COMPOSITION AND METHOD USING IT

A composition with collagen, palmitoyl tripeptide-1, tetrapeptide-7, and tetrapeptide-10 stimulates collagen production, addressing skin aging by enhancing skin firmness and reducing wrinkles.

FR3153999B3Active Publication Date: 2025-11-07LOREAL SA
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Patent Information

Application Number
FR2023013140
Authority / Receiving Office
FR · FR
Patent Type
Utility models
Current Assignee / Owner
Priority Date
2023-10-13
Filing Date
2023-11-28
Publication Date
2025-11-07
Estimated Expiration
2033-11-28

AI Technical Summary

Technical Problem

Existing cosmetic products are inadequate in effectively resisting skin aging due to insufficient collagen production with age.

Method used

A composition comprising collagen, palmitoyl tripeptide-1, palmitoyl tetrapeptide-7, and palmitoyl tetrapeptide-10, which stimulate the production of collagen III and IV to enhance skin elasticity and resistance to aging.

Benefits of technology

The composition effectively stimulates collagen production, resulting in improved skin firmness, reduced wrinkles, and enhanced resistance to UV damage.

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Abstract

COMPOSITION AND METHOD USING IT The present invention relates to a composition comprising: (i) at least one collagen; (ii) palmitoyl tripeptide-1; (iii) palmitoyl tetrapeptide-7; and (iv) palmitoyl tetrapeptide-10. The present invention also relates to a non-therapeutic method for the treatment of keratinous materials, comprising the application of said composition to the keratinous materials. Figure for the abstract: none
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Description

Title of the invention: COMPOSITION AND METHOD USING IT technical field

[0001] The present invention relates to a composition. In particular, the present invention relates to a composition for the care of keratinous materials. The present invention also relates to a non-therapeutic method for the care of keratinous materials. PRIOR TECHNOLOGY

[0002] Human skin consists of three compartments, namely a superficial compartment, which is the epidermis, the dermis and a deep compartment, which is the hypodermis.

[0003] The dermis is primarily composed of fibroblasts and an extracellular matrix (ECM). This extracellular matrix consists of various macromolecules responsible for the skin's mechanical resistance, suppleness, tone, and elasticity, as well as physiologically important functions (hydration, thermoregulation, and regulation of skin permeability). These macromolecules include, in particular, collagens, elastin, and glycoconjugates (glycoproteins and proteoglycans).

[0004] Collagens represent 70% of the proteins in the ECM. Naturally, collagens are constantly renewed, but this renewal decreases with age, resulting in thinning of the dermis.

[0005] A wide variety of cosmetic products have been used to care for the skin, for example, to resist skin aging by stimulating collagen production. However, some cosmetic products on the market are not satisfactory in terms of resisting skin aging.

[0006] Thus, there is always a need to formulate a skin care composition that can effectively resist skin aging. Summary of the invention

[0007] An object of the present invention is therefore to develop a skin care composition which can effectively resist skin aging.

[0008] Another object of the present invention is to propose a cosmetic skin care process.

[0009] The inventors have now discovered that the composition of the present invention can effectively resist skin aging.

[0010] Consequently, in a first aspect, the present invention proposes a composition comprising: i. at least one collagen; ii. palmitoyl tripeptide-1; iii. of palmitoyl tetrapeptide-7; and iv. of palmitoyl tetrapeptide-10.

[0011] The inventors have discovered that the composition of the present invention can effectively resist skin aging by stimulating the production of collagen III and IV.

[0012] In a second aspect, the present invention proposes a non-therapeutic method for the treatment of keratinous materials, comprising the application of the composition according to the first aspect of the present invention on the keratinous materials.

[0013] In a third aspect, the present invention proposes a use of the composition according to the first aspect of the present invention to provide an anti-aging effect on keratinous materials.

[0014] Other subjects, features, aspects, and advantages of the invention will become even clearer upon reading the description and examples that follow. DETAILED DESCRIPTION OF THE INVENTION

[0015] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as that commonly understood by a person skilled in the art in the field covered by the present invention. Where the definition of a term in the present invention conflicts with the meaning commonly understood by a person skilled in the art in the field covered by the present invention, the definition described in the present invention shall apply.

[0016] In what follows and unless otherwise indicated, the limits of a range of values ​​are included in that range, in particular, in the expressions "between...and..." and "from...to...".

[0017] Moreover, the expression "at least one" used in this description is equivalent to the expression "one or more".

[0018] Throughout this application, the term "comprising" shall be interpreted as encompassing all the specifically mentioned features as well as optional, additional, unspecified features. As used herein, the use of the term "comprising" also discloses the embodiment in which no features other than the specifically mentioned features are present (i.e., "consisting of").

[0019] Unless otherwise specified, all numerical values ​​expressing a quantity of ingredients and the like used in the description and claims shall be understood as modified by the term "approximately". Accordingly, unless otherwise stated, the numerical values ​​and parameters described These are approximate values ​​that can be changed depending on the desired objective, if applicable.

[0020] For the purposes of the present invention, the term "keratinous materials" is intended to cover human skin and mucous membranes such as the lips. Facial skin is considered in particular according to the present invention.

[0021] In the present invention, all percentages refer, unless otherwise specified, to a percentage by weight.

[0022] According to the first aspect, the composition of the present invention comprises: i. at least one collagen; ii. palmitoyl tripeptide-1; iii. of palmitoyl tetrapeptide-7; and iv. of palmitoyl tetrapeptide-10. Collagen

[0023] According to the first aspect, the composition of the present invention comprises at least one collagen.

[0024] For the purposes of the present invention, collagen can be any type of collagen from any source. In this regard, reference will be made to the different types of collagen mentioned in the studies by Van der Rest and Garonne, 1990, Biochem., vol. 72, 473-484 or 1991, Faseb Journal, vol. 5, 2814-2823, or disclosed in CN109593126A.

[0025] Preferably, the collagen is chosen from type I, III and V collagens.

[0026] More preferably, the composition according to the present invention comprises type III collagen. Preferably, the collagen is water-soluble.

[0027] It goes without saying that, according to the present invention, a mixture of different types of collagen in any proportion and / or of different origins can be used.

[0028] Advantageously, collagen is present in the composition of the present invention in a quantity of dry matter ranging from 0.005 ppm to 1000 ppm, preferably from 0.01 ppm to 500 ppm, more preferably from 0.05 ppm to 100 ppm, most preferably from 0.05 ppm to 4 ppm, relative to the total weight of the composition. Palmitoyl tripeptide-1

[0029] The composition of the present invention comprises palmitoyl tripeptide-1.

[0030] Palmitoyl tripeptide-1 has a glycine-histidine-lysine (GHK) amino acid sequence. Its chemical name is N-(l-oxohexadecyl)glycyl-L-histidyl-L-lysine and its structure is as follows:

[0031] This is a matrikine signal peptide, which acts on the dermis to promote the synthesis of extracellular matrix such as collagen and glycosaminoglycans, strengthen the dermis and make the skin thicker, firmer, with smoothed wrinkles and more resistant to UV.

[0032] Its synthesis can be found in CN108218956A and CN114891063B.

[0033] Palmitoyl tripeptide-1 is commercially available.

[0034] Advantageously, palmitoyl tripeptide-1 is present in the composition of the present invention in an amount ranging from 0.0002 ppm to 200 ppm, preferably from 0.001 ppm to 100 ppm, more preferably from 0.005 ppm to 50 ppm, most preferably from 0.01 ppm to 1 ppm, relative to the total weight of the composition. Palmitoyl tetrapeptide-7

[0035] The composition of the present invention comprises palmitoyl tetrapeptide-7.

[0036] Palmitoyl tetrapeptide-7, also known as palmitoyl tetrapeptide-3, has the amino acid sequence glycine-glutamine-proline-arginine (GQPR). Its chemical name is N-(l-oxohexadecyl)glycyl-L-glutaminyl-L-prolyl-L-arginine. Palmitoyl tetrapeptide-7 has the following structure:

[0037] Palmitoyl tetrapeptide-7 is an active fragment of immunoglobulin IgG, which can significantly reduce the level of inflammatory factor IL-6 in the cellular inflammation process, particularly in cells damaged by UV, and can reduce the deepening of skin wrinkles caused by inflammation and restore skin vitality.

[0038] Its synthesis can be found in CN112830956B.

[0039] Palmitoyl tripeptide-7 is commercially available.

[0040] Advantageously, palmitoyl tetrapeptide-7 is present in the composition of the present invention in an amount ranging from 0.0001 ppm to 100 ppm, preferably from 0.0005 ppm to 50 ppm, more preferably from 0.001 ppm to 25 ppm, most preferably from 0.005 ppm to 0.5 ppm, relative to the total weight of the composition. Palmitoyl tetrapeptide-10

[0041] The composition of the present invention comprises palmitoyl tetrapeptide-10.

[0042] Palmitoyl tetrapeptide-10 has a chemical name N2-(l-oxohexadecyl)-L-lysyl-L-threonyl-L-phenylalanyl-L-lysine.

[0043] Palmitoyl tetrapeptide-10 has the following structure:

[0044] Palmitoyl tetrapeptide-10 is commercially available.

[0045] Advantageously, palmitoyl tetrapeptide-10 is present in the composition of the present invention in an amount ranging from 0.0001 ppm to 10 ppm, preferably from 0.0005 ppm to 5 ppm, more preferably from 0.001 ppm to 1 ppm, most preferably from 0.002 ppm to 0.02 ppm, relative to the total weight of the composition. Acetyl hexapeptide-8

[0046] Preferably, the composition of the present invention comprises acetyl hexapeptide-8.

[0047] Acetyl hexapeptide-8 has a chemical name N-acetyl-L-alpha-glutamyl-L-alpha-glutamyl-L-methionyl-L-glutaminyl-L-arginyl-L-argininamide.

[0048] Acetyl hexapeptide-8 has the following structure:

[0049] Acetyl hexapeptide-8 is commercially available.

[0050] Advantageously, acetyl hexapeptide-8 is present in the composition of the present invention in an amount ranging from 0.001 ppm to 30 ppm, preferably from 0.005 ppm to 10 ppm, more preferably from 0.01 ppm to 5 ppm, by total weight of the composition. Aqueous phase

[0051] The composition of the present invention may include an aqueous phase.

[0052] Preferably, the aqueous phase comprises water.

[0053] Advantageously, water is present in the composition of the present invention in an amount ranging from 50% by weight to 99.99% by weight, preferably from 70% by weight to 99.99% by weight, more preferably from 80% by weight to 99.6% by weight, relative to the total weight of the composition.

[0054] Optionally, the aqueous phase comprises a water-miscible organic solvent (at room temperature at 25 °C) selected from monoalcohols, glycols and polyols having 2 to 20 carbon atoms, such as octyldodecanol, glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and mixtures thereof, so as to provide a hydrating effect.

[0055] Advantageously, the aqueous phase is present in the composition of the present invention in an amount ranging from 60% by weight to 99.99% by weight, preferably from 70% by weight to 99.99% by weight, more preferably from 80% by weight to 99.6% by weight, relative to the total weight of the composition. Additional cosmetic active ingredients

[0056] The composition of the present invention may include an additional cosmetic active ingredient in addition to the cosmetic active ingredients as defined above.

[0057] A person skilled in the art can adjust the type and quantity of additional cosmetic active ingredients according to the end use of the composition according to the present invention. Additional adjuvants or additives

[0058] The composition of the present invention may also include conventional cosmetic adjuvants or additives, for example, perfumes, chelating agents, preservatives and bactericides, surfactants, thickeners, pH regulators, and mixtures thereof.

[0059] A person skilled in the art can choose the quantity of additional adjuvants or additives so as not to have a negative impact on the final use of the composition according to the present invention.

[0060] According to a particularly preferred embodiment, the present invention proposes a composition comprising, in relation to the total weight of the composition: i. from 0.05 ppm to 100 ppm of at least one collagen; ii. from 0.005 ppm to 50 ppm of palmitoyl tripeptide-1; iii. from 0.001 ppm to 25 ppm of palmitoyl tetrapeptide-7; iv. 0.001 ppm to 1 ppm of palmitoyl tetrapeptide-10; and v. optionally from 0.01 ppm to 5 ppm of acetyl hexapeptide-8. pharmaceutical form and process

[0061] The composition of the present invention is in the form of an emulsion, a cream, a lotion or a hydrogel, and can be used as a toner, a lotion, a light cream, a nourishing cream, a night mask or an eye cream.

[0062] The composition of the present invention can be used for the care of keratinous materials. In particular, the composition of the present invention can provide benefits for skin radiance, forehead wrinkles, fine lines in the nasolabial area, and ptosis of the lower part of the face.

[0063] According to the second aspect, the present invention proposes a non-therapeutic method for the treatment of keratinous materials, comprising the application of the composition according to the first aspect of the present invention to the keratinous materials.

[0064] In certain embodiments, the present invention proposes a non-therapeutic method for anti-aging keratinous materials, comprising the application of the composition according to the first aspect of the present invention on keratinous materials.

[0065] In particular, keratinous material is the skin, especially facial skin.

[0066] In a third aspect, the present invention proposes a use of the composition according to the first aspect of the present invention to provide an anti- aging on keratinous materials.

[0067] In particular, keratinous material is the skin, especially facial skin. EXAMPLES

[0068] The following examples are given by way of non-limiting illustrations of the present invention.

[0069] The main raw materials used, their trade names and suppliers are listed in Table 1.

[0070] [Table 1] Table 1 INCI name Trade name Supplier Collagen 164.88° COLLAGEN (H0102) SHANXI JINBO BIO-PHARMACEUT ICAL Palmitoyl tetrapeptide-10 CRYSTALIDE MB AL SEDERMA (CRODA) Acetyl hexapeptide-8 ARGIRELINE AMPLIFIED PEPTIDE SOLUTION LIPOTEC Palmitoyl tripeptide-1 (and) Palmitoyl tetrapeptide-7 MATRIXYL 3000 SEDERMA (CRODA)

[0071] Inventive Examples 1 and 2 and Comparative Examples 1 and 2

[0072] The compositions of Inventive Examples (IE) 1 and 2 and Comparative Examples (CE) 1 and 2 were prepared based on the quantities of active ingredients given in Table 2, and the remainder is water. The quantities are given in ppm by weight of active ingredients relative to the total weight of the composition.

[0073] [Table 2] Table 2 Components El. 1 EC. 1 EC. 2 EI.2 Collagen 4 4 4 0.05 Palmitoyl tetrapeptide-10 0.02 / 0.02 0.002 Acetyl hexapeptide-8 / 0.05 0.05 0.05 Palmitoyl tripeptide-1 1 1 / 0.01 Palmitoyl tetrapeptide-7 0.5 0.5 / 0.005

[0074] The compositions of Inventive Examples 1 and 2 represent compositions according to the present invention.

[0075] The composition of comparative example 1 does not include palmitoyl te- trapeptide-10.

[0076] The composition of comparative example 2 does not include palmitoyl tripeptide-1 or palmitoyl tetrapeptide-7.

[0077] Preparation process:

[0078] The compositions listed above were prepared as follows, taking the composition of inventive example 2 for example, by adding collagen, palmitoyl tetrapeptide-10, acetyl hexapeptide-8 and palmitoyl tripeptide-1 (and) palmitoyl tetrapeptide-7 gently into water with stirring at room temperature to obtain a homogeneous mixture. Assessment

[0079] The effect of the above-prepared compositions on the production of collagen III and collagen IV was tested as follows. 1. Cell inoculation:

[0080] The fibroblasts were revived, and when the pose rate reached approximately 60%, the cells were seeded into 6-well plates and cultured overnight in an incubator with CO2 (37°C, 5% CO2). 1. Preparing the solution:

[0081] The working solutions were prepared according to the test groups listed in Table 3.

[0082] [Table 3]Table 3 Sample Groups Indicator Methods Blank Control (BC) / 1. Collagen IV + IF 2. Collagen III + qRT-PCR Negative Control (NC) / Positive Control (PC) TGF-

[31] Test Samples According to Composition of El. 1 According to Composition of EC.1 According to Composition of EC.2 According to Composition of EI.2 1. Administration:

[0083] The groups were administered according to Table 3. Culture medium was added to each well for the blank control group and the negative control group. The same volume of culture medium containing TGF-

[31] was added to each well for the positive control group. The same volume of culture solution containing the corresponding concentration of active ingredients in the culture medium was added to each well for the test sample groups. 1. UVA irradiation: all groups except the blank control group were subjected to UVA irradiation. After irradiation, they were placed in an incubator with CO2 (37 °C, 5% CO2) for subsequent culture. 2. Immunofluorescence detection and gene expression detection were performed.

[0084] The rate of improvement and the rate of overregulation were calculated according to the following equations:

[0085] Improvement rate (%) = (test group - NC group) / NC group * 100%

[0086] Overregulation rate (%) = (test group - BC group) / BC group * 100%

[0087] When analyzed with the t-test, with respect to the BC group, significance is represented by #, the value p<0.05 is represented by #, the value p<0.01 is represented by # #; with respect to the NC group, significance is represented by *, the value p<0.05 is represented by * and the value p<0.01 is represented by **.

[0088] The PCR data for collagen III have been summarized in Table 4.

[0089] [Table 4] Table 4 Mean ET P-value Overregulation Rate (%) BC 1.00 0.08 / / NC 0.45 0.07 0.001## / PC 0.66 0.07 0.023* 46.67 Composition of El. 1 0.72 0.09 0.013* 60.00 Composition of EC.1 0.69 0.11 0.029* 53.33 Composition of EC.2 0.67 0.10 0.032* 48.89 Composition of El.2 0.83 0.14 0.013* 84.44

[0090] Table 4 shows that the compositions of inventive examples 1 and 2 show better results on the production of collagen III compared to the compositions of comparative examples 1 and 2.

[0091] The PCR data for collagen IV have been summarized in Table 5.

[0092] [Table 5] Table 5 Mean AND P-value Improvement Rate (%) BC 1.00 0.07 / / NC 0.48 0.05 0.001## / PC 1.61 0.02 0.000** 235.42 Composition of El. 1 2.06 0.15 0.000** 329.17 Composition of EC.1 1.90 0.19 0.000** 295.83 Composition of EC.2 1.70 0.15 0.000** 254.17

[0093] It can be seen in Table 5 that the composition of inventive example 1 shows a better result on the production of collagen IV compared to the compositions of comparative examples 1 and 2.

Claims

Demands

1. Composition comprising: (i) at least one collagen; (ii) palmitoyl tripeptide-1; (iii) palmitoyl tetrapeptide-7; and (iv) palmitoyl tetrapeptide-10.

2. Composition according to claim 1, wherein the collagen is selected from type I, III or V collagens, preferably the collagen is water-soluble.

3. Composition according to claim 1 or 2, wherein collagen is present in a dry matter quantity from 0.005 ppm to 1000 ppm, preferably from 0.01 ppm to 500 ppm, more preferably from 0.05 ppm to 100 ppm, most preferably from 0.05 ppm to 4 ppm, relative to the total weight of the composition.

4. Composition according to any one of claims 1 to 3, wherein palmitoyl tripeptide-1 is present in an amount from 0.0002 ppm to 200 ppm, preferably from 0.001 ppm to 100 ppm, more preferably from 0.005 ppm to 50 ppm, most preferably from 0.01 ppm to 1 ppm, relative to the total weight of the composition.

5. Composition according to any one of claims 1 to 4, wherein palmitoyl tetrapeptide-7 is present in an amount from 0.0001 ppm to 100 ppm, preferably from 0.0005 ppm to 50 ppm, more preferably from 0.001 ppm to 25 ppm, most preferably from 0.005 ppm to 0.5 ppm, relative to the total weight of the composition.

6. Composition according to any one of claims 1 to 5, wherein palmitoyl tetrapeptide-10 is present in an amount from 0.0001 ppm to 10 ppm, preferably from 0.0005 ppm to 5 ppm, more preferably from 0.001 ppm to 1 ppm, most preferably from 0.002 ppm to 0.02 ppm, relative to the total weight of the composition.

7. Composition according to any one of claims 1 to 6, further comprising acetyl hexapeptide-8.

8. Composition according to claim 7, wherein acetyl hexapeptide-8 is present in an amount from 0.001 ppm to 30 ppm, preferably from 0.005 ppm to 10 ppm, more preferably from 0.01 ppm to 5 ppm, relative to the total weight of the composition.

9. Composition according to claim 1, comprising, in relation to the total weight of the composition: (i) from 0.05 ppm to 100 ppm of at least one collagen selected from type I, III and V collagens; (ii) from 0.005 ppm to 50 ppm of palmitoyl tripeptide-1; (iii) from 0.001 ppm to 25 ppm of palmitoyl tetrapeptide-7; (iv) 0.001 ppm to 1 ppm of palmitoyl tetrapeptide-10; and (v) optionally, from 0.01 ppm to 5 ppm of acetyl hexapeptide-8.

10. Non-therapeutic method for the treatment of keratinous materials, comprising the application of the composition according to any one of claims 1 to 9 on keratinous materials.