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    • 专利摘要:
    The peptide comprises from 3 to 10 amino acids of which at least the sequence K * (Ac) GH or K * (Ac) HG and may further comprise a modification at the N-terminus, preferably an acylation, and / or C-terminal ; K * is selected from the group consisting of lysine (Lys, K), ornithine (Orn), diaminobutyric acid (Dab), diaminopropionic acid (Dap) and a hydroxylated derivative thereof; K * (Ac) corresponds to a lysine, ornithine, diaminobutyric acid, diaminopropionic acid or a hydroxylated derivative thereof, acetylated on the amine of their side hydrocarbon chain. The two preferred peptides are Pal-K (Ac) GH and Pal-K (Ac) HG. This peptide can be used for a cosmetic treatment, especially anti-aging, anti-wrinkles and fine lines, to improve the mechanical properties of the skin, firmness / tone / elasticity / suppleness, to increase the density and volume of the skin, to a restructuring effect, healing, and / or to fight against stretch marks.
    公开号:FR3052453A1
    申请号:FR1655468
    申请日:2016-06-14
    公开日:2017-12-15
    发明作者:Olivier Peschard；Anne Doucet；Richard Leroux；Philippe Mondon
    申请人:Sederma SA；
    IPC主号:
    专利说明:

    The present invention relates to novel peptides, compositions comprising them and cosmetic uses of said peptides. It is more particularly peptides for the treatment of the skin and its integuments, mammals, humans or animals.
    It concerns the cosmetics industry (topically or orally), hygiene and personal care products and dermo-pharmacy.
    Peptides have an important signal function and coordinate many biochemical processes. As a result, they have become unavoidable and promising active ingredients, particularly in the cosmetics industry, where new compounds are constantly being researched that can beautify the skin and the integuments, that is to say, from improve the general condition.
    The present inventors have been more particularly interested in searching for new peptides having an activity on the main constitutive molecules of the extracellular matrix (ECM) dermal which decreases with age, and more particularly active on the synthesis of collagen I, elastin and hyaluronic acid, and also active on the synthesis of glycoproteins such as fibronectin.
    The loss of density and thickness of the dermis are related to a reduction of synthesis of macromolecules during aging by dermal fibroblasts cells in charge of their manufacture.
    Collagen I is the most abundant protein in the dermis and is essential for firm skin. Elastin is synthesized and secreted in the extracellular dermal space. It constitutes the major component up to 90% of the elastic fibers.
    Fibronectin is a glycoprotein found in the extracellular matrix, which plays a key role in cell adhesion to the extracellular matrix. It can simultaneously bind to the cell and other extracellular matrix molecules, such as collagen or another fibronectin molecule. For this, the fibronectin molecules assemble to form adhesive elastic fibers on the surface of many cells. This determines the mechanical properties (elasticity, suppleness and firmness) of the skin. Hyaluronic acid is an essential component of the dermis. The interest of hyaluronic acid lies in its viscoelastic properties and its ability to capture water. Thus it fills the spaces between the collagen and elastin fibers, in the dermis. This contributes to the suppleness of the skin and prevents the formation of wrinkles. This substance decreases with age, the skin dries and wrinkles. The increase of collagen IV and laminin is also sought. It helps to restore / strengthen the dermis / epidermis junction (JDE). Collagen IV forms a two-dimensional network and is one of the major components of the dermis / epidermis junction. Laminins are also contained in the basal layer and participate in the anchoring of cell surfaces to the basal lamina. Together, these two essential components of the JDE ensure the keratinocyte of the basal lamina a better anchoring and contribute to maintain the flexibility of repornme.
    The reduction of protein synthesis with age is felt at the level of the JDE. Thus collagen IV is more fragmented and at the same time less produced, as are laminins, which in some areas leads to an alteration of the JDE and a poorer communication between melanocytes, keratinocytes and JDE and less flexibility of the system. The interest in stimulating the synthesis of these two proteins therefore clearly appears.
    The stimulated synthesis of these molecules will result from the results on the embellishment and the general state of the skin, in terms of mechanical properties: a skin that is denser, regonflated, firmer, more toned, more supple and elastic, the peptide having a healing effect, volumizing, plumping, and therefore anti-wrinkles, and at the level of imperfections of the complexion (more homogeneous color and more brightness).
    Numerous peptides or peptide mixtures having properties on the MEC and anti-aging applications have already been proposed, in particular by the Applicant, such as the Pal-KTTKS (SEQ ID No. 1) sold under the trademark MATRIXYL ™, the Pal mixture. -GHK and Pal-GQPR (SEQ ID No. 2) under the trademark MATRIXYL 3000 ™ or more recently Pal-KM02K under the trademark MATRIXYL Synth-6 ™ (M02 corresponding to a dioxygenated methionine). Other known peptides are mentioned later in the description.
    The object of the present invention is to propose other peptides capable of improving the general state of the skin and superficial body growths, and more particularly peptides which are active on the synthesis of ECM proteins. In addition, it aims to provide peptides sufficiently effective to be used alone or in combination, in proportions of a few ppm, and can be used in the form of topical composition, including cosmetic.
    The present invention provides a peptide comprising from 3 to 10 amino acids including at least one peptide sequence K * (Ac) GH or a peptide sequence K * (Ac) HG and which may comprise a modification at the N-terminus and / or C-terminus wherein: • K * is selected from the group consisting of: a lysine (Lys, K), an omithine (Om), a diaminobutyric acid (Dab), a diaminopropionic acid (Dap) and a hydroxyl derivative of lysine; • K * (Ac) corresponds to a lysine, omithine, diaminobutyric acid, diaminopropionic acid or a hydroxylated derivative thereof, acetylated on the amine of their side hydrocarbon chain; Said modification at the N-terminus is -CO-Ri or -SO 2 -R 1; Said modification at the C-terminus is chosen from the group comprising -ORi, -NH2, -NHRi and -NRiR2; and R1 and R2 being, independently of one another, chosen from an alkyl, aryl, aralkyl, alkylaryl, alkoxy and aryloxy group, which may be linear, branched, cyclic, polycyclic, unsaturated, hydroxylated, carbonylated, phosphorylated and or sulfur, said group having 1 to 24 carbon atoms, and may have in its backbone heteroatom O, S and / or N.
    By convention, the N-terminus is that of the amino acid shown to the left of the peptide formula and the C-terminus is that of the amino acid shown to the right of the formula.
    As shown in the table below, the diaminobutyric acid and the diaminopropionic acid are analogues of lysine according to the present invention, comprising respectively a side chain of 3, 2 and 1 carbon atom (s). instead of 4 for lysine and ending with an amine NH2 function The number of carbon playing the role of spacer more or less long. According to the invention, it is on this lateral amine function that an acetyl - (CO) CFF group is grafted.
    The hydroxylated derivatives of K * include a hydroxyl radical on the hydrocarbon side chain, such as, for example, hydroxylysine of formula:
    The amino acids of the peptide according to the invention other than those of the inventive sequences K * (Ac) HG and / or K * (Ac) GH can be chosen from 20 natural amino acids or their derivatives or analogues, preferably chosen from the lysine, histidine, glycine, alanine and an amino acid K * as defined according to the invention, more preferably glycine or alanine.
    The peptide according to the invention may comprise several times the inventive sequence K * (Ac) HG and / or K * (Ac) GH.
    Preferably according to the invention K * is a lysine, K * (Ac) corresponding to an ε-acetylated lysine.
    Also preferably, the peptide comprises either a modification at the N-terminus or a modification at the C-terminus corresponding to a group R 1 and / or R 2 as defined above preferably having 3 to 24 carbon atoms, to form a fatty chain and thus increasing the lipophilic character of the peptide and its penetrating power in the skin.
    According to a preferred possibility, the peptide according to the invention: comprises at the C-terminal end a short modification OMe, OEt and NH2 or is free of modification (comprises an OH terminus), preferably free of modification; and comprises at the N-terminus a modification, preferably an acylation -CO-Ri, more preferably with a group Ri of 3 to 24 carbon atoms, and more preferably selected from an octanoyl (C8), decanoyl (CIO) , lauroyl (C12), myristoyl (C14), palmitoyl (Cl6), stearoyl (Cl8), biotinoyl, elaidoyl, oleoyl and lipoyl.
    According to another possibility, the peptide according to the invention comprises at the C-terminal end a modification, preferably -ORi with R 1, an alkyl chain of 3 to 24 carbons; and comprises at the N-terminus a short change NHRt with R1 an alkyl chain of 1 to 3 carbons or is free of modification (includes an NH 2 terminus), preferably free of modification.
    According to other preferred characteristics, the peptide according to the invention is a small peptide comprising from 3 to 6 amino acids, more preferably comprising 3 amino acids corresponding to the sequence according to the invention K * (Ac) HG or the sequence K * (Ac) GH, that is corresponding to the tripeptides of formulas:
    (1) (2) wherein: X is when present at the N-terminus modification; and Z is when present at the C-terminus modification.
    The preferred peptides according to the invention are Pal-K (Ac) HG and Pal-K (Ac) GH, corresponding to a palmitoylated modification at the N-terminus and free of modifications at the C-terminus (OH terminus).
    The detailed description of in vitro tests given below shows that such peptides have an activity on the MEC marker molecules, active from a few ppm, and which can be used alone or as a mixture to improve the appearance and general condition of the skin and its integuments, and in particular for the treatment and / or prevention of signs of aging, and / or imperfections of the skin and its integuments. The inventors have shown that the peptides according to the invention have in particular a pro-collagen activity.
    Tests also show that they have a higher activity than the corresponding sequence peptide comprising a nonacetylated amino acid K *.
    The peptides according to the invention may be optically pure, or consist of L or D isomers or a mixture thereof. The naturally occurring L-isomers may be preferred.
    The peptides may be in the form of salts, especially hydrochloric or acetic salt.
    The present invention also covers derivatives (with modification and / or addition of a chemical function but without change in the carbon skeleton) and the like (with modification and / or addition of a chemical function but with a further change in the skeleton carbon), complexes with other species such as a metal ion (eg copper, zinc, manganese, magnesium, and others).
    The present invention also provides a composition, in particular a topical composition, comprising at least one peptide according to the invention in a physiologically acceptable medium. Depending on the excipient and the peptide assay, this composition will constitute, for example, a concentrated active ingredient or a less concentrated final composition directly intended for the client or patient.
    By "physiologically acceptable medium" is meant according to the present invention, without being limiting, an aqueous or hydroalcoholic solution, a water-in-oil emulsion, an oil-in-water emulsion, a microemulsion, an aqueous gel, an anhydrous gel , a serum, a dispersion of vesicles, a powder. "Physiologically acceptable" means that the compositions are suitable for topical or transdermal use, in contact with the mucous membranes, the nails, the scalp, the hair, the hairs and the skin of mammals and more particularly human, compositions which can be ingested or injected into the skin, without risk of toxicity, incompatibility, instability, allergic response, and others. This "physiologically acceptable medium" forms what is conventionally called the excipient of the composition.
    The peptides according to the invention may be solubilized in a lipophilic or hydrophilic matrix with, if appropriate, a solubilizer, depending on the future application.
    The peptide may be combined with other active ingredients at effective concentrations that can act synergistically or in a reinforcing manner to achieve the desired effects described for the invention, such as the following agents: anti-aging, anti-wrinkle and fine lines, lightening, pro-pigmenting, moisturizing, moisturizing, slimming, anti-acne, anti-inflammatory, anti-oxidant, acting on the radiance of the complexion, anti-glycation, volumizing, restructuring, anti-carbonylation, dermo-relaxants, anti- hair regrowth, acting on the stratum corneum, on the dermis-epidermis junction, on the production of protein HSPs, on the firmness, elasticity, tone of the skin, the regrowth of hair (eyelashes, eyebrows, for example), etc. . These active ingredients can be obtained from plant materials, such as plant extracts or vegetable or fermentation products.
    More specifically, the peptides may be combined with at least one of the compounds selected from vitamin B3 compounds, compounds such as niacinamide or tocopherol, retinoid compounds such as retinol, hexamidine, α-acid and the like. lipoic, resveratrol or DHEA, hyaluronic acid, peptides, especially N-acetyl-Tyr-Arg-O-hexadecyl, Pal-VGVAPG (SEQ ID NO 3), Pal-KTTKS (SEQ ID NO: 1) , Pal-GHK, Pal-KM02K (M02 corresponding to a dioxygenated methionine) and Pal-GQPR (SEQ ID No. 2), which are conventional active ingredients used in topical cosmetic or dermopharmaceutical compositions.
    The composition according to the invention can be applied to the face, the body, the décolleté, the scalp, the hair, the eyelashes, the hairs, in any form or vehicle known to those skilled in the art, in particular in the form of a solution, dispersion, emulsion, paste or powder, individually or premixed or be conveyed individually or premixed with vectors such as macrocapsules, microcapsules or nanocapsules, macrospheres, microspheres, or nanospheres, liposomes, oleosomes or chylomicrons, macroparticles, microparticles or nanoparticles, macro-sponges, micro-sponges or nanoepongs, microemulsions or nanoemulsions, or adsorbed on powdery organic polymers, talcs, bentonites, spores or exines and other mineral or organic carriers.
    In cosmetics in particular, applications can be proposed especially in the skincare ranges of the face, body, hair and body hair and makeup-care ranges, including eyelashes and eyebrows. In general, the peptides according to the present invention can be used in any form, in a bound form, incorporated or adsorbed on macro-, micro-, and nanoparticles, or on macro-, micro- and nanocapsules. for the treatment of textiles, natural or synthetic fibers, wool, and any material intended to come into contact with the skin and which may be used in clothing, night or daywear, handkerchiefs, or the tissues, in order to exert its cosmetic or therapeutic effect through this skin / textile contact and to allow a continuous topical delivery.
    The "International Cosmetic Ingredient Dictionaiy and Handbook" (16th edition, 2016) published by the "Personal Care Products Council" (formerly the "Cosmetic, Toiletry, and Fragrance Association") describes a wide variety, without limitation, of cosmetic ingredients and pharmaceuticals commonly used in the skin care industry, which are suitable for use as additional ingredients in the compositions of the present invention. Other additional skin care actives that are particularly useful can be found in Sederma's commercial literature and at www.sederma.com.
    The following commercial active agents may also be mentioned: betaine, glycerol, Actimoist Bio 2 ™ (Active Organics), AquaCacteen ™ (Mibelle AG Cosmetics), Aquaphyline ™ (Silab), AquaregulK ™ (Solabia) , Carciline ™ (Greentech), Codiavelane ™ (Biotech Marine), Dermaflux ™ (Arch Chemicals, Inc.), Hydra'Flow ™ (Sochibo), Hydromoist ™ (Symrise), RenovHyal ™ (Soliance), Seamoss ™ (Biotech Marine) , Argireline ™ (trade name for acetyl hexapeptide-3, Lipotec), spilanthol or Acmella oleracea extract known as Gatuline Expression ™, an extract of Boswellia serrata known as Boswellin ™, Deepaline PVB ™ ( Seppic), Syn-AKE ™ (Pentapharm), Ameliox ™, Bioxilift ™ (Silab), PhytoCellTec ™ Aigan (Mibelle), Papilactyl D ™ (Silab), Preventhelia ™ (Lipotec), or the following assets offered by Sederma: Subliskin ™ , Venuceane ™, Moist 24 ™, Vegesome Moist 24 ™, Essenskin ™, Juvinity ™, Revidrat ™, Resistem ™, Chronod yn ™, Kombuchka ™, Chromocare ™, Calmosensine ™, Glycokin factor S ™, Biobustyl ™, Idealift ™, Ceramide 2 ™, Ceramide A2 ™, Ceramide H03 ™, Legance ™, Intenslim ™, Prodizia ™, Senestem ™, Beautifeye ™, Pacifeel ™, Sebuless ™, Majestem ™, Apiscalp ™, NG Unsaponifiable Shea Butter ™, Citystem ™ or mixtures of these active ingredients. Among the plant extracts that can be combined with a peptide according to the invention, mention may be made in particular of ivy extracts, for example climbing ivy (Hedera helix), Bupleurum chinensis, Bupleurum falcatum, arnica ( Arnica montana L), rosemary (Rosmarinus ojficinalis N), marigold (Calendula officinalis), sage (Salvia officinalis L), ginseng (Panax ginseng), ginko biloba, St. John's wort (Hyperycum perforatum), butcher's broom (Ruscus aculeatus L), of Ulmaria (Filipendula ulmaria L), Orthosiphon (Orthosiphon stamincus benth), Algae (Fucus vesiculosus), Birch (Betula alba), Green Tea, Kola nut (Cola nipida), chestnut, bamboo, Centella asiatica, heather, fucus, willow, piloselle, escin extracts, cangzhu extracts, chrysanthellum indicum extracts, plants of the genus Armeniacea, Atractylodis platicodon, Sinnomenum, Pharbitidis , Flemingia, from Coleus as C. forskohlii, C. blu mei, C. esquirolii, C. scutellaroides, C. xanthantus and C. barbatus, as a raciness extract of Coleus barbatus, extracts of Ballot, Guioa, Davallia, Terminalia, Barringtonia, Trema, Antirobia, Cecropia, Argania, Dioscoreae as Dioscorea opposita or mexico, extracts of Ammi visnaga, Siegesbeckia, in particular Siegesbeckia orientalis, plant extracts of the family Ericaceae, in particular extracts of blueberries (Vaccinium angustifollium) from Arctostaphylos uva ursi, Aloe vera, plants containing sterols (in particular phytosterols), Manjistha (extract of plants of the genus Rubia, in particular Rubia cordifolia), Guggal (extract of plants of the genus Commiphora, in particular Commiphora mukul), an extract of kola, chamomile, violet trellis, Piper methysticum (Kava Kava from Sederma), Bacopa monieri (Bacocalmine ™, Sederma) and sea whip, Glycyrrhiza glabra, mulberry, tea tree, Larrea divaricata, Rabdosia rubescens, Euglena gracilis, Fibraurea recisa hirudinea, Chaparral sorghum, sunflower flower, Enantia chlorantha, Mitracarpe of the genus Spermacocea, Buchu barosma, Lawsonia inermis L., Adiantium capillus-veneris L., Chelidonium majus, from Luffa cylindrical, from "Japanese Mandarin" (Citrus reticulata blanco var. unshiu), Camellia sinensis, Imperata cylindrical, Glaucium flavum, Cupressus sempervirens, Polygonatum multiflorum, loveyly hemsleya, Sambucus nigra, Phaseolus lunatus, Centaurium, Macrocystis pyrifera, Tumera diffusa, Anemarrhena asphodeloides, of Portulaca pilosa, with Humulus lupulus, Arabica coffee, llex paraguariensis, Globularia cordifolia, Oxydendron arboreum, Albizzia julibrissin, Zingiber zerumbet smith, Marrubium vulgare, Apium graveolens (celery) or Leontopodium alpinum (or eldelweiss) or orchids.
    The compositions of the present invention may include other peptides, including, but not limited to, di-, tri-, tetra-, penta- and hexapeptides and derivatives thereof. According to a particular embodiment, the concentration of the additional peptide in the composition varies between 1 × 10 -7% and 20%, preferably between 1 × 10 -6% and 10%, preferably between 1 × 10 -5% and 5%, by weight. . The term "peptide" herein refers to peptides containing 10 amino acids or less, their derivatives, isomers and complexes with other species such as a metal ion (e.g. copper, zinc, manganese, magnesium, and others). The term "peptides" refers to both natural peptides and synthetic peptides. It also refers to compositions which contain peptides and which are found in nature, and / or which are commercially available.
    Nonlimiting examples of dipeptides that may be used in the context of the present invention include Camosin (beta-AH), YR, VW, NF, DF, KT, KC, CK, KP, KK, TT, PA, PM or PP. Non-limiting examples of tripeptides include RKR, HGG, GKH, GGH, GHG, KFK, KAvaK, ΚβΑΚ, KAbuK, KAcaK, KPK, KVK, KMOK, KM02K, PPL, PPR, SPR, QPA, LPA or SPA.
    Non-limiting examples of tetrapeptides are RSRK (SEQ ID NO: 4), GQPR (SEQ ID NO: 5), KTFK (SEQ ID NO: 6), KTAK (SEQ ID NO: 7), KAYK (SEQ ID NO: 8) or KFYK (SEQ ID NO. ID NO 9). A non-limiting example of a pentapeptide is KTTKS (SEQ ID NO: 10) and hexapeptides GKTTKS (SEQ ID NO: 11) and VGVAPG (SEQ ID NO: 12). Other peptides that can be used in the context of the present invention may be chosen from, without this list being limiting: lipophilic derivatives of peptides, preferably the myristoyl and palmitoyl derivatives, and the complexes with the metal ions mentioned above (eg copper tripeptide complex HGG). Preferred dipeptides include, for example, N-Palmitoyl-beta-Ala-His, N-Acetyl-Tyr-Arg-hexadecyl ester (Calmosensine ™, Idealift ™, Sederma), Pal-KT, Pal-RT (Sederma). Preferred tripeptides include N-Pal-Gly-Lys-His, (Pal-GKH, Sederma), copper derivative of HGG (Lamin ™, Sigma), Pal-GHK, lipospondin (N-Elaidoyl-KFK) and its conservative substitution analogues, N-Acetyl-RKR-NH2 (Peptide CK +), N-Biot-GHK (Sederma), Pal-KAvaK, Pal-KpAlaK, Pal-KAbuK, Pal-KAcaK, Pal-KM02K (Sederma) and their derivatives.
    Mention may also be made here of the anti-aging tripeptides of general formula X-Pro * -Pro * -Xaa-Y described in application WO2015181688 with Xaa selected from Leu, Arg, Lys, Ala, Ser, and Asp, at the N-terminus , X chosen from H, -CO-Ri and -SO 2 -R 1 and at the C-terminal end Y chosen from OH, OR 1, NH 2, NHR 1 or NR 1 R 2, R 1 and R 2 being, independently of one another, chosen from a alkyl, aryl, aralkyl, alkylaryl, alkoxy and aryloxy group, which may be linear, branched, cyclic, polycyclic, unsaturated, hydroxylated, carbonylated, phosphorylated and / or sulfurized, said group possibly possessing in its backbone a heteroatom particularly O, S and / or or N, and Pro * corresponding to Proline, an analogue or derivative thereof; comprising, for example, Myr-PPL-OH and Myr-PPR-OH.
    Mention may also be made here also of the pro-pigmenting and / or pro-Mec dipeptides and tripeptides of the general formula X- (Xaal) n-Pro * -Xaa2-Y described in the application WO 2014/080376, with n = 0, 1 or 2, Xa a hydrophobic amino acid selected from Ala, Val, Met, Leu, Iso, Phe, Pro, and analogs or derivatives thereof; or a polar amino acid selected from Ser, Thr, Tyr, Asp, Glu and derivatives and analogs thereof; and when n = 2 the two amino acids Xaai may be the same or different; Xaa2 a hydrophobic amino acid selected from Ala, Val, Met, Leu, Iso, Phe, and analogs or derivatives thereof; a basic amino acid selected from Arg, Lys, His, and derivatives and analogs thereof; at the N-terminus of the peptide, X is selected from H, -CO-Ri and -SO 2 -R 1; at the C-terminal end of the peptide, Y is chosen from OH, OR 1, NH 2, NHR 1 or NR 1 R 2, R 1 and R 2 being, independently of one another, chosen from an alkyl, aryl, aralkyl, alkylaryl, alkoxy and aryloxy group; which can be linear, branched, cyclic, polycyclic, unsaturated, hydroxylated, carbonylated, phosphorylated and / or sulfurized, said group possibly having in its backbone a heteroatom, in particular O, S and / or N; Pro * corresponding to Proline, an analogue or derivative thereof; comprising, for example, Pal-SPR-OH, Pal-PPR-OH, Pal-QPA-OH, Pal-LPA-OH, Myr-SPA-OH, Pal-PM-OH, Pal-PA-OH and Pal-PP peptides. -OH.
    Tetrapeptide derivatives which may be used in the context of the present invention include, but are not limited to, Pal-GQPR (Sederma) (SEQ ID NO 2), Pal-KTFK or Ela-KTFK (SEQ ID NO 13), Ela-KTAK (SEQ ID No. 14), Ela-KAYK (SEQ ID No. 15) or Ela-KFYK (SEQ ID No. 16). Useful pentapeptide derivatives are, but are not limited to, Pal-KTTKS (SEQ ID NO: 1) (MATRIXYL ™, Sederma), N-Pal-Tyr-Gly-Gly-Phe-X (SEQ ID NO: 17) with X being Leu or Pro, N-Pal-His-Leu-Asp-Ile-Ile-X with X being Trp, Phe, Tyr, Tic, 7-hydroxy-Tic or Tpi (SEQ ID No. 18), or their mixture. Useful hexapeptide derivatives include, but are not limited to: N-Pal-VGVAPG (SEQ ID NO: 3), Pal-GKTTKS (SEQ ID NO: 19), and derivatives. Pal-GHK and Pal-GQPR (SEQ ID No. 2) (Matrixyl ™ 3000, Sederma) can also be mentioned.
    The preferred commercially available compositions containing a tripeptide or derivative include Sederma Biopeptide-CL ™, Maxilip ™ or Biobustyl ™. The preferred commercially available compositions of tetrapeptides include: RIGIN ™, Eyeliss ™, Matrixyl ™ Reloaded and Matrixyl 3000 ™, which contain between 50 and 500 ppm of Pal-GQPR (SEQ ID NO 2) and an excipient, proposed by Sederma.
    The following commercial peptides may also be mentioned as additional active ingredients: Vialox ™ (INCI name = Pentapeptide-3 (synthetic peptide including alanine, arginine, isoleucine, glycine and proline)), Syn-ake ™ (β-Ala-Pro) -Dab-NH-Bzl) or Syn-Coll ™ (Pal-Lys-Val-Lys-OH) sold by DSM, Argireline ™ (Glu-Glu-Glu-Met-Gln-Arg-Arg-NH2) (INCI name = Acetyl hexapeptide-3) (SEQ ID No. 20), Leuphasyl ™ (Tyr-D-Ala-Gly-Phe-Leu) (SEQ ID No. 21), Aldenine ™ (Gly-His-Lys) , Trylagen ™ (INCI name = Pseudoalteromonas Ferment Extract, Hydro lyzed Wheat Protein, Hydro Lyzed Soy Protein, Tripeptide-10 Citrulline (product of the reaction of Citmylline and Tripeptide-10 (synthetic peptide consisting of aspartic acid, isoleucine and lysine)), Tripeptide-1), Eyeseryl ™ (Ac-P-Ala-His-Ser-His) (SEQ ID No. 22), Serilesine ™ (Ser-Ile-Lys-Val-Ala-Val ) (SEQ ID NO. 23) or Decorinyl ™ (INCI name: Tripeptide-10 Citrulline = p produced by the reaction of Citrulline and Tripeptide-10 (synthetic peptide consisting of aspartic acid, isoleucine and lysine) sold by Lipotec, Collaxyl ™ (Gly-Pro-Gln-Gly-Pro-Gln (SEQ ID No. 24)) or Quintescine ™ (Cys-Gly) sold by Ashland, Cytokinol ™ LS (casein hydrolyzate) sold by Laboratoires Serobiologiques / Cognis, Kollaren ™ (Gly-His-Lys), ΓΙΡ2000 ™ (Pal-Val-Tyr-Val) or Meliprene ™ (INCI name = Monofluoroheptapeptide-1: product of the reaction of acetic acid and a synthetic peptide containing arginine, glycine, glutamic acid, histidine, norleucine, p-fluorophenylalanine and tryptophan) sold by the European Institute of Cell Biology, Neutrazen ™ (Pal-His-D-Phe-Arg-NH2) sold by the company Innovations, or BONT-L-Peptide ™ (INCI name = Palmitoyl Hexapeptide- 19: product of the reaction of palmitic acid and Hexapeptide-19 (synthetic peptide consisting of asparagine, aspartic acid, lysine and methionine), Timp-Peptide ™ (INCI name = Acetyl Hexapeptide-20: product obtained by acetylation of Hexapeptide-20 (synthetic peptide consisting of alanine, glycine, lysine, valine and proline) or ECM Modulin ™ (INCI name = Palmitoyl Tripeptide-28: product of the reaction of palmitic acid and Tripeptide-28 (synthetic peptide consisting of arginine, lysine and phenylalanine) sold by the company Infinite Activos.
    The present invention thus proposes the use of at least one peptide according to the invention or a composition comprising it, as defined above, for a non-therapeutic cosmetic treatment to improve the general condition of the skin and / or its integuments and treat imperfections.
    Preferably according to the invention, the treatment is topical.
    The peptide according to the invention is more particularly recommended according to the invention for an anti-aging treatment, in particular a treatment: anti-wrinkles and fine lines; and / or improving the mechanical properties of the skin: firmness, tone, elasticity and / or suppleness; and / or healing; and / or increasing the density and volume of the skin (volumizing effect, plumping and / or restructuring); and / or to fight against stretch marks; and / or to improve the homogeneity and / or radiance of the complexion. Other applications are of course conceivable for the peptides according to the invention (alone or in combination), for example moisturizing, slimming, detoxification, anti-glycation, anti-free radicals, tensors, anti-fatigue, anti-bags and / or dark circles. , calming, action on the growth of hair and hair, action on the radiance of the complexion, pigmentation, on the scalp, etc. as a preventive or curative.
    The present invention covers a cosmetic, non-therapeutic topical treatment method for improving the appearance and the general condition of the skin and its integuments, including the topical application to the skin of a subject who has require an effective amount of a peptide or a mixture of peptides according to the invention or a composition according to the invention comprising said peptide or the mixture of peptides, the peptides being as defined above.
    By "topical treatment" or "topical use" is meant an application that is intended to act at the place where it is applied: skin, mucous membrane, appendages.
    The peptide or the composition according to the invention may be applied locally to the targeted zones. The "effective" amount depends on various factors, such as age, condition of the patient, severity of the disorder or pathology, and the mode of administration. An effective amount means a non-toxic amount sufficient to achieve the desired effect.
    In a cosmetic composition according to the invention, the peptides to be present in an effective amount may be in proportions of between 0.000001% and 15% relative to the total weight of the composition, preferably between 0.00001% and 5%, more preferably between 0.0001% and 0.01% (between 1 and 100 ppm) for topical cosmetic application, depending on the destination of the composition and the desired effect more or less pronounced. The peptides may be present in the compositions according to the invention in variable relative proportions, in equivalent amounts, or on the contrary in different proportions.
    All percentages and ratios used in this application are by weight of the total composition and all measurements are made at 25 ° C unless otherwise specified. For example, for a cosmetic facial treatment, the European Cosmetics Directive has fixed a standard application amount of a cream of 2.72 mg / cm 2 / day / person and for a lotion for the body of 0.5 mg / cm2 / day / person.
    According to other particularities, the cosmetic treatment method according to the invention may be associated with one or more other treatment methods aimed at the skin, such as, for example, treatments by light therapy, by heat or by aromatherapy.
    According to the invention, it is possible to propose devices with several compartments or kits intended for the implementation of the method described above, and which could include, by way of example, and without being limiting, in a first compartment a composition containing a peptide of the invention and in a second compartment an additional excipient and / or active, the compositions contained in said first and second compartments being here considered as a combination composition for simultaneous use, separate or spread in the especially in one of the treatments defined above.
    The treatment method according to the invention is more particularly adapted to slow the degradation of the molecules of the dermal extracellular matrix and / or to act on the JDE via the stimulation of collagen IV and / or laminin. Other applications are of course conceivable for the peptides according to the invention (alone or in combination), for example moisturizing, slimming, detoxification, anti-glycation, anti-free radicals, tensors, anti-fatigue, anti-bags and / or dark circles. , calming, action on the growth of hair and hair, action on the radiance of the complexion, pigmentation, on the scalp, etc. as a preventive or curative.
    The following examples describe and illustrate certain aspects of the invention. They should not be perceived as limiting the disclosure, as they provide mainly information useful for its understanding and implementation. A) Synthesis Example of a Peptide According to the Invention: Pal-K (Ac) HG The peptide Pal-K (Ac) HG is prepared by peptide synthesis. The glycine is coupled with a resin via its terminal acid function (with a coupling agent, for example DCC (diclyclohexylcarbodiimide) / NHS (N-hydroxysuccinimide) or HBTU (2- (1H-benzotriazol-1-yl) -1, 3,3-tetramethyluronium hexafluorophosphate) / HOBT (1-hydroxy-benzotriazole)). The glycine thus protected is then reacted with a histidine derivative in the presence of a coupling agent, and then the same operation is carried out to add the previously acetylated lysine. This is then acylated on its amine function with an activated palmitic acid derivative (palmitoyl chloride for example) in the presence of a base. After cleavage of the peptide resin, precipitation of the peptide, washing and drying, the product palmitoyl-lysyl-glycyl-histidine acetylated in solid form is obtained.
    This procedure is applicable to obtain the Pal-K (Ac) HG by inverting the glycine and rhistidine initially.
    B) Preparation of a Composition According to the Invention Comprising the Pal-K (Ac) HG Peptide of Example A) or the Pal-K (Ac) GH
    Starting materials: the pure peptide, synthesized according to the synthesis method explained above; excipient: a mixture of fatty esters, chosen so as to form an oily matrix, for example intended to form a composition without water for the subsequent formulation of cosmetic compositions without water.
    Procedure: The peptide is mixed with the excipient and gently stirred and heated until solubilization and total limpidity. C) In vitro evaluations
    The peptides according to the invention have a number of remarkable effects presented below. Peptides prepared according to A) above and dissolved in an excipient were tested in vitro and showed activities which are presented hereinafter. 1) ELISA Protocol Assays
    Normal human fibroblasts (FHN) in culture are placed in contact with the test products or their excipient (negative control) for 72 hours. After contact, the culture supernatants are removed and the syntheses of the dermal macromolecules are estimated by ELISA assays. An estimate of cell viability is made by Hoechst assay and allows to weight the data obtained. Results for the Pal-K (Ac) HG Table 1:
    Table 2:
    Table 3:
    The results show that the peptide Pal-K (Ac) HG according to the invention stimulates the synthesis of collagens I and IV and fibronectin on normal human fibroblasts at concentrations of a few ppm and in significant proportions. The results also show that the peptide Pal-K (Ac) HG according to the invention is advantageously more active than its nonacetylated version on lysine (Pal-KHG) for collagens I and IV, while has no decline in activity on fibronectin. Results for the Pal-Kf AcIGH Table 4:
    Table 5:
    Table 6:
    Table 7:
    Table 8:
    The results show that the peptide Pal-K (Ac) GH according to the invention stimulates the synthesis of collagens I and IV, fibronectin, elastin and hyaluronic acid on normal human fibroblasts at concentrations of a few ppm and in significant proportions. The results also show that the peptide Pal-K (Ac) GH according to the invention is advantageously more active than its nonacetylated version on lysine (Pal-KHG) for collagen I (at 7 ppm) and IV (at 10 ppm), elastin above 10 ppm and hyaluronic acid very largely from 3 ppm. 2) Immunofluorescence Assays Protocol
    Normal human fibroblasts (FHN) are cultured for 24 hours. The cells are placed in contact or not with the test products or their excipient at different concentrations for 6 days for collagen I or 14 days for elastin (DMEMc 5% S VF). The synthesis of collagen I and elastin produced by the cells in extracellular matrix form is then quantified by immunoblotting on the fixed mats. A count of Hoechst-labeled nuclei is performed in parallel in order to have an estimate of the viability and to weight the data. Results Table 9:
    Table 10:
    Table 11:
    The results confirm that the peptide Pal-K (Ac) HG according to the invention stimulates the synthesis of collagens I and IV, and show that they strongly stimulate the synthesis of elastin. The results also confirm that the peptide Pal-K (Ac) HG according to the invention is advantageously more active than its nonacetylated version on lysine (Pal-KHG) for collagens I and IV, and advantageously reveals a very strong activity. on elastin while the non-acetylated version had no activity on this target.
    D) GALENIC
    Different formulations are described below. Additional active cosmetic ingredients, possibly resulting in support and / or in addition to the activity of the active ingredient according to the invention, may be added in the appropriate phase according to their hydrophobic or hydrophilic nature. These ingredients can be of any category depending on their function (s), the place of application (body, face, neck, bust, hands, hair, eyelashes, eyebrows, hair, etc.), the desired end effect and the targeted consumer, for example antioxidant, moisturizing, nourishing, protective, smoothing, remodeling, volumizing (lipofiling), acting on the radiance of the complexion, anti-stain, concealer, anti-glycation, slimming, soothing, myogenic relaxing, anti-redness, anti-vergetures, etc. They are mentioned above in the description. 1) Cream form, for example an anti-aging day cream for the face
    Protocol: Weigh phase A and heat it to 75 ° C in a water bath. Weigh phase B and let it swell for 20 minutes. Melt phase C until dissolved and add to phase B. Heat phase (B + C) at 75 ° C in a water bath. Pour phase A into phase (B + C) with Staro stirring. Extemporally, add phase D to phase (A + B + C). At about 45 ° C add phase E and neutralize with phase F. Thoroughly homogenize. At 35 ° C, add phase G. Thoroughly homogenize. pH: 6.20.
    Examples of ingredients that can be added to this formulation: • CALMOSENSINE ™: sedative active ingredient marketed by Sederma (WO1998 / 07744) containing the lipo-dipeptide Tyr-Arg. It reduces feelings of discomfort. • SEBULESS ™: active ingredient marketed by Sederma including an extract of Syringa vulgaris obtained by cell culture in vitro, sebum regulator purifying, mattifies and refreshes the complexion, blurs the imperfections. • PRODIZIA ™: active ingredient marketed by Sederma including Albizia julibrissin extract, which promotes the visible reduction of signs of fatigue: dark circles, puffiness, dullness and pulled features in repairing and protecting the skin from damage caused by glycation. • PACIFEEL ™: active ingredient marketed by Sederma, including an extract of natural origin from the plant Mirabilis jalapa (Belle de nuit) that relieves feelings of discomfort (itching, tingling), reduces the redness of sensitive and reactive skin. • MAJESTEM ™: an active ingredient based on leontopodium alpinum plant cells obtained by cell culture in-vitro and titrated with luteopodic acid; tightens the relaxed skin of the neck, raises the cheekbones and smooths the wrinkles around the eye. 2) Form gel, for example a firming salt for the body
    Protocol: Disperse Ultrez 10 in water and allow to swell for 15 minutes. Heat phase B until dissolved and add to phase A. Weigh and mix phase C. Mix phase D and add it to phase C; well homogenize. Add the phase (C + D) to the phase (A + B). Then add phase E. Allow to swell for 1 hour. Well homogenize. Neutralize with phase F. Finally, add phase G. pH: 6.10.
    Examples of ingredients that can be added to this formulation: • AOUALANCE ™: osmoprotective moisturizing active ingredient marketed by Sederma (WO2009 / 104118) composed of homarine and erythritol. • LEGANCE ™: anti-aging active ingredient marketed by Sederma, corresponding to an extract of Zingiber zerumbet Smith obtained by supercritical CO 2 in a water-soluble excipient and titrated in zerumbone. It is an overall anti-aging ingredient for the legs. It improves their appearance and comfort by reducing water retention, improving microcirculation and refining fat tissue. • BODYFIT ™ active ingredient marketed by Sederma (WO 2004/024695) slimming / firming. • JUVINITY ™: Active ingredient marketed by Sederma (WO 2011/125039) which reduces the signs of aging on the face and décolleté, smooths wrinkles, restructures and densifies the dermis. Can be used as reinforcement of activity. 3) Compact powder form
    Protocol: Weigh phase A and mix. Weigh phase B and pour it into phase B. Pour A + B into the mixer and mix. Add phase C to A + B in several times and mix each time. Add phase D. Check at each step for homogeneity.
    Example of an ingredient that can be added to this formulation: • VEGESOME MOIST 24 ™. an ingredient marketed by Sederma specifically designed for the formulation of moisturizing makeup powders; it is a powder composed of hollow particles of 25 μηι (Lycopodium clavatum exins) loaded with an extract of Impera ata cylindrica having moisturizing properties. 4) Other cream form (face or body)
    Protocol: Weigh phase A and heat it to 75 ° C in a water bath. Weigh phase B and let it swell for 20 minutes. Melt phase C until dissolved and add to phase B. Heat phase (B + C) at 75 ° C in a water bath. Pour phase A into phase (B + C) with Staro stirring. Extemporally, add phase D to phase (A + B + C). At about 45 ° C add phase E and neutralize with phase F. Thoroughly homogenize. At 35 ° C, add phase G. Thoroughly homogenize. pH: 6.20.
    Examples of ingredients that can be added to this formulation: • SUBLISKIN ™: active ingredient marketed by Sederma (W02009 / 055663) that hydrates and smooths the skin while allowing it to withstand external aggressions. • VENUCEANE ™: active ingredient marketed by Sederma (WO2002 / 066668) which prevents visible signs of photoaging (spots, wrinkles, dryness ...), protects cell structures from damage caused by UV and reinforces the integrity of the skin . • KOMBUCHKA ™: active ingredient acting on the radiance of the complexion, marketed by Sederma (W02004 / 012650). • INTENSUIVI ™: slimming active ingredient marketed by Sederma. It is a synergistic combination of extracts of Globularia cordifolia obtained by plant cell culture, Zingiber zerumbet Smith titrated in zerumbone and vegetable caffeine obtained by supercritical CO2 extraction. • CITYSTEM ™: an active ingredient based on plant cells obtained in vitro from Marrubium vulgare with a high concentration of Forsythoside B; used against attacks of pollution: makes the skin soft and smooth, refines skin texture, reduces the visibility of blackheads, leaving the skin radiant and purified.
    权利要求:
    Claims (14)
    [1" id="c-fr-0001]
    A peptide comprising from 3 to 10 amino acids including at least the peptide sequence K * (Ac) GH or the peptide sequence K * (Ac) HG and which may comprise a modification at the N-terminus and / or C terminus, in which K * is selected from the group consisting of a lysine (Lys, K), an omithine (Om), a diaminobutyric acid (Dab), a diaminopropionic acid (Dap) and a hydroxylated derivative thereof; • K * (Ac) corresponds to a lysine, omithine, diaminobutyric acid, diaminopropionic acid or a hydroxylated derivative thereof, acetylated on the amine of their side hydrocarbon chain; Said modification at the N-terminus is -CO-Ri or -SO 2 -R 1; Said modification at the C-terminus is chosen from the group comprising -ORi, -NH2, -NHRi and -NRiR2; and R 1 and R 2 being, independently of one another, chosen from an alkyl, allyl, aralkyl, alkylaryl, alkoxy and aryloxy group, which may be linear, branched, cyclic, polycyclic, unsaturated, hydroxylated, carbonylated, phosphorylated and or sulfur, said group having 1 to 24 carbon atoms and may have in its backbone heteroatom O, S and / or N.
    [2" id="c-fr-0002]
    2. Peptide according to claim 1, characterized in that K * is a lysine, K * (Ac) corresponding to an ε-acetylated lysine.
    [3" id="c-fr-0003]
    3. Peptide according to claim 1 or 2, characterized in that said group R1 and / or R2 comprises from 3 to 24 carbon atoms.
    [4" id="c-fr-0004]
    4. Peptide according to one of claims 1 to 3, characterized in that it comprises an acyl group -CO-Ri modified at the N-terminus.
    [5" id="c-fr-0005]
    Peptide according to claim 4, characterized in that the acyl group -CO-Rj is chosen from octanoyl (Cg), decanoyl (Cio), lauroyl (C12), myristoyl (Cm), palmitoyl (Cm) and stearoyl ( C18), biotinoyl, elaidoyl, oleoyl and lipoyl.
    [6" id="c-fr-0006]
    6. Peptide according to one of claims 1 to 5, characterized in that it comprises a modification at the N-terminus and is free of modification at the C-terminus.
    [7" id="c-fr-0007]
    7. Peptide according to one of claims 1 to 6 of formulas:

    O) (2) where X is when present at the N-terminal change and Z when present at the C-terminal change.
    [8" id="c-fr-0008]
    Peptide according to claim 7, corresponding to Pal-K (Ac) GH or Pal-K (Ac) HG.
    [9" id="c-fr-0009]
    9. Cosmetic composition comprising as active ingredient an effective amount of at least one peptide according to any one of claims 1 to 8 in a physiologically acceptable medium.
    [10" id="c-fr-0010]
    10. Composition according to claim 9, characterized in that it comprises at least one additional active ingredient selected from the compounds of vitamin B3, niacinamide, tocopherol, retinoid compounds, hexamidine, α-lipoic acid. resveratrol, DHEA, hyaluronic acid and peptides selected from N-acetyl-Tyr-Arg-O-hexadecyl, Pal-VGVAPG (SEQ ID NO 3), Pal-KTTKS (SEQ ID No. 1), Pal-GHK, Pal-KM02K and Pal-GQPR (SEQ ID NO 2).
    [11" id="c-fr-0011]
    11. Use of at least one peptide according to any one of claims 1 to 8 or a composition according to claim 9 or 10 for a non-therapeutic cosmetic treatment to improve the general condition of the skin and / or its dander and treat imperfections.
    [12" id="c-fr-0012]
    12. Use according to claim 11 for topical treatment.
    [13" id="c-fr-0013]
    13. Use according to claim 11 or 12, for an anti-aging treatment of the skin and / or its integuments.
    [14" id="c-fr-0014]
    14. Use according to one of claims 11 to 13 for a treatment: anti-wrinkles and fine lines; and / or improving the mechanical properties of the skin: firmness, tone, elasticity, and / or suppleness; and / or healing; and / or increasing the density and volume of the skin (volumizing effect, plumping and / or restructuring); and / or to fight against stretch marks, and / or to improve the homogeneity and radiance of the complexion.
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    同族专利:
    公开号 | 公开日
    KR20190018692A|2019-02-25|
    US20190153030A1|2019-05-23|
    EP3468983A1|2019-04-17|
    CN109311939A|2019-02-05|
    US11001607B2|2021-05-11|
    FR3052453B1|2018-05-18|
    WO2017216177A1|2017-12-21|
    EP3468983B1|2020-01-22|
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    法律状态:
    2017-05-10| PLFP| Fee payment|Year of fee payment: 2 |
    2017-12-15| PLSC| Search report ready|Effective date: 20171215 |
    2018-05-16| PLFP| Fee payment|Year of fee payment: 3 |
    2020-05-04| PLFP| Fee payment|Year of fee payment: 5 |
    2021-05-20| PLFP| Fee payment|Year of fee payment: 6 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1655468A|FR3052453B1|2016-06-14|2016-06-14|PEPTIDE, COMPOSITION COMPRISING SAME AND USES IN PARTICULAR COSMETICS|
    FR1655468|2016-06-14|FR1655468A| FR3052453B1|2016-06-14|2016-06-14|PEPTIDE, COMPOSITION COMPRISING SAME AND USES IN PARTICULAR COSMETICS|
    KR1020197001209A| KR20190018692A|2016-06-14|2017-06-13|Peptides, compositions comprising the peptides, and their use especially in cosmetics|
    US16/307,548| US11001607B2|2016-06-14|2017-06-13|Peptide, composition comprising said peptide and uses thereof, in particular cosmetic uses|
    CN201780037005.3A| CN109311939A|2016-06-14|2017-06-13|Peptide, composition comprising the peptide and application thereof, especially cosmetic use|
    PCT/EP2017/064439| WO2017216177A1|2016-06-14|2017-06-13|Peptide, composition comprising said peptide and uses thereof, in particular cosmetic uses|
    EP17731843.3A| EP3468983B1|2016-06-14|2017-06-13|Peptide, composition comprising said peptide and uses thereof, in particular cosmetic uses|
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