FR2898811A1 - Cosmetic composition useful in anti-aging cosmetic product, comprises carnosine derivative or its salts and pseudodipeptide containing glutamic acid and tryptophan derivative - Google Patents
Cosmetic composition useful in anti-aging cosmetic product, comprises carnosine derivative or its salts and pseudodipeptide containing glutamic acid and tryptophan derivative Download PDFInfo
- Publication number
- FR2898811A1 FR2898811A1 FR0650989A FR0650989A FR2898811A1 FR 2898811 A1 FR2898811 A1 FR 2898811A1 FR 0650989 A FR0650989 A FR 0650989A FR 0650989 A FR0650989 A FR 0650989A FR 2898811 A1 FR2898811 A1 FR 2898811A1
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- derivative
- cosmetic composition
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- pseudodipeptide
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- 239000002537 cosmetic Substances 0.000 title claims abstract description 50
- CQOVPNPJLQNMDC-ZETCQYMHSA-N carnosine Chemical class [NH3+]CCC(=O)N[C@H](C([O-])=O)CC1=CNC=N1 CQOVPNPJLQNMDC-ZETCQYMHSA-N 0.000 title claims abstract description 21
- 150000003839 salts Chemical class 0.000 title claims abstract description 20
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 title claims abstract description 18
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 title claims abstract description 15
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- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 title abstract description 11
- ZQTUNIWBUQUKAM-UHFFFAOYSA-N [3-[2-(1h-imidazol-1-ium-4-yl)ethylamino]-3-oxopropyl]azanium;dichloride Chemical group Cl.Cl.NCCC(=O)NCCC1=CN=CN1 ZQTUNIWBUQUKAM-UHFFFAOYSA-N 0.000 claims description 9
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Description
COMPOSITION COSMETIQUE ANTI-AGE DE PREFERENCE POUR LE JOURANTI-AGING COSMETIC COMPOSITION OF PREFERENCE FOR THE DAY
L'invention concerne le domaine des produits cosmétiques et vise à offrir une nouvelle composition cosmétique qui permet de lutter contre le vieillissement cutané contenant l'association d'au moins deux polypeptides et, plus particulièrement, l'association d'au moins deux pseudopeptides synthétiques. The invention relates to the field of cosmetic products and aims to provide a novel cosmetic composition that makes it possible to combat cutaneous aging containing the combination of at least two polypeptides and, more particularly, the combination of at least two synthetic pseudopeptides. .
Par composition cosmétique capable de lutter contre le vieillissement cutané , on entend toute composition cosmétique capable d'empêcher et/ou de limiter l'apparition des signes du vieillissement cutané. By cosmetic composition capable of combating cutaneous aging is meant any cosmetic composition capable of preventing and / or limiting the appearance of the signs of skin aging.
On entend également toute composition cosmétique capable, lorsque la peau présente déjà des signes d'un vieillissement cutané, de corriger et/ou d'amoindrir ces signes de vieillissement. Les signes cliniques du vieillissement cutané sont notamment la présence de fines ridules puis des rides plus ou moins profondes, une désorganisation du grain de la peau avec un microrelief moins uniforme et de nature anisotrope, une perte de fermeté et de tonicité de la peau, une peau sèche, un amincissement de l'épaisseur de la peau.... It also means any cosmetic composition capable, when the skin already has signs of skin aging, to correct and / or reduce these signs of aging. The clinical signs of skin aging include the presence of fine wrinkles and more or less deep wrinkles, disorganization of the skin grain with a less uniform microrelief and anisotropic nature, a loss of firmness and tone of the skin, a dry skin, a thinning of the thickness of the skin ....
Il existe deux types de vieillissement cutané, le vieillissement intrinsèque ou chronologique induit par des processus génétiquement programmés et le vieillissement actinique lié aux expositions solaires. Ce dernier type de vieillissement est également appelé héliodermie. There are two types of skin aging, intrinsic or chronological aging induced by genetically programmed processes and actinic aging related to solar exposures. This last type of aging is also called heliodermia.
Le vieillissement cutané se caractérise par l'amincissement de l'épaisseur de la peau, avec une perte de 6% de l'épaisseur de la peau dès la naissance tous les dix ans (Robert et al., 2001, J. Méd. Esth. et Chir. Derm., vol. 28, pages 27-35). En effet, la prolifération des kératinocytes de l'épiderme ralentit au cours du temps ce qui provoque un amincissement tissulaire et une altération de la fonction de barrière. Skin aging is characterized by the thinning of skin thickness, with a loss of 6% of the thickness of the skin from birth every ten years (Robert et al., 2001, J. Med. and Chir Derm, vol 28, pages 27-35). In fact, the proliferation of keratinocytes in the epidermis slows down over time, which causes tissue thinning and an alteration of the barrier function.
Au niveau du derme, le métabolisme des fibroblastes ralentit également avec l'âge et leur capacité à synthétiser la matrice extracellulaire diminue ce qui provoque une atrophie du derme (Benoît et al., 2000, IFSCC Magazine, vol. 3, pages 11-17). Cette modification quantitative s'accompagne d'une modification qualitative de la composition de cette matrice extracellulaire. La quantité de collagène décline avec l'âge (Shuster et al., 1975, Brit. J. Dermatol., vol. 93, pages 639-43). En effet, la synthèse des collagènes fibrillaires (de type I et III en particulier) diminue légèrement avec l'âge mais de façon moindre pour le collagène de type III. La synthèse d'élastine et de fibronectine augmente avec l'âge (Robert et al., 2001, J. Méd. Esth. et Chir. Derm., vol. 28, pages 27-35). Parallèlement, la concentration effective de protéoglycanes et de glycosaminoglycanes dans le derme diminue, ce fait est particulièrement net pour l'acide hyaluronique qui devient indétectable à partir de 60 ans (Alirezai et Meynadier, 1997, Nouv. Dermatol., vol. 16, pages 41-47). Cette modification qualitative de la composition de la matrice extracellulaire cutanée modifie les propriétés mécaniques de la peau dont l'élasticité diminue et qui devient moins résistante à la pression. Cette modification se manifeste également par une perte d'hydratation des tissus. In the dermis, fibroblast metabolism also slows with age and their ability to synthesize the extracellular matrix decreases causing atrophy of the dermis (Benoît et al., 2000, IFSCC Magazine, vol 3, pages 11-17 ). This quantitative modification is accompanied by a qualitative modification of the composition of this extracellular matrix. The amount of collagen declines with age (Shuster et al., 1975, Brit J. Dermatol., Vol 93, pages 639-43). Indeed, the synthesis of fibrillar collagens (type I and III in particular) decreases slightly with age but less so for type III collagen. The synthesis of elastin and fibronectin increases with age (Robert et al., 2001, J. Med., Esth., And Chir, Derm, 28, pages 27-35). At the same time, the effective concentration of proteoglycans and glycosaminoglycans in the dermis decreases, this fact is particularly clear for hyaluronic acid which becomes undetectable from the age of 60 (Alirezai and Meynadier, 1997, New Dermatol., Vol 16, pages 41-47). This qualitative modification of the composition of the cutaneous extracellular matrix modifies the mechanical properties of the skin, the elasticity of which decreases and becomes less resistant to pressure. This modification is also manifested by a loss of tissue hydration.
La modification qualitative de la composition de la matrice extracellulaire cutanée est aggravée et accélérée par l'activité catabolique liée à l'âge. En effet, toutes les cellules de l'organisme sont capables de produire des enzymes protéolytiques pouvant s'attaquer à certains des constituants de la matrice extracellulaire comme les fibres de collagène et d'élastine. Ces enzymes sont respectivement appelées collagénases et élastases. Lors du vieillissement chronologique, une augmentation de l'activité élastasique des fibroblastes a pu être mis en évidence in vitro (Pelletier-Lebon et al., 1989, Cutaneous development, aging and repair, vol. 18, pages 341-345, Fidia Research Series, Liviana Press). Cette augmentation semble être un processus intrinsèque au niveau de la régulation des gènes et de leurs transcrits. L'augmentation de l'activité de ces protéases entraîne une augmentation de la libération de peptides pouvant agir sur les cellules et modifier leur phénotype. Par exemple, le récepteur de l'élastine activé par des peptides de l'élastine augmente la production d'élastases par les fibroblastes (Archilla-Marcos et Robert, 1993, Clin. Physiol. Biochem., vol. 10, pages 86-91). The qualitative change in the composition of the cutaneous extracellular matrix is aggravated and accelerated by age-related catabolic activity. Indeed, all cells of the body are able to produce proteolytic enzymes that can attack some of the constituents of the extracellular matrix such as collagen and elastin fibers. These enzymes are respectively called collagenases and elastases. During chronological aging, an increase in the elastase activity of fibroblasts could be demonstrated in vitro (Pelletier-Lebon et al., 1989, Cutaneous development, aging and repair, vol 18, pages 341-345, Fidia Research Series, Liviana Press). This increase appears to be an intrinsic process in the regulation of genes and their transcripts. The increase in the activity of these proteases causes an increase in the release of peptides that can act on the cells and modify their phenotype. For example, the elastin receptor activated by elastin peptides increases the production of elastases by fibroblasts (Archilla-Marcos and Robert, 1993, Clin Physiol Biochem, Vol 10, pages 86-91). ).
Le vieillissement actinique est induit par l'accumulation de radicaux libres dérivés de l'oxygène au niveau de la peau. Cet excès de radicaux libres ne peut plus être neutralisé par les défenses anti-radicalaires endogènes et entraîne des modifications chimiques des constituants cellulaires et extracellulaires (Benoît et al., 2000, IFSCC Magazine, vol. 3, pages 11-17). Lors du vieillissement actinique, d'importantes modifications enzymatiques conditionnent la dégradation de la matrice extracellulaire du derme. En effet, les réactions induites par les radicaux libres dérivés de l'oxygène dégradent notamment le collagène dont les molécules sont coupées et libèrent des peptides activateurs des polynucléaires, ces derniers accentuant la dégradation du tissu conjonctif (Alirezai et Meynadier, 1997, Nouv. Actinic aging is induced by the accumulation of free radicals derived from oxygen in the skin. This excess of free radicals can no longer be neutralized by the endogenous anti-free radical defenses and leads to chemical modifications of the cellular and extracellular constituents (Benoît et al., 2000, IFSCC Magazine, vol 3, pages 11-17). During actinic aging, important enzymatic modifications condition the degradation of the extracellular matrix of the dermis. In fact, the reactions induced by the free radicals derived from oxygen degrade the collagen whose molecules are cut off and release polynuclear activating peptides, the latter accentuating the degradation of the connective tissue (Alirezai and Meynadier, 1997, Nouv.
Dermatol., vol. 16, pages 41-47). De plus, l'activité élastasique de la peau augmente à la suite d'irradiations par les UV (Labat-Robert et al., 2000, J. Photochem. Photobiol., vol. 57, pages 113-118). Dermatol., Vol. 16, pages 41-47). In addition, the elastasic activity of the skin increases as a result of UV irradiation (Labat-Robert et al., 2000, J. Photochem Photobiol., Vol 57, pages 113-118).
Il a été démontré et observé en microscopie électronique que des contacts existent entre fibres nerveuses et cellules cutanées de toutes sortes (kératinocytes, mélanocytes, cellules immunitaires, fibroblastes, adipocytes,...). Le système nerveux participe donc à l'anatomie et à la physiologie cutanée. Les cellules cutanées sont capables non seulement de produire des neuromédiateurs mais aussi d'en être les cibles dans la mesure où elles possèdent des récepteurs. A titre d'exemple, les kératinocytes synthétisent des neuromédiateurs cutanés et possèdent des récepteurs au neuropeptide qu'est la substance P. Les cellules nerveuses ne sont douées que d'un faible potentiel de régénération (ou de renouvellement). Le vieillissement cutané entraîne une neurodégénérescence et une perturbation des connexions du réseau nerveux cutané. It has been demonstrated and observed by electron microscopy that contacts exist between nerve fibers and cutaneous cells of all kinds (keratinocytes, melanocytes, immune cells, fibroblasts, adipocytes, etc.). The nervous system thus participates in anatomy and cutaneous physiology. Cutaneous cells are able not only to produce neuromediators but also to be targets because they have receptors. For example, keratinocytes synthesize cutaneous neuromediators and have neuropeptide receptors that are the substance P. Nerve cells have only a low regeneration (or renewal) potential. Skin aging causes neurodegeneration and disruption of the connections of the cutaneous nervous system.
Ainsi, une composition cosmétique utile pour lutter contre le vieillissement cutané doit contenir des actifs présentant une activité anti-radicalaire et capables de conserver les capacités réactives fonctionnelles des cellules nerveuses et de les protéger des agressions. Les travaux de la Demanderesse ont permis de mettre en évidence que l'association d'un dérivé de carnosine et d'un pseudodipeptide et, plus particulièrement, d'un pseudoodipeptide contenant au moins de l'acide glutamique permet de répondre aux problèmes techniques cités ci-dessus. Ainsi, la présente invention concerne une composition cosmétique comprenant au moins un dérivé de carnosine ou un de ses sels et au moins un pseudodipeptide contenant de l'acide glutamique et un dérivé de tryptophane. Thus, a cosmetic composition that is useful for combating cutaneous aging must contain active agents that exhibit anti-radical activity and that are capable of retaining the functional reactive capacities of nerve cells and protecting them from attack. The work of the Applicant has made it possible to demonstrate that the combination of a carnosine derivative and a pseudodipeptide and, more particularly, of a pseudoodipeptide containing at least glutamic acid makes it possible to respond to the technical problems mentioned. above. Thus, the present invention relates to a cosmetic composition comprising at least one carnosine derivative or a salt thereof and at least one pseudodipeptide containing glutamic acid and a tryptophan derivative.
Dans le cadre de la présente invention, la composition cosmétique contient au moins un dérivé de carnosine ou un de ses sels. La carnosine, dipeptide de formule C9H1403N4 est l'association de deux acides aminés que sont l'histidine et la (3-alanine. Cette molécule est présente naturellement dans les cellules vivantes et, en particulier, dans les cellules nerveuses et les cellules musculaires qui contiennent des taux de carnosine élevés. Par dérivé de la carnosine , on entend dans le cadre de la présente invention, d'une part, un pseudodipeptide contenant de l'histidine (ou un dérivé d'histidine) et de la (3-alanine (ou un dérivé de 13-alanine) mais dans lequel la liaison reliant ces deux acides aminés (ou dérivés) est une liaison pseudopeptidique et, d'autre part, un pseudodipeptide dans lequel au moins un des deux acides aminés choisis parmi l'histidine et la b-alanine est un dérivé dudit acide aminé et la liaison est une liaison peptidique classique. Par liaison pseudopeptidique , on entend toute liaison capable de remplacer une liaison peptidique classique telle qu'une liaison rétro, inverso, rétroinverso, carba (liaison CH2-CH2) et aza. Dans le cadre de la présente invention, on entend par dérivé d'acide aminé , quel que soit l'acide aminé considéré, un énantiomère, un diastéréoisomère, un acide aminé naturel de conformation D, un acide aminé dérivé après action enzymatique, un acide aminé protégé par une fonction chimique, un acide aminé auquel un groupement a été ajouté et/ou supprimé. Ce groupement, lorsqu'il est ajouté, est susceptible d'apporter de meilleures propriétés au pseudodipeptide selon l'invention. Ainsi, par exemple, un tel groupement peut être ajouté en vue de faciliter une meilleure pénétration dans la peau, ces groupements étant, par exemple, des radicaux de type "oléyl", "stéaryl", "palmityl", etc.... De plus, par exemple, il se peut, pour des motifs de résistance ou d'efficacité, que le dérivé d'acide aminé soit un acide aminé modifié sur ses fonctions acides carboxyliques et/ou sur ses fonctions amines. Ainsi, un dérivé d'acide aminé selon l'invention est un acide aminé modifié par acylation ou acétylation sur sa fonction amine et/ou par amidation ou estérification sur sa fonction carboxylique, la fonction carboxylique dudit dérivé d'acide aminé peut être également supprimée. In the context of the present invention, the cosmetic composition contains at least one carnosine derivative or one of its salts. Carnosine, a dipeptide of the formula C9H1403N4, is the combination of two amino acids, histidine and (3-alanine), which is naturally present in living cells and, in particular, in nerve cells and muscle cells. In the context of the present invention, carnosine derivative is understood to mean, on the one hand, a pseudodipeptide containing histidine (or a histidine derivative) and (3-alanine). (or a 13-alanine derivative) but in which the bond connecting these two amino acids (or derivatives) is a pseudopeptide bond and, on the other hand, a pseudodipeptide in which at least one of the two amino acids chosen from histidine and the β-alanine is a derivative of said amino acid and the linkage is a conventional peptide bond. <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> <br/> A pseudopeptide binding is any binding capable of replacing a conventional peptide bond such ro, inverso, retroinverso, carba (CH2-CH2 bond) and aza. In the context of the present invention, the term "amino acid derivative", regardless of the amino acid considered, an enantiomer, a diastereoisomer, a natural amino acid conformation D, an amino acid derived after enzymatic action, an acid amine protected by a chemical function, an amino acid to which a group has been added and / or deleted. This group, when added, is likely to bring better properties to the pseudodipeptide according to the invention. Thus, for example, such a group may be added in order to facilitate better penetration into the skin, these groups being, for example, radicals of the "oleyl", "stearyl", "palmityl", etc. type. In addition, for example, it may be, for reasons of resistance or efficiency, that the amino acid derivative is an amino acid modified on its carboxylic acid functions and / or on its amine functions. Thus, an amino acid derivative according to the invention is an amino acid modified by acylation or acetylation on its amine function and / or by amidation or esterification on its carboxylic function, the carboxylic function of said amino acid derivative can also be suppressed .
De façon avantageuse, le dérivé de carnosine mis en oeuvre dans le cadre de la présente invention est la 13-alanyl-L-histamine, également connue sous le nom de décarboxy-carnosine ou de carcinine, l'histidine de la carnosine ayant été remplacée par l'histamine par suppression de la fonction carboxylique. Ce dérivé est d'une très grande stabilité et résiste à l'hydrolyse enzymatique. Il peut être d'origine naturelle ou d'origine synthétique. En ce qui concerne l'origine naturelle d'un tel dérivé, il a été découvert dans le tissu cardiaque du crustacé Carcinus maenas (Arnould et Frentz, 1975, Comp. Biochem. Physiol., vol. 50, pages 59-66) et, depuis lors, a été identifié dans les tissus de mammifères riches en histamine tels que le coeur, le rein, l'estomac et l'intestin. L'homme du métier connaît des méthodes pour extraire et/ou purifier un tel dérivé. Par origine synthétique , on entend dans le cadre de la présente invention de la (3-alanyl-L-histamine, sous forme pure ou en solution, à différentes concentrations, obtenue par synthèse chimique. Un procédé de synthèse chimique d'un tel dérivé est notamment décrit dans l'article de Babizhayev et al., 1994, Biochem J., vol. 304, pages 509-516. Les sels et plus particulièrement les sels d'addition d'un dérivé de carnosine utilisables dans le cadre de la présente invention sont notamment choisis parmi les sels d'addition avec un acide tels que les chlorhydrates, les bromhydrates, les sulfates, les sulfonates, les carboxylates, les citrates, les succinates, les tartrates, les lactates, les tosylates, les benzènesultonates, les phosphates et les acétates et les sels d'addition avec une base telles que la soude, la potasse, l'ammoniaque, les amines ou les alcanolamines et les mélanges de ceux-ci. Un sel d'addition particulièrement préféré dans le cadre de la présente invention est le chlorhydrate. Ainsi, un composé préféré en tant que sel d'un dérivé de carnosine utilisé dans le cadre de la présente invention est le chlorhydrate de décarboxy-carnosine. Ce composé est notamment commercialisé sous forme d'une solution hydroglycolique par la société Exsymol (Monaco, Principauté de Monaco) sous la dénomination Alistin . La composition cosmétique dans le cadre de la présente invention contenant un dérivé de carnosine et/ou un de ses sels en association avec un pseudodipeptide contenant de l'acide glutamique et un dérivé de tryptophane permet d'améliorer la capacité de la peau à se défendre contre les dommages induits par les UV et, donc, de lutter contre le vieillissement actinique. En effet, l'effet protecteur du chlorhydrate de décarboxycarnosine utilisé à 0,1% sur la SuperOxyde Dismutase (SOD) naturelle de la peau a été évalué ex vivo sur une fraction cutanée épiderme-derme irradiée par les UVA et UVB suivi par la mesure de la réduction du cytochrome C par l'anion superoxyde (02-). Ce test a permis de montrer une augmentation de 43% de la capacité de la peau à se défendre contre les dommages induits par les UV en présence de chlorhydrate de décarboxy-carnosine. De plus, sur des surnageants de cultures primaires de fibroblastes humains soumis à une irradiation aux UVA à 30 J/cm2, en présence ou non de chlorhydrate de décarboxy-carnosine, le malondialdéhyde (MDA) libéré lors d'une réaction radicalaire en chaîne à l'intérieur des membranes cellulaires a été dosé par réaction avec l'acide thiobarbiturique. Ce test a permis de mettre en évidence le rôle anti-radicalaire du chlorhydrate de décarboxycarnosine qui, à 0,005%, inhibe quasi-totalement les substances réactives avec l'acide thiobarbiturique (TBars). Dans la composition cosmétique de la présente invention, le dérivé de carnosine ou l'un de ses sels tels que définis précédemment représente de 0,0001 à 10% en poids, avantageusement de 0,0001 à 1% en poids, plus particulièrement de 0,0005 à 0,5% en poids et, tout particulièrement, de 0,001 à 0,2% en poids par rapport au poids total de ladite composition. Advantageously, the carnosine derivative used in the context of the present invention is 13-alanyl-L-histamine, also known under the name of decarboxy carnosine or carcinine, the carnosine histidine having been replaced. by histamine by suppression of the carboxylic function. This derivative is very stable and resistant to enzymatic hydrolysis. It can be of natural origin or of synthetic origin. As regards the natural origin of such a derivative, it has been found in the heart tissue of crustacean Carcinus maenas (Arnould and Frentz, 1975, Biochem Physiol., Vol 50, pages 59-66) and since then has been identified in histamine-rich mammalian tissues such as the heart, kidney, stomach and intestine. Those skilled in the art know methods for extracting and / or purifying such a derivative. By synthetic origin is meant in the context of the present invention of (3-alanyl-L-histamine, in pure form or in solution, at different concentrations, obtained by chemical synthesis A chemical synthesis process of such a derivative is particularly described in the article by Babizhayev et al., 1994, Biochem J., vol 304, pages 509-516 .The salts and more particularly the addition salts of a carnosine derivative that can be used in the context of The present invention is especially chosen from acid addition salts such as hydrochlorides, hydrobromides, sulphates, sulphonates, carboxylates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates and addition salts with a base such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines and mixtures thereof.A particularly preferred addition salt in the context of the present invention. presen the invention is the hydrochloride. Thus, a preferred compound as a salt of a carnosine derivative used in the context of the present invention is decarboxy carnosine hydrochloride. This compound is in particular marketed in the form of a glycolic solution by the company Exsymol (Monaco, Principality of Monaco) under the name Alistin. The cosmetic composition in the context of the present invention containing a carnosine derivative and / or a salt thereof in combination with a pseudodipeptide containing glutamic acid and a tryptophan derivative improves the ability of the skin to defend itself against UV-induced damage and therefore fight against actinic aging. Indeed, the protective effect of decarboxycarnosine hydrochloride used at 0.1% on the natural Superoxide Dismutase (SOD) of the skin was evaluated ex vivo on an epidermal-dermal fraction irradiated with UVA and UVB followed by measurement. reduction of cytochrome C by superoxide anion (02-). This test showed a 43% increase in the skin's ability to defend against UV-induced damage in the presence of decarboxy carnosine hydrochloride. In addition, on supernatants from primary cultures of human fibroblasts subjected to UVA irradiation at 30 J / cm 2, in the presence or absence of decarboxy carnosine hydrochloride, the malondialdehyde (MDA) released during a free radical chain reaction. the interior of the cell membranes was determined by reaction with thiobarbituric acid. This test made it possible to highlight the anti-radical role of decarboxycarnosine hydrochloride which, at 0.005%, almost completely inhibits substances reactive with thiobarbituric acid (TBars). In the cosmetic composition of the present invention, the carnosine derivative or a salt thereof as defined above represents from 0.0001 to 10% by weight, advantageously from 0.0001 to 1% by weight, more particularly from 0 to , 0005 to 0.5% by weight and, especially, from 0.001 to 0.2% by weight relative to the total weight of said composition.
Dans le cadre de la présente invention, la composition cosmétique contient, associé au dérivé de carnosine ou à l'un de ses sels, un pseudodipeptide contenant de l'acide glutamique et un dérivé de tryptophane. Un dérivé de tryptophane préféré dans le cadre de la présente invention est le dérivé dans lequel la fonction carboxylique du tryptophane a été supprimée. Ainsi, le pseudodipeptide contentant de l'acide glutamique et un dérivé de tryptophane mis en oeuvre dans le cadre de la présente invention est avantageusement le L-glutamylamidoethyl indole de formule : HOOC O H2N H H H Le pseudodipeptide contenant de l'acide glutamique et un dérivé de tryptophane mis en oeuvre dans le cadre de la présente invention et tel que précédemment défini est d'origine synthétique et se trouve avantageusement sous forme d'une solution aqueuse stable. On peut, à titre d'exemple, utiliser la solution aqueuse stable de L-glutamylamidoethyl indole synthétique commercialisée par la société Exsymol (Monaco, Principauté de Monaco) sous la marque GLISTIN . L'activité neurotrophique et antineurodégénérescence du pseudodipeptide contenant de l'acide glutamique et un dérivé de tryptophane et, en particulier, du L-glutamylamidoethyl indole avantageusement associé à un dérivé de carnosine ou à l'un de sels a été mis en évidence. En effet, le L-glutamylamidoethyl indole est capable de protéger des cellules nerveuses PC12 irradiées par des UVB à 285 nm mais cette protection n'est pas uniquement due à un effet anti-oxydant du L-glutamylamidoethyl indole. Cet effet prépondérant est qualifié d'effet neurotrophique, c'est- à-dire capable de jouer le rôle de facteurs neurospécifiques tels que le NGF (pour Nerve Growth Factor). La croissance des cellules nerveuses passe par un stade de différenciation, de cellules précurseurs indifférenciées (morphologiquement indistinctes) vers des cellules nerveuses morphologiquement caractéristiques de par la présence de dendrites. Le processus de différenciation se produit sous l'effet de facteurs neurotrophiques tels que le NGF. Les cellules nerveuses PC12 cultivées dans un milieu riche en NGF conduisent à une différenciation optimale caractérisée par la présence de dendrites et d'un important réseau neuronal, alors qu'un défaut de NGF conduit à un réseau altéré et à la mort par apoptose des cellules (neurodégénérescence). Or l'apport de L-glutamylamidoethyl indole à des concentrations de l'ordre de 0,05 à 0,1 mg/ml permet de suppléer au défaut de NGF en maintenant l'intégrité du réseau neuronal et permet d'éviter la neurodégénérescence ainsi que la mort apoptotique des cellules nerveuses. L'action du L-glutamylamidoethyl indole pourrait s'expliquer via l'expression de neuropeptides et d'interleukines puisque, 5 jours après la différenciation des cellules nerveuses PC12, le L-glutamylamidoethyl indole favorise l'expression du neuropeptide Y (NPY), du peptide intestinal vasoactif (VIP pour Vasoactive Intestinal Peptide) et de l'interleukine 6. Dans la composition cosmétique de la présente invention, le pseudodipeptide contenant de l'acide glutamique et un dérivé de tryptophane tel que précédemment défini représente de 0,0001 à 10% en poids, avantageusement de 0,0001 à 1% en poids, plus particulièrement de 0,0005 à 0,1% en poids et, tout particulièrement, de 0,001 à 0,01% en poids par rapport au poids total de ladite composition. In the context of the present invention, the cosmetic composition contains, associated with the carnosine derivative or one of its salts, a pseudodipeptide containing glutamic acid and a tryptophan derivative. A preferred tryptophan derivative in the context of the present invention is the derivative in which the carboxylic function of tryptophan has been suppressed. Thus, the pseudodipeptide containing glutamic acid and a tryptophan derivative used in the context of the present invention is advantageously L-glutamylamidoethyl indole of formula: HOOC O H2N HHH The pseudodipeptide containing glutamic acid and a derivative Tryptophan used in the context of the present invention and as defined above is of synthetic origin and is advantageously in the form of a stable aqueous solution. By way of example, it is possible to use the stable aqueous solution of synthetic L-glutamylamidoethyl indole marketed by Exsymol (Monaco, Principality of Monaco) under the trademark GLISTIN. The neurotrophic and antineurodegenerative activity of the pseudodipeptide containing glutamic acid and a derivative of tryptophan and, in particular, L-glutamylamidoethyl indole advantageously associated with a carnosine derivative or with one of salts has been demonstrated. Indeed, L-glutamylamidoethyl indole is capable of protecting irradiated PC12 nerve cells with UVB at 285 nm, but this protection is not solely due to an anti-oxidant effect of L-glutamylamidoethyl indole. This preponderant effect is called a neurotrophic effect, that is to say capable of acting as neurospecific factors such as NGF (for Nerve Growth Factor). The growth of nerve cells goes through a stage of differentiation, from undifferentiated (morphologically indistinct) precursor cells to morphologically characteristic nerve cells by the presence of dendrites. The differentiation process occurs under the effect of neurotrophic factors such as NGF. PC12 nerve cells cultured in a medium rich in NGF lead to an optimal differentiation characterized by the presence of dendrites and an important neuronal network, whereas a defect of NGF leads to an altered network and to the death by apoptosis of the cells (neurodegeneration). However, the intake of L-glutamylamidoethyl indole at concentrations of the order of 0.05 to 0.1 mg / ml makes it possible to compensate for the defect of NGF by maintaining the integrity of the neuronal network and makes it possible to avoid neurodegeneration as well. than the apoptotic death of nerve cells. The action of L-glutamylamidoethyl indole could be explained by the expression of neuropeptides and interleukins since, 5 days after the differentiation of PC12 nerve cells, L-glutamylamidoethyl indole promotes the expression of neuropeptide Y (NPY), vasoactive intestinal peptide (VIP for Vasoactive Intestinal Peptide) and interleukin 6. In the cosmetic composition of the present invention, the pseudodipeptide containing glutamic acid and a tryptophan derivative as defined above is from 0.0001 to 10% by weight, advantageously from 0.0001 to 1% by weight, more particularly from 0.0005 to 0.1% by weight and, more particularly, from 0.001 to 0.01% by weight relative to the total weight of said composition.
La composition cosmétique selon la présente invention peut en outre contenir un autre polypeptide et, plus particulièrement, un tétrapeptide. De façon préférée, le tétrapeptide que peut contenir la composition cosmétique selon l'invention est un tétrapeptide dérivé de l'hormone de jeunesse et, avantageusement, un tétrapeptide acétylé dérivé de l'hormone de jeunesse. Ce tétrapeptide est d'origine synthétique et se trouve sous la forme d'une solution aqueuse. Il s'agit de façon particulièrement préférée du tétrapeptide acétylé dérivé de l'hormone de jeunesse commercialisé par la société Institut Européen de Biologie Cellulaire (Ramonville-Saint-Agne, France) sous la marque THYMULEN 4 . Ce tétrapeptide est capable de compenser la perte naturelle des facteurs thymiques liée au déclin du thymus avec l'âge, de favoriser la synthèse des cytokines et la croissance des kératinocytes et de moduler l'immunovigilence cutanée des cellules de Langerhans en induisant la synthèse du facteur de croissance des polynucléaires et des macrophages (GM-CSF pour Granulocyte Macrophage Colony Stimulating Factor). Dans la composition cosmétique selon l'invention, le tétrapeptide tel que défini précédemment représente de 0,0001 à 10% en poids, avantageusement de 0,0001 à 1% en poids, plus particulièrement de 0,0001 à 0,1% en poids et, tout particulièrement, de 0,0002 à 0,01% en poids et, plus particulièrement encore, de 0,0002 à 0,001% en poids par rapport au poids total de ladite composition. The cosmetic composition according to the present invention may further contain another polypeptide and, more particularly, a tetrapeptide. Preferably, the tetrapeptide that can contain the cosmetic composition according to the invention is a tetrapeptide derived from the youth hormone and, advantageously, an acetylated tetrapeptide derived from the youth hormone. This tetrapeptide is of synthetic origin and is in the form of an aqueous solution. This is particularly preferably acetylated tetrapeptide derived from the youth hormone marketed by the European Institute of Cell Biology (Ramonville-Saint-Agne, France) under the trademark THYMULEN 4. This tetrapeptide is able to compensate for the natural loss of thymic factors related to the decline of the thymus with age, to promote the synthesis of cytokines and the growth of keratinocytes and to modulate cutaneous immunovigilence of Langerhans cells by inducing factor synthesis. polynuclear and macrophage growth (GM-CSF for Granulocyte Macrophage Colony Stimulating Factor). In the cosmetic composition according to the invention, the tetrapeptide as defined above represents from 0.0001 to 10% by weight, advantageously from 0.0001 to 1% by weight, more particularly from 0.0001 to 0.1% by weight. and, most preferably, from 0.0002 to 0.01% by weight and even more preferably from 0.0002 to 0.001% by weight relative to the total weight of said composition.
La composition cosmétique de la présente invention à application topique peut constituer notamment une composition de protection, de traitement ou de soin cosmétique ou dermatologique pour le visage, pour le cou, pour les mains ou pour le corps, comme, par exemple, crèmes de jour, crèmes de nuit, crèmes ou huiles solaires, laits corporels), une composition de maquillage (par exemple fond de teint) ou une composition de bronzage artificiel. La composition cosmétique de la présente invention est, dans une forme de mise en oeuvre préférée, un soin de jour. The cosmetic composition of the present invention for topical application can constitute in particular a composition for the protection, treatment or cosmetic or dermatological treatment for the face, the neck, the hands or the body, such as, for example, day creams. , night creams, sun creams or oils, body milks), a makeup composition (for example a foundation) or an artificial tanning composition. The cosmetic composition of the present invention is, in a preferred embodiment, a day care.
La composition cosmétique selon la présente invention peut contenir un ou plusieurs autres composants connus de l'homme du métier, comme des agents de formulation ou additifs d'usage connu et classique dans les compositions cosmétiques. A titre d'exemple et de façon non limitative, de tels agents de formulation et additifs peuvent être des gélifiants hydrophiles ou lipophiles, des additifs hydrophiles ou lipophiles, des adoucissants, des colorants, des agents solubilisants, des agents de texture (sorbitol), des parfums, des charges, des absorbeurs d'odeur, des actifs filmogènes, des conservateurs, des tensio-actifs, des émulsionnants, des huiles, des glycols, des vitamines, des filtres solaires,.... Grâce à ses connaissances en matière de cosmétiques, l'homme du métier saura quels agents de formulation ajouter à la composition cosmétique selon l'invention et en quelles quantités en fonction des propriétés recherchées. The cosmetic composition according to the present invention may contain one or more other components known to those skilled in the art, such as formulating agents or additives of known and conventional use in cosmetic compositions. By way of example and without limitation, such formulating agents and additives may be hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, softeners, dyes, solubilizing agents, texturing agents (sorbitol), perfumes, fillers, odor absorbers, film-forming active agents, preservatives, surfactants, emulsifiers, oils, glycols, vitamins, sunscreens, .... of cosmetics, those skilled in the art will know which formulating agents to add to the cosmetic composition according to the invention and in what quantities according to the desired properties.
De plus, la composition cosmétique selon la présente invention peut se présenter sous toute forme connue de l'homme du métier dans le domaine de la cosmétique sans aucune autre restriction galénique particulière autre que celle pour l'application sur la peau. Ainsi, la composition cosmétique selon l'invention peut avoir la forme d'une solution ou suspension aqueuse, alcoolique ou d'une suspension huileuse ou d'une solution ou d'une dispersion de type lotion ou sérum, d'une émulsion de consistance liquide ou semi-liquide de type lait, obtenues par dispersion d'une phase grasse dans une phase aqueuse (émulsion Huile dans Eau H/E) ou inversement (Eau dans Huile : E/H), ou d'une suspension ou émulsion de consistance molle du type crème H/E ou E/H ou d'un gel aqueux ou anhydre, d'un onguent, d'une lotion, d'un masque ou encore de microcapsules ou microparticules, ou d'une dispersion vésiculaire de type ionique et/ou non ionique. On peut également envisager les formulations cosmétiques selon l'invention sous la forme d'une mousse ou encore sous forme de compositions pour aérosol comprenant également un agent propulseur sous pression. In addition, the cosmetic composition according to the present invention may be in any form known to those skilled in the field of cosmetics without any other particular pharmaceutical restriction other than that for application to the skin. Thus, the cosmetic composition according to the invention may have the form of an aqueous solution, or an alcoholic suspension or an oily suspension or a solution or dispersion of the lotion or serum type, of a consistency emulsion. liquid or semi-liquid milk-type, obtained by dispersion of a fatty phase in an aqueous phase (oil in water emulsion O / W) or conversely (water in oil: W / O), or a suspension or emulsion of soft consistency of the O / W or W / O cream type or of an aqueous or anhydrous gel, an ointment, a lotion, a mask or else microcapsules or microparticles, or a vesicular dispersion of the type ionic and / or nonionic. It is also possible to envisage the cosmetic formulations according to the invention in the form of a foam or in the form of aerosol compositions also comprising a propellant under pressure.
La présente invention concerne également l'utilisation d'un dérivé de la carnosine ou de l'un de ses sels et d'au moins un pseudodipeptide contenant de l'acide glutamique et un dérivé de tryptophane, et/ou d'une composition cosmétique telle que précédemment définie dans un produit cosmétique anti-âge. The present invention also relates to the use of a derivative of carnosine or of one of its salts and of at least one pseudodipeptide containing glutamic acid and a tryptophan derivative, and / or a cosmetic composition as previously defined in an anti-aging cosmetic product.
Enfin, la présente invention concerne un procédé cosmétique destiné à empêcher et/ou à limiter l'apparition des signes du vieillissement cutané et/ou à les corriger et/ou à les amoindrir. Ce procédé comprend les étapes consistant à appliquer une quantité suffisante d'une composition cosmétique selon l'invention. Par quantité suffisante , on entend dans le cadre de la présente invention une quantité capable de diminuer et/ou d'amoindrir les fines ridules et/ou les rides plus ou moins profondes, capable de réorganiser le grain de la peau, d'uniformiser le microrelief de la peau, capable de restaurer et/ou d'améliorer la fermeté et la tonicité de la peau etc.... De préférence, dans le procédé cosmétique selon l'invention, l'application de la composition cosmétique est effectuée le jour au moment du réveil et/ou à toute heure de la journée. Finally, the present invention relates to a cosmetic process for preventing and / or limiting the appearance of the signs of skin aging and / or to correct and / or reduce them. This method comprises the steps of applying a sufficient amount of a cosmetic composition according to the invention. By sufficient quantity is meant in the context of the present invention an amount capable of reducing and / or reducing fine fine lines and / or wrinkles of greater or lesser depth, capable of rearranging the grain of the skin, of uniformizing the skin. microrelief of the skin, capable of restoring and / or improving the firmness and the tonicity of the skin, etc. Preferably, in the cosmetic process according to the invention, the application of the cosmetic composition is carried out on the day when waking up and / or at any time of the day.
D'autres avantages et caractéristiques de l'invention apparaîtront à la lecture des exemples de formulation ci-après qui sont donnés à titre illustratif et ne sauraient être interprétés comme limitant la portée de l'invention. 1. Exemple de crème pour le jour selon la présente invention. % MONOSTEARATE DE GLYCEROL AE 2,50 CETEARYL ISONONANOATE 12,00 BHT 0,02 CETEARYL GLUCOSIDE 3,50 TRIGLYCERIDES C8 CIO 4,00 DIMETHICONE 5,00 CARBOMER 0,25 EDTA DISODIQUE 0,10 GLYCERINE 5,00 SODIUM HYDROXIDE 0,111 DIMETHICONE 1,00 THYMULEN 0,70 GLISTIN 0,50 ALISTIN 0,05 PARFUM 0,20 CONSERVATEUR 0,50 EAU DEMINERALISEE Q.S.P 100 II. Exemple de gel pour le jour selon la présente invention. Other advantages and characteristics of the invention will appear on reading the examples of formulation below which are given for illustrative purposes and can not be interpreted as limiting the scope of the invention. 1. Example of cream for the day according to the present invention. % GLYCEROL MONOSTEARATE AE 2.50 CETEARYL ISONONANOATE 12.00 BHT 0.02 CETEARYL GLUCOSIDE 3.50 TRIGLYCERIDES C8 CIO 4.00 DIMETHICONE 5.00 CARBOMER 0.25 DISODIUM EDTA 0.10 GLYCERIN 5.00 SODIUM HYDROXIDE 0.111 DIMETHICONE 1 , 00 THYMULEN 0.70 GLISTIN 0.50 ALISTIN 0.05 PERFUME 0.20 PRESERVATIVE 0.50 DEMINERALIZED WATER QSP 100 II. Example of a gel for the day according to the present invention.
CETEARYL OCTANOATE 4,00 POLYDECENE 5,50 TRIGLYCERIDES C8 CIO 2,00 DIMETHICONE 1,00 DL ALPHA TOCOPHEROL 0,02 PEMULEN TRI 0,25 ISONONANOATE D'ISONONYLE 3,00 DERIVE DE CELLULOSE 0,20 GLYCERINE 5,00 EDTA DISODIQUE 0,05 SODIUM HYDROXIDE 0,09 CARBOMER 1,30 THYMULEN 0,60 GLISTIN 0,50 ALISTIN 0,05 PARFUM 0,20 CONSERVATEUR 0,50 EAU DEMINERALISEE Q.S.P 100 CETEARYL OCTANOATE 4.00 POLYDECENE 5.50 TRIGLYCERIDES C8 CIO 2.00 DIMETHICONE 1.00 DL ALPHA TOCOPHEROL 0.02 PEMULEN TRI 0.25 ISONONYLATED ISONONYLATE 3.00 CELLULOSE DERIVED 0.20 GLYCERIN 5.00 DISODIUM EDTA 0 , 05 SODIUM HYDROXIDE 0.09 CARBOMER 1.30 THYMULEN 0.60 GLISTIN 0.50 ALISTIN 0.05 PERFUME 0.20 PRESERVATIVE 0.50 DEMINERALIZED WATER QSP 100
Claims (12)
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111035816A (en) * | 2019-12-30 | 2020-04-21 | 嫦娥创新（武汉）生物科技有限公司 | Composition for maintaining microecological balance of female lower reproductive system and application |
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| Publication number | Publication date |
|---|---|
| FR2898811B1 (en) | 2012-04-06 |
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