FR2668365A1 - Use in cosmetics of N-acetyl peptides endowed with biological activity - Google Patents

Use in cosmetics of N-acetyl peptides endowed with biological activity Download PDF

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FR2668365A1
FR2668365A1 FR9013349A FR9013349A FR2668365A1 FR 2668365 A1 FR2668365 A1 FR 2668365A1 FR 9013349 A FR9013349 A FR 9013349A FR 9013349 A FR9013349 A FR 9013349A FR 2668365 A1 FR2668365 A1 FR 2668365A1
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cosmetic preparations
preparations according
peptide
sequence
glycyl
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FR2668365B1 (en
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Lintner Karl
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Sederma SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Cosmetics (AREA)

Abstract

This patent describes the production and use in cosmetics of products derived from a reaction between a biologically active oligopeptide and a fatty acid, for facilitating passage through the skin and effecting penetration of the peptide to its site of action.

Description

Le domaine des protéines et des peptides dotés d'une activité biologique spécifique est caractérisé par le très grand nombre de protéines (enzymes, protéines de transport et de structure) et de peptides de taille variable (facteurs de croissance, hormones, neurotransmetteurs). Cette grande diversité résulte de la possibilité pratiquement illimitée de combiner les acides aminés en chaines plus ou moins longues de séquence variable.The field of proteins and peptides with specific biological activity is characterized by the very large number of proteins (enzymes, transport and structural proteins) and peptides of variable size (growth factors, hormones, neurotransmitters). This great diversity results from the practically unlimited possibility of combining amino acids into more or less long chains of variable sequence.

Les protéines et les peptides ont en commun leur structure chimique : enchaînement d'acides aminés ; leur nature physico-chimique : plutôt hydrosolubles que lipophiles ; leur mode de dégradation "in vivo" : action ciblée relativement spécifique pour chaque séquence (stimulateur, inhibiteur, effecteur de processus métaboliques).Proteins and peptides have in common their chemical structure: chain of amino acids; their physico-chemical nature: rather water-soluble than lipophilic; their "in vivo" degradation mode: relatively specific targeted action for each sequence (stimulator, inhibitor, effector of metabolic processes).

Alors que ce dernier point rend les protéines et les peptides (polypeptides et oligopeptides) très interessants dans les domaines pharmaceutique et cosmétique, certains paramètres décrits plus haut limitent leur emploi dans ces domaines. En ce qui concerne l'application topique, le degré d'hydrosolubilité, l'absence de lipophilie marquée ainsi que la taille moyenne des peptides, couplés à la présence plus ou moins importante de charges électriques sur les molécules, sont responsables du fait que les peptides, même de petite taille, ne pénètrent que difficilement à travers les couches superficielles de la peau.While this last point makes proteins and peptides (polypeptides and oligopeptides) very interesting in the pharmaceutical and cosmetic fields, certain parameters described above limit their use in these fields. With regard to topical application, the degree of water solubility, the absence of marked lipophilicity as well as the average size of the peptides, coupled with the more or less significant presence of electrical charges on the molecules, are responsible for the fact that the Even small peptides penetrate only with difficulty through the surface layers of the skin.

Un grand nombre de peptides biologiquement actifs, appelés biopeptides dans ce qui suit, pourraient trouver leur application dans les produits cosmétiques destinés aux soins préventifs ou réparateurs de la peau : les inhibiteurs de la protéolyse (élastase, collagénase), les stimulateurs de la synthèse du collagène, de l'élastine, de la réticuline ou de la laminine, les peptides anti-inflammatoires, les peptides à action cicatrisante, les peptides chemotactiques, vasodilatateurs et autres.A large number of biologically active peptides, called biopeptides in the following, could find their application in cosmetic products intended for preventive or repairing skin care: proteolysis inhibitors (elastase, collagenase), stimulators of the synthesis of collagen, elastin, reticulin or laminin, anti-inflammatory peptides, healing peptides, chemotactic peptides, vasodilators and others.

Quelles sont les limites d'utilisation de ces peptides dans les préparations cosmétiques ?
Du fait, de la difficulté qu'ont ces substances à pénétrer le stratum corneum, on pourrait penser qu'une augmentation de la concentration du peptide permettrait de surmonter la lenteur de la diffusion transcutanée. Mais le prix très élevé des peptides de synthèse et les risques de sensibilisation ou d'allergie interdisent cette voie. What are the limits of use of these peptides in cosmetic preparations?
Because of the difficulty these substances have in penetrating the stratum corneum, one might think that an increase in the concentration of the peptide would make it possible to overcome the slowness of transcutaneous diffusion. But the very high price of synthetic peptides and the risks of sensitization or allergy prohibit this path.

Ces peptides, de séquence connue et décrits dans 8rature, sont actifs "in vivo" et "in vitro" à des concentrations très faibles, de l'ordre de milli-, micro- et nanomoles par litre.These peptides, of known sequence and described in 8rature, are active "in vivo" and "in vitro" at very low concentrations, of the order of milli-, micro- and nanomoles per liter.

Pour amener les biopeptides de la surface de la peau vers les cellules cibles de l'épiderme, en utilisant des concentrations de cet ordre de grandeur, les possibilites sont limitées.To bring biopeptides from the surface of the skin to the target cells of the epidermis, using concentrations of this order of magnitude, the possibilities are limited.

L'objet du présent brevet est l'utilisation des acides gras, composants naturels de la peau (acide oléique, palmitique, linoléique et autres) comme vecteurs de peptides. Nous avons découvert que la plupart des biopeptides d'intérêt cosmétique conservent leur activité biologique naturelle, même si ce peptide est acylé du côté N-terminal par un acide gras du type décrit. Ce lipopeptide acquiert un caractère lipophile beaucoup plus marqué, devient émulsifiable avec les composants lipophiles d'une préparation cosmétique et peut traverser le stratum corneum, soit par voie intercellulaire soit par voie intracellulaire.The subject of this patent is the use of fatty acids, natural components of the skin (oleic, palmitic, linoleic and others) as vectors of peptides. We have discovered that most biopeptides of cosmetic interest retain their natural biological activity, even if this peptide is acylated on the N-terminal side by a fatty acid of the type described. This lipopeptide acquires a much more marked lipophilic character, becomes emulsifiable with the lipophilic components of a cosmetic preparation and can cross the stratum corneum, either by intercellular or intracellular route.

Ces lipopeptides ont la formule générale suivante R1-NH-X-COOR2, où R1 est une chaine aliphatique de 2 à 22 atomes, sature ou insaturée, ou portant un ou plusieurs groupes hydroxyl ; ou X est un oligopeptide de 2 à 20 acides amines, de séquence et d'activité biologique définie ; ou R2 = H, ester méthylique ou éthylique, amide, méthylamide ou diméthylamide
Quelques exemples non limitatifs vont illustrer les possibilités d'utilisation de ces lipo-biopeptides.These lipopeptides have the following general formula R1-NH-X-COOR2, where R1 is an aliphatic chain of 2 to 22 atoms, saturated or unsaturated, or carrying one or more hydroxyl groups; or X is an oligopeptide of 2 to 20 amino acids, of defined sequence and biological activity; or R2 = H, methyl or ethyl ester, amide, methylamide or dimethylamide
Some nonlimiting examples will illustrate the possibilities of using these lipo-biopeptides.

Carnosine : la carnosine est un dipeptide de séquence B-Ala-His, qui se trouve présent dans divers tissus animaux. Au niveau physiologique et pharmacologique, son activité a été decrite comme étant antioxydante (BABIZHAYEN M.A. (1989) B.B.A. 1004, 363-371], cicatrisante (L. SOO YOUNG (1983) Hanguk. Saenghwa
Hakkoe Chi, 16 (2), 181 - 187] .et anti-inflammatoire.Carnosine: Carnosine is a dipeptide of sequence B-Ala-His, which is found in various animal tissues. Physiologically and pharmacologically, its activity has been described as antioxidant (BABIZHAYEN MA (1989) BBA 1004, 363-371], healing (L. SOO YOUNG (1983) Hanguk. Saenghwa
Hakkoe Chi, 16 (2), 181 - 187]. And anti-inflammatory.

L'utilisation de ce peptide par voie topique n'a pas été envisagée du fait de son faible pouvoir de penétration cutanée.The use of this peptide topically has not been envisaged because of its low skin penetration power.

Le couplage de la carnosine avec un acide gras choisi dans la série des acides gras saturés ou insaturés de longueur C12 à C18 (palmitique, stéarique, oléique, linoléique etc ...) par voie de synthese (méthode des anhydrides mixtes, de carbodiimide et d'autres bien connues par l'homme de l'art de la synthese peptidique) donne un produit huileux mais pur, après purification par chromatographie. Ce produit conserve l'activité antioxydante de la carnosine. I1 peut être facilement incorporé dans la phase grasse d'une formulation cosmétique ou dans des préparations de liposomes.The coupling of carnosine with a fatty acid chosen from the series of saturated or unsaturated fatty acids of length C12 to C18 (palmitic, stearic, oleic, linoleic, etc.) by synthesis (method of mixed anhydrides, carbodiimide and others well known to those skilled in the art of peptide synthesis) give an oily but pure product, after purification by chromatography. This product retains the antioxidant activity of carnosine. It can be easily incorporated into the fatty phase of a cosmetic formulation or into liposome preparations.

Les études de pénétration cutanée par autohistoradiographie ont montré que la lipo-carnosine traverse le stratum corneum alors que la carnosine ne le fait que de façon très limitée dans un même laps de temps.Skin penetration studies by autohistoradiography have shown that lipo-carnosine crosses the stratum corneum whereas carnosine does so only in a very limited way in the same period of time.

Gly-His-Lys : ce peptide est un facteur de croissance cellulaire spécifique des cellules du foie, surtout quand il se présente sous forme de sel de cuivre LPICKART L. et al (1973) Biochem.Gly-His-Lys: this peptide is a cell growth factor specific to liver cells, especially when it is in the form of copper salt LPICKART L. et al (1973) Biochem.

Res. Commun. 54, 562-566]. I1 a egalement été décrit comme stimulateur de la synthèse du collagene sur des fibroblastes en culture (MAQUANT F.X. et al (1988 FEBS letters, 238 (2), 181187]. Son caractère hydrosoluble et hydrophile ainsi que les charges électriques (sur le groupe amino et carboxyl ainsi que sur le noyau imidazole et sur la Lysine) rendent son passage transcutané difficile. La réaction avec un acide gras, comme décrit plus haut, permet de garder l'activité stimulatrice de la synthèse de collagène. Le même type d'étude autohistoradiographique sur le peptide marqué à l'iode sur le noyau imidazole de l'histidine révèle une meilleure pénétration du lipobiopeptide par rapport au peptide seul.Res. Common. 54, 562-566]. It has also been described as a stimulator of the synthesis of collagen on fibroblasts in culture (MAQUANT FX et al (1988 FEBS letters, 238 (2), 181187]. Its water-soluble and hydrophilic nature as well as electrical charges (on the amino group and carboxyl as well as on the imidazole nucleus and on Lysine) make its transcutaneous passage difficult. The reaction with a fatty acid, as described above, makes it possible to keep the activity stimulating the synthesis of collagen. The same type of study Autohistoradiographic study on the peptide labeled with iodine on the imidazole nucleus of histidine reveals better penetration of the lipobiopeptide compared to the peptide alone.

Fragments de laminine et peptides chemotactiques : certaines séquences oligopeptidiques ont la capacité de reproduire des fonctions spécifiques des protéines dont elles sont issues : le pentapeptide Tyr-Arg-Gly-Asp-Ser de la laminine, glycoprotéine de poids moléculaire 800.000, est la séquence la plus courte qui favorise l'attachement des cellules entre elles. Cette action simule la fonction de la protéine entière. Plus la séquence peptidique est longue, moins le peptide passera facilement à travers la peau. La modification par la N-acylation permet, comme dans les autres cas, de faire pénétrer le peptide dans le stratum granulosum de l'épiderme.Laminin fragments and chemotactic peptides: certain oligopeptide sequences have the capacity to reproduce specific functions of the proteins from which they originate: the Tyr-Arg-Gly-Asp-Ser pentapeptide of laminin, glycoprotein of molecular weight 800,000, is the sequence the shorter which promotes the attachment of cells to each other. This action simulates the function of the whole protein. The longer the peptide sequence, the less easily the peptide will pass through the skin. The modification by N-acylation allows, as in the other cases, to make the peptide penetrate into the stratum granulosum of the epidermis.

Un comportement et une fonction similaire peuvent être décrits pour la séquence Arg-Gly-Asp de la fibronectine, pour la séquence Gly-Pro-Arg-Pro qui inhibe la fibrinolyse, pour la séquence Val-Gly-Pro-Val-Gly, fragment de l'éîastine, pour les peptides vasodilatateurs qui peuvent améliorer la microcirculation dans la peau ou les vasoconstricteurs qui permettent d'atténuer les tâches de rougeurs diffuses. A similar behavior and function can be described for the Arg-Gly-Asp sequence of fibronectin, for the Gly-Pro-Arg-Pro sequence which inhibits fibrinolysis, for the Val-Gly-Pro-Val-Gly sequence, fragment eastin, for vasodilator peptides which can improve microcirculation in the skin or vasoconstrictors which help to reduce spots of diffuse redness.

Concernant les peptides d'activité biologique qui peuvent etre rendus lipophiles et ainsi capables d'un passage transcutané, il est impossible d'en dresser une liste exhaustive.Concerning the peptides of biological activity which can be made lipophilic and thus capable of a transcutaneous passage, it is impossible to draw up an exhaustive list.

On peut toutefois citer, sans être limitatif, les peptides stimulateurs de la croissance cellulaire, les peptides stimulateurs de la synthèse protéique, de la lipolyse, de la mélanogénese, les inhibiteurs peptidiques de l'hydrolyse enzymatique en général, et de la lipogénèse, les peptides responsables d'une action spécifique sur le cuir chevelu.Mention may however be made, without being limiting, of peptides which stimulate cell growth, peptides which stimulate protein synthesis, lipolysis, melanogenesis, peptide inhibitors of enzymatic hydrolysis in general, and lipogenesis, peptides responsible for a specific action on the scalp.

Les lipoaminoacides sont une classe à part, dans la mesure où un acide aminé ne constitue pas encore un peptide et n'a pas en soi une activité spécifique.Lipoamino acids are a class apart, since an amino acid does not yet constitute a peptide and does not in itself have a specific activity.

Les produits faisant l'objet de l'invention peuvent être formulés dans toutes les présentations habituelles de la cosmétologie telles que cremes, laits ou huiles ainsi que gels, lotions et toniques. I1 peut également s' agir de préparations liposomales, de micro- ou nanocapsules, de micro- ou nanoparticules.The products which are the subject of the invention can be formulated in all the usual presentations of cosmetology such as creams, milks or oils as well as gels, lotions and tonics. It can also be liposomal preparations, micro- or nanocapsules, micro- or nanoparticles.

La dose d'utilisation de ces composés va dépendre du peptide et de son activité spécifique. Elle pourra s'échelonner de 10-6 à 10-2 molaire. The dose of use of these compounds will depend on the peptide and its specific activity. It can range from 10-6 to 10-2 molar.

Claims (17)

REVENDICATIONS 1. Préparations cosmétiques caractérisées en ce qu'elles 1. Cosmetic preparations characterized in that they contiennent un ou plusieurs lipopeptides de formule  contain one or more lipopeptides of formula générale general R1 -NH-X-COOR2  R1 -NH-X-COOR2 ou R1 est une chaine aliphatique de 2 à 22 atomes, saturée where R1 is an aliphatic chain of 2 to 22 atoms, saturated ou insaturée, ou portant un ou plusieurs groupes hydroxyles or unsaturated, or carrying one or more hydroxyl groups ou X est un oligopeptide de 2 à 20 acides aminés, de or X is an oligopeptide of 2 to 20 amino acids, of séquence et d'activite biologique définie ; ou R2 = H, ester defined sequence and biological activity; where R2 = H, ester methylique ou éthylique, amide, methylamide ou diméthylamides.  methyl or ethyl, amide, methylamide or dimethylamides. 2. Préparations cosmétiques selon la revendication 1 2. Cosmetic preparations according to claim 1 caractérisées en ce que la chaine aliphatique est sature. characterized in that the aliphatic chain is saturated. 3. Préparations cosmétiques selon les revendications 1 et 2 3. Cosmetic preparations according to claims 1 and 2 caractérisées en ce que la chaine aliphatique est hydroxyle characterized in that the aliphatic chain is hydroxyl avec 1 à 3 groupements hydroxyles. with 1 to 3 hydroxyl groups. 4. Préparations cosmétiques selon les revendications 1 4. Cosmetic preparations according to claims 1 à 3 caractérisées en ce que la chaine aliphatique est to 3 characterized in that the aliphatic chain is insaturee avec 1 à 6 doubles liaisons. unsaturated with 1 to 6 double bonds. 5. Préparations cosmétiques selon les revendications 1 à 4, 5. Cosmetic preparations according to claims 1 to 4, caractérisées en ce que le peptide a la séquence B-Alanyl-  characterized in that the peptide has the sequence B-Alanyl- Histidine. Histidine. 6. Préparations cosmétiques selon les revendications 1 à 4,6. Cosmetic preparations according to claims 1 to 4, caractérisées en ce que le peptide a la séquence Glycyl characterized in that the peptide has the sequence Glycyl Histidyl-Lysine. Histidyl-Lysine. 7. Préparations cosmétiques selon l'une quelconque des 7. Cosmetic preparations according to any one of revendications 1 à 4 caractérisées en ce que le peptide a Claims 1 to 4, characterized in that the peptide has la séquence Arginyl-Glycyl-Aspartyl. the Arginyl-Glycyl-Aspartyl sequence. 8. Préparations cosmétiques selon l'une quelconque des 8. Cosmetic preparations according to any one of revendications 1 à 4, caractérisées en ce que le claims 1 to 4, characterized in that the peptide a la séquence Glycyl-Prolyl-Arginyl-Proline.  peptide has the sequence Glycyl-Prolyl-Arginyl-Proline. 9. Préparations cosmétiques selon l'une quelconque des 9. Cosmetic preparations according to any one of revendications 1 à 4, caractérisées en ce que le peptide Claims 1 to 4, characterized in that the peptide a la séquence Tyrosyl-Arginyl-Glycyl-Aspartyl-Sérine. has the sequence Tyrosyl-Arginyl-Glycyl-Aspartyl-Serine. 10. Préparations cosmétiques selon l'une quelconque des10. Cosmetic preparations according to any one of revendications 1 à 4, caractérisées en ce que le peptide Claims 1 to 4, characterized in that the peptide a la séquence Valyl-Prolyl-Glycyl-Valyl-Glycine. has the sequence Valyl-Prolyl-Glycyl-Valyl-Glycine. 11. Préparations cosmétiques selon l'une quelconque des11. Cosmetic preparations according to any one of revendications de 1 à 10, caractérisées en ce que R1 est claims 1 to 10, characterized in that R1 is l'acide palmitique. palmitic acid. 12. Préparations cosmétiques selon l'une quelconque des12. Cosmetic preparations according to any one of revendications de 1 à 10, caractérisées en ce que R1 est claims 1 to 10, characterized in that R1 is l'acide oléique. oleic acid. 13. Préparations cosmétiques selon l'une quelconque des13. Cosmetic preparations according to any one of revendications de 1 à 10, caractérisées en ce que R1 est claims 1 to 10, characterized in that R1 is l'acide linoléique. linoleic acid. 14. Préparations cosmétiques selon l'une quelconque des14. Cosmetic preparations according to any one of revendications de 1 à 10, caractérisées en ce que R1 est claims 1 to 10, characterized in that R1 is l'acide aleurétique. aleuretic acid. 15. Préparations cosmétiques selon l'une quelconque des15. Cosmetic preparations according to any one of revendications 1 à 14 caractérisées en ce qu'elles peuvent Claims 1 to 14, characterized in that they can être des crèmes, laits, huiles, gels, lotions et toniques. be creams, milks, oils, gels, lotions and tonics. 16. Préparations cosmétiques selon l'une quelconque des16. Cosmetic preparations according to any one of revendications de 1 à 14 caractérisées en ce qu'elles Claims 1 to 14, characterized in that they peuvent être encapsulées dans des vésicules du type can be encapsulated in vesicles of the type liposomes, micro- ou nanocapsules. liposomes, micro- or nanocapsules. 17. Préparations cosmétiques selon l'une quelconque des 17. Cosmetic preparations according to any one of revendications de 1 à 16, caractérisées en ce que la dose claims 1 to 16, characterized in that the dose d'utilisation est comprise entre 10-6 et 10-2 molaire.  of use is between 10-6 and 10-2 molar.
FR9013349A 1990-10-25 1990-10-25 USE IN COSMETICS OF N-ACETYLPEPTIDES HAVING BIOLOGICAL ACTIVITY. Expired - Lifetime FR2668365B1 (en)

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WO1998007744A1 (en) * 1996-08-23 1998-02-26 Sederma S.A. Synthetic peptides and their use in cosmetic or dermopharmaceutical compositions
WO1998007752A1 (en) * 1996-08-23 1998-02-26 Regents Of The University Of Minnesota Self-assembling amphiphiles for construction of peptide secondary structures
WO1998009611A1 (en) * 1996-09-09 1998-03-12 Societe D'exploitation De Produits Pour Les Industries Chimiques - Seppic Cosmetic use of compounds with lipoaminoacid structure and cosmetic compositions with soothing activity incorporating some of these compounds
FR2753096A1 (en) * 1996-09-09 1998-03-13 Seppic Sa N-Lauroyl-aminoacid cosmetic soothing agent
FR2756565A1 (en) * 1996-12-04 1998-06-05 Oreal NEW DERIVATIVES OF HISTIDINE AND THEIR USE IN COSMETICS OR PHARMACY
FR2776188A1 (en) * 1998-03-20 1999-09-24 Fabre Pierre Dermo Cosmetique Glycylglycine oleamide to combat the effects of skin aging
FR2778917A1 (en) * 1998-05-25 1999-11-26 Oreal NOVEL HISTIDINE DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF AND USES
WO1999062482A1 (en) * 1998-05-29 1999-12-09 Showa Denko K.K. Surfactant for use in external preparations for skin and external preparation for skin containing the same
FR2786693A1 (en) * 1998-12-04 2000-06-09 Dior Christian Parfums Topical slimming compositions containing a L-tyrosine-L-arginine synthetic peptide
WO2000062743A2 (en) * 1999-04-19 2000-10-26 The Procter & Gamble Company Skin care compositions containing combination of skin care actives
WO2001043701A2 (en) * 1999-12-17 2001-06-21 Sederma Cosmetic or dermopharmaceutical compositions containing the n-palmytoyl-gly-hys-lys tripeptide
FR2810323A1 (en) * 2000-06-16 2001-12-21 Shiseido Int France Elaidyl-lysyl-phenylalanyl-lysine useful as an anti-ageing additive in cosmetic compositions
JP2002524487A (en) * 1998-09-15 2002-08-06 セデルマ エス．アー． Use of a peptide for scarring, moisturizing and improving skin appearance as a cosmetic or dermatological agent during natural aging or hyperaging (sun dermatitis, contamination)
WO2004060393A2 (en) * 2002-12-30 2004-07-22 Thorel Jean-Noel Cutaneous metabolic bio-activator
EP1449517A1 (en) * 2003-02-21 2004-08-25 Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C. Use of N-Lauroylaminoacids as cosmetic and pharmaceutical slimming agents
WO2011125040A2 (en) 2010-04-08 2011-10-13 Sederma New polyterpene type compounds, compositions containing them and topical uses thereof
US8361516B2 (en) 2006-08-03 2013-01-29 Sederma Composition comprising sarsasapogenin
US8507649B2 (en) 2006-05-05 2013-08-13 Sederma Cosmetic compositions comprising at least one peptide with at least one immobilized aromatic cycle
US20140309173A1 (en) * 2013-03-13 2014-10-16 Neocutis Sa Peptides For Skin Rejuvenation And Methods Of Using The Same
US10286030B2 (en) 2016-02-04 2019-05-14 Alastin Skincare, Inc Compositions and methods for invasive and non-invasive procedural skincare
US10493011B2 (en) 2017-08-03 2019-12-03 ALASTIN Skincare, Inc. Peptide compositions and methods for ameliorating skin laxity and body contour
US11103455B2 (en) 2018-08-02 2021-08-31 ALASTIN Skincare, Inc. Liposomal compositions and methods of use
WO2021170754A1 (en) 2020-02-28 2021-09-02 Sederma Recombinant microalgae able to produce kttks peptides, polypeptides, or proteins and their derivatives and associated method and uses thereof

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