WO2021204309A1 - Pentapeptide dérivé de la caséine et composition le comprenant ainsi que son utilisation topique - Google Patents
Pentapeptide dérivé de la caséine et composition le comprenant ainsi que son utilisation topique Download PDFInfo
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- WO2021204309A1 WO2021204309A1 PCT/CZ2021/050042 CZ2021050042W WO2021204309A1 WO 2021204309 A1 WO2021204309 A1 WO 2021204309A1 CZ 2021050042 W CZ2021050042 W CZ 2021050042W WO 2021204309 A1 WO2021204309 A1 WO 2021204309A1
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- pentapeptide
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000012755 real-time RT-PCR analysis Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
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- 238000010839 reverse transcription Methods 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
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- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
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- A61K9/0012—Galenical forms characterised by the site of application
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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- A61Q19/08—Anti-ageing preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
- C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
- C07K14/4701—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals not used
- C07K14/4732—Casein
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
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- A61K38/00—Medicinal preparations containing peptides
Definitions
- the present invention relates to casein-derived X-Asn-Pro-Trp-Asp-Gln-Z pentapeptide, composition comprising thereof, and its topical use. It relates more particularly to use of casein-derived peptides for treating the skin of humans or animals for cosmetic and dermo-pharmaceutical purposes.
- Skin as a barrier protects the body from biological and chemical factors, regulates the passage of molecules and protects against physical influences such as UV radiation. These external factors often damage the skin and induce appropriate cellular responses that eventually cause skin aging [1, 2].
- Old skin has impaired barrier function with altered permeability to various substances [3, 4], mostly due to a decrease in lipid content in the stratum corneum. It is considered that the aged skin losses approximately 30% of ceramides (a waxy lipid molecules) [5]. In some diseases, such as atopic dermatitis, the skin barrier is also impaired, allowing microbial and allergen penetration [6] . For this reason, the improvement of the skin barrier is one of the main trends not only in cosmetology but also in dermatology.
- the human epidermis mainly consists of four layers: stratum basale (SB), stratum spinosum (SS), stratum granulosum (SG) and stratum comeum (SC). Keratinocytes after proliferation in SB differentiate and migrate upward through SS into the SC. Different sets of keratin intermediate filaments are expressed in different layers. Keratins are elastic fibrous proteins and form heterodimers between acidic (type I) and basic (type II) proteins. Keratins make filaments and form a three-dimensional cytoskeleton in the cytoplasm and around the nucleus. These filaments are anchored to desmosomes, which are junctional complexes utilized for cell-cell adhesion [7, 8].
- SB stratum basale
- SS stratum spinosum
- SG stratum granulosum
- SC stratum comeum
- Cornification is similar to the cell death of lens epithelial cells and red blood cells in the respect that typical apoptosis-related proteins (e.g. caspase-3) are not activated. [9, 10].
- the SC is the most outer layer and is composed of keratinocytes with completed keratinization. [11, 12].
- TJ tight junctions
- Tight junctions are very complex structures which form a paracellular barrier to tightly regulate passage of molecules in a highly selective manner across the epithelium [15].
- Tight junctions consist of claudins, occludins, tricellulin, zonula occludens and junction adhesion molecules.
- the structure of tight junction complexes differs between different layers of the epidermis [16].
- TJs were proved to have the ability to compensate for damaged or even completely missing SC. This phenomenon was manifested by increased expression of TJ proteins such as ZO-1 or occludin that resulted in a blockage of molecules at TJ positive sites [18, 19].
- NPWDQ Peptide Asn-Pro-Trp-Asp-Gln
- the subject-matter of the invention concerns a casein-derived pentapeptide as an enhancer of skin cells having a general formula I
- X is -NHX 1 group of asparagine at the N-terminal end of the peptapeptide, wherein X 1 is selected from a group comprising H, acetyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, elaidoyl, oleoyl, biotinoyl or lipoyl; Z is -COZ 1 group of glutamine at the C-terminal end of the peptapeptide, wherein Z 1 is selected from a group comprising OH, OCH3, OCH2CH3 or NH2.
- X 1 is H or acetyl and Z 1 is OH or NH2 .
- the pentapeptide of the general formula I according to the present invention may be optically pure or be composed of L- or D-isomers or a mixture thereof.
- L-isomers which are those found in nature, are preferred.
- the pentapeptide of the present invention may be in the form of salts, especially salts of hydrochloric acid or acetic acid, or any salts commonly used in cosmetics.
- the present invention also encompasses derivatives of the pentapeptides of the present invention and their complexes with other species such as metal ion (e.g. copper, zinc, manganese, magnesium, and other).
- metal ion e.g. copper, zinc, manganese, magnesium, and other.
- Another embodiment according to the present invention is a topical composition comprising at least one pentapeptide of the general formula I as defined above.
- a concentration of the pentapeptide of the general formula I is in the range of 0.001 to 70 % (w/w), preferably in the range of 0.001 to 0.5 % (w/w), more preferably from 0.001 to 0.05% (w/w).
- Amount of the pentapeptide depends on the purpose of the composition and the desired final effect.
- This invention also includes the topical composition, that contains at least one pentapeptide according to the invention in a medium suitable for the topical skin application that may be selected from a group comprising a cream (a water- in-oil or oil-in-water emulsion, a micro- or nano-emulsion), a serum (aqueous or hydro-alcoholic solution or gel, sterile or nonsterile), anhydrous gel, a paste, a dispersion of vesicles, a powder, nanofibers, macro-, micro-, or nano-capsules, macro-, micro- or nano-spheres, liposomes, oleosomes or chylomicrons, macro-, micro-, or nanoparticles or macro-, micro- or nano- sponges, which may be adsorbed on organic polymer powders, talcs, bentonites and other inorganic or organic supports.
- a cream a water- in-oil or oil-in-water emulsion, a micro- or nano
- the composition is in a form selected from a group comprising cream, serum or nanofibers.
- the concentration of the pentapeptide of the general formula I is in the range of 0.001 to 1 % (w/w), preferably 0.001 % to 0.05 % (w/w).
- the topical composition according to the present invention containing at least one pentapeptide in combination with other common ingredients used in cosmetic or dermo- pharmaceutical products.
- composition in the form of a cream additionally comprises at least one cosmetic and dermo-pharmaceutical auxiliary ingredient selected from a group comprising oil, wax, butter, emulsifier, auxiliary active ingredient and preservative.
- cosmetic and dermo-pharmaceutical auxiliary ingredient selected from a group comprising oil, wax, butter, emulsifier, auxiliary active ingredient and preservative.
- the amount of oil, wax, butter or a mixture thereof in the composition according to the present invention is in the range of 20 to 55 % (w/w).
- the amount of emulsifier in the composition according to the present invention is in the range of 2 to 7 % (w/w).
- the amount of auxiliary active ingredient in the composition according to the present invention is in range of 0.001 to 10 % (w/w).
- the amount of preservative in the composition according to the present invention is in range of 0.8 to 1.2 % (w/w).
- the oil is selected from a group comprising argan, coconut, avocado, almond, sesame, olive, sunflower, hemp, jojoba, macadamia, castor oil;
- the butter is selected from a group comprising cocoa butter, shea butter, avocado butter; and
- the wax is selected from a group comprising lanolin, beeswax, camauba, candelilla wax and petrolatum.
- the emulsifier is preferably selected from a group comprising glyceryl stearate, lecithin, steryl alcohol, sorbitan oleate, polysorbate, stearic acid, cetyl alcohol and cetearyl alcohol, sodium acrylate, sodium acryloyldimethyl taurate copolymer, isohexadecane, polysorbate 80.
- the topical composition according to the present invention containing at least one pentapeptide according to the invention may also be combined with other auxiliary active ingredients that can have synergistic or additional effect to enhance or extend the desired activity described in the invention. That might comprise following agents: anti-aging, anti-fine lines and anti-wrinkle, lightening, whitening, anti-spots, pro-pigmenting, hydrating, moisturizing, humectants, slimming, exfoliating, anti-acne, anti-redness, anti-inflammatory, antioxidants, radical scavengers, acting on skin brightness of complexion, anti-glycation, volumizing, restructuring, rejuvenating, regenerating, anti-carbonylation, dermo-relaxing, improving stratum corneum, dermo-epidermal junction, HSP protein production, firmness, elasticity and tone of skin, collagen boosters, eye contours (dark circles and under eye bags), promoting blood circulation etc.
- auxiliary active ingredients that can have synergistic or
- auxiliary active ingredients may be synthetic or obtained from plant, bacteria, fungi cell cultures or products of their fermentation.
- the auxiliary active ingredient is selected from a group comprising vitamins A, D, E, K, C, B-group vitamins, coenzyme Q10, allantoin, bisabolol, lactic acid, aminoacids, peptides, preferably Acetyl Hexapeptide-8, Palmitoyl Tripeptide- 1 , Copper tripeptide- 1, Saccharomyces peptides, Hexapeptide-1, and proteins preferably rice, soy protein, quinoa protein or wheat protein; polysaccharides, preferably hyaluronic acid or its pharmaceutically and cosmetically acceptable salt, carboxymethyl glucan, schizophyllan, glucomannan; panthenol; urea; glycerin; plant extracts, preferably aloe vera extract, cammomile extract, acai extract, green tea extract, algae extract, oat extract
- preservative is selected from the group comprising aromatic acids and derivatives thereof, preferably benzoic acid, salicylic acid, dehydroacetic acid, parabens; alcohols preferably ethanol, isopropanol, benzyl alcohol, phenoxyethanol, phenethyl alcohol; imidazole derivatives preferably hydantoin, imidazolidinyl urea; cationic surfactants preferably benzalkonium chloride.
- aromatic acids and derivatives thereof preferably benzoic acid, salicylic acid, dehydroacetic acid, parabens
- alcohols preferably ethanol, isopropanol, benzyl alcohol, phenoxyethanol, phenethyl alcohol
- imidazole derivatives preferably hydantoin, imidazolidinyl urea
- cationic surfactants preferably benzalkonium chloride.
- the topical composition according to the present invention is in the form of a serum comprising the pentapeptide of the general formula I according to the present invention in a concentration from 0.001 to 1 % (w/w), preferably 0.01 to 0.5 % (w/w).
- topical composition according to the present invention can preferably contain at least one water-soluble auxiliary active ingredient in range of 0.001 to 10 % (w/w) and at least one a preservative as defined above.
- the water soluble auxiliary active ingredient is selected from the group comprising of vitamin C; group B vitamins; aminoacids, peptides preferably Acetyl Hexapeptide-8 Argiline, Palmitoyl Tripeptide, Copper tripeptide- 1, Saccharomyces peptides, Hexapeptide-1, and proteins preferably rice protein, soy protein, quinoa or wheat protein; further water-soluble polysaccharides preferably hyaluronic acid or its pharmaceutically and cosmetically acceptable salt, carboxymethyl glucan, schizophyllan, glucomannan; panthenol; urea; glycerin; plant extracts preferably aloe vera extract, cammomile extract, acai extract, green tea extract, algae extract, oat extract, cannabis extract, cranberry extract; bacteria preferably Lactobacillus, Thalassospira, Bifidobacterium, Halobacterium or fungi extracts from Agaricus subrufescens
- Average molecular weight of hyaluronic acid or its pharmaceutically and cosmetically acceptable salt as the auxiliary active ingredient is in the range of 4x 10 2 to 4x 10 6 g/mol, preferably lx 10 4 to l,5x 10 6 g/mol.
- the amount of water in the composition according to the present invention in the form of the cream or the serum corresponds the amount of water added up to 100 % (w/w) of the composition.
- the topical composition it is in the form of nanofibers comprising the pentapeptide of the general formula I as defined above and its concentration is in the range of 0.07 to 70 % (w/w), preferably 0.07 to 7 % (w/w), and at least one auxiliary polymer.
- nanofibers can contain additionally hyaluronic acid or its pharmaceutically and cosmetically acceptable salt.
- concentration in nanofibers in the topical composition according to the present invention is in the range of 5 to 80% (w/w) and a concentration of auxiliary polymer is in the range of 10 to 94 % (w/w).
- Average molecular weight of hyaluronic acid or its pharmaceutically and cosmetically acceptable salt is in the range of lx 10 4 to 3x 10 6 g/mol.
- the auxiliary polymer is selected from a group comprising polyethylene oxide, polyvinyl alcohol or a mixture thereof. Average molecular weight of the auxiliary polymer is in the range of lx 10 4 to 9x 10 5 g/mol.
- the topical composition it further comprises at least one auxiliary active ingredient as defined above.
- the nanofibers are in the form of a water-soluble, dry layer.
- pentapeptide of the general formula I according to the present invention or use of the cosmetic and dermo-pharmaceutical compositions containing said pentapeptide to improve the skin condition and appearance. More specifically, the pentapeptide according to the invention shows antioxidant activity, improves skin barrier function by stimulation of production of adhesion, tight junction and comification proteins, and it also increases skin hydration by induction of filaggrin, whose degradation products are part of the skin natural moisturizing factor.
- the said pentapeptide according to the present invention is an enhancer of skin cells especially by additional effect, thus by enhancing keratinization - a process that occurs only in the skin cells.
- the said pentapeptide according to the present invention is also useful for restoration of the skin barrier function in vivo in human epidermis and for upregulation of the gene expression of proteins involved in the skin barrier function and hydration in vivo in human epidermis
- the said pentapeptide of the topical composition according to the invention is dedicated for normal skin as well as for the skin with disrupted barrier function associated with various skin diseases.
- the pentapeptide of the general formula I according to the present invention and the topical composition according to the present invention for use for treatment of skin.
- skin diseases selected from a group comprising atopic dermatitis, psoriasis, peeling skin disease, ichthyosis.
- cosmetic treatment of skin preferably for use for cosmetic treatment of skin.
- Cosmetically and pharmaceutically acceptable salts of hyaluronic acid are said to be those formed from acids which form non-toxic acid anions selected from a group comprising sodium, potassium, calcium, magnesium, zinc.
- % w/w of components in the topical composition according to the present invention are related to the total weight of the composition.
- Average molecular weight of hyaluronic acid or its pharmaceutically and cosmetically acceptable salts is determined by SEC-MALS (multi-angle light scattering coupled with size exclusion chromatography) or by calculation from kinematic viscosity of 0.05 % solution in a salt solution buffered with phosphate.
- Fig. 1 Cytotoxicity of NPWDQ and acetyl-Asn-Pro-Trp-Asp-Gln (ac-NPWDQ). The data represent mean+SEM from at least 3 independent experiments.
- Fig. 2 Antioxidant activity of NPWDQ and ac-NPWDQ. The data represent mean+SEM from at least 3 independent experiments. Student’s T-test was used for the statistical analysis (* p ⁇ 0.05, ** p ⁇ 0.01, *** p ⁇ 0.001).
- Fig. 3. Primary dermal irritation index (PDII) for NPWDQ. NPWDQ peptide was applied in occlusion on volar forearm of 15 volunteers for 18 h. The exposed skin was then evaluated and scored for the signs of irritation and PDII was calculated. There were no signs of dermal irritation in tested concentrations of NPWDQ peptide: 200 and 100 pg/ml and PDII was below 0,5 (limit for non-irritating agents).
- Fig. 4 Recovery of TEWL (Transepidermal water loss) in human skin in vivo after invasion of the skin barriers by removal of upper layers SC with a tape and application of NPWDQ.
- NPWDQ peptide 200 pg/ml in PBS
- TEWL was measured immediately after tape stripping and after 48 h treatment with NPWDQ.
- Peptide NPWDQ contributed to faster recovery of TEWL in comparison with the control (PBS).
- Student’s T-test was used for the statistical analysis (* p ⁇ 0.05, ** p ⁇ 0.01, *** p ⁇ 0.001).
- Fig. 5 Downregulation of TEWL in human skin after treatment with acetylated NPWDQ (ac-NPWDQ).
- ac-NPWDQ acetylated NPWDQ
- Fig. 6 Upregulation of skin hydration after treatment with acetylated NPWDQ (ac-NPWDQ).
- ac-NPWDQ acetylated NPWDQ
- Split-face study on 16 volunteers showed that 6 weeks application of ac-NPWDQ (0,001%) cause upregulation of skin hydration by 8%.
- Student’ s T-test was used for the statistical analysis (* p ⁇ 0.05, ** p ⁇ 0.01, *** p ⁇ 0.001).
- NPWDQ and ac-NPWDQ (acetylated) peptides that were synthesized were tested on NIH-3T3 mouse embryonic fibroblasts.
- the cells were seeded into 96-well plates and cultured for 24 hours.
- Cell viability was measured 24 hours after treatment with the peptides using the 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyl- tetrazolium bromide (MTT) assay.
- MTT stock solution (20 pi; concentration 5 mg/ml) was added to the cell culture medium (200 m ⁇ ) into each well. The plates were incubated for 2.5 h at 37 °C.
- Example 2 Antioxidant activity of NPWDQ and ac-NPWDQ peptides.
- the antioxidant activity of NPWDQ and ac-NPWDQ that were synthesized was determined using 2,2-diphenyl- 1-picrylhydrazyl (DPPH; Sigma- Aldrich) as a stable free radical which in the presence of an antioxidant changes color from purple to yellow.
- DPPH 2,2-diphenyl- 1-picrylhydrazyl
- the DPPH assay was performed as described previously (Brand -Williams et al., 1995) with slight modifications. Briefly, 100 m ⁇ of the 0,01 % DPPH diluted in methanol was added to 100 m ⁇ of the tested substance diluted in 50 mM Tris pH 7,1 in 96-well plate. After 15 min, the absorbance was measured at 515 nm using a VersaMax microplate reader (Molecular Devices).
- NPWDQ and ac-NPWDQ peptides showed a significant, direct antioxidant activity. They showed an ability for a direct scavenging of free radicals in tested concentrations (Fig.2). Student’s T-test was used for the statistical analysis. (* p ⁇ 0.05,
- Example 3 Upregulation of tight junction proteins and adhesion molecules in HaCaT keratinocytes by NPWDQ and ac-NPWDQ treatment.
- HaCaT keratinocytes were seeded in 6-well plate and cultivated for 24 h. After that, they were treated with 100 pg/ml of NPWDQ or ac-NPWDQ that were synthesized (see Examples 8 and 9) and incubated for 48 h.
- the total RNA was isolated from the samples using RNAse mini kit (Qiagen) according to the instructions provided by the producer. The concentration and purity of isolated RNA was determined using a NanoDropTM One/OneC Microvolume UV-Vis spectrophotometer using a 260/280 absorption ratio.
- RNA 1 pg was used for reverse transcription reaction performed with High Capacity RNA to cDNA Kit (Invitrogen) in GenePro thermal cycler (Bioer Technology) according to the manufacturer’s instructions.
- qRT-PCR quantitative, real-time PCR
- TJP1, TJP2, CDH1, OCLN TaqMan gene expression probes
- Applied Biosystems TaqMan Fast Advanced Mastermix
- RPL13A was used as a reference gene. The data were analysed using the 2 DDa method.
- Table 1 Expression of the genes encoding tight junction proteins TJP1, TJP2, OCLN and adhesive molecules CDH1, DSG1 in HaCaT keratinocytes after treatment with NPWDQ (100 pg/ml) for 48 h.
- the gene expression was determined by qRT-PCR.
- the data represent mean+SEM from at least 3 independent experiments. Student’s T-test was used for the statistical analysis (* p ⁇ 0.05, ** p ⁇ 0.01, *** p ⁇ 0.001).
- Table 2 Expression of the genes encoding tight junction proteins TJP1, TJP2, OCLN and adhesive molecules CDH1, DSG1 in HaCaT keratinocytes after treatment with ac-NPWDQ (100 pg/ml) for 48 h. The gene expression was determined by qRT-PCR. The data represent mean+SEM from at least 3 independent experiments. Student’s T-test was used for the statistical analysis (* p ⁇ 0.05, ** p ⁇ 0.01, *** p ⁇ 0.001). Table 2
- the dermal irritation patch test was performed with NPWDQ that was synthesized (see Example 8) applied in occlusion on volar forearm of 15 volunteers.
- the peptide was applied in phosphate-buffered saline (PBS) in concentrations 100 and 200 pg/ml for 18 h, PBS was applied as a negative control.
- PBS phosphate-buffered saline
- the primary dermal skin irritation index was then calculated.
- NPWDQ peptide has no irritating effect on human skin (Fig.3).
- Example 5 Restoration of the skin barrier function in vivo in human epidermis by NPWDQ treatment.
- TEWL Skin barrier on two 1,5 cm 2 areas distant 2 cm from each other on volar forearm of 10 volunteers was impaired by tape stripping (15 D-Squame discs per each place, CuDerm) of the upper layers of SC.
- TEWL was measured in both places using a TM 30 tewameter (CK electronics) and then, 0,2 mg/ml NPWDQ peptide that was synthesized (see Example 8) in PBS or PBS alone was applied six times during 48 h at 8 a.m., 2 p.m. and 8 p.m. each day on the two tested areas. After 48 h we measured TEWL again and observed its bigger decrease in the place where the peptide was applied.
- the taped-stripped epidermis of the ten volunteers treated with NPWDQ that was synthesized was after the TEWL measurement as described in Example 5 sampled using a suction blister method.
- the epidermis was homogenized, and RNA was isolated from the samples by the guanidine thiocyanate-phenol extraction method using RNAzol Reagent (Molecular Research Center) and RNAse mini kit (Qiagen) according to the instructions provided by the producer.
- the further procedure (RT-PCR and real-time qPCR) was performed as described in Example 3.
- TJP1 tight junction protein 1
- CDH1 cadherin 1
- DSG1 desmoglein 1
- comification proteins like involucrin (IVL) and filaggrin (FLG)
- UCA urocanic acid
- PCA pyrrolidone carboxylic acid
- NMF natural moisturizing factor
- TJP1 tight junction protein 1
- CDH1 adhesive molecules cadherin 1
- DSG1 desmoglein 1
- FLG filaggrin
- Example 7 Improvement of skin barrier function in vivo by acetylated NPWDQ.
- acetylated NPWDQ (ac-NPWDQ) was synthesized (see Examples 9) in cream (0,001%) on one half of the face for 6 weeks twice a day. On the other half placebo cream was applied.
- the TEWF was measured using a TM 30 tewameter (CK electronics) at the beginning of the study and then after 2, 4 and 6 weeks. After 6 weeks of ac-NPWDQ application we observed a downregulation of TEWF by 15% in comparison with the placebo (fig.5). Additionally, the peptide application led to upregulation of skin hydration by 8% (fig.6).
- NPWDQ peptide and its derivatives were synthetized by standard solid phase peptide synthesis protocol using Fmoc/tBu strategy on Wang resin [25, 26]. The resulting peptides were cleaved from the resin, and the sidechains were deprotected using TFA/FEO/CFECh/anisol/TIS (85:5:5/2.5/2.5) mixture.
- the first part of the synthesis was performed as described in Example 8. After Fmoc- deprotection and washing, mixture of acetanhydride and pyridine (1/1, v/v) in DMF was added into the reactor. N-terminal acetylation was carried out for 30 minutes. The resulting peptide was cleaved from the resin and the sidechains were deprotected using TFA/H20/CH2C12/anisol/TIS (85:5:5/2.5/2.5) cocktail.
- the first part of the synthesis was performed as described in Example 8. After Fmoc-deprotection and washing, lauric acid and DIC was added to resin for N-terminal lauroylation. Reaction was carried out for 24 hours. The resulting peptide was cleaved from the resin and the sidechains were deprotected using TFA/H20/CH2C12/anisol/TIS (85:5:5/2.5/2.5) cocktail.
- Example 11 Composition comprising pentapep tides according to the invention: cream with NPWDQ or ac-NPWDQ.
- oil and water phases are prepared, they are heated to 70 °C. Next, both phases are mixed together and emulsified while stirring (290 rpm/min). After stirring, the emulsion is cooled to 40 °C and the active ingredient phase and preservative are added. pH is checked and in case it is not between 5.2 to+ 6.5 it is adjusted with 1 -50% citric acid or 1-50 % KOH or
- Example 12 Composition with the peptides of the invention: a serum with NPWDQ or its derivatives.
- Example of serum containing the pentapeptide of the invention NPWDQ.
- the peptide NPWDQ is added to water and stirred till complete dissolution.
- phenoxyethanol and sodium hyaluronate are mixed with water till complete dissolution.
- Example 13 Composition with the peptides of the invention: a nanofiber layer with NPWDQ or its derivatives.
- Example of a nanofiber layer containing the peptide of the invention NPWDQ. Table 17.
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Abstract
L'invention concerne un pentapeptide dérivé de la caséine utilisé en tant qu'activateur des cellules de la peau ayant une formule générale I dans laquelle : X est un groupe –NHX1 d'asparagine à l'extrémité N-terminale du pentapeptide, dans laquelle X1 est choisi dans un groupe comprenant H, acétyle, octanoyle, décanoyle, lauroyle, myristoyle, palmitoyle, stéaroyle, élaïdoyle, oléoyle, biotinoyle ou lipoyle ; Z représente un groupe –COZ1 de glutamine à l'extrémité C-terminale du pentapeptide, dans laquelle Z1 est choisi dans un groupe comprenant OH, OCH3, OCH2CH3 ou NH2 ; et une composition topique le comprenant ainsi que son utilisation topique.
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| CZPV2020-207 | 2020-04-09 | ||
| CZ2020207A CZ308812B6 (cs) | 2020-04-09 | 2020-04-09 | Pentapeptid odvozený od kaseinu a kompozice, která jej zahrnuje a jejich topické použit |
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| CN117285595A (zh) * | 2023-11-27 | 2023-12-26 | 中国科学院烟台海岸带研究所 | 一种具有肠屏障保护功能的五肽lk5及其应用 |
| CN117304264A (zh) * | 2023-11-27 | 2023-12-29 | 中国科学院烟台海岸带研究所 | 一种具有肠屏障保护功能的五肽rp5及其应用 |
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Cited By (5)
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| WO2023186193A1 (fr) * | 2022-03-31 | 2023-10-05 | Contipro A.S. | Hexapeptide, composition comprenant celui-ci et son utilisation topique |
| CN117285595A (zh) * | 2023-11-27 | 2023-12-26 | 中国科学院烟台海岸带研究所 | 一种具有肠屏障保护功能的五肽lk5及其应用 |
| CN117304264A (zh) * | 2023-11-27 | 2023-12-29 | 中国科学院烟台海岸带研究所 | 一种具有肠屏障保护功能的五肽rp5及其应用 |
| CN117285595B (zh) * | 2023-11-27 | 2024-01-26 | 中国科学院烟台海岸带研究所 | 一种具有肠屏障保护功能的五肽lk5及其应用 |
| CN117304264B (zh) * | 2023-11-27 | 2024-02-06 | 中国科学院烟台海岸带研究所 | 一种具有肠屏障保护功能的五肽rp5及其应用 |
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| Publication number | Publication date |
|---|---|
| CZ2020207A3 (cs) | 2021-06-02 |
| CZ308812B6 (cs) | 2021-06-02 |
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