WO2010032891A1 - Nouveau palmitoyltripeptide et composition cosmétique anti-rides le contenant - Google Patents

Nouveau palmitoyltripeptide et composition cosmétique anti-rides le contenant Download PDF

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Publication number
WO2010032891A1
WO2010032891A1 PCT/KR2008/005595 KR2008005595W WO2010032891A1 WO 2010032891 A1 WO2010032891 A1 WO 2010032891A1 KR 2008005595 W KR2008005595 W KR 2008005595W WO 2010032891 A1 WO2010032891 A1 WO 2010032891A1
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WO
WIPO (PCT)
Prior art keywords
skin
pro
hyp
resin
gly
Prior art date
Application number
PCT/KR2008/005595
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English (en)
Inventor
Jeong Keun Hwang
Jin Kyo Jung
Young Hoon Ahn
Soon Min Bae
Jun Seob Shin
Hyuk Kwang Jeong
Original Assignee
Maim Co., Ltd.
Morechem Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Maim Co., Ltd., Morechem Co., Ltd. filed Critical Maim Co., Ltd.
Publication of WO2010032891A1 publication Critical patent/WO2010032891A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
    • 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
    • A61Q19/08—Anti-ageing preparations
    • 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
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala

Definitions

  • the present invention relates to a novel pept ide-derived compound and anti-skin aging cosmetic composition comprising the same as an active ingredient.
  • ⁇ 3> Functioning to protect the body from various external threats and being in contact with various external stimuli, the skin is prone to aging. As skin tissues age, they decrease in their ability to produce protein fibers and substrate mass and thus become thinner, leading to a reduction in skin elasticity and the formation of wrinkles.
  • compounds known to be useful to improve skin appearance and physiological functions including those associated with fine wrinkles, furrows, aging, and photo- damaged skin. For example, much is known about the effects of vitamin C and retinoid on the skin. In fact, these compounds are widely used in cosmetic compositions of world-wide distribution. In addition to desirable effects, however, side effects associated with storage and skin irritation are reported for conventional skin-care composition.
  • Peptides are known to show skin-care effects while causing slight irritation. Almost free of side effects for the skin, peptides, the main components of all proteins can be advantageously used for skin rejuvenation. Recent studies have reported that when used in cosmetic compositions for wrinkle improvement, peptides or peptide derivatives show faster skin improvement effects than do retinols, which are generally used as anti- wrinkle agents, and that they can be safely applied to sensitive regions, such as those around the eyes, e.g., eyelids, because of the absence of side effects even when heavily used.
  • peptide derivatives known to be ingredients in anti-wrinkle cosmetics.
  • peptide derivatives are typical tri- to hex- apeptide derivatives, such as Palm-Gly-His-Lys, Palm-Gly-Gln-Pro-Arg, etc.
  • Some cosmetics made of compositions comprising the peptide derivatives have now been coming into the market.
  • the peptide derivatives can activate collagen within the soft tissue of the skin, thus leading to wrinkle removal and skin rejuvenation.
  • Collagen is composed predominantly of glycine, proline and hydroxyproline, with the main characteristic being a high content of hydroxyproline, which is found in few proteins other than collagen.
  • collagen contains the tripeptide sequence pattern Gly-Pro-Hyp in its chains.
  • an object of the present invention is to provide a novel palmitolytripeptide derivative having an amphipathic structure composed of a lipophilic palmitoyl moiety and a hydrophilic tripeptide Gly-Pro-Hyp moiety, which can overcome the skin barrier which the hydrophilic tripeptide Gly-Pro-Hyp alone cannot.
  • Another object of the present invention is to provide a method for preparing the novel palmitoyltripeptide derivative.
  • the present invention provides a novel palmitolytripeptide, represented by palmitoyl-glycinyl-prolinyl- hydroxyproline (Palm-Gly-Pro-Hyp) or the following structural formula I:
  • the present invention provides a method for preparing the palmitolytripeptide compound (Palm-Gly- Pro-Hyp), comprising attaching hydroxyproline, proline and glycine to a resin in that order with the aid of 2-(4-nitrophenyl)sulfonylethoxycarboxyl-amino acid (Nsc-amino acid) as a mediator to synthesize glycinyl-prol inyl- hydroxyprolinyl-resin (Gly-Pro-Hyp-resin) , introducing a palmitoyl group into the glycinyl-prol inyl-hydroxyprolinyl-resin to afford palmitoyl-glycinyl- prolinyl-hydroxyproline-resin (Palm-Gly-Pro-Hyp-resin), and removing the resin and side chain-protecting group from the palm
  • the present invention provides a cosmetic composition for lifting wrinkles and delaying skin aging, comprising the palmitoyltripeptide compound as an active ingredient.
  • the cosmetic composition may be in the form of a skin lotion, nutrient lotion or nutrient cream.
  • the cosmetic composition comprises the palmitoyltripeptide compound in an amount from 0.0001 to 0.1 % by weight
  • the novel palmitoyltripeptide compound of the present invention can effectively pass through the skin barrier thanks to the lipophilic moiety thereof, the cosmetic composition has greatly improved delaying of skin aging, lifting of wrinkles, and maintaining of skin elasticity.
  • the cosmetic composition according to the present invention is excellent in terms of long-term storage, safety to the skin, and convenience of use.
  • FIG. 1 is a graph showing an MTT assay result for the palmitoyltripeptide compound (Palm-Gly-Pro-Hyp) of the present invention.
  • FIG. 2 is a graph showing effects of the palmitoyltripeptide compound (Palm-Gly-Pro-Hyp) of the present invention on collagen synthesis.
  • FIG. 3 is a graph showing the improvement in skin wrinkles after using the cosmetic composition with time (in weeks).
  • FIG. 4 is a strain-time curve obtained in an assay with the cosmetic compositions of the present invention for skin elasticity.
  • FIG. 5 is a graph showing the improvement in skin elasticity after using the cosmetic composition with time (in weeks).
  • FIG. 6 is a photograph showing Moire topography for assaying the cosmetic compositions of the present invention for improvements in skin lifting.
  • FIG. 7 is a graph showing the improvement in skin lifting after using the cosmetic composition with time.
  • the present invention pertains to a novel peptide derivative Palm-Gly- Pro-Hyp and an anti-wrinkle cosmetic composition comprising the same as an active ingredient.
  • the method of the present invention comprises 1) coupling the three amino acid residues consecutively with a resin 2) introducing a palmitoyl moiety, and 3) removing the resin and side-chain protecting groups.
  • Nsc-amino acid used in the synthesis method of the present invention, has advantages from a variety of aspects. To begin with, Nsc-amino acid is more stable and thus can be easily handled at room temperature. In addition, Nsc- amino acid decomposes more slowly in DMF, a typical solvent for peptide synthesis, so that the Nsc moiety can be removed under more mild conditions than is Fmoc.
  • Nsc-amino acid can be advantageously applied to conventional methods in which peptides are synthesized from a solution of amino acids in a suitable solvent in a reactor.
  • Nsc-amino acids avoid various side reactions causing damage to the amino acids before the desired reaction.
  • Nsc-amino acids are economically favorable because they are cheaper than Fmoc-amino acids.
  • the constitution of the present invention is as follows: (1) the novel palmitoyltripept ide Palm-Gly-Pro-Hyp is prepared using a solid-phase peptide synthesis method based on Nsc-amino acid; and, (2) cosmetic compositions containing a solution of the palmitoyltripeptide in an amount of from 0.001-0.1% by dry weight and preferably in an amount of 0.01% by dry weight are analyzed for cosmetic effects.
  • the following examples are given only for the purpose of illustrating the present invention, and do not limit the present invention for any reason.
  • Palm Palmitoyl
  • DIPEA Di isopropyl ethyl amine
  • Tr i isopropyl si lane
  • the novel peptide derivative Palm-Gly-Pro-Hyp according to the present invention was prepared using a solid-phase peptide synthesis method and analyzed by HPLC and MaIdi-TOF mass spectrometry.
  • the resin was incubated for 1 hour with 5.33 g (1.2 eq) of Nsc- Hyp(tBu)-0H, together with 50 mL of DMF and 7 mL (4 eq) of DIPEA, washed, and treated for 10 min with a mixture of 2:1 methanol : DIPEA in MC, followed by washing with excess MC/DMF (1:1). After the Nsc moiety was deprotected with 50 mL of a 20% piperidine solution in DMF, the remaining Hyp-resin was washed three times with DMF. The amino acid immobilized onto the resin was measured to be in an amount of 0.64 mmol/g of resin.
  • Palm-Gly-Pro-Hyp O.lg was dissolved at room temperature in 12 g of butylene glycol and then mixed with 1 g of the solubilisant LRI, 5 g of ethanol, 0.4 g of Phenonip and 81.4 g of purified water by stirring. The resulting aqueous solution was adjusted to a pH of 5.3 with triethanolamine.
  • ⁇ 84> Generally, cells can be grown ex vivo while suspended in a liquid medium or adhering to the bottom of a culture flask in a monolayer manner. In association with skin tests, monolayer cultures are employed because skin cells, that is, fibroblasts, keratinocytes, endocrine cells, etc. are grown in adherent culture. Monolayer culture methods are advantageous in that they give relatively quick test results and require only small amounts of samples for analysis thus allowing various samples to be screened. Also, they enjoy the advantage of low cost.
  • monolayer culture methods have the following disadvantages: only water-soluble samples can be used astest subjects because they must be dissolved in culture media; there is a significant difference between in vivo and in vitro test results; no barriers exist against toxic materials because they are applied directly to cells.
  • a 3D culture method has been developed in which different skin cells constituting the actual skin are cultured together in one system.
  • the artificial 3D cell culture is widely applied to studies on intercellular action (signaling, material transfer between cells).
  • a 3D cell culture there is the artificial dermis D.E. (dermal equivalent) culture system in which keratinocytes are additionally seeded.
  • the artificial dermis D.E. is cultured for a predetermined period of time and keratinocytes are seeded on the collagen sheet to construct a culture system.
  • the seeded keratinocytes form a keratinized barrier on the collagen sheet while some of them migrate to the collagen sheet layer.
  • the keratinized barrier is formed, the resulting may serve to effectively dampen the toxicity which may present when the product itself or highly concentrated additives are used for the test.
  • the 3D culture system is useful in tests for protein synthesis or to analyze cell proliferation, cell metabolism, immune substances, etc.
  • DMEM is selected for fibroblasts, and SFM for keratinocytes.
  • D.E (Dermal Equivalent) culture system a dermal equivalent was prepared by culturing fibroblasts on a collagen matrix in a Transwell culture system.
  • keratinocytes wereseeded and cultured in the culture system to form a keratinized barrier.
  • FIG. 1 is a plot a graph showing results of the MTT assay with the peptide compound (Palm-Gly-Pro-Hyp) of the present invention.
  • Collagen is a long, fibrous structural protein which is a major component of the extracellular matrix (ECM). Thus, the biosynthesis and degradation of collagen is very closely related to the health of the ECM.
  • procollagens Various types of collagens (Types I, II, III, IV and V) are synthesized as precursor molecules called procollagens. ⁇ iO7> These procollagens contain additional peptide sequences, usually called
  • pro-peptides at both the amino-terminal and the carboxy-terminal ends.
  • propeptides The function of these propeptides is to facilitate the winding of procollagen molecules into a triple-helical conformationwithin the endoplasmic reticulum.
  • the propeptides are cleaved off from the collagen triple helix molecule during its secretion, after which, the triple helix collagens polymerize into extracellular collagen fibrils.
  • the amount of the free pro-peptides stoichiometrically reflects the amount of collagen molecules of interest.
  • the Pro-collagen Type I C-peptide (PIP) assay kit useful in this assay was commercially available from TAKARA.
  • the pro-peptides in the artificial skin culture were quantitatively analyzed as follows.
  • ⁇ iO9> (a) 100 ⁇ L of antibody-POD conjugate solution was transferred into one micro-well. Immediately then, 20 ⁇ L of a sample or standard material was added to the wel 1.
  • FIG. 2 is a plot showing effects of the peptide compound (PaIm-GIy-Pro- Hyp) of the present invention on collagen synthesis.
  • ⁇ 132> Mean reactivity was calculated as follows. ⁇ 133> [(15 subjects O point + O subject x 1 point + O subject x 2 points + O subject x 3 points + O subject x 4 points) + (15 subjects XO point + O subject x 1 point + O subject x 2 points + O subject x 3 points + O subject x 4 points)] x 100/(2 rounds x 4 points x 15 subjects)- 0%
  • compositions of Examples 3 to 5 were found to be safe to the body without causing skin irritation.
  • Table 8 summarizes the results of the stability test of the cosmetic formulations.
  • the replicas thus prepared were analyzed using a Visitometer (Skin- Visiometer SV 600, Courage & Khazaha, Germany). This analysis was conducted in a spectrophotometry manner. For example, the light intensity generated upon the passage of the light from an artificial light source through the silicon material was analyzed using Lambert & Beer's Law, and the degree of improvement in the skin wrinkleswas measured.
  • the assessment parameter used in the assessment of the visiometer was R2 for maximum roughness. Smaller R2 values described better improvements in skin wrinkles, that is, decreases in wrinkle depth, expressed in arbitrary units.
  • Table 9 reports the improvements (%) in skin wrinklesassessed in the assay.
  • ⁇ i75> For example, a 2-mm-diameter circular aperture of the probe was brought into close contact with the saved skin and a controlled vacuum was applied to the skin through the aperture of the probe, so that the skin was pulled into the probe.
  • the penetration depth (maximum 3 mm) of the skin was determined by a non-contact optical system using IR light. For this, the light intensity detected inside the probe using the pulled skin as a barrier was compared to that when the skin was not drawn into the probe.
  • the skin near the pulled area was fixed by an outer ring of the probe, with the application of a
  • FIG. 4 is a strain-time curve obtained from the assay of the cosmetic compositions for skin elasticity.
  • Table 10 reports improvements (%) in skin elasticity as a result of the use of the cosmetic composition.
  • the Moire system included a measurement device, lighting fixtures, and a high-resolution digital camera (Olympus E-330, Japan).
  • a measurement device for standardization, conditions for the tomography (measurement direction, position, etc.) were fixed. Particularly, parts near the mouth were selected as test regions because significant skin sagging was generated there.
  • FIG. 6 is a photograph showing Moire tomography for assaying the cosmetic compositions of the present invention for improved skin lifting.

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  • Proteomics, Peptides & Aminoacids (AREA)
  • Gerontology & Geriatric Medicine (AREA)
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Abstract

La présente invention concerne un nouveau composé palmitoyltripeptide et une composition cosmétique anti-rides le comprenant comme principe actif. Ayant la capacité de passer efficacement à travers la barrière de la peau grâce à son groupe lipophile, le nouveau composé entraîne de grandes améliorations dans les rides de la peau et son élasticité. Ainsi, le composé peut favoriser la synthèse de collagène dans les tissus de peau blessés, fournissant d’excellentes propriétés de renouvellement de la peau.
PCT/KR2008/005595 2008-09-16 2008-09-22 Nouveau palmitoyltripeptide et composition cosmétique anti-rides le contenant WO2010032891A1 (fr)

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KR1020080090704A KR101093685B1 (ko) 2008-09-16 2008-09-16 신규한 팔미토일트리펩타이드와 이를 함유하는 주름개선 화장품 조성물
KR10-2008-0090704 2008-09-16

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012128438A1 (fr) * 2011-03-22 2012-09-27 주식회사 셀인바이오 Dipeptide palmitoylique dans lequel une glycylproline ou une glycylhydroxyproline est liée à l'acide palmitique et procédé pour le produire
WO2015111857A1 (fr) * 2014-01-27 2015-07-30 (주)셀인바이오 Dérivé peptidique et composition cosmétique fonctionnelle contenant ce dernier
WO2016133773A1 (fr) * 2015-02-19 2016-08-25 Elc Management Llc Nouvelle stratégie de remodelage cutané
CN107759660A (zh) * 2017-12-05 2018-03-06 陕西慧康生物科技有限责任公司 一种三肽‑29的液‑固相合成方法
TWI675849B (zh) * 2016-10-04 2019-11-01 南韓商賽特瑞恩股份有限公司 化合物或其美容學上可接受的鹽用於減少皺紋之用途
CN112754955A (zh) * 2021-02-07 2021-05-07 西南大学 一种豆腐柴果胶面膜液及其制备方法
CN113350233A (zh) * 2021-05-24 2021-09-07 上海优康化妆品有限公司 一种抗衰组合物及其制备方法及用途

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KR101051812B1 (ko) * 2011-03-14 2011-07-26 주식회사 참 존 신규 세라마이드 유도체 및 그 제조방법
KR101889322B1 (ko) 2016-08-17 2018-08-20 (주)진셀팜 주름 개선 및 항노화 효과를 가지는 펩타이드, 및 이의 용도
KR101886123B1 (ko) 2016-08-17 2018-08-07 (주)진셀팜 주름 개선용 펩타이드, 및 이의 용도
KR101900745B1 (ko) 2016-08-17 2018-09-20 (주)진셀팜 주름 개선 및 미백 효과를 가지는 펩타이드, 및 이의 용도
KR101907902B1 (ko) 2017-02-23 2018-12-10 김현성 펩타이드를 함유하는 리포좀 조성물
KR102014602B1 (ko) 2017-10-19 2019-08-29 주식회사 삼성인터네셔널 기미 개선용 화장료 조성물
KR102035275B1 (ko) * 2017-11-30 2019-11-18 에이앤펩주식회사 피부투과와 효능이 개선된 화장품 소재용 신규 펩타이드 유도체 개발

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US20070048245A1 (en) * 2005-09-01 2007-03-01 Belfer William A Cosmetic composition to accelerate repair of functional wrinkles
JP2007091637A (ja) * 2005-09-29 2007-04-12 Fancl Corp Ｉ型コラーゲン産生促進用組成物
US20070166267A1 (en) * 2006-01-18 2007-07-19 Grant Industries, Inc. Anti-wrinkle composition

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Publication number Priority date Publication date Assignee Title
US20070048245A1 (en) * 2005-09-01 2007-03-01 Belfer William A Cosmetic composition to accelerate repair of functional wrinkles
JP2007091637A (ja) * 2005-09-29 2007-04-12 Fancl Corp Ｉ型コラーゲン産生促進用組成物
US20070166267A1 (en) * 2006-01-18 2007-07-19 Grant Industries, Inc. Anti-wrinkle composition

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012128438A1 (fr) * 2011-03-22 2012-09-27 주식회사 셀인바이오 Dipeptide palmitoylique dans lequel une glycylproline ou une glycylhydroxyproline est liée à l'acide palmitique et procédé pour le produire
WO2015111857A1 (fr) * 2014-01-27 2015-07-30 (주)셀인바이오 Dérivé peptidique et composition cosmétique fonctionnelle contenant ce dernier
JP2017505341A (ja) * 2014-01-27 2017-02-16 チェリンバイオ コ−、リミテッドＣｅｌｌｉｎｂｉｏ Ｃｏ．， Ｌｔｄ ペプチド誘導体及びこれを含む機能性化粧品の組成物
WO2016133773A1 (fr) * 2015-02-19 2016-08-25 Elc Management Llc Nouvelle stratégie de remodelage cutané
TWI675849B (zh) * 2016-10-04 2019-11-01 南韓商賽特瑞恩股份有限公司 化合物或其美容學上可接受的鹽用於減少皺紋之用途
CN107759660A (zh) * 2017-12-05 2018-03-06 陕西慧康生物科技有限责任公司 一种三肽‑29的液‑固相合成方法
CN112754955A (zh) * 2021-02-07 2021-05-07 西南大学 一种豆腐柴果胶面膜液及其制备方法
CN113350233A (zh) * 2021-05-24 2021-09-07 上海优康化妆品有限公司 一种抗衰组合物及其制备方法及用途

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