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    • 专利摘要:
    The peptide has the general formula X - Pro * - Pro * - Xaa - Y wherein: Xaa is selected from Leucine (Leu, L), Arginine (Arg, R), Lysine (Lys, K), Alanine (Ala, A), Serine (Ser, S), and Aspartic Acid (Asp, D); At the N-terminal end of the peptide, X is chosen from H, -CO-R 1 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 and alkylaryl group, alkoxy and aryloxy, which may 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; and • Pro * corresponding to Proline, an analogue or derivative thereof. The peptide is adapted to stimulate the synthesis of the molecules constituting the dermal extracellular matrix, in particular collagen 1 and 4 and elastin. It can be used for a cosmetic treatment including anti-aging, anti-wrinkles and fine lines, to improve the mechanical properties of the skin, firmness / tonicity / elasticity / suppleness, to increase the density and volume of the skin, for an effect restructuring and / or to fight against stretch marks.
    公开号:FR3021319A1
    申请号:FR1454632
    申请日:2014-05-22
    公开日:2015-11-27
    发明作者:Olivier Peschard；Anne Doucet；Roux Richard Le；Philippe Mondon
    申请人:Sederma SA；
    IPC主号:
    专利说明:

    [0001] The present invention relates to novel peptides, compositions comprising them and cosmetic, therapeutic or cosmeceutical uses of said peptides. It is more particularly peptides for the treatment of the skin and its integuments, mammals, humans or animals.
    [0002] It concerns the cosmetics industry, hygiene and personal care products, cosmeceuticals 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 finding 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 and elastin and also active on the synthesis of glycoproteins such as fibronectin.
    [0003] 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.
    [0004] 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. 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 better anchoring and help maintain the suppleness of the epidermis. 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 appears clearly. The stimulated synthesis of these molecules will result from the results on the beautification and the general state of the skin, mainly in terms of mechanical properties: a denser skin, regonflated, firmer, more toned, more supple and elastic, the peptide having a volumizing effect, plumping, and therefore anti-wrinkle. Numerous peptides or mixtures of peptides having properties on the ECM 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 MATRIXYL ™ brand, the Pal mixture. -GHK and Pal-GQPR (SEQ ID No. 2) under the trademark MATRIXYLTm 3000 or more recently Pal-KMO2K under the trademark MATRIXYL Synthe-6Tm (M02 corresponding to a methionine dioxygenated). Other known peptides are mentioned later in the description. Moreover, the patent application WO2010071132 describes a series of eight peptides (-tri, -tetra, penta and -hexa peptides) derived from fermented milk and having been selected because they are not digested by the enzymes of the digestive tract. and that they are able to penetrate the epithelial cells of the intestine. The authors further showed that at concentrations of about 40 ppm, stimulation of collagen synthesis and increased proliferation of epidermal cells was observed. Thanks to these properties, the authors recommend that these peptides, extracted naturally or synthesized, can be advantageously ingested as cosmeceuticals having anti-aging properties. The eight peptides have a PP sequence (Asn-Ile-Pro-Pro-Leu (NIPPL, SEQ ID No. 3), Ile-Pro-Pro (IPP), Ile-Pro-Pro-Leu (IPPL, SEQ ID No. 4), Val-Pro-Pro (VPP), Val-Pro-Pro-Phe (VPPF, SEQ ID No. 5), Pro-Val-Val-Pro-Pro-Pro (PVVVPP, SEQ ID No. 6), Phe-Pro-Pro-Gln (FPPQ, SEQ ID No. 7) and Leu-Pro-Pro-Thr (LPPT, SEQ ID No. 8) and among them two peptides (IPPL tetrapeptide (SEQ ID No. 4) and Pentapeptide NIPPL (SEQ ID NO: 3) comprise the more precise sequence of PPL amino acids NIPPL (SEQ ID NO: 3) is presented as the preferred peptide with the best result in collagen production by fribroblasts: +30 About 50% relative to the control for a concentration of about 55 ppm, against + 10% only compared to the control for a concentration of about 44 ppm for the IPPL peptide (SEQ ID No. 4).
    [0005] 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, its purpose is to propose peptides that are sufficiently effective to be used alone or in combination, in proportions of a few ppm, and can be used in the form of a topical composition, in particular a cosmetic composition. The present invention provides peptides of general formula: X - Pro * - Pro * - Xaa - Y (I) With: - Xaa is selected from Leucine (Leu, L), Arginine (Arg, R), Lysine (Lys, K), Alanine (Ala, A), Serine (Ser, S), and Aspartic Acid (Asp, D); at the N-terminus of the peptide, X is chosen from H, -CO-R 1 and -50 2 -R 1 - at the C-terminal end of the peptide, Y is chosen from OH, R 1, NH 2, NHR 1 or NR 1 R 2, R 1 and R 2; being, independently of one another, selected from an alkyl, aryl, aralkyl, alkylaryl, alkoxy and aryloxy group, which may be linear, branched, cyclic, polycyclic, unsaturated, hydroxylated, carbonylated, phosphorylated and / or sulfur-containing, group which may have in its backbone a heteroatom particularly O, S and / or N; Pro * corresponding to Proline, an analogue or a derivative thereof. 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, especially with regard to collagen 1 and collagen 4 and pro-elastin activity.
    [0006] The present invention covers the following derivatives or analogues of proline: 1) from cycles of different size (eg 4 or 6 bonds); 2) resulting from the modification of the relative position (a or (3) of the acid function (COOH) with respect to the nitrogen of the cycle 3) resulting from substitutions on the cycle modifying its size and / or its polarity. 4) from the combination of the previous items. They can be represented by the following general formula II: ## STR1 ## The present invention preferably provides the following analogous compounds shown in the following Table 1 possessing a nitrogen atom. in the ring such as proline (5-cycle and COOH at a): 30 Compound name Chemical structure azetidine-2-carboxylic acid 4-cycle and COOH 13-proline (or pyrrolidine-3-carboxylic acid) 5-cycle and COOH in (3 pipecolic acid Cycle at 6 and COOH at a nipecotic acid Cycle at 6 and COOH at (3 thio-proline (or thiazolidine-4-carboxylic Cycle at 5 and COOH at a + S at position 4 acid) 4- hydroxy-proline Cycle at 5 and COOH at α + OH at position 4 3,4-dehydro-proline Cycle at 5 and COOH at α + unsaturation 3-4 Other compounds resulting from the substitution of proline by an R group are Non-limiting examples are given in Table 2 below: Grouping R Position piperidin-4 -yl 1 on phenyl nitrogen; dimethyl phenyl; OH; NH2; F; F2; CF3; benzyl; cyclohexyl; oxo; bromobenzyl; SH; phenoxy phenyl; dimethyl; phenyl oxo, cyclohexyl 4 + 5 Proline can also be substituted by substituted analogs having a 6-bonded ring as exemplified in the following Table 3: Compound name Chemical structure 3-carboxy-morpholine 6-oxygenated + COOH cycle in 3-position 2-carboxy-morpholine 6-oxygenated + COOH cycle in 2-position Tic (or 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) and its hydroxylated derivative 6-COOH cycle in 2-position on this ring + phenyl in position 4 + 5 Tiq (or 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid) 6-COOH ring in position 6 on this ring + indole in position 4 + 5 According to the invention, preferably in formula I: - if X is H then Y is selected from OR ', NH2, NHR1 or NR1R2 and if Y is OH then X is -CO-R1 or -502-R1; peptides in which in the formula I, X = H and Y = OH are excluded, to favor peptides having a substitution at one of the N-terminal or C-terminal ends because they have a better bioavailability (skin penetration power). most important) ; and / or - Pro * is the Proline, natural amino acid; and / or Xaa is chosen from Leucine (Leu, L) and Arginine (Arg, R). Thus, two preferred peptides according to the invention are X-PPL-Y and X-PPR-Y. According to other preferred features of the invention: R 1 and / or R 2 is an alkyl chain of 1 to 24 carbon atoms, preferably a lipophilic alkyl chain of 3 to 24 carbon atoms; and / or - X is an acyl group CO-R 1 and Y is chosen from OH, OMe, OEt and NH 2, preferably OH; X is preferably selected from octanoyl (C8), decanoyl (C10), lauroyl (C12), myristoyl (C14), palmitoyl (C16), stearoyl (C18), biotinoyl, elaidoyl, oleoyl and lipoyl; more preferably selected from lauroyl (C12), myristoyl (C14) and palmitoyl (C16); and / or - Y is OH and X is selected from palmitoyl (C16), myristoyl (C14) and lauroyl (C12); more preferably myristoyl (C14). The preferred peptides according to the invention are Myr-PPL-OH and Myr-PPR-OH. 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 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 carbon skeleton), 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 dosage, this composition will for example constitute a concentrated active ingredient or a less concentrated final composition directly intended for the customer 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 mucous membranes, nails, scalp, hair, hair and mammalian skin and more particularly human, ingestible compositions. or injected into the skin, without risk of toxicity, incompatibility, instability, allergic response, and others. This "physiologically acceptable medium" forms what is conventionally referred to as the excipient of the composition.
    [0007] 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. . 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 CTFA ("International cosmetic ingredient dictionary & handbook" (13th Ed. 2010) published by "The Cosmetic, Toiletry, and Fragrance Association, Inc.", Washington, DC) describes a wide variety, without limitation, of cosmetic and pharmaceutical ingredients commonly used in the skin care industry, which are suitable for use as additional ingredients in the compositions of the present invention.
    [0008] 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 as examples: betaine, glycerol, Actimoist Bio 2TM (Active Organics), AquaCacteenTM (Mibelle AG Cosmetics), AquaphylineTM (Silab), AquaregulKTM (Solabia), CarcilineTM (Greentech) ), CodiavelaneTM (Biotech Marine), DermafluxTM (Arch Chemicals, Inc.), Hydra'FlowTM (Sochibo), Hydromoist LTM (Symrise), RenovHyal TM (Soliance), SeamossTM (Biotech Marine), ArgirelineTM (trade name acetyl hexapeptide) -3 of Lipotec), spilanthol or an extract of Acmella oleracea known as Gatuline ExpressionTM, an extract of Boswellia serrata known as BoswellinTM, Deepaline PVBTM (Seppic), Syn-AKETM (Pentapharm), AmelioxTM, BioxiliftTM ( Silab), PhytoCellTecTMArgan (Mibelle), Papilactyl DTM (Silab), PreventheliaTM (Lipotec), SubliskinTM (Sederma), VenuceaneTM (Sederma), Moist 24TM (Sederma), Vegesome Moist 24TM (Sederma), EssenskinTM (Sederma), Juvini tyTM ( Sederma), RevidratTM (Sederma), ResistemTM (Sederma), Chrono dynTM (Sederma), KombuchkaTM (Sederma), ChromocareTM (Sederma), CalmosensineTM (Sederma), Glycokin factor STM (Sederma), BiobustylTM (Sederma), IdealiftTM (Sederma), Ceramide 2TM, Ceramide A2TM and Ceramide HO3TM (Sederma), LeganceTM (Sederma), IntenslimTM (Sederma), ProdiziaTM (Sederma), SenestemTm (Sederma), BeautifeyeTm (Sederma), Pacifeel (Sederma), Sebulessi'm (Sedenna), NG Unsaponifiables of Shea ButterTM (Sederma) or mixtures of those -this. 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 officinalis N), Marigold (Calendula officinalis), Sage (Salvia officinalis L), Ginseng (Panax ginseng), Ginko biloba, St. John's Wort (Hyperycum Perforatum), Ruscus (Ruscus aculeatus L), of Ulmaria (Filipendula ulmaria L), Orthosiphon (Orthosiphon Stamincus Benth), Algae (Fucus Vesiculosus), Birch (Betula alba), Green Tea, Kola nut (Cola Nipida), horse 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. blumei, C. e squirolii, C. scutellaroides, C. xanthantus and C. barbatus, as an extract of raciness of Coleus barbatus, extracts of Ballot, Guioa, Davallia, Terminalia, Barringtonia, Trema, antirobia, cecropia, argania, dioscoreae as Dioscorea opposita or Mexican 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, alpe vera, plants containing sterols (especially 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 clover, Piper methysticum (Kava Sederma kava), Bacopa monieri (BacocalmineTM, Sederma) and sea whip, Glycyrrhiza glabra, mulberry, tea tree, Larrea divaricata, Rabdosia ru bescens, Euglena gracilis, Fibraurea recisa Hirudinea, Chaparral Sorghum, sunflower, Enantia chlorantha, Mitracarpe of the genus Spermacocea, Buchu barosma, Lawsonia inermis L., Adiantium Capillus-Veneris L., of Chelidonium majus, Luffa cylindrical, Japanese Mandarin (Citrus reticulata Blanco var. unshiu), Camelia sinensis, Imperata cylindrical, Glaucium Flavum, Cupressus Sempervirens, Polygonatum multiflorum, loveyly hemsleya, Sambucus Nigra, Phaseolus lunatus, Centaurium, Macrocystis Pyrifera, Turnera Diffusa, Anemarrhena asphodeloides, of Portulaca pilosa, Humulus lupulus, Arabica coffee, Ilex Paraguariensis, Globularia Cordifolia, Oxydendron arboreum, Albizzia julibrissin and Zingiber zerumbet smith. 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 can be used in the context of the present invention include Camosin (beta-AH), YR, VW, NF, DF, KT, KC, CK, KP, KK or TT. Non-limiting examples of tripeptides include RKR, HGG, GKH, GGH, GHG, KFK, KPK, KMOK, KMO2K or KAvaK. Non-limiting examples of tetrapeptides are RSRK (SEQ ID NO: 9), GQPR (SEQ ID NO: 10), or KTFK (SEQ ID NO: 11). A non-limiting example of pentapeptide is KTTKS (SEQ ID NO: 12) and hexapeptides GKTTKS (SEQ ID NO: 13) and VGVAPG (SEQ ID NO: 14). 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). The preferred tripeptides include N-Pal-Gly-Lys-His, (Pal-GKH, Sederma), the copper derivative of HGG (LaminTM, Sigma), lipospondin (N-Elaidoyl-KFK) and its conservative substitution analogues , N-Acetyl-RKR-NH2 (Peptide CK +), N-Biot-GHK (Sederma), Pal-KM02K (Sederma) and their derivatives. Tetrapeptide derivatives which may be used in the context of the present invention include, but are not limited to, N-Pal-GQPR (Sederma, SEQ ID No. 2) and Ela-KTFK (SEQ ID No. 15). Useful pentapeptide derivatives are, but are not limited to, N-Pal-KTTKS (MATRIXYL ™, Sederma, SEQ ID No. 1), N-Pal-Tyr-Gly-Gly-Phe-X (SEQ ID No. 16) with X being Met or Leu or their mixture. Useful hexapeptide derivatives include, but are not limited to: N-Pal-VGVAPG (SEQ ID NO: 17), Pal-GKTTKS (SEQ ID NO: 18), and derivatives. We can also mention the mixture Pal-GHK and Pal-GQPR (SEQ ID NO: 2) (MatrixylTM 3000, Sederma). Preferred commercially available compositions containing a tripeptide or derivative include Biopeptide-CLTM, MaxilipTM or Sederma BiobustylTM. Preferred commercially available compositions of tetrapeptide sources include: RIGINTM Eyeliss ™, Matrixyl ™ Reloaded and Matrixyl 3000 ™, which contain between 50 and 500 ppm of palGQPR (SEQ ID NO: 2) and an excipient, provided by Sederma. The following commercial peptides may also be mentioned as additional active ingredients: VialoxTM, Syn-akeTM or Syn-Co11TM (Pentapharm), Hydroxyprolisilane CNTM (Exsymol), Argireline TM, LeuphasylTM, AldenineTM, TrylgenTM, EyeserylTM, SerilesineTM or DecorinylTM (Lipotec) , CollaxylTM or QuintescineTM (Vincience), BONT-L-PeptideTM (Infinitec Activos), CytokinolTMLS (Serobiological Laboratories / Cognis), KollarenTM, IP2000TM or MelipreneTM (European Institute of Cell Biology), NeutrazenTM (Innovations), ECM-ProtectTM (Atrium Innovations) ), Timp-PeptideTM, ECM ModulinTM (lnfinitec Activos). The present invention also proposes a cosmetic, cosmeceutical or therapeutic topical treatment method for improving the appearance and general condition of the skin and its integuments, comprising the topical application to the skin of a subject which requires 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 peptide mixture, the peptides being as defined hereinabove. 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.
    [0009] 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, are generally in proportions of between 0.000001% and 15% relative to the total weight of the composition, more preferably between 0.0001. % and 5%, 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 set a standard application amount of a cream of 2.72 mg / cm2 / 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, more particularly adapted to the treatment - anti overall age; and / or - anti-wrinkles and fine lines (cutaneous relief smoothes out filled wrinkles), and / or - improving the mechanical properties of the skin, firmness / elasticity / tonicity, and / or - increasing the density and the volume of the skin ( volumizing effect, plumping), - and / or restructuring, and / or - to fight against stretch marks. 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. A composition according to the invention comprising at least one of the peptides defined by formula I is suitable for a therapeutic treatment of skin deficient in molecules constituting the dermal extracellular matrix.
    [0010] The following examples describe and illustrate certain aspects of the invention. They should not be perceived as limiting the disclosure, as they mainly provide useful information for its understanding and implementation. A) Synthesis Example of a Peptide According to the Invention: Myr-PPL-OH The Myr-PPL-OH peptide is prepared by peptide synthesis. The leucine 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) -l, 1, 3,3-tetramethyluronium hexafluorophosphate) / HOBT (1-hydroxy-benzotriazole)). The thus protected leucine is then reacted with a proline derivative in the presence of a coupling agent, followed by the same operation to add the second proline. This is then acylated on its amine function with an activated myristic acid derivative (myristoyl chloride for example) in the presence of a base. After precipitation, washing and drying, the product myristoyl-prolyl-prolyl-leucine is obtained in solid form. This same synthesis process can be applied to the peptides of the formula I according to the invention, for example to the Myr-PPR-OH peptide. B) Preparation of a Composition According to the Invention Comprising the Myr-PPL-OH Peptide of Example A) 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.
    [0011] 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 assays Protocol Normal human fibroblasts (FHN) in culture are put in contact with the products to be tested or their excipient (negative control) during 72h. At the end of the contact, the culture supernatants are taken 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.
    [0012] Results Table 4: Collagen I Product Concentration% of variation / control Significance (Student test) Myr-PPA-OH 3 ppm + 40 p <0.05 Myr-PPA-OH 7 ppm + 143 p <0.01 Myr-PPS- OH 3 ppm + 70 p <0.01 Myr-PPS-OH 7 ppm + 172 p <0.01 Myr-PPD-OH 1 ppm + 27 p <0.05 Myr-PPD-OH 3 ppm + 57 p <0 , 01 Myr-PPD-OH 7 ppm + 44 p <0.01 Myr-PPK-OH 3 ppm + 75 p <0.01 Myr-PPK-OH 4 ppm + 68 p <0.05 Myr-PPK-OH 5 ppm + 145 p <0.01 Myr-PPL-OH 1 ppm + 34 p <0.05 Myr-PPL-OH 3 ppm + 59 p <0.01 Myr-PPL-OH 5 ppm + 87 p <0.01 Myr-PPR-OH 3 ppm + 90 p <0.01 Myr-PPR-OH 4 ppm + 163 p <0.01 Myr-PPR-OH 5 ppm + 160 p <0.01 Table 5: Collagen IV Product Concentration% variation / control Significance (Student test) Myr-PPA-OH 7 ppm + 54 p <0.05 Myr-PPS-OH 3 ppm + 28 p <0.01 Myr-PPS-OH 7 ppm + 42 p <0, 01 Myr-PPD-OH 1 ppm + 23 p <0.01 Myr-PPD-OH 3 ppm + 37 p <0.01 Myr-PPK-OH 3 ppm + 37 p <0.05 Myr-PPK-OH 4 ppm + 52 p <0.01 Myr-PPK-OH 5 ppm + 64 p <0.01 Myr-PPK-OH 6 ppm + 57 p <0.01 Myr-PPL-OH 1 ppm + 38 p <0.01 Myr -PPL-OH 3 ppm + 51 p <0.01 Myr-PPL-OH 5 ppm + 83 p <0.01 Myr-PPL-OH 7 ppm + 159 p <0.01 Myr-PPR-OH 3 ppm + 49 p <0.01 Myr -PPR-OH 4 ppm + 64 p <0.01 Myr-PPR-OH 5 ppm + 104 p <0.01 Myr-PPR-OH 6 ppm + 93 p <0.01 Table 6: Fibronectin Product Concentration% of variation / control Significance (Student's test) Myr-PPA-OH 1 ppm + 25 p <0.05 Myr-PPA-OH 7 ppm + 60 p <0.01 Myr-PPS-OH 1 ppm + 28 p <0.01 Myr -PPS-OH 7 ppm + 87 p <0.01 Myr-PPD-OH 1 ppm + 53 p <0.01 Myr-PPD-OH 3 ppm + 44 p <0.01 Myr-PPD-OH 7 ppm + 48 p <0.01 Myr-PPK-OH 3 ppm + 32 p <0.05 Myr-PPK-OH 5 ppm + 46 p <0.01 Myr-PPL-OH 3 ppm + 73 p <0.01 Myr-PPL -OH 5 ppm + 41 p <0.05 Myr-PPL-OH 7 ppm + 66 p <0.01 Myr-PPR-OH 4 ppm + 27 p <0.01 Table 7: Laminin Product Concentration% of variation / control Significance (Student test) Myr-PPA-OH 1 ppm + 40 p <0.05 Myr-PPA-OH 3 ppm + 80 p <0.01 Myr-PPA-OH 7 ppm + 143 p <0.01 Myr-PPS -OH 7 ppm + 41 p <0.01 Myr-PPD-OH 3 ppm + 23 p <0.05 Myr-PPK-OH 1 ppm + 34 p <0.05 Myr-PPK-OH 3 ppm + 102 p < 0.01 Myr-PPK-OH 5 ppm + 92 p <0.01 Myr-PPL-OH 1 ppm + 29 p <0.05 Myr-PPL-OH 3 ppm + 83 p <0.01 Myr-PPL-OH 5 ppm + 53 p <0.01 Myr-PPL -OH 7 ppm + 41 p <0.05 Myr-PPR-OH 3 ppm + 24 p <0.01 Myr-PPR-OH 4 ppm + 39 p <0.01 Table 8: Elastin Product Concentration% of variation / control Significance (Student test) Myr-PPA-OH 7 ppm + 57 p <0.05 Myr-PPA-OH 10 ppm + 92 p <0.01 Myr-PPS-OH 3 ppm + 60 p <0.05 Myr-PPS -OH 7 ppm + 117 p <0.01 Myr-PPD-OH 1 ppm + 63 p <0.01 Myr-PPD-OH 3 ppm + 65 p <0.01 Myr-PPD-OH 7 ppm + 123 p < 0.01 Myr-PPD-OH 10 ppm + 85 p <0.05 Myr-PPK-OH 3 ppm + 46 p <0.05 Myr-PPL-OH 5 ppm + 86 p <0.05 Myr-PPL-OH 7 ppm + 137 p <0.01 Myr-PPR-OH 5 ppm + 81 p <0.01 The results show that the peptides according to the invention stimulate the synthesis of collagens I and IV, fibronectin, laminins and elastin on fibroblasts normal humans at concentrations of a few ppm and in significant proportions, with a predominant activity for Myr-PPR-OH and Myr-PPL-OH. 2) Immunofluorescence assays Protocol Normal human fibroblasts (HHN) 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% FCS). 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: Collagen I Product Concentration% of variation / Significance control (Mann Whitney U-test) Myr-PPL-OH Myr-PPL-OH 3 ppm 7 ppm + 68 p <0.01 p <0.01 + 95 Table 10 : Elastin Product Concentration% of variation / Significance control (Mann Whitney U-test) Myr-PPL-OH 2 ppm + 183 p <0.01 Myr-PPL-OH 3 ppm + 259 p <0.01 Myr-PPL-OH 7 ppm + 145 p <0.01 Myr-PPR-OH 2 ppm + 148 p <0.01 Myr-PPR-OH 3 ppm + 141 p <0.01 Myr-PPR-OH 7 ppm + 44 p <0.01 D) GALENIC Various 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 Ingredient (INCI name)% by weight Phase A Sorbitan Stearate 3.00 Cyclopentasiloxane (and) Cyclohexasiloxane 2.00 Ethylhexyl Palmitate 3.00 Glyceryl Stearate (and) PEG-100 Stearate 3.00 Ethylhexyl Methoxycinnamate 1.00 Ethylhexyl Dimethyl PABA 1.00 Phase B Demineralized Water Qs 100 Ultrez 10 (Carbomer) 0.40 Phase C Glycerin 5.00 Preservative qs15 Phase D 3.00 Peptide according to the invention in a fat carrier Phase E Potassium Sorbate 0.10 Phase F Sodium Hydroxide 30% (Sodium Hydroxide) 0.60 Demineralized Water 6.00 G Phase Perfume 0.10 Protocol: Weigh phase A and heat it at 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: CALMOSENSINETm: sedative active ingredient marketed by Sederma (W01998 / 07744) containing lipo-dipeptide Tyr-Arg. It reduces feelings of discomfort. - SEBULESSTm: active ingredient marketed by Sederma comprising an extract of Syringa vulgaris obtained by cell culture in vitro, sebum regulator purifying, mattifies and refreshes the complexion, blurring imperfections. - PRODIZIATM: active ingredient marketed by Sederma including an extract of Albizia julibrissin, which promotes the visible reduction of signs of fatigue: dark circles, pockets, dull complexion and drawn features by repairing and protecting the skin from damage caused by glycation. - PACIFEELTm: active ingredient marketed by Sederma, including an extract of natural origin from the plant Mirabilis jalapa (Belle de nuit) which relieves feelings of discomfort (itching, tingling), reduces the redness of sensitive and reactive skin. 2) Gel form, for example firming gel for the body Ingredient (INCI name)% by weight Phase A Qs 100 Demineralized water Ultrez 10 (Carbomer) 0.20 Phase B PEG 400 5.00 Preservatives qs Phase C Dimethicone 4.00 Pemulen TR2 (Acrylates / C10-30 Alkyl Acrylate Cross Polymer) 0.20 Phase D 1.00 Tween 20 (Polysorbate 20) 2.00 Peptide in Fat Carrier Phase E Potassium Sorbate (Potassium Sorbate) 0.10 Phase F Hydroxide sodium 30% (Sodium Hydroxide) 0.60 Demineralized water 5.00 Phase G Fragrance 0.10 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: AQUALANCETm: osmoprotective moisturizing active ingredient marketed by Sederma (WO2009 / 104118) composed of homarine and erythritol. - LEGANCETm: anti-aging active ingredient marketed by Sederma, corresponding to an extract of Zingiber zerumbet Smith obtained by supercritical CO2 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. - BODYFITTm: active ingredient marketed by Sederma (WO 2004/024695) slimming / firming. JUVINITYTM: Active ingredient marketed by Sederma (WO 2011/125039) which reduces the signs of aging on the face and décolleté, smoothes wrinkles, restructures and densifies the dermis. Can be used as reinforcement of activity. 3) Compact powder form Ingredient (INCI name)% by weight Phase A Talc Qsp 100 Kaolin 2.00 Calcium Stearate 1.00 Mica 4.00 Silica 1.00 Bismuth Oxychloride 2.00 Potassium Sorbate qs Phenoxyethanol qs Phase B Unipure Black LC 989 HLC [CI 77499 (and) Hydrogenated Lecithin] 0.20 Unipure Red LC 381 HLC [CI 77491 (and) Hydrogenated Lecithin] 0.60 Unipure Yellow LC 182 HLC [CI 77492 (and) Hydrogenated Lecithin] 1.00 Covapearl Star Gold 2302 AS [CI 77891 (and) CI 77491 (and) Synthetic 0.50 Fluorphlogopite (and) Triethoxycaprylylsilane] Covapearl Brown 838 HLC [CI 77491 (and) Mica (and) Hydrogenated 1.00 Lecithin) Covapearl Dark Blue 637 [CI 77510 (&) CI 77891 (&) Mica] 0.10 Phase C Crodamol PTIS-LQ- (MV) [Pentaelythrityl Tetraisostearate] 4.00 Peptide according to the invention in a fatty matrix 3.00 Phase D Perfume 0.30 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 241m, an ingredient marketed by Sederma specifically designed for the formulation of moisturizing makeup powders; it is a powder composed of hollow particles of 25 μm (exines of Lycopodium clavatum) loaded with an extract of Imperata cylindrica having moisturizing properties. 4) Other cream form (face or body) Ingredient (INCI name)% by weight Phase A Arlacel 170 (Glyceryl Stearate (and) PEG-100 Stearate) 5.50 Abil Wax 2434 (Stearoxy Dimethicone) 3.00 Acetulan (Cetyl Acetate) (and) Acetylated Lanolin Alcohol 1.50 Crodacol C 90 (Cetyl Alcohol) 1.50 Ore Ore 3.00 Shea Butter 5.00 Unsaponifiable Shea 1.00 Parsol MCX (Ethylhexyl Methoxicinnamate) 3.50 Phase B Demineralized Water Qs 100 Phase C 0.20 Carbopol 940 (Carbomer) Phase D Demineralized Water 2.00 Triethanolamine 99% (Triethanolamine) 0.20 Phase E Propylene Glycol 0.10 Mixed Parabens Phase F Sodium Hydroxide 30% (Sodium Hydroxide) 5.00 Water demineralized qs Phase G Peptide according to the invention in a hydrophilic matrix 2.00 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: - SUBLISKINTm: active ingredient marketed by Sederma (WO2009 / 055663) which hydrates and smooths the skin while allowing it to withstand external aggressions. - VENUCEANETm: 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. - KOMBUCHKATm: active ingredient acting on the radiance of the complexion, marketed by Sederma (WO2004 / 01265 0). - INTENSLIMTm: 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.
    权利要求:
    Claims (13)
    [0001]
    REVENDICATIONS1. Peptide of general formula: X - Pro * - Pro * - Xaa - Y (1) with: - Xaa is chosen from Leucine (Leu, L), Arginine (Arg, R), Lysine (Lys, K) Alanine (Ala, A), Serine (Ser, S), and Aspartic Acid (Asp, D); at the N-terminus of the peptide, X is chosen from H, -CO-R 1 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 may be linear, branched, cyclic, polycyclic, unsaturated, hydroxylated, carbonylated, phosphorylated and / or sulfurized, said grouping may have in its backbone a heteroatom particularly O, S and / or N; and Pro * corresponding to Proline, an analogue or a derivative thereof.
    [0002]
    Peptide according to claim 1, characterized in that if X is H then Y is selected from OR1, NH2, NHR1 or NR1R2 and if Y is OH then X is -CO-R1 or -502-R1.
    [0003]
    3. Peptide according to one of the preceding claims, characterized in that in formula I, Pro * is Proline.
    [0004]
    Peptide according to one of the preceding claims, characterized in that Xaa is chosen from Leucine (Leu, L) and Arginine (Arg, R), the peptide being X-PPL-Y or X-PPR-Y. .
    [0005]
    5. Peptide according to one of the preceding claims, characterized in that R1 and / or R2 is an alkyl chain of 1 to 24 carbon atoms.
    [0006]
    Peptide according to claim 5, characterized in that R1 and / or R2 is an alkyl chain of 3 to 24 carbon atoms.
    [0007]
    7. Peptide according to one of the preceding claims, characterized in that X is an acyl group CO-R1 and Y is selected from OH, OMe, OEt and NH2.
    [0008]
    Peptide according to claim 7, characterized in that Y is OH.
    [0009]
    9. Peptide according to one of the preceding claims, characterized in that X is an acyl group CO-R1 selected from octanoyl (C8), decanoyl (C10), lauroyl (C12), myristoyl (C14), palmitoyl (C16). , stearoyl (C18), biotinoyl, elaidoyl, oleoyl and lipoyl.
    [0010]
    10. Peptide according to the preceding claim, characterized in that X is selected from a myristoyl (C14) or a palmitoyl (C16).
    [0011]
    Peptide according to claim 10, characterized in that X is a myristoyl.
    [0012]
    12. Peptide according to claim 11, selected from Myr-PPL-OH and Myr-PPR-OH.
    [0013]
    13. Topical composition, comprising as active ingredient at least one peptide according to any one of the preceding claims in a physiologically acceptable medium. Use of at least one peptide according to any one of claims 1 to 12 or A composition according to claim 13 for non-therapeutic cosmetic treatment for improving the general condition and appearance of the skin and / or its integuments. 15. Use according to claim 14, for the treatment of signs of aging and / or imperfections of the skin and its integuments. 16. Use according to claim 14 or 15 for topical cosmetic treatment. 17. Use according to one of claims 14 to 16 for a treatment: - Anti-wrinkles and fine lines, and / or - Improving the mechanical properties of the skin, firmness / tone / elasticity / flexibility, and / or - Increasing the density and the volume of the skin (volumizing, plumping effect), and / or - Restructuring), and / or - To fight against stretch marks.
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    2021-05-20| PLFP| Fee payment|Year of fee payment: 8 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1454632|2014-05-22|
    FR1454632A|FR3021319B1|2014-05-22|2014-05-22|PEPTIDES, COMPOSITIONS COMPRISING THE SAME, AND PARTICULARLY COSMETIC USES|FR1454632A| FR3021319B1|2014-05-22|2014-05-22|PEPTIDES, COMPOSITIONS COMPRISING THE SAME, AND PARTICULARLY COSMETIC USES|
    EP15732391.6A| EP3145943A1|2014-05-22|2015-05-21|Peptides, compositions comprising them and uses in particular cosmetic uses|
    US15/312,402| US10668000B2|2014-05-22|2015-05-21|Peptides, compositions comprising them and uses in particular cosmetic uses|
    PCT/IB2015/053737| WO2015181688A1|2014-05-22|2015-05-21|Peptides, compositions comprising them and uses in particular cosmetic uses|
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