WO2000040611A1 - Slimming cosmetic compositions - Google Patents

Slimming cosmetic compositions Download PDF

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Publication number
WO2000040611A1
WO2000040611A1 PCT/FR1999/003110 FR9903110W WO0040611A1 WO 2000040611 A1 WO2000040611 A1 WO 2000040611A1 FR 9903110 W FR9903110 W FR 9903110W WO 0040611 A1 WO0040611 A1 WO 0040611A1
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Prior art keywords
pth
peptides according
peptides
peptide
cosmetic
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PCT/FR1999/003110
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French (fr)
Inventor
Karl Lintner
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Sederma S.A.
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Priority to AU15698/00A priority Critical patent/AU1569800A/en
Publication of WO2000040611A1 publication Critical patent/WO2000040611A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K14/00Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575Hormones
    • C07K14/635Parathyroid hormone (parathormone); Parathyroid hormone-related peptides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08Tripeptides
    • C07K5/0802Tripeptides with the first amino acid being neutral
    • C07K5/0804Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides

Definitions

  • Adrenergic substances (adrenaline and the like) are well known for their impressive capacity to stimulate lipolysis in adipocytes, but their use is strictly prohibited in cosmetics and dermopharmaceucy.
  • pTH Para-thyroid hormone
  • pTH Para-thyroid hormone
  • 1-34 Para-thyroid hormone
  • the hybrid peptides obtained by grafting the Ser-Nal dipeptide on the ⁇ -terminal side in the sequences described above, did not demonstrate lipolytic activity greater than that of the initial sequences.
  • the in vitro activity is found in vivo after topical application, and therefore in an approach relating to cosmetics. Due to their shorter lengths, the industrial synthesis of these peptides becomes economically realistic, and due to the high lipolytic activity of the sequences described here, it is entirely possible to use these peptides in all cosmetic and dermopharmaceutical compositions.
  • the peptide, minimal sequence consists of Gly-Lys-His when the undecapeptide, longest sequence, corresponds to His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-
  • R H, or an alkyl chain, linear or branched, saturated or unsaturated, hydroxylated or sulfurized or not, containing 1 to 24 carbon atoms, preferably 12 to 18 carbon atoms
  • AA is all or part of the following peptide sequence His-Asn-Leu-Gly-Lys - His-Leu-Asn-Ser-Met-Glu (pTH (9-19)), preferably Gly-Lys-His-Leu-Asn (pTH (12-16)) or even Gly-
  • the peptides which respond to the sequences described above have a real and significant lipolytic activity by the topical route which is usable in cosmetics and dermopharmacy.
  • the peptides which are the subject of the patent, can be obtained either by conventional chemical synthesis (in solid phase or in homogeneous liquid phase), or by enzymatic synthesis (Kullman et al, J. Biol. Chem. 1980, 255, 8234) from constituent amino acids or their derivatives.
  • the peptides can also be obtained by fermentation of a strain of bacteria modified or not by genetic engineering, to produce the desired sequences or their different fragments.
  • the peptides can be obtained by extraction of proteins of animal or vegetable origin, preferably vegetable, followed by a controlled hydrolysis which releases the peptide fragments in question, with the stipulation that the released fragments correspond to the peptide sequences pTH (9- n) with n between 10 and 19 inclusive. Many proteins found in plants are likely to contain these sequences within their structure.
  • the controlled hydrolysis makes it possible to release these peptide fragments.
  • Peptide 1 His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu, i.e. the longest sequence described in this patent
  • Peptide 2 His-Asn-Leu-Gly-Lys-His -Leu-Asn
  • Peptide 3 Gly-Lys-His-Leu-Asn- S er-Met-Glu
  • Peptide 4 Gly-Lys-His-Leu-Asn
  • Peptide 5 Gly-Lys-His, the shortest sequence in this patent. Human adipocytes (obtained from plastic surgery waste) are suspended in a survival medium.
  • One of the 4 preceding peptides is then added at different concentrations and, after 2 hours of incubation at 37 ° C., the amount of glycerol and fatty acids released in the external medium is measured.
  • the following table shows the amounts of glycerol released (nmol / 2.5.10 5 cells / 2hr) as well as the percentage increase (compared to basal level) observed with the peptides tested under these conditions under a final concentration of 1.10 "6 M.
  • Example n ° 5 Lipolytic activity in vivo An in vivo test, carried out on 15 women aged 35 to 62 years for four weeks, consisted in monitoring the evolution of two parameters, the perimeter of the thighs measured using one centimeter and the thickness of the adipose layer determined using the ultrasound technique. The results given below therefore relate to the differences observed between the values obtained for these two parameters between time 0 and at the end of the test, ie 4 weeks later.
  • Example No. 1 The gel described in Example No. 1 was used, except that the peptide was absent from the placebo gel.
  • the lipolytic peptides are used alone or in combination with one another , in a finished cosmetic or dermopharmaceutical product, in any galenic form: O / W and W / O emulsions, milks, lotions, gelling and viscous polymers, surfactants and emulsifiers, ointments, hair lotions, shampoos, soaps, powders, sticks and pencils , sprays, body oils.
  • these peptides in the form of a solution, dispersion, emulsion, or encapsulated in vectors such as macro-, micro- or nan ocapsules, liposomes or chylomicrons, or included in macro-, micro- or nanoparticles, or in micro-sponges, or adsorbed on powdery organic polymers, talcs, bentonites and other mineral supports.
  • concentration of use of these peptides can vary between 0.000001 and 1% (w / w), preferably between 0.0001 and 0.1% in the finished product.
  • peptides can be combined in cosmetic compositions with any other ingredient usually used in cosmetics: extraction and / or synthetic lipids, gelling and viscosifying polymers, surfactants and emulsifiers, water-soluble or liposoluble active principles, extracts from other plants, tissue extracts, marine extracts, etc.
  • peptides are obtained by extraction of plant proteins, followed by enzymatic hydrolysis so as to generate peptide fragments of average size less than 1500 daltons, part of the released fragments having to contain at least one of the sequences corresponding to pTH (9-n ) with n between 10 and 19 inclusive.
  • lipolysis stimulating agents such as caffeine, theophylline, xanthine derivatives in general is particularly advantageous for carrying out the invention.
  • peptides are used in cosmetic or dermopharmaceutical compositions for cosmetic applications with lipolytic activity for skin care, particularly the slimming treatment of overweight thighs and hips, in the treatment of cellulite and in skin tightening.
  • peptides or the cosmetic or dermopharmaceutical compositions containing them are used for the preparation of a medicament for skin care, particularly for the slimming treatment of overweight thighs and hips, in the treatment of cellulite and in firming skin.

Abstract

The invention relates to peptide sequences derived from the parathyroid hormone (pTh), whereby said sequences exhibit lipolytic activity that is used to advantageous effect in cosmetic or dermatological slimming products that are administered topically. Said activity is enhanced when the peptides are chemically modified so as to increase their lipophilicity. The peptides can be obtained by means of synthesis, biotechnology or by moderate hydrolysis of plant proteins.

Description

TITRE Compositions cosmétiques amincissantes TITLE Slimming cosmetic compositions
L'industrie cosmétique est en permanence à la recherche de nouveaux ingrédients actifs possédant des activités lipolytiques, pour les intégrer dans des produits dits amincissants. De nombreuses substances (molécules pures comme les dérivés de 5 xanthine; mélanges complexes comme certains extraits de plantes, ...) sont proposées et utilisées.The cosmetic industry is constantly looking for new active ingredients with lipolytic activities, to integrate them into so-called slimming products. Many substances (pure molecules such as 5 xanthine derivatives; complex mixtures such as certain plant extracts, etc.) are proposed and used.
Le marché demande néanmoins des nouveautés et des produits toujours plus actifs. Les substances adrénergiques (adrénaline et analogues) sont bien connues pour leur impressionnante capacité à stimuler la lipolyse dans les adipocytes mais, leur emploi ι o est formellement interdit en cosmétique et en dermopharmaceucie.The market nevertheless demands new and ever more active products. Adrenergic substances (adrenaline and the like) are well known for their impressive capacity to stimulate lipolysis in adipocytes, but their use is strictly prohibited in cosmetics and dermopharmaceucy.
Récemment, d'autres classes de substances, de nature différente, ont été identifiées comme étant également capables de stimuler, à des degrés divers, la lipolyse des triglycérides dans les adipocytes humains et/ou animaux. Il s'agit de peptides de courte chaîne à caractère hormonal comme, par exemple,Recently, other classes of substances, of different nature, have been identified as also capable of stimulating, to varying degrees, the lipolysis of triglycerides in human and / or animal adipocytes. These are short chain peptides of a hormonal nature such as, for example,
15 l'hormone para-thyroïdienne (pTH (1-84)) ou son fragment pTH (1-34).Para-thyroid hormone (pTH (1-84)) or its fragment pTH (1-34).
Ces peptides sont susceptibles de stimuler la lipolyse, aussi bien in vitro qu' vivo, par le biais de l'activation de l'adénylate cyclase membranaire (par exemple: Tanigushi A. et al. J. Lip. Res. (1987) 28 .490-496). Malheureusement, le plus petit des deux peptides mentionnés ci-dessus, le pTH (1-These peptides are capable of stimulating lipolysis, both in vitro and in vivo, through the activation of the membrane adenylate cyclase (for example: Tanigushi A. et al. J. Lip. Res. (1987) 28 .490-496). Unfortunately, the smaller of the two peptides mentioned above, pTH (1-
20 34), comporte une séquence de 34 acides aminés (H-Ser-Nal-Ser-Glu-Ile-Gln-Leu-34), has a sequence of 34 amino acids (H-Ser-Nal-Ser-Glu-Ile-Gln-Leu-
Met-His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu-Arg-Nal-Glu-Trp-Leu-Arg- Lys-Lys-Leu-Gln-Asp-Val-His-Asn-Phe-OH), ce qui rend sa synthèse à l'échelle industrielle très difficile, et par conséquent son utilisation incompatible avec les exigences économiques du marché cosmétique visé.Met-His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu-Arg-Nal-Glu-Trp-Leu-Arg- Lys-Lys-Leu-Gln-Asp-Val-His- Asn-Phe-OH), which makes its synthesis on an industrial scale very difficult, and therefore its use incompatible with the economic requirements of the targeted cosmetic market.
25 Récemment, un brevet a décrit l'utilisation de fragments de ce pTH (1-34), Ν-acylés ou non, composés de 3 à 10 acides aminés, dont la séquence débutait par Ser-Val, pour leurs effets amincissants par voie topique (FR 98 09193). Au vu de l'ensemble de la littérature scientifique (par exemple: Taniguchi A. et al. (1987) J. ofLipid Res.28 :490-494), la présence des deux acides aminés Ν-terminaux25 Recently, a patent described the use of fragments of this pTH (1-34), Ν-acylated or not, composed of 3 to 10 amino acids, whose sequence started with Ser-Val, for their slimming effects by the topical (FR 98 09193). In view of all of the scientific literature (for example: Taniguchi A. et al. (1987) J. of Lipid Res. 28: 490-494), the presence of the two Ν-terminal amino acids
30 (Ser-Nal) semblait alors être obligatoire. L'objet du présent brevet est la double découverte que l'activité lipolytique, tant in vivo qu'w vitro, était portée par des fragments peptidiques, dérivé de la pTH:30 (Ser-Nal) then seemed to be compulsory. The object of this patent is the double discovery that the lipolytic activity, both in vivo and in vitro, was carried by peptide fragments, derived from pTH:
- même si le coté N-peptidique ne contient pas la séquence classique Ser-Val,- even if the N-peptide side does not contain the classic Ser-Val sequence,
- même si le peptide n'est constitué que de 3 à 11 acides aminés. Ces peptides correspondent donc à des fragments qui déclinent toutes les possibilités de longueur et de clivage de la pTH (9-19).- even if the peptide only consists of 3 to 11 amino acids. These peptides therefore correspond to fragments which decline all the possibilities of length and cleavage of pTH (9-19).
Les peptides hybrides, obtenus par greffage du dipeptide Ser-Nal du coté Ν-terminal dans les séquences décrites ci-dessus, n'ont pas démontré d'activité lipolytique supérieure à celle des séquences initiales. De manière surprenante, l'activité in vitro se retrouve in vivo après application par voie topique, et donc dans une approche relevant de la cosmétique. De par leurs longueurs plus courtes, la synthèse industrielle de ces peptides devient économiquement réaliste, et de par la forte activité lipolytique des séquences décrite ici, il est tout à fait possible d'utiliser ces peptides dans toutes compositions cosmétiques et dermopharmaceutiques.The hybrid peptides, obtained by grafting the Ser-Nal dipeptide on the Ν-terminal side in the sequences described above, did not demonstrate lipolytic activity greater than that of the initial sequences. Surprisingly, the in vitro activity is found in vivo after topical application, and therefore in an approach relating to cosmetics. Due to their shorter lengths, the industrial synthesis of these peptides becomes economically realistic, and due to the high lipolytic activity of the sequences described here, it is entirely possible to use these peptides in all cosmetic and dermopharmaceutical compositions.
Le peptide, séquence minimale, est constitué de Gly-Lys-His quand l'undécapeptide, séquence la plus longue, correspond à His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-The peptide, minimal sequence, consists of Gly-Lys-His when the undecapeptide, longest sequence, corresponds to His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-
Glu.Glue.
Enfin, tout comme dans le brevet FR 98 09193, afin de rendre tous ces peptides encore plus actif par voie topique, il est avantageux de les rendre lipophiles par un greffage d'un acide gras de plus ou moins longue chaîne (mirystyl, palmityl, stéaryl, lipoyl...) sur l'aminé Ν-terminale et/ou d'estérifîer le groupe carboxyle du peptide. Sont donc concernés par ce brevet, les divers fragments du peptide pTH (9-19), caractérisés en ce qu'ils contiennent la séquence de structure générale suivante:
Figure imgf000004_0001
où R = H, ou une chaîne alkoyle, linéaire ou branchée, saturée ou insaturée, hydroxylée ou soufrée ou non, contenant 1 à 24 atomes de carbone, préférentiellement 12 à 18 atomes de carbone, et R2 = OH ou OR3 ou NR R5 avec R3 = une chaîne alkyle de Ci à C24, préférentiellement soit Ci à C3, soit C14 à C18 et avec R-jR5 étant indépendamment l'un de l'autre = H ou une chaîne alkyle de 1 à 12 atomes de carbone, préférentiellement de 1 à 3 atomes de carbone, et AA est tout ou partie de la séquence peptidique suivante His-Asn-Leu-Gly-Lys- His-Leu-Asn-Ser-Met-Glu (pTH (9-19)), préférentiellement Gly-Lys-His-Leu-Asn (pTH (12-16)) ou même Gly-Lys-His (pTH (12-14)).
Finally, as in patent FR 98 09193, in order to make all these peptides even more active topically, it is advantageous to make them lipophilic by grafting a fatty acid of more or less long chain (mirystyl, palmityl, stearyl, lipoyl ...) on the Ν-terminal amine and / or to esterify the carboxyl group of the peptide. Are therefore concerned by this patent, the various fragments of the peptide pTH (9-19), characterized in that they contain the following sequence of general structure:
Figure imgf000004_0001
where R = H, or an alkyl chain, linear or branched, saturated or unsaturated, hydroxylated or sulfurized or not, containing 1 to 24 carbon atoms, preferably 12 to 18 carbon atoms, and R 2 = OH or OR 3 or NR R 5 with R 3 = an alkyl chain from C 1 to C 24 , preferably either C 1 to C 3 or C 14 to C 18 and with R-jR 5 being independently each other = H or an alkyl chain of 1 to 12 carbon atoms, preferably 1 to 3 carbon atoms, and AA is all or part of the following peptide sequence His-Asn-Leu-Gly-Lys - His-Leu-Asn-Ser-Met-Glu (pTH (9-19)), preferably Gly-Lys-His-Leu-Asn (pTH (12-16)) or even Gly-Lys-His (pTH (12 -14)).
Les peptides qui répondent aux séquences décrites ci dessus possèdent une réelle et importante activité lipolytique par voie topique qui est utilisable en cosmétique et dermopharmacie.The peptides which respond to the sequences described above have a real and significant lipolytic activity by the topical route which is usable in cosmetics and dermopharmacy.
Les peptides, objets du brevet, peuvent être obtenus soit par synthèse chimique classique (en phase solide ou en phase homogène liquide), soit par synthèse enzymatique (Kullman et al, J. Biol. Chem. 1980, 255, 8234) à partir des acides aminés constitutifs ou de leurs dérivés.The peptides, which are the subject of the patent, can be obtained either by conventional chemical synthesis (in solid phase or in homogeneous liquid phase), or by enzymatic synthesis (Kullman et al, J. Biol. Chem. 1980, 255, 8234) from constituent amino acids or their derivatives.
Les peptides peuvent être obtenus également par fermentation d'une souche de bactéries modifiées ou non par génie génétique, pour produire les séquences recherchées ou leurs différents fragments.The peptides can also be obtained by fermentation of a strain of bacteria modified or not by genetic engineering, to produce the desired sequences or their different fragments.
Enfin, les peptides peuvent être obtenus par extraction de protéines d'origine animale ou végétale, préférentiellement végétale, suivie d'une hydrolyse contrôlée qui libère les fragments peptidiques en question, avec la stipulation que les fragments libérés correspondent aux séquences peptidiques pTH(9-n) avec n compris entre 10 et 19 inclus. De nombreuses protéines trouvées dans les plantes sont susceptibles de contenir ces séquences au sein de leur structure. L'hydrolyse ménagée permet de dégager ces fragments peptidiques.Finally, the peptides can be obtained by extraction of proteins of animal or vegetable origin, preferably vegetable, followed by a controlled hydrolysis which releases the peptide fragments in question, with the stipulation that the released fragments correspond to the peptide sequences pTH (9- n) with n between 10 and 19 inclusive. Many proteins found in plants are likely to contain these sequences within their structure. The controlled hydrolysis makes it possible to release these peptide fragments.
Pour réaliser l'invention, il est possible, mais non nécessaire, d'extraire soit les protéines concernées d'abord et de les hydrolyser ensuite, soit d'effectuer l'hydrolyse d'abord sur un extrait brut et de purifier les fragments peptidiques ensuite. On peut également utiliser l'hydrolysât sans en extraire les fragments peptidiques en question, en s'assurant toutefois d'avoir arrêté la réaction enzymatique d'hydrolyse à temps et de doser la présence des peptides en question par des moyens analytiques appropriés (traçage par radioactivité, immunofluorescence ou immunoprécipitation avec des anticorps spécifiques, etc.). D'autres procédés plus simples ou plus complexes conduisant à des produits moins chers ou plus purs sont facilement envisageables par l'homme de l'art connaissant le métier de l'extraction et de la purification des protéines et peptides.To carry out the invention, it is possible, but not necessary, to extract either the proteins concerned first and then hydrolyze them, or to carry out the hydrolysis first on a crude extract and to purify the peptide fragments then. It is also possible to use the hydrolyzate without extracting the peptide fragments in question therefrom, making sure however to have stopped the enzymatic hydrolysis reaction in time and to measure the presence of the peptides in question by appropriate analytical means (tracing by radioactivity, immunofluorescence or immunoprecipitation with specific antibodies, etc.). Other simpler or more complex processes leading to cheaper or purer products are easily conceivable by those skilled in the art knowing the art of extracting and purifying proteins and peptides.
A titre d'exemple illustrant l'invention, on cite quelques formules cosmétiques représentatives mais non limitatives de l'invention:By way of example illustrating the invention, a few cosmetic formulas which are representative but not limiting of the invention are cited:
Exemple n° 1: Gel amincissantExample 1: Slimming gel
Carbopol 1342R 0,3Carbopol 1342R 0.3
Propylène glycol 2,0Propylene glycol 2.0
Glycérine 1,0Glycerin 1.0
Vaseline blanche 1,5White petrolatum 1.5
Cylomethicone 6,0Cylomethicone 6.0
Alcool cétylique 0,5Cetyl alcohol 0.5
LubrajelR MS 10 triéthanolamine 0,3LubrajelR MS 10 triethanolamine 0.3
Gly-Lys-His 0,01Gly-Lys-His 0.01
Eau, conservateurs, parfum qsp 100 g.Water, preservatives, perfume qs 100 g.
Exemple n°2: Crème amincissanteExample 2: Slimming cream
Stéareth-21 2.4Steareth-21 2.4
Stéareth-2 2.6Steareth-2 2.6
PPG-15 stéaryl éther 8.0PPG-15 stearyl ether 8.0
Cire d'abeille 0.5Beeswax 0.5
Stéaroxy diméthicone 3.0Stearoxy dimethicone 3.0
Propylène glycol 3.0Propylene glycol 3.0
CarbopolR 941 0.25CarbopolR 941 0.25
Triéthanolamine 0.250.25 triethanolamine
N-Palmitoyl-Gly-Lys-His-Leu-Asn 0.01N-Palmitoyl-Gly-Lys-His-Leu-Asn 0.01
Caféine 1.0Caffeine 1.0
Eau, conservateurs, parfums qsp 100 gWater, preservatives, perfumes qs 100 g
-emple n° 3: Lotion alcoolique-ample 3: Alcoholic lotion
Ethanol 5.0Ethanol 5.0
Propylène glycol 2.0 Diméthicone copolyol 0.5Propylene glycol 2.0 Dimethicone copolyol 0.5
PPG- 1 -PEG-9 lauryl glycol éther 0.6PPG- 1 -PEG-9 lauryl glycol ether 0.6
N-Palmitoyl-His-Asn-Leu-Gly-Lys-His 0.001 eau, conservateurs, parfum qsp 100 g L'activité des peptides sera démontrée par les deux exemples suivants:N-Palmitoyl-His-Asn-Leu-Gly-Lys-His 0.001 water, preservatives, perfume qs 100 g The activity of the peptides will be demonstrated by the following two examples:
Exemple n° 4: Activité lipolytique in vitro Dans cet exemple, 5 séquences peptidiques ont été testées:Example 4: Lipolytic activity in vitro In this example, 5 peptide sequences were tested:
Peptide 1 : His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu, soit la séquence la plus longue décrite dans ce brevet, Peptide 2: His-Asn-Leu-Gly-Lys-His-Leu-Asn,Peptide 1: His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu, i.e. the longest sequence described in this patent, Peptide 2: His-Asn-Leu-Gly-Lys-His -Leu-Asn,
Peptide 3: Gly-Lys-His-Leu-Asn- S er-Met-Glu, Peptide 4: Gly-Lys-His-Leu-Asn,Peptide 3: Gly-Lys-His-Leu-Asn- S er-Met-Glu, Peptide 4: Gly-Lys-His-Leu-Asn,
Peptide 5: Gly-Lys-His, soit la séquence la plus courte de ce brevet. Des adipocytes humains (obtenus à partir de déchets de chirurgie plastique) sont mis en suspension dans un milieu de survie.Peptide 5: Gly-Lys-His, the shortest sequence in this patent. Human adipocytes (obtained from plastic surgery waste) are suspended in a survival medium.
On ajoute alors, à différentes concentrations, l'un des 4 peptides précédents et, après 2 heures d'incubation à 37°C, on mesure la quantité de glycérol et d'acides gras libérés dans le milieu extérieur.One of the 4 preceding peptides is then added at different concentrations and, after 2 hours of incubation at 37 ° C., the amount of glycerol and fatty acids released in the external medium is measured.
Dans les mêmes conditions, le métabolisme lipolytique de base et une série de contrôles positifs sont réalisés, respectivement en l'absence du peptide testé ou en présence de différentes concentrations de pTH (1-34) qui est alors considéré comme produit de référence.Under the same conditions, the basic lipolytic metabolism and a series of positive controls are carried out, respectively in the absence of the peptide tested or in the presence of different concentrations of pTH (1-34) which is then considered as a reference product.
Le tableau suivant montre les quantités de glycérol libéré (nmol/2,5.105 cellules/2hr) ainsi que le pourcentage d'augmentation (par rapport au niveau basai) observé avec les peptides testés dans ces conditions sous une concentration finale de 1.10"6M .The following table shows the amounts of glycerol released (nmol / 2.5.10 5 cells / 2hr) as well as the percentage increase (compared to basal level) observed with the peptides tested under these conditions under a final concentration of 1.10 "6 M.
Basai pTH (1-34) Peptide 1 Peptide 2 Peptide 3 Peptide 4 Peptide 5 Ôlycérol 17,5 ± 1,1 30,5 ± 1,1 27,7 ± 0,8 24,3 ±0,8 25,6 ± 0,9 23,7 ± 0,5 20,3 ±0,6Basai pTH (1-34) Peptide 1 Peptide 2 Peptide 3 Peptide 4 Peptide 5 Olycerol 17.5 ± 1.1 30.5 ± 1.1 27.7 ± 0.8 24.3 ± 0.8 25.6 ± 0.9 23.7 ± 0.5 20.3 ± 0.6
A % - + 75,1 + 58,2 + 39.2 + 46,2 + 35,4 + 16,8A% - + 75.1 + 58.2 + 39.2 + 46.2 + 35.4 + 16.8
Dans les mêmes conditions expérimentales, on peut également suivre la variation de la concentration d'AMPc (Adénosine monophosphate cyclique) dans le milieu cellulaire. Lorsque des concentrations inférieures de peptides ont été testées, un effet concentration dépendant a été mis en évidence sur la libération de glycérol, ce qui démontre bien la spécificité du mécanisme biochimique et physiologique mis enjeu. Exemple n° 5: Activité lipolytique in vivo Un test in vivo, effectué sur 15 femmes âgées de 35 à 62 ans pendant quatre semaines, a consisté à suivre l'évolution de deux paramètres, le périmètre des cuisses mesuré à l'aide d'un centimètre et l'épaisseur de la couche adipeuse déterminée à l'aide de la technique d'échographie (ultrasons). Les résultats donnés plus loin concernent donc les différences observées entre les valeurs obtenues pour ces deux paramètres entre le temps 0 et en fin de test, soit 4 semaines plus tard.Under the same experimental conditions, it is also possible to follow the variation in the concentration of cAMP (cyclic adenosine monophosphate) in the cell medium. When lower concentrations of peptides were tested, a concentration dependent effect was demonstrated on the release of glycerol, which clearly demonstrates the specificity of the biochemical and physiological mechanism involved. Example n ° 5: Lipolytic activity in vivo An in vivo test, carried out on 15 women aged 35 to 62 years for four weeks, consisted in monitoring the evolution of two parameters, the perimeter of the thighs measured using one centimeter and the thickness of the adipose layer determined using the ultrasound technique. The results given below therefore relate to the differences observed between the values obtained for these two parameters between time 0 and at the end of the test, ie 4 weeks later.
Le gel décrit dans l'exemple n°l a été utilisé, si ce n'est que le peptide était absent du gel placebo.The gel described in Example No. 1 was used, except that the peptide was absent from the placebo gel.
Après 4 semaines de traitement biquotidien avec des gels (un gel placebo et un gel contenant le peptide Gly-Lys-His-Leu-Asn, on constate une évolution favorable du périmètre et de l'épaisseur de la couche adipeuse sur les cuisses traitées à la préparation contenant le peptide lipolytique: -12% et -14% respectivement, alors que les variations des valeurs de ces deux paramètres sur les cuisses traitées au placebo ne sont pas significatives. Les peptides à caractère lipolytique sont utilisés seuls ou en association entre eux, dans un produit cosmétique ou dermopharmaceutique fini, dans toute forme galénique: émulsions H/E et E/H, laits, lotions, polymères gélifiants et viscosants, tensioactifs et émulsifiants, pommades, lotions capillaires, shampooings, savons, poudres, sticks et crayons, sprays, huiles corporelles. Il est possible d'utiliser ces peptides sous forme de solution, de dispersion, d'émulsion, ou encapsulés dans des vecteurs comme les macro-, micro- ou nanocapsules, les liposomes ou les chylomicrons, ou inclus dans des macro-, micro- ou nanoparticules, ou dans des microéponges, ou adsorbés sur des polymères organiques poudreux, les talcs, bentonites et autres supports minéraux. La concentration d'utilisation de ces peptides peut varier entre 0.000001 et 1% (p/p), préférentiellement entre 0.0001 et 0.1% dans le produit fini. Ces peptides peuvent être combinés dans les compositions cosmétiques avec tout autre ingrédient habituellement utilisé en cosmétique: lipides d'extraction et/ou de synthèse, polymères gélifiants et viscosants, tensioactifs et émulsifiants, principes actifs hydro- ou liposolubles, extraits d'autres plantes, extraits tissulaires, extraits marins, etc.After 4 weeks of twice-daily treatment with gels (a placebo gel and a gel containing the Gly-Lys-His-Leu-Asn peptide, there is a favorable change in the perimeter and thickness of the fatty layer on the thighs treated with the preparation containing the lipolytic peptide: -12% and -14% respectively, while the variations in the values of these two parameters on the thighs treated with placebo are not significant. The lipolytic peptides are used alone or in combination with one another , in a finished cosmetic or dermopharmaceutical product, in any galenic form: O / W and W / O emulsions, milks, lotions, gelling and viscous polymers, surfactants and emulsifiers, ointments, hair lotions, shampoos, soaps, powders, sticks and pencils , sprays, body oils. It is possible to use these peptides in the form of a solution, dispersion, emulsion, or encapsulated in vectors such as macro-, micro- or nan ocapsules, liposomes or chylomicrons, or included in macro-, micro- or nanoparticles, or in micro-sponges, or adsorbed on powdery organic polymers, talcs, bentonites and other mineral supports. The concentration of use of these peptides can vary between 0.000001 and 1% (w / w), preferably between 0.0001 and 0.1% in the finished product. These peptides can be combined in cosmetic compositions with any other ingredient usually used in cosmetics: extraction and / or synthetic lipids, gelling and viscosifying polymers, surfactants and emulsifiers, water-soluble or liposoluble active principles, extracts from other plants, tissue extracts, marine extracts, etc.
Ces peptides sont obtenus par extraction de protéines de plantes, suivie d'hydrolyse enzymatique de façon à générer des fragments peptidiques de taille moyenne inférieure à 1500 daltons, une partie des fragments libérés devant contenir au moins une des séquences correspondant au pTH (9-n) avec n compris entre 10 et 19 inclus. La combinaison avec d'autres agents stimulant la lipolyse tels que la caféine, la théophylline, les dérivés de xanthine en général est particulièrement avantageuse pour réaliser l'invention.These peptides are obtained by extraction of plant proteins, followed by enzymatic hydrolysis so as to generate peptide fragments of average size less than 1500 daltons, part of the released fragments having to contain at least one of the sequences corresponding to pTH (9-n ) with n between 10 and 19 inclusive. The combination with other lipolysis stimulating agents such as caffeine, theophylline, xanthine derivatives in general is particularly advantageous for carrying out the invention.
Ces peptides sont utilisés dans des compositions cosmétiques ou dermopharmaceutiques pour des applications cosmétiques à activité lipolytique pour les soins de la peau, particulièrement le traitement amincissant des surcharges pondérales des cuisses et des hanches, dans le traitement de la cellulite et dans le raffermissement cutané.These peptides are used in cosmetic or dermopharmaceutical compositions for cosmetic applications with lipolytic activity for skin care, particularly the slimming treatment of overweight thighs and hips, in the treatment of cellulite and in skin tightening.
Ces peptides ou les compositions cosmétiques ou dermopharmaceutiques les contenant sont utilisées pour la préparation d'un médicament pour les soins de la peau, particulièrement pour le traitement amincissant des surcharges pondérales des cuisses et des hanches, dans le traitement de la cellulite et dans le raffermissement cutané. These peptides or the cosmetic or dermopharmaceutical compositions containing them are used for the preparation of a medicament for skin care, particularly for the slimming treatment of overweight thighs and hips, in the treatment of cellulite and in firming skin.

Claims

Revendications claims
1. Peptides fragments du pTH(l-34) de structure suivante:1. Peptide fragments of pTH (l-34) with the following structure:
Rι-NH-AA-R2 avecRι-NH-AA-R 2 with
R\ = H, ou une chaîne alkoyle, linéaire ou branchée, saturée ou insaturée, hydroxylée ou soufrée ou non, contenant 1 à 24 atomes de carbone, préférentiellement 12 à 18 atomes de carbone,R \ = H, or an alkyl chain, linear or branched, saturated or unsaturated, hydroxylated or sulfurized or not, containing 1 to 24 carbon atoms, preferably 12 to 18 carbon atoms,
R = OH ou OR3 ou NR4R5 avec R3 = une chaîne alkyle de Ci à C24, préférentiellement soit Ci à C3, soit C14 à 8 et avec R.jR5 étant indépendamment l'un de l'autre = H ou une chaîne alkyle de 1 à 12 atomes de carbone, préférentiellement de 1 à 3 atomes de carbone,R = OH or OR 3 or NR 4 R 5 with R 3 = an alkyl chain of Ci to C 24 , preferably either Ci to C 3 , or C 14 to 8 and with R.jR 5 being independently one of the other = H or an alkyl chain of 1 to 12 carbon atoms, preferably of 1 to 3 carbon atoms,
AA est, tout ou partie de longueur variable de la séquence peptidique suivante His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu (pTH(9-19)), dont préférentiellement Gly-Lys-His-Leu-Asn (pTH(12-16)) ou Gly-Lys-His (pTH(12-14)), mais à l'exclusion des séquences (pTH(9-18)), (pTH(10-18)), (pTH(l l-18)), (pTH(12-18)), (pTH(13-18)), (pTH(14-18)), (pTH(9-17)),AA is, all or part of variable length of the following peptide sequence His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu (pTH (9-19)), of which preferably Gly-Lys- His-Leu-Asn (pTH (12-16)) or Gly-Lys-His (pTH (12-14)), but excluding the sequences (pTH (9-18)), (pTH (10-18 )), (pTH (11-18)), (pTH (12-18)), (pTH (13-18)), (pTH (14-18)), (pTH (9-17)),
(pTH(9-16)), (pTH(9-15)), (pTH(9-14)), (pTH(9-13)).(pTH (9-16)), (pTH (9-15)), (pTH (9-14)), (pTH (9-13)).
2. Peptides selon la revendication 1 obtenus par synthèse chimique, par voie enzymatique, par fermentation ou par extraction de protéines d'origine végétale.2. Peptides according to claim 1 obtained by chemical synthesis, by enzymatic route, by fermentation or by extraction of proteins of vegetable origin.
3. Peptides selon 1 à 2 obtenus par synthèse peptidique classique en phase homogène ou hétérogène ou par synthèse enzymatique à partir des acides aminés constitutifs.3. Peptides according to 1 to 2 obtained by conventional peptide synthesis in homogeneous or heterogeneous phase or by enzymatic synthesis from the constituent amino acids.
4. Peptides selon les revendications 1 à 3 obtenus par extraction de protéines de plantes, suivie d'hydrolyse enzymatique de façon à générer des fragments peptidiques de taille moyenne inférieure à 1500 daltons, une partie des fragments libérés devant contenir au moins une des séquence correspondant au pTH (9-n) avec n compris entre 10 et 19 inclus.4. Peptides according to claims 1 to 3 obtained by extraction of plant proteins, followed by enzymatic hydrolysis so as to generate peptide fragments of average size less than 1500 daltons, part of the released fragments having to contain at least one of the corresponding sequence pTH (9-n) with n between 10 and 19 inclusive.
5. Peptides selon les revendications 1 à 4 caractérisés en ce que leur lipophilie est augmentée par greffage d'un acide gras de plus ou moins longue chaîne (mirystyl, palmityl, stéaryl, lipoyl...) sur l'aminé N-terminale et/ou d'estérifier le groupe carboxyle du peptide. 5. Peptides according to claims 1 to 4, characterized in that their lipophilicity is increased by grafting a fatty acid of more or less long chain (mirystyl, palmityl, stearyl, lipoyl, etc.) onto the N-terminal amine and / or to esterify the carboxyl group of the peptide.
6. Utilisation des peptides, selon les revendications 1 à 5, seuls ou en association entre eux, dans un produit cosmétique ou dermopharmaceutique fini, à des concentrations variant entre 0.000001 et 1% (p/p), préférentiellement entre 0.0001 et 0.1%. 6. Use of the peptides according to claims 1 to 5, alone or in combination with one another, in a finished cosmetic or dermopharmaceutical product, at concentrations varying between 0.000001 and 1% (w / w), preferably between 0.0001 and 0.1%.
7. Utilisation des peptides, selon les revendications 1 à 5 et la revendication 6, seuls ou en association entre eux, dans un produit cosmétique ou dermopharmaceutique fini, sous forme de solution, de dispersion, d'émulsion, ou encapsulées dans des vecteurs comme les macro-, micro- ou nanocapsules, des liposomes ou des chylomicrons, ou inclus dans des macro-, micro-ou nanoparticules, ou dans des microéponges, ou adsorbés sur des polymères organiques poudreux, les talcs, bentonites et autres supports minéraux. 7. Use of the peptides according to claims 1 to 5 and claim 6, alone or in combination with one another, in a finished cosmetic or dermopharmaceutical product, in the form of a solution, dispersion, emulsion, or encapsulated in vectors such as macro-, micro- or nanocapsules, liposomes or chylomicrons, or included in macro-, micro- or nanoparticles, or in micro-sponges, or adsorbed on powdery organic polymers, talcs, bentonites and other mineral supports.
8. Utilisation des peptides, selon les revendications 1 à 5 et 6 à 7, seuls ou en association entre eux, dans un produit cosmétique ou dermopharmaceutique fini, dans toute forme galénique: émulsions H/E et E/H, laits, lotions, polymères gélifiants et viscosants, tensioactifs et émulsifiants, pommades, lotions capillaires, shampooings, savons, poudres, sticks et crayons, sprays, huiles corporelles. 8. Use of the peptides, according to claims 1 to 5 and 6 to 7, alone or in combination with one another, in a finished cosmetic or dermopharmaceutical product, in any galenical form: O / W and W / O emulsions, milks, lotions, gelling and viscosifying polymers, surfactants and emulsifiers, ointments, hair lotions, shampoos, soaps, powders, sticks and pencils, sprays, body oils.
9. Utilisation des peptides selon les revendications 1 à 5 et 6 à 8, seuls ou en association entre eux, dans un produit cosmétique ou dermopharmaceutique fini, avec tout autre ingrédient habituellement utilisé: lipides d'extraction et ou de synthèse, polymères gélifiants et viscosants, tensioactifs et émulsifiants, principes actifs hydro- ou liposolubles, extraits de plantes, extraits tissulaires, extraits marins, caféine, théophylline, dérivés de la xanthine et autres agents lipolytiques.9. Use of the peptides according to claims 1 to 5 and 6 to 8, alone or in combination with one another, in a finished cosmetic or dermopharmaceutical product, with any other ingredient usually used: extraction and or synthetic lipids, gelling polymers and viscosants, surfactants and emulsifiers, water- or fat-soluble active ingredients, plant extracts, tissue extracts, marine extracts, caffeine, theophylline, xanthine derivatives and other lipolytic agents.
10. Compositions cosmétiques ou dermopharmaceutiques renfermant les peptides selon les revendications 1 à 5 et 6 à 9 utilisées dans les applications cosmétiques à activité lipolytique pour les soins de la peau, particulièrement le traitement amincissant des surcharges pondérales des cuisses et des hanches, dans le traitement de la cellulite et dans le raffermissement cutané.10. Cosmetic or dermopharmaceutical compositions containing the peptides according to claims 1 to 5 and 6 to 9 used in cosmetic applications with lipolytic activity for skin care, particularly the slimming treatment of overweight thighs and hips, in the treatment cellulite and in skin tightening.
11. Utilisation des peptides selon les revendications 1 à 5, ou d'une composition cosmétique ou dermopharmaceutique renfermant les peptides selon les revendications 6 à 9, pour la préparation d'un médicament pour les soins de la peau, particulièrement pour le traitement amincissant des surcharges pondérales des cuisses et des hanches, dans le traitement de la cellulite et dans le raffermissement cutané. 11. Use of the peptides according to claims 1 to 5, or of a cosmetic or dermopharmaceutical composition containing the peptides according to claims 6 to 9, for the preparation of a medicament for skin care, particularly for the slimming treatment of overweight thighs and hips, in the treatment of cellulite and in skin tightening.
PCT/FR1999/003110 1998-12-30 1999-12-09 Slimming cosmetic compositions WO2000040611A1 (en)

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