  • the dosage may vary depending on the age, sex, weight, pathology and severity of the subject to be administered, the route of administration or the judgment of the prescriber. Application amount determination based on these factors is within the level of skill in the art.
  • compositions according to one aspect of the invention may include additives such as diluents, excipients, lubricants, binders, disintegrants, buffers, dispersants, surfactants, colorants, flavoring or sweetening agents as needed.
  • additives such as diluents, excipients, lubricants, binders, disintegrants, buffers, dispersants, surfactants, colorants, flavoring or sweetening agents as needed.
  • Compositions according to one aspect of the present invention may be prepared by conventional methods in the art.
  • composition according to an aspect of the present invention may increase collagen production, inhibit collagen production inhibitor secretion, and may inhibit or improve skin wrinkles and prevent aging.
  • Preferred embodiments according to one aspect of the invention include the most optimal mode known to the inventor for carrying out one aspect of the invention. Variations of the preferred embodiments may become apparent to those skilled in the art upon reading the foregoing description. The inventors expect skilled artisans to employ such variations as appropriate, and the inventors expect the various aspects of the invention to be practiced in a manner different from that described herein. Accordingly, this specification includes all modifications and equivalents of the subject matter referred to in the appended claims, as permitted by patent law. Moreover, any combination of the above-mentioned elements within all possible variations is included herein unless expressly stated to the contrary or apparently contradictory in context.
  • Peptides having the novel activity of SEQ ID NO: 1 were prepared according to solid phase peptide synthesis known in the art. Specifically, peptides were synthesized by coupling amino acids one by one from the C-terminus through Fmoc solid phase synthesis (SPPS) using ASP48S (Peptron, Inc., Daejeon, Korea). As follows, the first amino acid at the C-terminus of the peptides was attached to the resin. For example:
  • HBTU [2- (1H-Benzotriazole-1-yl) -1,1,3,3-tetamethylaminium hexafluorophosphate] / HOBt [N-Hydroxxybenzotriazole] / NMM [4-Methylmorpholine] is used as the coupling reagent. It was. Fmoc removal was performed using piperidine in DMF in 20% of DMF.
  • Each peptide was synthesized by repeating a process of reacting the amino acids with each other, washing with a solvent, and then deprotecting the amino acid using the state in which the amino acid protecting group was bound to the solid support.
  • the synthesized peptide was separated from the resin and purified by HPLC. The success of the synthesis was confirmed by LC / MS and lyophilized.
  • Peptides CP-55 and CP-56 were also prepared based on the same method as the preparation of CP-54, in which only the basic skeleton of the peptide was substituted for the corresponding sequence of each peptide.
  • human skin fibroblasts are cultured to improve collagen synthesis effect. After treating TGF- ⁇ (positive control) and each peptide known to be present, relative collagen synthesis of the positive control group and each peptide-treated experimental group was determined based on the control group without any treatment by absorbance measurement method. Calculated.
  • the CCD-986SK (ATCC® CRL-1947 TM ), a human skin fibroblast, was used.
  • the cell lines were placed in DMEM medium containing 10% FBS and penicillin-Streptomycin antibiotics and seeded in a 100 mm culture dish, followed by incubation in a 37 ° C., 5% CO 2 incubator. . While checking the growth rate and state of each cell every day, subcultures were performed at a ratio of 1: 2 to 1: 3 at intervals of 2 to 3 days to maintain a good state of the cells.
  • the cultured CCD-986SK cells were placed in a 24-well plate at 2 ⁇ 10 4 cells per well, and then cultured for 24 hours.
  • the culture medium was removed and washed with PBS, followed by starvation treatment for 2 hours with serum-free medium without serum. Thereafter divided into a control group (no control), a positive control group treated with TGF- ⁇ 20ng / ml and an experimental group treated with the addition of 10 mM peptide so that the final concentration of the peptide according to an aspect of the present invention is 50 ⁇ M each group Was incubated at 5% CO 2 , 37 ° C for 24 hours.
  • the cultures were collected and the amount of collagen was measured using the ELISA (procollagen type IC-peptide EIA kit) method.
  • washing buffer 100 ⁇ l of color reagent (TMBZ) was added thereto, and incubated at room temperature for 15 minutes, followed by 100 ⁇ l of 1N sulfuric acid. It was then measured with an ELISA reader at 450 nm.
  • TMBZ color reagent
  • Collagen synthesis degree derived through the above experimental method was calculated and expressed as a relative value when the control (control) is 100%, as shown in Table 2 below.
  • the peptides CP-54, CP-55, CP-56 having a novel activity according to the present invention showed that the collagen synthesis degree increased by more than 10% compared to the control.
  • the peptide having a novel activity according to an aspect of the present invention and a composition comprising the same show collagen synthesis effects. These effects are to improve the wrinkles and anti-aging of the skin, it can be seen that the peptide and the composition comprising the same according to an aspect of the present invention can have a variety of excellent effects in improving the skin condition.
  • the peptide having a novel activity has collagen synthesis activity, and it is expected that the functional cosmetic composition for wrinkle improvement and anti-aging may be developed using the peptide.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
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  • Proteomics, Peptides & Aminoacids (AREA)
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Abstract

La présente invention concerne un peptide ayant une nouvelle activité et une composition le comprenant et, plus particulièrement, un peptide ayant une nouvelle activité présentant une efficacité pour la synthèse du collagène et une composition pour améliorer les rides et prévenir le vieillissement le comprenant. Le peptide ayant une nouvelle activité et la composition le comprenant selon la présente invention ont un effet remarquable dans la synthèse du collagène, ce qui permet de fournir une composition pour améliorer les rides et prévenir le vieillissement.
PCT/KR2017/004288 2016-04-21 2017-04-21 Peptide efficace pour augmenter la génération de collagène et composition le comprenant Ceased WO2017183942A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2016-0048749 2016-04-21
KR20160048749 2016-04-21

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WO2017183942A2 true WO2017183942A2 (fr) 2017-10-26
WO2017183942A3 WO2017183942A3 (fr) 2018-08-02

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Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4439510B2 (ja) * 2005-03-22 2010-03-24 ロート製薬株式会社 新規ペプチド
KR100721144B1 (ko) * 2006-03-22 2007-05-25 (주)아르떼르화장품 펩타이드 혼합물을 포함하는 주름개선용 화장료 조성물
ES2691070T3 (es) * 2012-05-11 2018-11-23 Kael-Gemvax Co.,Ltd Péptidos antiinflamatorios y composición que comprende los mismos
WO2016006733A1 (fr) * 2014-07-09 2016-01-14 강원대학교산학협력단 Composition contenant des fragments peptidiques dérivés du facteur de croissance des fibroblastes pour la cicatrisation des plaies ou l'inhibition de la formation des rides
WO2016190660A1 (fr) * 2015-05-26 2016-12-01 주식회사 젬백스앤카엘 Nouveau peptide et composition le contenant

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