KR101949270B1 - Agent for peptide or protein stabilization - Google Patents
Agent for peptide or protein stabilization Download PDFInfo
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- KR101949270B1 KR101949270B1 KR1020110126601A KR20110126601A KR101949270B1 KR 101949270 B1 KR101949270 B1 KR 101949270B1 KR 1020110126601 A KR1020110126601 A KR 1020110126601A KR 20110126601 A KR20110126601 A KR 20110126601A KR 101949270 B1 KR101949270 B1 KR 101949270B1
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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
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Abstract
The present invention discloses compositions for stabilizing peptides or proteins comprising at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof. At least one of a peptide and a protein; And a composition comprising at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein, and derivatives thereof. The present invention also encompasses one or more of peptides and proteins; And at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein, and derivatives thereof to prepare a composition.
Description
The present invention relates to a preparation for stabilizing a peptide or protein.
Protein is a polymeric organism that constitutes the body of all living things and is a linkage of many amino acids. It is important as a constituent of the body of an organism and as a catalytic material for various chemical reactions in a cell. On the basis of these properties, proteins are widely used in various fields such as foods, medicines or cosmetics.
The present invention is intended to provide a composition in which a peptide or protein stabilizer and a peptide or protein are stably maintained. The present invention also provides a method for stabilizing a peptide or protein.
One aspect of the present invention provides a peptide or protein stabilizing agent comprising at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof.
Another aspect of the invention is a pharmaceutical composition comprising at least one of a peptide and a protein; And a composition comprising at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof.
Yet another aspect of the present invention is a method for the production of a peptide comprising at least one of a peptide and a protein; And at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein, and derivatives thereof, to prepare a composition.
At least one selected from the group consisting of panthenol, polyalcohol ester compound, casein and derivatives thereof of the present invention is excellent in stabilizing a peptide or protein. The composition comprising at least one of the peptides and proteins according to one aspect of the present invention comprises at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof, whereby the peptide or protein is not degraded for a long period of time And can be stably maintained. Particularly, in the case of a composition containing a peptide or protein in a dissolved state, since the degradation of the peptide or protein is hardly achieved by containing at least one selected from the group consisting of panthenol, polyalcohol ester compound, casein and derivatives thereof, It is not necessary to dissolve the peptide or protein and it is easy to store and circulate the peptide or protein in a state containing the peptide or protein.
The peptide or protein is used in various fields such as foods, medicines or cosmetics, but it is not easy to formulate it due to instability under external physical and chemical conditions, especially high temperature conditions. In addition, when the peptide or protein is dissolved, it is easily decomposed. Therefore, when the peptide or protein is dissolved, it is inconvenient to dissolve it immediately before use. In order to solve such problems, attempts have been made to stabilize peptides or proteins by incorporating saccharides such as sucrose, trehalose, fructose, mannitol and the like into a composition containing at least one of peptides and proteins. However, no.
Hereinafter, the present invention will be described in detail.
An aspect of the present invention provides a peptide or protein stabilizing agent comprising at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof. One or more selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof may physically and chemically protect the peptide or protein to prevent degradation of the peptide or protein, so that the peptide or protein can be stably maintained for a long period of time .
One aspect of the present invention is a method for detecting a protein comprising at least one of a peptide and a protein; And a composition comprising at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein, and derivatives thereof. The composition includes at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof, so that the peptide or protein contained therein can be stably maintained without being decomposed for a long period of time.
One aspect of the present invention is a method for detecting a protein comprising at least one of a peptide and a protein; And at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein, and derivatives thereof, to prepare a composition. In this way, the peptide or protein can be stably maintained for a long period without decomposition by mixing at least one selected from the group consisting of a peptide or protein and a panthenol, polyalcohol ester compound, casein and derivatives thereof.
In this specification, panthenol is an alcohol derivative of pantothenic acid, which is one of the vitamin B group, and can be expressed by the following formula (1).
As used herein, derivatives of panthenol include all compounds that can be obtained by chemically modifying a part of panthenol, including hydrogen or a specific atomic group substituted with another atom or atomic group. More specifically, the derivatives of panthenol include allantoin calcium pantothenate, calcium pantothenate, ethyl dicarboethoxy pantothenate (C 17 H 29 NO 9 , formula (2)), hydroxyethyl plate toten amide MEA (hydroxyethyl Pantothenamide MEA, C 13 H 26 N 2 O 6, formula 3), the plate toten amide MEA (Pantothenamide MEA, C 11 H 22 N 2 O 5, formula 4), pantothenic acid (pantothenic Acid , C 9 H 17 NO 5 (Chemical Formula 5), Pantothenoyl Dipeptide-13, Sodium Pantothenate, PanthenylEthylether, PanthenylEthylether It includes acetate, C 13 H 25 NO 5 , formula 6), and carbonyl Pantheon triacetate (panthenyl triacetate, C 15 H 25 NO 7, at least one selected from the group consisting of formula (7)).
In the present specification, a polyalcohol ester-based compound means a compound containing a polyalcohol ester group. In one aspect of the present invention, a polyalcohol ester compound and a derivative thereof include a compound in which a polyalcohol and stearic acid are ester-bonded, and specifically, polyglyceryl stearate, polyglyceryl distearate, PEG stearate, PEG distearate, polyglyceryl methyl glucoside distearate or PEG methyl glucose distearate, more specifically polyglyceryl-3 methyl glucose distearate or PEG-20 methyl glucose distearate do. In another aspect of the present invention, the polyalcohol ester based compound includes a compound that acts as a surfactant.
In this specification, a casein derivative is a concept including all the compounds obtainable by chemically changing a part of casein. In one aspect of the present invention, the casein or a derivative thereof includes a casein hydrolyzate obtained by hydrolyzing casein with an acid or an enzyme, or a casein salt such as casein sodium. In one aspect of the present invention, the casein or a derivative thereof may stabilize other proteins contained in the composition besides itself.
In one aspect of the present invention, the peptide means a polymeric molecule of amino acid, and is a concept comprising from 2 to 10 amino acids, 10 to 20 or 20 or more linked polypeptides. In another aspect of the invention, the peptide comprises about 10 amino acids linked.
In one aspect of the invention, a protein generally includes all materials that can be classified as proteins.
In one aspect of the invention, the peptide or protein may generally refer to an efficacious ingredient included in a pharmaceutical, cosmetic or food composition. In another aspect of the invention, the peptides or proteins include those extracted from animals or plants. In another aspect of the invention, the peptide or protein comprises at least one of growth factors, hormones, interferons, vaccines, recombinant proteins, recombinant peptides and enzymes. More specifically, the peptide or protein may be selected from the group consisting of Epidermal Growth Factor, basic Fibroblast Growth Factor, Platelet Derived Growth Factor, Vascular Endothelial Growth Factor ), Tyrosine kinase ligand, interleukin 1 alpha, interleukin 1 beta, interleukin 1 beta, interleukin 17 alpha, CC motif chemokine ligand 5 (CC Motif Chemokine Ligand 5), Human Growth Hormone, Insulin, Acyl Coenzyme A Desaturase, Albumin, Alkaline Phosphatase, Aminopeptidase, Amylase Amylase, amyloglucosidase, Apo-Lactoferrin, Arthrospira extract, Bromelain, Casein, Catalase, Cellulase, Collagen, Crystallins, Cytochrome C, Deoxyribonuclease, Elastin, Elastin, Fibronectin, Ficin, Fish Plasma Protein, Galactose Dehydrogenase, Gelatin, Gelidium Pulchrum Protein, But are not limited to, Gliadin, Glucose Oxidase, Glycoproteins, Hemoglobin, Hesperidinase, Horseradish Peroxidase, Human Placental Enzymes, Placental Protein, Human Placental Protein, Hyaluronidase, Hydroxysteroid Ox Reducing Agent, Lactoferrin, Lactoglobulin, Lactobacillus, Lactobacillus, Lactobacillus, Lactobacillus, Lactobacillus, Idreductus, Kallikrein, Keratin, Laccase, Lactate Dehydrogenase, Lactis Proteinum, Lactoperoxidase, Ligninase, Lipase, Lupinus Albus Protein, Lysozyme, Lysozyme Beta-Glucan, Macrocystis, Lactobacillus, (Oryza Sativa (Rice) Bran Protein), Oryza sativa (Rice) Bran Protein, Milk Protein, Milk Protein, Nacre Protein, Oryza sativa (Rice) Seed Protein, Oxido Reductases, Pancreatin, Papain, Papain Beta-Glucan, Pepsin ), Protease (Protease), prune Clostridium Histolyticum Collagenase, Serralysin, Serum Albumin Protein (Prunus Amygdalus Dulcis (Sweet Almond) Protein), r-Clostridium Histolyticum Collagenase, Albumin, Serum Protein, Silk, Soluble Elastin, Soluble Keratin, Soluble Proteoglycan, Soybean Peroxidase, Subtilisin, ), Sutilains, trypsin, tyrosinase, urease, Whey Protein, Zein, aFGF (Fibroblast Growth Factor), FGF-1, FGF 2, FGF-7, FGF-10, insulin-like growth factor (IGF-1), IGF-2, keratinocyte growth factor (KGF) Nerve Growth Factor (β-NGF), Protein PIGF-1CG (Protein PIGF-1CG), Transforming Growth Factor (TGF) Tissue inhibitors of TGF-beta-1, TGF-3, Thioredoxin, Stem Cell Factor, Il-2, IL-10, IL-4 and metalloproteinase- Inhibitor of Metalloproteinases-2, Placenta Growth Factor, fetal liver kinase-2, Superoxide dismutase (SOD), Tripartite motif-containing protein, thymosin (thymosin), human beta defensin (human Beta defensin), called general, botox ® botulinum toxin (botulinum toxin) and polio, diphtheria, whooping cough, measles, rubella, typhoid and para-typhoid, cholera, plague, tuberculosis, It is recommended that vaccines against chronic infections caused by Staphylococcus aureus or Streptococcus, Tetanus, Flu, Yellow fever, Encephalitis, Rocky Acid Fever, Typhus or Hepatitis B One selected from the group consisting of the antigens used It includes but is not a single, limited. In another aspect of the present invention, when the panthenol, the polyalcohol ester compound, the casein and the derivative thereof is casein or a derivative thereof, at least one selected from the peptide and the protein does not contain a casein or a milk protein .
In one aspect of the invention, a composition comprising a peptide or protein can be formulated into a composition comprising the peptide or protein, the viscosity of the composition comprising the peptide or protein, or the storage conditions such as the storage temperature and duration of the composition comprising the peptide or protein, , Polyalcohol ester compounds, casein, and derivatives thereof, in various amounts. More specifically, 0.1 to 50% by weight, specifically 0.5 to 30% by weight, more specifically 1 to 20% by weight, based on the total weight of the composition, of at least one member selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof . When it is contained in the above weight percentage, it is not only suitable for exhibiting the intended effect of the present invention but also can satisfy both the stability and safety of the composition and may be suitably included in the above range in terms of cost effectiveness.
In one aspect of the present invention, the weight ratio of at least one peptide selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof is 50,000,000: 1 to 1: 1 or 1: 1 to 1: 50,000,000 , Specifically 10,000,000: 1 to 1: 1 or 1: 1 to 1: 10,000,000, more specifically 500,000: 1 to 1: 1 or 1: 1 to 500,000. When it is contained in the above weight ratio, it is not only suitable for exhibiting the intended effect of the present invention but also can satisfy both stability and safety of the composition, and may be appropriate in terms of cost effectiveness.
In one aspect of the invention, a composition comprising at least one of a peptide and a protein may have a viscosity of from 5,000 cP to 30,000 cP. In another aspect of the invention, a composition comprising at least one of a peptide and a protein may have a viscosity of 8,000 cP to 25,000 cP. In another aspect of the invention, a composition comprising at least one of a peptide and a protein may have a viscosity of from 10,000 cP to 20,000 cP. When the composition comprising at least one of the peptide and the protein has a viscosity in the range as described above, the peptide or protein stabilizing effect of the panthenol, polyalcohol ester compound, casein or a derivative thereof can be better exhibited.
A method of stabilizing a peptide or protein according to one aspect of the present invention includes: at least one of a peptide and a protein; And at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein, and derivatives thereof, to prepare the composition, and then the resulting composition is stirred at a temperature of -30 캜 to 30 캜, specifically, At a refrigeration condition of -10 ° C to 10 ° C and at a room temperature of 4 ° C to 30 ° C.
One aspect of the present invention provides a cosmetic, pharmaceutical or food composition comprising a peptide or protein stabilizing agent comprising at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof. Another aspect of the invention is a pharmaceutical composition comprising at least one of a peptide and a protein; And a cosmetic, pharmaceutical or food composition comprising at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof. Yet another aspect of the present invention is a method for the production of a peptide comprising at least one of a peptide and a protein; And at least one selected from the group consisting of panthenol, polyalcohol ester compounds, casein and derivatives thereof to prepare a cosmetic, pharmaceutical or food composition.
The cosmetic composition according to the present invention may be provided in all formulations suitable for topical application. For example, emulsions obtained by dispersing an oil phase in an aqueous phase, emulsions obtained by dispersing a water phase in an oil phase, suspensions, powders, pastes, micro needles, foam or aerosol compositions As shown in FIG. These compositions may be prepared according to conventional methods in the art.
The cosmetic composition according to the present invention may contain, in addition to the above-mentioned substances, other ingredients which can give a synergistic effect to the main effect, so long as they do not impair the main effect. The cosmetic composition according to the present invention may further comprise a moisturizing agent, an emollient agent, an ultraviolet absorber, a preservative, a bactericide, an antioxidant, a pH adjuster, an organic or inorganic pigment, a perfume, a cold agent or an antiperspirant agent. The compounding amount of the above components can be easily selected by those skilled in the art within a range not to impair the objects and effects of the present invention. The amount thereof may be 0.01 to 5% by weight, specifically 0.01 to 3% by weight, have.
The pharmaceutical composition according to one aspect of the present invention is not limited to the treatment of a specific disease but includes a composition that can be used for medicinal purposes including a peptide or a protein and can be exemplified by a pharmaceutical composition for promoting skin regeneration and wound healing, But is not limited to.
The pharmaceutical composition according to one aspect of the present invention may be administered orally, rectally, topically, transdermally, intravenously, intramuscularly, intraperitoneally, subcutaneously, and the like.
Formulations for oral administration may be in the form of tablets, pills, soft and hard capsules, granules, powders, granules, solutions, emulsions or pellets, It is not. These formulations may contain, in addition to the active ingredient, a diluent such as lactose, dextrose, sucrose, mannitol, sorbitol, cellulose or glycine, a lubricant such as silica, talc, stearic acid or polyethylene glycol, or a binder such as magnesium aluminum Silicate, starch paste, gelatin, tragacanth, methylcellulose, sodium carboxymethylcellulose or polyvinylpyrrolidine). And may optionally contain pharmaceutical additives such as disintegrants, absorbents, colorants, flavors, or sweeteners. The tablets may be prepared by conventional mixing, granulating or coating methods.
Formulations for parenteral administration may be, but are not limited to, injections, drops, lozenges, ointments, gels, creams, suspensions, emulsions, suppositories, patches or spraying agents.
The effective ingredients of the pharmaceutical composition according to one aspect of the present invention will vary depending on the age, sex, weight, pathological condition and severity of the subject to be administered, route of administration, or judgment of the prescriber. Determination of the amount of application based on these factors is within the level of ordinary skill in the art and its daily dose is, for example, from 0.1 mg / kg / day to 100 mg / kg / day, more specifically from 5 mg / kg / day to 50 mg / / Day, but is not limited thereto.
The formulation of the food composition according to one aspect of the present invention is not particularly limited, but can be formulated into, for example, tablets, granules, drinks, caramels, diet bars and the like. The food composition of each formulation can be blended with the ingredients commonly used in the field in addition to the active ingredient without difficulty by those skilled in the art depending on the purpose of formulation or use, and synergistic effect can be obtained when the composition is applied simultaneously with other ingredients.
The dosage of the active ingredient is within the level of those skilled in the art, and its daily dose may vary depending on various factors such as the age, health condition, and complications of the subject to be administered.
Hereinafter, the constitution and effects of the present invention will be described in more detail with reference to Examples, Comparative Examples and Experimental Examples. However, these examples, comparative examples, and experimental examples are provided for illustrative purposes only in order to facilitate understanding of the present invention, and the scope and scope of the present invention are not limited thereto.
[Example 1 and Comparative Examples 1 to 5] Preparation of cosmetic composition
The cosmetic composition (emulsion) of Example 1 and Comparative Examples 1 to 5 was prepared in a conventional manner (unit: wt%) with the composition shown in Table 1 below. Example 1 includes panthenol, and Comparative Examples 1 to 4 include saccharides.
To prepare the preparation method more specifically, first, the oil component was added to the aqueous phase component and mixed thoroughly at 7000 rpm for 3 minutes. After that, the epithelial growth factor solution was added and homogenized by homomixing for 1-2 minutes.
[Experimental Example 1] Evaluation of protein stability of panthenol
To examine the stability of the epithelial growth factor contained in the composition of Example 1 and Comparative Examples 1 to 5, each composition was stored at 4 ° C, 25 ° C and 50 ° C, and the content thereof was measured by ELISA (Enzyme-Linked Immunosorbent Assay ). After 2 weeks of storage at 4 ° C and 25 ° C, the contents were measured. After 2 weeks of storage at 25 ° C, the contents were stored at 4 ° C for 2 weeks. The relative thermal stability (%) The results are shown in the table below.
As can be seen from the above results, the stability of the epithelial growth factor in the composition of the present invention is better than that of the composition of the comparative examples. In other words, it can be confirmed that the panthenol inhibits the decrease of the protein content, thereby enhancing the stability of the protein composition.
[Example 2 and Comparative Examples 6 to 8] Preparation of cosmetic composition
(Emulsion) of Example 2 and Comparative Examples 6 to 8 were prepared in substantially the same manner as in Example 1 and Comparative Examples 1 to 5 (unit:% by weight). Example 1 includes polyglyceryl-3 methyl glucose distearate which is a polyalcohol ester compound, while Comparative Examples 6 to 8 do not.
(0.65: 0.175: 0.175)
[Experimental Example 2] Evaluation of protein stability of polyalcohol ester compound
To determine the stability of the epithelial growth factor contained in the composition of Example 2 and Comparative Examples 6 to 8, the epithelial growth factor content of each composition was measured (initial value), and it was measured at 4 ° C and 25 ° C for 1 year After storage, the content of epithelial growth factor was confirmed by ELISA. The results are shown in the table below.
As can be seen from the above results, it may be helpful to stabilize the hydrogeneide-based material (hydrogene lecithin / C 12 -16 alcohol / palmitic acid) or a saccharide fatty acid ester which has been used as a component for forming a protein the expected surface active agent is high (C 14 -22 alcohol / C 12 -20-alkyl glucoside or a sucrose fatty acid ester), epidermal growth factor content after one year of comparative example composition than the composition of example containing. This means that the polyalcohol ester compound can increase the stability of the protein, which means that the effect is more excellent when stored in a refrigerator than at room temperature. Thus, it can be confirmed that the polyalcohol ester compound has the effect of stabilizing the protein because it inhibits the decrease of the protein content over a long storage period.
[Examples 3 and 4 and Comparative Examples 9 to 14] Preparation of cosmetic composition
(Emulsion) of Examples 3 and 4 and Comparative Examples 9 to 14 were prepared in substantially the same manner as in Example 1 and Comparative Examples 1 to 5 (unit: wt%). Example 3 contains casein hydrolyzate and Example 4 contains casein sodium, while Comparative Examples 9 to 14 do not.
[Experimental Example 3] Evaluation of protein stability of casein and its derivatives
In order to examine the stability of the epithelial growth factor contained in the compositions of Examples 3 and 4 and Comparative Examples 9 to 14, the initial content of epithelial growth factor of each composition was confirmed by ELISA. After 1 year storage at 4 ° C, 25 ° C and 45 ° C, the content of epithelial growth factor was measured by the same method, and the relative thermal stability (%) of each storage temperature was obtained The following table shows.
As can be seen from the above results, the content of epithelial growth factor after one year of the composition of the present invention was lower than that of the composition of Comparative Examples including lactoferrin, gelatin, glycoprotein (glycoprotein), whey or L-theanine, high. This means that casein and its derivatives can increase the stability of the epithelial growth factor, and especially when stored at room temperature or below, the effect is more excellent. Thus, it can be confirmed that casein and its derivatives inhibit the decrease of epithelial cell growth factor content during a long storage period, thereby enhancing the stability of the epithelial growth factor composition.
Formulation examples of the composition according to one aspect of the present invention will now be described in more detail, but the composition can be applied to various formulations, which are not intended to limit the invention but rather to illustrate it specifically.
[Formulation Example 1] Flexible lotion
Flexible lotions are prepared in a conventional manner according to the compositions listed in the table below.
[Formulation Example 2] Nutritional lotion (Milk lotion)
Nutritional lotion is prepared according to the composition shown in the table below by a conventional method.
[Formulation Example 3] Nourishing cream
Nutritive creams are prepared in a conventional manner according to the ingredients listed in the table below.
[Formulation Example 4] Massage cream
Massage creams are prepared in a conventional manner according to the composition shown in the table below.
[Formulation Example 5] Pack
Prepare the pack in the usual manner according to the composition listed in the table below.
[Formulation Example 6]
Injections are prepared in a conventional manner according to the composition shown in the table below.
[Formulation Example 7] ointment
Ointment is prepared by a conventional method according to the composition shown in the following table.
Claims (15)
A composition for promoting skin regeneration and wound healing, comprising panthenol in a weight ratio of 1: 1 to 1:10.
Wherein the composition comprises from 1 to 20% by weight, based on the total weight of the composition, of panthenol.
Wherein the composition has a viscosity of from 5,000 cP to 30,000 cP.
Wherein the composition is a cosmetic composition.
Wherein the composition is a pharmaceutical composition.
Wherein the step of preparing the composition comprises mixing the panthenol at 1 to 20% by weight based on the total weight of the composition to prepare a composition.
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| KR1020110126601A KR101949270B1 (en) | 2010-11-30 | 2011-11-30 | Agent for peptide or protein stabilization |
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| KR20100120841 | 2010-11-30 | ||
| KR1020100120841 | 2010-11-30 | ||
| KR1020110126601A KR101949270B1 (en) | 2010-11-30 | 2011-11-30 | Agent for peptide or protein stabilization |
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| KR1020170146214A Division KR101949272B1 (en) | 2010-11-30 | 2017-11-03 | Agent for peptide or protein stabilization |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US11337942B2 (en) | 2019-12-16 | 2022-05-24 | Gentribio Inc. | External use composition comprising paeonol and panthenol or pharmaceutically acceptable salts thereof as active ingredients |
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| CN104644532B (en) * | 2013-11-20 | 2019-08-09 | 株式会社爱茉莉太平洋 | Use the low viscosity cosmetic composition of naturally occurring emulsifying agent |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005516048A (en) * | 2002-01-30 | 2005-06-02 | ザ プロクター アンド ギャンブル カンパニー | Topical skin and / or hair composition containing hydrolyzed protein |
| US20060159646A1 (en) * | 2003-08-11 | 2006-07-20 | Velasco Andres F | Hair regenerator |
| WO2008079898A1 (en) | 2006-12-20 | 2008-07-03 | Pharmwest, Inc. | Methods and topical formulations comprising colloidal metal for treating or preventing skin conditions |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11337942B2 (en) | 2019-12-16 | 2022-05-24 | Gentribio Inc. | External use composition comprising paeonol and panthenol or pharmaceutically acceptable salts thereof as active ingredients |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101949272B1 (en) | 2019-02-19 |
| WO2012074285A2 (en) | 2012-06-07 |
| WO2012074285A3 (en) | 2012-08-23 |
| KR20170125780A (en) | 2017-11-15 |
| KR20120059429A (en) | 2012-06-08 |
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