WO2015187951A1 - Compositions and methods for improving skin quality - Google Patents
Compositions and methods for improving skin quality Download PDFInfo
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- WO2015187951A1 WO2015187951A1 PCT/US2015/034199 US2015034199W WO2015187951A1 WO 2015187951 A1 WO2015187951 A1 WO 2015187951A1 US 2015034199 W US2015034199 W US 2015034199W WO 2015187951 A1 WO2015187951 A1 WO 2015187951A1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—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
- A61K8/86—Polyethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/32—Proteins, polypeptides; Degradation products or derivatives thereof, e.g. albumin, collagen, fibrin, gelatin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/77—Polymers containing oxygen of oxiranes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/1703—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
- A61K38/1709—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
- A61K38/1748—Keratin; Cytokeratin
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- A—HUMAN NECESSITIES
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/44—Medicaments
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- A—HUMAN NECESSITIES
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0028—Polypeptides; Proteins; Degradation products thereof
- A61L26/0047—Specific proteins or polypeptides not covered by groups A61L26/0033 - A61L26/0042
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- A—HUMAN NECESSITIES
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/0066—Medicaments; Biocides
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61Q19/007—Preparations for dry skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/252—Polypeptides, proteins, e.g. glycoproteins, lipoproteins, cytokines
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- A—HUMAN NECESSITIES
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/412—Tissue-regenerating or healing or proliferative agents
Definitions
- the invention relates to the field of skin treatment.
- the integument or skin is the largest organ of the body, making up 16% of body weight, with a surface area of 1.8m 2 .
- the skin has several functions, the most important being to form a physical barrier to the environment, allowing and limiting the inward and outward passage of water, electrolytes and various substances while providing protection against micro-organisms, ultraviolet radiation, toxic agents and mechanical insults.
- the epidermis comprises five layers: stratum corneum, stratum lucidum, stratum granulosum, stratum spinosum, and stratum basale.
- the stratum corneum is the outermost of the five layers of the epidermis and is largely responsible for the vital barrier function of the skin.
- the structure of the stratum corneum has been described as a "brick and mortar" type structure.
- the corneocytes are the bricks.
- a corneocyte is a protein complex that is made of tiny threads of keratin in an organized matrix. The keratin can hold large amounts of water between the fibers/threads.
- the stratum corneum contains about 12-16 layers of corneocytes and each corneocyte has a mean thickness of approximately 1 micrometer.
- the "mortar" between the corneocytes contains free fatty acids and ceramides that are released from lamellar bodies in keratinocytes as they mature to the stratum corneum. Because there are two types of lipids, this layer is referred to as a lamellar lipid bilayer. This lipid bilayer plays a major role in maintaining the barrier properties of the skin. Corneocytes also contain a natural moisturizing factor (NMF), which is a collection of water-soluble compounds. These compounds compose approximately 20-30% of the dry weight of the corneocyte. NMF components absorb water from the atmosphere and combine it with their own water content allowing the outermost layers of the stratum corneum to stay hydrated despite exposure to the elements.
- NMF moisturizing factor
- the epidermis plays a large role in defending a body against infection and preventing excessive water loss through the skin. Because the risk of infection and water loss rises dramatically when the epidermal barrier is breached, natural processes for wound healing exist in order to repair the breach as quickly as possible and protect the body. It is becoming clear that smaller and less obvious breaches of the epidermis are also problematic. Studies of atopic dermatitis indicate that, at least in some cases, the condition is associated with a genetic defect in the epidermal barrier which allows irritants, microbes and allergens to penetrate the skin and cause the adverse reactions commonly associated with atopic dermatitis.
- Non-healing wounds affect about 3 to 6 million people in the United States, with persons 65 years and older accounting for 85% of these events. Non-healing wounds result in enormous health care expenditures, with the total cost estimated at more than $3 billion per year. Further, atopic dermatitis now affects 10-20% of children in the United States and direct healthcare costs exceeded $3 billion per year in 2013 according to the National Institute of Arthritis and Musculoskeletal and Skin Disease.
- compositions and methods for the protection of skin and for improving skin quality such as dryness, redness, scaliness, itchiness, rash, ability to resist or manage infection, or ability to heal a wound.
- compositions and methods that solve the problems or inadequacies of the prior art.
- methods for improving skin quality in a subject comprising administering to the skin a pharmaceutical composition comprising a polypeptide covalently bound to a hydrophilic polymer and/or a polysaccharide covalently bound to a hydrophilic polymer.
- a composition containing a keratin polypeptide and a hydrophilic polymer improves one or more skin qualities when applied to the skin. Skin qualities include, but are not limited to, dryness, redness, scaliness, itchiness, rash, ability to resist or manage infection, and ability to heal a wound.
- the hydrophilic polymer has a formula selected from:
- Ri is hydroxyl, carboxyl, ethylamine, 2-pyrrolidone, hydroxyethyl methacrylic acid, methylamine, phosphonic acid, sulfonic acid, hydroxyl, or S04 " ; wherein R2 is hydrogen, methyloxazoline, ethyloxazoline, or propyloxazoline; and wherein "n” is between 1 and 1,500.
- the "n” in formula Ia, Ib or Ic is between 1 and 1000, 1 and 500, 1 and 250, or 1 and 125.
- the "n" in formula Ia, Ib or Ic is between about 100 and about 125. In still other embodiments, the "n” is about 114.
- Fig. 1 is a chemical structure of a functionally reactive succinimidyl valerate in the terminal position of a polyethylene glycol polymer.
- Fig. 2 is a graph showing the effect of 100 ⁇ g/mL of keratin-polyethylene glycol DPBS composition on primary human adult keratinocytes relative to media alone.
- a cell includes a plurality of cells, including mixtures thereof.
- atopic dermatitis is used herein to refer to a skin condition also known as eczema that can include or lead to one or more of, dryness, rash, redness, itchiness, and fluid-filled sores.
- composition is intended to include a combination of active agent and another compound or composition, inert (for example, a detectable agent or label) or active, such as an adjuvant.
- compositions and methods include the recited elements, but not excluding others.
- Consisting essentially of when used to define compositions and methods shall mean excluding other elements of any essential significance to the combination.
- a composition consisting essentially of the elements as defined herein would not exclude trace contaminants from the isolation and purification method and pharmaceutically acceptable carriers, such as phosphate buffered saline, preservatives, and the like.
- Consisting of shall mean excluding more than trace elements of other ingredients and substantial method steps for administering the compositions of this invention. Embodiments defined by each of these transition terms are within the scope of this invention.
- covalently bound means that a covalent bond exists between a portion of the hydrophilic polymer and the polypeptide, or vice- versa. Accordingly, the term “covalently bound” refers to both direct covalent bonds (a sharing of pairs of electrons between the atoms of the hydrophilic polymer and the polypeptide) and indirect covalent bonds (a sharing of pairs of electrons between atoms of the hydrophilic polymer and the composition comprising the polypeptide, or vice-versa).
- the term "epidermal breach” refers to a loss or reduction of a barrier property in at least the stratum corneum of the skin.
- a “barrier property” refers to an ability to impede the entry or exit of a compound or microorganism through the skin.
- the epidermal breach comprises a wound. In other embodiments, the epidermal breach is that caused by atopic dermatitis.
- the term "epidermal breach” further includes burns, sores including mouth sores such as canker sores, and surgical incisions including cosmetic surgery incisions and oral surgery incisions.
- mammal for purposes of treatment refers to any animal classified as a mammal, including human, domestic and farm animals, nonhuman primates, and zoo, sports, or pet animals, such as dogs, horses, cats, cows, etc.
- a "pharmaceutical composition” is intended to include the combination of an active agent with a pharmaceutically acceptable carrier or excipient, inert or active, making the composition suitable for diagnostic or therapeutic use in vivo or ex vivo.
- pharmaceutically acceptable carrier means a carrier or excipient that is useful in preparing a pharmaceutical composition that is generally safe and non-toxic, and includes a carrier that is acceptable for veterinary and/or human pharmaceutical use.
- pharmaceutically acceptable carrier encompasses any of the standard pharmaceutical carriers, such as a phosphate buffered saline solution, water, and emulsions, such as an oil/water or water/oil emulsion, and various types of wetting agents.
- carrier encompasses any excipient, diluent, filler, salt, buffer, stabilizer, solubilizer, lipid, stabilizer, or other material well known in the art for use in pharmaceutical formulations and as described further below.
- the pharmaceutical compositions also can include preservatives.
- a "pharmaceutically acceptable carrier” as used in the specification and claims includes both one and more than one such carrier.
- a desired response is a skin quality improvement.
- a desired biological or medical response is achieved following administration of multiple or dosages of the composition to the subject over a period of days, weeks, or years.
- subject is defined herein to include animals. In some embodiments, the animal is a non-mammal such as a reptile or a bird.
- the animal is a mammal, including, but not limited to, primates (e.g., humans), cows, sheep, goats, horses, dogs, cats, rabbits, rats, mice and the like.
- the subject is a human. In some embodiments, the subject is a child.
- wound refers herein to an injury to skin wherein at least a portion of the epidermal layer of the skin is damaged.
- the term “wound” includes a first-degree abrasion, a second-degree abrasion, a third-degree abrasion, a laceration, an incision, a puncture wound, and a penetration wound.
- compositions comprising a polypeptide covalently bound to a hydrophilic polymer and/or a polysaccharide covalently bound to a hydrophilic polymer.
- the polypeptides bound to the hydrophilic polymer include, but are not limited to, polypeptides of keratin, collagen, elastin, fibroin, milk-derived proteins such as casein, beta- lactoglobulin and alpha-lactalbumin, and grain proteins such as wheat protein. Hydrophobic polypeptides such as keratin may be preferred in certain embodiments.
- compositions comprising a hydrophilic polymer covalently bound to a polysaccharide such as chitosan, chitin, or chitin glucan.
- a composition containing a keratin polypeptide and a hydrophilic polymer improves one or more skin qualities when applied to the skin.
- Skin qualities include, but are not limited to, dryness, redness, scaliness, itchiness, rash, ability to resist or manage infection, and ability to heal an epidermal breach including a wound.
- the term "keratin” refers to a family of fibrous structural proteins that are found in the hair, skin, nails, claws and hooves of mammals (a-keratins) and in the scales, claws and shells of reptiles, the feathers, beaks, and claws of birds and the quills of porcupines ( ⁇ -keratins).
- Alpha-keratins are also known as cytokeratins and are further subdivided into soft a-keratins (epithelial cytokeratins) and hard ⁇ -keratins (trichocyte keratins). All keratins are heteropolymers of type I and type II keratins.
- KRTl KRT2, KRT3, KRT4, KRT5, KRT6A, KRT6B, KRT6C, KRT7, KRT8, KRT9, KRT10, KRTl 2, KRT13, KRTl 4, KRT15, KRTl 6, KRTl 7, KRTl 8, KRTl 9, KRT20, KRT23, KRT24, KRT25, KRT26, KRT27, KRT28, KRT31, KRT32, KRT33A, KRT33B, KRT34, KRT35, KRT36, KRT37, KRT38, KRT39, KRT40, KRT71, KRT72, KRT73, KRT74, KRT75, KRT76, KRT77, KRT78, KRT79, KRT80, KRT81, KRT82, KRT83, KRT84, KRT85, KRT86, KRT222.
- a keratin polypeptide of the present invention may be encoded by one or more genes selected from KRT1, KRT2, KRT3, KRT4, KRT5, KRT6A, KRT6B, KRT6C, KRT7, KRT8, KRT9, KRT10, KRT12, KRT13, KRT14, KRT15, KRT16, KRT17, KRT18, KRT19, KRT20, KRT23, KRT24, KRT25, KRT26, KRT27, KRT28, KRT31, KRT32, KRT33A, KRT33B, KRT34, KRT35, KRT36, KRT37, KRT38, KRT39, KRT40, KRT71, KRT72, KRT73, KRT74, KRT75, KRT76, KRT77, KRT78, KRT79, KRT80, KRT81, KRT82, KRT83, KRT84, KRT85, KRT86, and KRT222.
- polypeptide is used in its broadest sense to refer to a compound of two of more subunit amino acids, amino acid analogs, or peptidomimetics.
- the subunits may be linked by peptide bonds. In another embodiment, the subunits may be linked by other bonds, e.g., ester, ether, etc.
- amino acid refers to either natural and/or unnatural or synthetic amino acids, including glycine and both the D or L optical isomers, and amino acid analogs and peptidomimetics.
- a peptide of three or more amino acids may be referred to as an oligopeptide if the peptide chain is short, e.g., less than about 25 amino acids.
- the term "polypeptide" can include full-length naturally occurring proteins as well as functional fragments of those proteins. Protein fragments are functional when they achieve the desired result of the full- length protein in the context of the present invention. For example, a keratin fragment that is covalently bound to a hydrophilic polymer is encompassed by the present invention when the keratin-hydrophilic polymer provides a skin improvement effect when applied to skin using the methods of the present invention.
- a polypeptide can be derived from natural sources or synthetically prepared, including through the use of large-scale protein expression mechanisms. The polypeptides may be hydrolyzed or non-hydrolyzed, and in some embodiments, the polypeptides are non-hydrolyzed.
- the keratin polypeptide can be naturally derived or synthetically prepared.
- the keratin polypeptide can be purified from various natural sources or commercially obtained.
- the keratin polypeptide can have a molecular weight from about 0.5 kDa to about 60 kDa, or from about 2 kDa to about 6 kDa, or from about 20 kDa to about 40 kDa.
- the keratin polypeptide is about 5 kDa.
- the keratin polypeptide is about 45kDa to about 55 kDa.
- the keratin polypeptide is about 52 kDa.
- hydrophilic polymer includes polypeptides, carbohydrates, nucleic acids, poly(ethylene glycol), poly(oxazoline), polyvinylpyrrolidone), poly(acrylamide), poly(acrylic acid), poly(allylamine), poly(hydroxyethyl methacrylate), poly(ethyleneimine), poly(vinylphosphonic acid), poly(vinyl sulfate), poly(vinylsulfonic acid), poly(vinyl alcohol), glycerol propoxylate, hydroxy ethyl starch (HES).
- the hydrophilic polymer is a synthetic hydrophilic polymer selected from the group consisting of: poly(ethylene glycol), poly(oxazoline), polyvinylpyrrolidone), poly(acrylamide), poly(acrylic acid),poly(allylamine), poly(hydroxyethyl methacrylate), poly(ethyleneimine), poly(vinylphosphonic acid), poly(vinyl sulfate), poly(vinylsulfonic acid), poly(vinyl alcohol), glycerol propoxylate, and hydroxyethyl starch (HES).
- synthetic hydrophilic polymer selected from the group consisting of: poly(ethylene glycol), poly(oxazoline), polyvinylpyrrolidone), poly(acrylamide), poly(acrylic acid),poly(allylamine), poly(hydroxyethyl methacrylate), poly(ethyleneimine), poly(vinylphosphonic acid), poly(vinyl sulfate), poly(vinylsulfonic acid), poly(vinyl alcohol
- the molecular weight of the hydrophilic polymer is between about 0.5 and about 80 kDa, between about 0.5 and about 40 kDa, or between about 0.5 and about 10 kDa. In some embodiments, the molecular weight of the hydrophilic polymer is between about 2 and about 10 kDa. In some embodiments, the molecular weight of the hydrophilic polymer is between about 20 and about 40 kDa. In one embodiment, the molecular weight of the hydrophilic polymer is about 5 kDa. In another embodiment, the molecular weight of the hydrophilic polymer is about 30 kDa.
- the hydrophilic polymer has a formula selected from:
- Ri is hydroxyl, carboxyl, ethylamine, 2-pyrrolidone, hydroxyethyl methacrylic acid, methylamine, phosphonic acid, sulfonic acid, hydroxyl, or S04 " ; wherein R2 is hydrogen, methyloxazoline, ethyloxazoline, or propyloxazoline; and wherein "n” is between 1 and 1,500.
- the "n” in formula la, lb or Ic is between 1 and 1000, 1 and 500, 1 and 250, or 1 and 125.
- the "n” in formula la, lb or Ic is between about 100 and about 125.
- the "n” is about 114.
- the "n" in formula la, lb or Ic may be selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 and 24.
- the hydrophilic polymer is covalently bound to a keratin polypeptide and the hydrophilic polymer has a formula of:
- n is between 1 and 1,500.
- the "n” in formula la, lb or Ic is between 1 and 1000, 1 and 500, 1 and 250, or 1 and 125.
- the "n” in formula la, lb or Ic is between 100 and 125.
- the "n” is about 114.
- the "n" in formula la, lb or Ic may be selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 and 24.
- the compounds of formula la are known to those of skill in the art as polyethylene glycol, or PEG, compounds.
- PEG polyethylene glycol
- the PEG compounds encompassed by the present invention are capable of being covalently bound to a polypeptide at reactive moiety on the polypeptide, or a polypeptide modified to include such a reactive moiety, however, the invention is not limited by the covalent attachment method.
- the PEG compound is functionalized to allow reaction with the polypeptide.
- the hydrophilic polymer is a PEG compound that covalently binds a polypeptide at a primary amine (e.g. a lysine residue). In other embodiments, the hydrophilic polymer is a PEG compound that covalently binds a polypeptide at a sulfhydryl (e.g. a cysteine residue).
- Non- limiting examples of hydrophilic PEG polymers that fall within the present invention are MS(PEG (Thermo Scientific, Rockford, IL, USA), MS(PEG (Thermo Scientific, Rockford, IL, USA), MS(PEG)i2 (Thermo Scientific, Rockford, IL, USA), MS(PEG 4 (Thermo Scientific, Rockford, IL, USA), TMS(PEG)i2 (Thermo Scientific, Rockford, IL, USA), TMM(PEG)i2 (Thermo Scientific, Rockford, IL, USA), MM(PEG)i 2 (Thermo Scientific, Rockford, IL, USA), MM(PEG)24 (Thermo Scientific, Rockford, IL, USA), and other N-hydroxysuccinimide functionalized PEGs, mPEG-Succinimidyl- Succinate (molecular weight of 2, 5, 10 20 or 30 kDa) (Laysan Bio., Inc., Arab
- Branched polyethylene glycol compositions include TMS(PEG)i 2 , TMM(PEG)i 2 , and any other multi-armed polyethylene glycol compositions.
- the hydrophilic polymer is an mPEG-Succinimidyl-Succinate polymer that is about 5 kDa and wherein "n" is about 114.
- Functionally reactive moieties present or introduced into polypeptides or polysaccharides of the present invention can react with functionally reactive moieties present or introduced into the hydrophilic polymers of the present invention to form covalent bonds between the polypeptide and hydrophilic polymer.
- functionally reactive moieties useful in the present invention include those used in click chemistry, maleimide chemistry, and NHS-esters, among others.
- Functionally reactive moieties involved in click chemistry include, but are not limited to, azides and alkynes that form a triazole ring via the Huisgen cycloaddition process (see U.S. Patent No. 7,375,234, incorporated herein in its entirety).
- the maleimide chemistry involves reaction of the maleimide olefin with a nucleophile, such as -OH, -SH or -NH 2 , to form a stable bond.
- a nucleophile such as -OH, -SH or -NH 2
- Other functionally reactive moieties include those described in Bioconjugate Techniques, Greg T. Hermanson, Academic Press, 2nd ed., 2008 (incorporated in its entirety herein).
- functionally active moieties are typically introduced at one or both ends of the polyethylene glycol polymer, as shown in Figure 1 where the functionally reactive succinimidyl valerate is shown in the terminal position of a polyethylene glycol polymer.
- Y-NH 2 R'OCH(OH)-X or Y-N CH-X hemiacetal or
- R ' is Ci-6 alkyl, C3-6 cycloalkyl, or an aryl group having 5-8 endocyclic atoms
- R is H, Ci-6 alkyl, C3-6 cycloalkyl, or an aryl group having 5-8 endocyclic atoms
- R is a carbonyl derivative of the form
- X and Y are each the polypeptide and the hydrophilic polymer, respectively.
- the keratin-hydrophilic polymer compounds described herein can be provided in a pharmaceutical composition.
- the pharmaceutical compositions include a therapeutically effective amount of a keratin-hydrophilic polymer compound described herein in combination with a pharmaceutically acceptable carrier.
- the pharmaceutical composition has antimicrobial properties.
- carrier encompasses any excipient, diluent, filler, salt, buffer, stabilizer, solubilizer, lipid, stabilizer, or other material well known in the art for use in pharmaceutical formulations.
- a carrier for use in a composition will depend upon the intended route of administration for the composition.
- the preparation of pharmaceutically acceptable carriers and formulations containing these materials is described in, e.g., Remington's Pharmaceutical Sciences, 21st Edition, University of the Sciences in Philadelphia, Lippincott, Williams & Wilkins, Philadelphia Pa., 2005.
- physiologically acceptable carriers include saline, glycerol, DMSO, buffers such as phosphate buffers, citrate buffer, and buffers with other organic acids; antioxidants including ascorbic acid; low molecular weight (less than about 10 residues) polypeptides; proteins, such as serum albumin, gelatin, or immunoglobulins; hydrophilic polymers such as polyvinylpyrrolidone; amino acids such as glycine, glutamine, asparagine, arginine or lysine; monosaccharides, disaccharides, and other carbohydrates including glucose, mannose, or dextrins; chelating agents such as EDTA; sugar alcohols such as mannitol or sorbitol; salt-forming counterions such as sodium; and/or nonionic surfactants such as TWEEN (ICI, Inc.; Bridgewater, New Jersey), polyethylene glycol (PEG), and PLURONICS (BASF; Florham Park, NJ).
- buffers such as phosphate buffers,
- compositions disclosed herein can advantageously comprise between about 0.1% and 99% by weight of the total of one or more of a keratin-hydrophilic polymer composition based on the weight of the total composition including carrier or diluent.
- the polypeptide -hydrophilic polymer and polysaccharide-hydrophilic polymer pharmaceutical compositions described above and elsewhere herein are administered to the skin of a subject for improving a quality of the skin.
- the term "skin” includes nails.
- administering refers to an administration that is oral, topical, intravenous, subcutaneous, transcutaneous, transdermal, intramuscular, intra-joint, parenteral, intra-arteriole, intradermal, intraventricular, intracranial, intraperitoneal, intralesional, intranasal, rectal, vaginal, by inhalation or via an implanted reservoir.
- parenteral includes subcutaneous, intravenous, intramuscular, intra-articular, intra-synovial, intrasternal, intrathecal, intrahepatic, intralesional, and intracranial injections or infusion techniques.
- Dosage forms for topical administration of the pharmaceutical compositions described herein include ointments, gels, pastes, liquids, solutions, creams, oils, foams, mousses, powders, aerosols, and sprays.
- the pharmaceutical compositions may also be applied to wound dressings such as patches, band aids, and gauze materials.
- Thickening agents, emollients, and stabilizers can be used to prepare the topical pharmaceutical compositions of the present invention.
- thickening agents include petrolatum, beeswax, xanthan gum, or polyethylene glycol, humectants such as sorbitol, emollients such as mineral oil, lanolin and its derivatives, or squalene.
- the pharmaceutical compositions described herein are admixed under sterile conditions with a pharmaceutically acceptable carrier and any preservatives, buffers, thickening agents, cosmetic agents, sunscreen agents, or propellants as can be required.
- the polypeptide -hydrophilic polymer and polysaccharide-hydrophilic polymer pharmaceutical compositions can be administered to the skin in a therapeutically effective amount.
- Those of skill in the art will understand that the specific dose level and frequency of dosage for any particular subject can be varied and will depend upon a variety of factors, including the activity of the specific compound employed, the metabolic stability and length of action of that compound, the species, age, body weight, general health, sex and diet of the subject, the mode and time of administration, rate of excretion, drug combination, and severity of the particular condition.
- the keratin-hydrophilic polymer pharmaceutical compositions are applied to the skin once, twice, three times, four times, five times, six times or more in a day.
- the keratin- hydrophilic polymer pharmaceutical compositions can be administered to the skin for any period of time including, but not limited to, about one day, about two days, about three days, about four days, about five days, about six days, about 1 week, about 2 weeks, about 3 weeks, about four weeks or more.
- Administration of a polypeptide-hydrophilic polymer and/or polysaccharide-hydrophilic polymer pharmaceutical composition to the skin in a therapeutically effective amount can result in an improvement of skin quality.
- Skin qualities include, but are not limited to, dryness, redness, scaliness, itchiness, rash, ability to resist or manage infection, and ability to heal an epidermal breach including an ability to heal a wound.
- administration of a therapeutically effective amount of a polypeptide-hydrophilic polymer and/or polysaccharide- hydrophilic polymer pharmaceutical composition to an area of skin that exhibits dryness results in a reduction of the size or severity of the dryness.
- administration of a therapeutically effective amount of a polypeptide-hydrophilic polymer and/or polysaccharide- hydrophilic polymer pharmaceutical composition to an area of skin that exhibits redness results in a reduction in the size or severity of the redness.
- administration of a therapeutically effective amount of a polypeptide-hydrophilic polymer and/or polysaccharide- hydrophilic polymer pharmaceutical composition to an area of skin that exhibits a rash results in a reduction in the size or severity of the rash.
- administration of a therapeutically effective amount of a polypeptide-hydrophilic polymer and/or polysaccharide- hydrophilic polymer pharmaceutical composition to an area of skin that exhibits itchiness results in a reduction in the size or severity of the itchiness. In some embodiments, administration of a therapeutically effective amount of a polypeptide-hydrophilic polymer and/or polysaccharide- hydrophilic polymer pharmaceutical composition to an area of skin that exhibits signs of an infection results in a reduction in the size or severity of the infection.
- administration of a therapeutically effective amount of a polypeptide-hydrophilic polymer and/or polysaccharide-hydrophilic polymer pharmaceutical composition to an area of skin results in a reduction of the likelihood of the onset of an infection on the skin as compared to a control.
- administration of a therapeutically effective amount of a polypeptide- hydrophilic polymer and/or polysaccharide-hydrophilic polymer pharmaceutical composition to an area of skin that contains a wound results in a faster or more complete reduction of the size of the wound as compared to a control.
- administration of a therapeutically effective amount of a polypeptide-hydrophilic polymer and/or polysaccharide-hydrophilic polymer pharmaceutical composition to an area of skin that contains a wound results in decreased scarring at the site the wound.
- a therapeutically effective amount of polypeptide-hydrophilic polymer and/or polysaccharide-hydrophilic polymer pharmaceutical composition repairs or covers an epidermal breach in an area of skin to which it is administered.
- the repair or cover can be in whole or in part, but the effect is to increase a barrier property of the skin to which it is administered.
- the barrier property relates to the inclusion or retention of water.
- the barrier property relates to the exclusion of an allergen or irritant. Allergens include those that are a causative factor in atopic dermatitis.
- the barrier property relates to the exclusion of a microorganism.
- microorganism includes, but is not limited to, a bacterium, virus, and a fungus.
- Bacteria include, but are not limited to, those that commonly gain entry through a breach in the skin such as Staphylococcus species (e.g. Staphylococcus aureus) Campylobacter species, Klebsiella pneumoniae, Escherichia coli, Capnocytophaga canimorsus, Vibrio vulnificus, Pseudomonas aeruginosa, Aeromonas hydrophila, and Salmonella species.
- Staphylococcus species e.g. Staphylococcus aureus
- Campylobacter species Klebsiella pneumoniae, Escherichia coli, Capnocytophaga canimorsus, Vibrio vulnificus, Pseudomonas aeruginosa, Aeromonas hydrophila
- Salmonella species e.g. Staphylococcus
- Keratin-polyethylene glycol compositions were prepared using the following equipment and materials:
- MS(PEG) 4 [MS4] Cat#22341 , lot # MI 162217, Thermo Scientific (Pierce) MS (PEG)i2; [MS12] Cat#22685, lot#MI162218, Thermo Scientific (Pierce) MS (PEG) 24 ; [MS24] Cat#22687, lot#MH161869, Thermo Scientific (Pierce) TMS (PEG)i2; [TMS 12] Cat# 22421 , lot#MD157106, Thermo Scientific (Pierce) Keratin [K] Cat# K3030, lot#lAG0185, Spectrum
- TMS 12 65 DMF to 100 mg of stock TMS 12
- Keratin-polyethylene glycol compositions were prepared using the following materials and equipment:
- reaction sample was prepared having ratios of keratin polypeptide and SVA PEG polymer (1 : 1).
- the sample was prepared as follows:
- K:P; 1 : l weighted out 50 mg of SVA PEG and added to 1 ml D-PBS + 5 mg keratin
- Amount [5 mg] of keratin was then added to 1 mL D-PBS and shaken by hand to solubilize. Amount of SVA PEG was weighted out and added to the PBS-keratin solutions. The SVA PEG amount was 50 mg. Tube was then shaken by hand and sealed with parafilm.
- Figure 2 is a graph showing the effect of 100 ⁇ g/mL of keratin-polyethylene glycol composition as described in Example 1 and Example 2 on primary human adult keratinocytes relative to media alone.
- the keratin-polyethylene glycol composition increased human keratinocyte migration in an Oris Cell Migration Assay.
- Primary keratinocytes were cultured in appropriate growth media with human keratinocyte growth supplement (HKGS) and pen/strep until cells reached confluence prior to seeding the assay.
- HKGS human keratinocyte growth supplement
- the Oris Cell Migration Assay a 96-well plate provided by Platypus Technologies, was seeded with 25,000 primary human keratinocytes with the Oris Cell Seeding Stoppers in place to prevent cell adhesion in the center of each well. The cells were incubated with growth medium plus HKSG for 24 hours then changed to media HKSG for 16 hours. When cells reached confluence the Oris Cell Seeding Stoppers were removed, exposing a uniform, circular "wound" in each well. Immediately upon removal of each stopper, test compounds were added at the indicated concentrations. SLP001 and SLP002 at 100, 50, 25, 10 ⁇ g/mL.
- a female of the age 12 with history of ingrown toenail infections treated the infection developing nail with the keratin-polyethylene glycol composition as described in Example 2.
- the toe(s) were first cleansed and then dried.
- the keratin-polyethylene glycol composition was then applied and left uncovered for 24-48 hours. Within 8 hours there was noticeable improvement and pain of the wound was gone. After 48 hours there was no noticeable sign of the wound under or around the toe(s).
- Over a period of 1 year the application of the keratin-polyethylene glycol composition was applied during each incident and the incidents were lessened overtime to now the female only has ingrown toenail infections very rarely.
- a wound on a dog's foreleg was initially treated by a vet with oral antibiotics and topical ointment for 2 weeks with no improvement.
- the dog also suffered with diarrhea and excess licking at the wound from both antibiotic treatments.
- the wound was cleansed each day prior to an application of keratin-polyethylene glycol composition as described in Example 2 once a day for 3 days.
- the wound was not covered.
- the dog was not bothered by the treatment. By the end of one month, the wound was gone and hair had grown back.
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US15/315,795 US11273118B2 (en) | 2014-06-04 | 2015-06-04 | Compositions and methods for improving skin quality |
JP2017516264A JP2017516869A (en) | 2014-06-04 | 2015-06-04 | Compositions and methods for improving skin quality |
CN201580033514.XA CN106470649A (en) | 2014-06-04 | 2015-06-04 | For improving compositionss and the method for skin quality |
CA2951038A CA2951038A1 (en) | 2014-06-04 | 2015-06-04 | Compositions and methods for improving skin quality |
EP15802421.6A EP3151796A4 (en) | 2014-06-04 | 2015-06-04 | Compositions and methods for improving skin quality |
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US201462007768P | 2014-06-04 | 2014-06-04 | |
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US (1) | US11273118B2 (en) |
EP (1) | EP3151796A4 (en) |
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Cited By (2)
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WO2018175871A1 (en) * | 2017-03-23 | 2018-09-27 | Tru-Hair Llc | Hair treatment intermediates and methods |
CN110312519A (en) * | 2017-01-31 | 2019-10-08 | 凯拉麦迪克斯有限公司 | Hair anticreep or hair growth-promoting composition for injection |
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RO132925A3 (en) * | 2018-06-12 | 2019-12-30 | Igor Statnîi | Multifunctional polymethylamine surface-active agent and process for preparing the same |
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FR2912650A1 (en) * | 2007-02-16 | 2008-08-22 | Oreal | Treating keratinous material, comprises applying composition comprising polymeric component having amino acid function cationic monomer unit, hydrophilic absorbent and hydrophilic absorbent comprising hydrophilic monomer repeating unit |
BRPI0705059B1 (en) * | 2007-06-28 | 2016-05-31 | Univ Rio De Janeiro | hydrolysates of keratin, process for their production and cosmetic compositions containing the same |
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FR2941231B1 (en) | 2009-01-16 | 2016-04-01 | Sederma Sa | NOVEL PEPTIDES, COMPOSITIONS COMPRISING THEM AND COSMETIC AND DERMO-PHARMACEUTICAL USES |
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2015
- 2015-06-04 JP JP2017516264A patent/JP2017516869A/en active Pending
- 2015-06-04 WO PCT/US2015/034199 patent/WO2015187951A1/en active Application Filing
- 2015-06-04 CN CN201580033514.XA patent/CN106470649A/en active Pending
- 2015-06-04 US US15/315,795 patent/US11273118B2/en active Active
- 2015-06-04 EP EP15802421.6A patent/EP3151796A4/en not_active Withdrawn
- 2015-06-04 CA CA2951038A patent/CA2951038A1/en not_active Abandoned
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US20080089930A1 (en) * | 1999-09-13 | 2008-04-17 | Keraplast Technologies, Ltd. | Keratin-Based Powders and Hydrogel for Pharmaceutical Applications |
US20110070276A1 (en) * | 2002-01-28 | 2011-03-24 | Keraplast Technologies, Ltd. | Bioactive keratin peptides |
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CN110312519A (en) * | 2017-01-31 | 2019-10-08 | 凯拉麦迪克斯有限公司 | Hair anticreep or hair growth-promoting composition for injection |
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US11273118B2 (en) | 2022-03-15 |
JP2017516869A (en) | 2017-06-22 |
US20170112754A1 (en) | 2017-04-27 |
EP3151796A4 (en) | 2018-01-10 |
CN106470649A (en) | 2017-03-01 |
EP3151796A1 (en) | 2017-04-12 |
CA2951038A1 (en) | 2015-12-10 |
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