WO2022185599A1 - Agent de réduction de protéine carbonylée pour les cheveux - Google Patents

Agent de réduction de protéine carbonylée pour les cheveux Download PDF

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WO2022185599A1
WO2022185599A1 PCT/JP2021/038092 JP2021038092W WO2022185599A1 WO 2022185599 A1 WO2022185599 A1 WO 2022185599A1 JP 2021038092 W JP2021038092 W JP 2021038092W WO 2022185599 A1 WO2022185599 A1 WO 2022185599A1
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hair
reducing agent
hydrogen atom
agent
carbon atoms
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PCT/JP2021/038092
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English (en)
Japanese (ja)
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直也 布施
真人 礒辺
正 松井
由香子 松江
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クラシエホームプロダクツ株式会社
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Priority to JP2023503365A priority Critical patent/JPWO2022185599A1/ja
Publication of WO2022185599A1 publication Critical patent/WO2022185599A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/22—Boron compounds
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/24—Phosphorous; Compounds thereof
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair

Definitions

  • the present invention relates to an agent, composition and method for reducing carbonylated protein in hair, which increases with age.
  • Patent Document 1 discloses prevention or improvement of gray hair or senile alopecia containing at least one active ingredient selected from the group consisting of berberbine, derivatives thereof, and salts thereof. agents, agents for suppressing or improving DNA damage in hair follicle-constituting cells, and agents for suppressing decrease in melanocyte stem cells.
  • Patent Document 2 discloses a peptide having an amino acid sequence of WY or a pharmaceutically acceptable salt or solvate thereof as an active ingredient.
  • a composition for improving the appearance of hair comprising:
  • an object of the present invention is to provide a new method and drug for improving age-related qualitative changes in hair.
  • the present inventors focused on black and gray hair in people aged 40 and over and analyzed age-related qualitative changes in hair.
  • the present inventors evaluated the degree of carbonylation, which is an index of aging, using white and black hair of women in each age group. As a result, the content of carbonylated proteins in hair increased with age, and there was a significant difference in carbonylation of white and black hair in women in their 50s and 60s compared to women in their 40s. .
  • Non-Patent Documents 1 and 2 relate to correlations between carbonylated proteins of the stratum corneum and physiological parameters of the skin. These documents show that protein carbonylation is inversely proportional to the water content of the stratum corneum, and that carbonylation of keratin proteins in each layer reduces the water retention capacity. The inventors thought that hair keratin protein might also cause a similar phenomenon by being carbonylated in the same way as skin keratin protein.
  • Non-Patent Document 3 reductive amination treatment with 5-ethyl-2-methylpyridine borane (PEMB) or Hantu ester can reduce carbonylated proteins in hair, which increases with age. showed that.
  • PEMB 5-ethyl-2-methylpyridine borane
  • Hantu ester can reduce carbonylated proteins in hair, which increases with age. showed that.
  • Non-Patent Document 4 Non-Patent Document 4
  • reductive amination treatment was possible for organic materials.
  • the present inventors have shown for the first time that reductive amination treatment is also useful for organic materials.
  • the present invention was made based on these findings.
  • the present invention provides a carbonylated protein-reducing agent for hair containing a reductive aminating agent containing a reducing agent, an acid catalyst and a nitrogen source.
  • the present invention also provides the agent for reducing carbonylated protein in hair, wherein the reducing agent is an organic borane complex or a compound represented by the following general formula (I).
  • R 1 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a carbohydrate having 1 to 16 carbon atoms, adenine dinucleotide or adenine dinucleotide phosphate
  • R 2 and R 3 respectively each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R 4 and R 5 each independently represent a hydrogen atom, -COO-R 6 or -CO-NR 6 R 7 , Each 7 independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • the present invention also provides that the reducing agent is 5-ethyl-2-methylpyridine borane (PEMB), 5-ethyl-2-methylpyridine borane complex, picoline borane complex, sodium cyanoborohydride (NaBH3CN) and trihydride.
  • the hair carbonylated protein-reducing agent is provided, which is at least one selected from the group consisting of sodium acetoxyborate.
  • the present invention also provides that the reducing agent is a compound represented by the general formula (I), R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and at least one of R 4 and R 5 is - Provided is the hair carbonylated protein-reducing agent represented by COO-R 6 , where R 6 represents an alkyl group having 1 to 3 carbon atoms.
  • the reducing agent is a compound represented by the general formula (I), R 1 represents a hydrogen atom, a carbohydrate having 1 to 16 carbon atoms, adenine dinucleotide or adenine dinucleotide phosphate, and R 4 represents a hydrogen atom, R 5 represents —CO—NR 6 R 7 , and R 6 and R 7 represent a hydrogen atom to provide the above carbonylated protein-reducing agent for hair.
  • R 1 represents a hydrogen atom, a carbohydrate having 1 to 16 carbon atoms, adenine dinucleotide or adenine dinucleotide phosphate
  • R 4 represents a hydrogen atom
  • R 5 represents —CO—NR 6 R 7
  • R 6 and R 7 represent a hydrogen atom to provide the above carbonylated protein-reducing agent for hair.
  • the reducing agent is at least selected from the group consisting of reduced nicotinamide adenine dinucleotide phosphate (NADPH), reduced nicotinamide adenine dinucleotide (NADH), reduced nicotinamide and Hantu ester.
  • NADPH reduced nicotinamide adenine dinucleotide phosphate
  • NADH reduced nicotinamide adenine dinucleotide
  • the present invention provides one of the above carbonylated protein-reducing agents for hair.
  • the present invention also provides the hair carbonylation protein-reducing agent, wherein the acid catalyst is at least one selected from the group consisting of acetic acid, citric acid, formic acid, propionic acid, phosphoric acid and oxalic acid.
  • the acid catalyst is at least one selected from the group consisting of acetic acid, citric acid, formic acid, propionic acid, phosphoric acid and oxalic acid.
  • the present invention also provides the hair carbonylation protein-reducing agent, wherein the nitrogen source is ammonia or an ammonium salt.
  • the present invention also provides a hair modification composition containing a reductive aminating agent containing a reducing agent, an acid catalyst and a nitrogen source, and a solvent.
  • the present invention also provides the hair-modifying composition, wherein the reducing agent is an organic borane complex or a compound represented by the general formula (I).
  • the present invention also provides that the reducing agent is 5-ethyl-2-methylpyridine borane (PEMB), 5-ethyl-2-methylpyridine borane complex, picoline borane complex, sodium cyanoborohydride (NaBH3CN) and trihydride.
  • the above hair modification composition which is at least one selected from the group consisting of sodium acetoxyborate.
  • the present invention also provides that the reducing agent is a compound represented by the general formula (I), R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and at least one of R 4 and R 5 is - Provided is the above hair modifying composition, which represents COO-R 6 , where R 6 represents an alkyl group having 1 to 3 carbon atoms.
  • the reducing agent is a compound represented by the general formula (I), wherein R 1 represents a carbohydrate having 1 to 16 carbon atoms, R 4 represents a hydrogen atom, and R 5 represents -CO- Provided is the above hair modifying composition, which represents NR 6 R 7 , wherein R 6 and R 7 represent hydrogen atoms.
  • the reducing agent is at least selected from the group consisting of reduced nicotinamide adenine dinucleotide phosphate (NADPH), reduced nicotinamide adenine dinucleotide (NADH), reduced nicotinamide and Hantu ester.
  • NADPH reduced nicotinamide adenine dinucleotide phosphate
  • NADH reduced nicotinamide adenine dinucleotide
  • Hantu ester is provided.
  • the present invention also provides the hair modifying composition, wherein the acid catalyst is at least one selected from the group consisting of acetic acid, citric acid, formic acid, propionic acid, phosphoric acid and oxalic acid.
  • the acid catalyst is at least one selected from the group consisting of acetic acid, citric acid, formic acid, propionic acid, phosphoric acid and oxalic acid.
  • the present invention also provides the hair modifying composition, wherein the nitrogen source is ammonia or an ammonium salt.
  • the present invention also provides the hair modifying composition, wherein the solvent is water or ethanol.
  • the present invention also provides an agent for improving water retention of hair containing a reductive aminating agent containing a reducing agent, an acid catalyst and a nitrogen source.
  • the present invention also provides a hair curvature reducing agent containing a reductive aminating agent comprising a reducing agent, an acid catalyst and a nitrogen source.
  • the present invention also provides a method for reducing carbonylated proteins in hair, comprising reductively aminating hair with a reducing agent in a solvent in the presence of an acid catalyst and a nitrogen source.
  • the present invention also provides a method for improving water retention of hair, comprising subjecting hair to reductive amination treatment with a reducing agent in a solvent in the presence of an acid catalyst and a nitrogen source.
  • the present invention also provides a method for reducing the curvature of hair, comprising reductively aminating hair with a reducing agent in a solvent in the presence of an acid catalyst and a nitrogen source.
  • the present invention can improve the water retention capacity of hair, which declines with aging.
  • the present invention can reduce the curvature of hair, which increases with aging, and improve the irregular shape of hair. Therefore, the present invention can contribute to further improvement of quality of life (QOL).
  • FIG. 1 shows measurement points for line mapping using optical microscopy images of untreated hair. Diagram showing the water behavior of black hair (diamond shape) and gray hair (triangle) in the cortex of a Japanese woman in her 50s. A diagram showing the localization of carbonylated proteins in cross sections of hair in each age group.
  • FIG. 4 is a diagram showing the ratio of average fluorescence intensity in cross sections of white hair and black hair in each age group.
  • FIG. 10 shows the average curvature of the hair of the same subject as in FIGS. 2 and 9.
  • FIG. FIG. 3 shows the level of introduction of amino groups in reductive amination-treated hair.
  • the present invention provides a carbonylated protein-reducing agent for hair containing a reductive aminating agent containing a reducing agent, an acid catalyst and a nitrogen source.
  • reducing carbonylated protein in hair means reducing the amount of carbonylated protein contained in hair.
  • hair includes both the hair shaft that emerges from the scalp and the hair root that resides within the scalp.
  • Reducing hair carbonylated proteins includes reducing carbonylated proteins in at least one of the hair cuticle, cortex and medulla.
  • reducing carbonylated protein as used herein includes suppressing an increase in carbonylated protein.
  • a carbonylated protein is a protein in which amino acids such as proline, arginine, lysine or threonine in the protein are oxidized by reactive oxygen species (ROS) and the like to become carbonyl derivatives.
  • ROS reactive oxygen species
  • the hair carbonylated protein-reducing agent of the present invention can modify hair through reduction of hair carbonylated protein. That is, the agent for reducing carbonylated protein in hair of the present invention can be used as a hair modifying agent.
  • modifying the hair includes improving the water retention capacity of the hair, reducing the average curvature of the hair, improving the irregular shape of the hair and improving the appearance of the hair. and so on.
  • reductive aminating agent refers to an agent capable of converting a carbonyl group of a carbonylated protein into an amino group by a reductive amination reaction.
  • a reductive amination reaction is a chemical reaction that converts an aldehyde or ketone to an amine.
  • a reductive aminating agent is a mixture comprising a reducing agent, an acid catalyst and a nitrogen source.
  • the reducing agent is used for the purpose of reducing the reaction intermediate imine to an amine.
  • a reducing agent for example, an organic borane complex can be used.
  • Organoborane complexes include, for example, 5-ethyl-2-methylpyridine borane (PEMB), 5-ethyl-2-methylpyridine borane complex, picoline borane complex, sodium cyanoborohydride (NaBH3CN) and sodium triacetoxyborohydride and so on. From the viewpoint of toxicity and safety, 5-ethyl-2-methylpyridine borane complex can be preferably used.
  • a compound having a 1,4-dihydropyridine structure represented by the following general formula (I) can be used as the reducing agent in the present invention.
  • R 1 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a carbohydrate having 1 to 16 carbon atoms.
  • Alkyl groups represented by R 1 can be, for example, methyl, ethyl, propyl, isopropyl and cyclopropyl groups.
  • R 2 and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R2 and R3 may be the same or different.
  • Alkyl groups represented by R 2 and R 3 can be, for example, methyl, ethyl, propyl, isopropyl and cyclopropyl groups.
  • R 4 and R 5 each independently represent a hydrogen atom, --COO--R 6 or --CO--NR 6 R 7 .
  • R4 and R5 may be the same or different.
  • R 6 and R 7 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R6 and R7 may be the same or different.
  • Alkyl groups represented by R 6 and R 7 can be, for example, methyl, ethyl, propyl, isopropyl and cyclopropyl groups.
  • alkyl group includes linear or branched alkyl groups.
  • Alkyl groups include, for example, methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl and hexyl groups. .
  • Carbohydrate includes monosaccharides, disaccharides, oligosaccharides, amino sugars, alditols, and the like.
  • Monosaccharides can be pyranosides or furanosides.
  • Carbohydrates can be, for example, D-glucose, D-mannose, D-galactose, D-allose, D-altrose, D-idose, D-talose, D-xylose, D-ribose and D-arabinose.
  • Carbohydrates may also have a structure in which two or more monosaccharides are linked by 1 to 3 phosphate groups.
  • a monosaccharide constituting a carbohydrate may be, for example, a nucleoside or a nucleotide in which ribose and a nucleobase are linked.
  • the carbohydrate can be, for example, adenine dinucleotide or adenine dinucleotide phosphate.
  • alkyl groups and carbohydrates may have substituents.
  • Substituents include, for example, halogen atoms, nitrogen atoms, sulfur atoms, hydroxyl groups, nitro groups, cyano groups, methoxy groups, ethoxy groups, carboxyl groups, carboxymethyl groups, carboxyethyl groups, methylenedioxy and the like.
  • Halogen atoms include fluorine, chlorine, bromine, iodine, and the like.
  • R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • at least one of R 4 and R 5 represents —COO—R 6
  • R 6 represents 1 to 3 carbon atoms.
  • the reducing agent in the present invention is preferably Hantu ester represented by the following formula (II).
  • R 1 represents a hydrogen atom or a carbohydrate having 1 to 16 carbon atoms
  • R 4 represents a hydrogen atom
  • R 5 represents —CO—NR 6 R 7
  • R 6 and R 7 represents a hydrogen atom.
  • R 1 represents a hydrogen atom, adenine dinucleotide or adenine dinucleotide phosphate
  • R 2 , R 3 and R 4 represent a hydrogen atom
  • R 5 represents —CO—NR 6 R 7 and R 6 and R7 each represent a hydrogen atom.
  • the reducing agent in the present invention is, for example, reduced nicotinamide adenine dinucleotide phosphate (NADPH), reduced nicotinamide adenine dinucleotide (NADH) or reduced nicotinamide.
  • NADPH/NADH are compounds having the structures shown below. A compound obtained by removing only the active site of NADH/NADPH is reduced niacinamide, both of which are biomolecules.
  • Hantu ester is preferably used as the reducing agent of the present invention from the viewpoint of economy and stability. Hantuester can be purchased in large quantities at low cost and is easy to store.
  • the compound represented by general formula (I) is used as a reducing agent in a reduced state. This compound functions as a reducing agent by releasing two electrons and becoming oxidized.
  • the compound represented by the general formula (I) as the reducing agent of the present invention, it is possible to reduce the burden on the environment and increase the safety to the human body. Moreover, since water, ethanol, or the like can be used as a solvent, safety to the human body can be further enhanced.
  • the compound of general formula (I) can be synthesized by any synthetic procedure known to those skilled in the art.
  • PEMB 5-ethyl-2-methylpyridine borane
  • PMB 5-ethyl-2-methylpyridine borane complex
  • picoline borane complex sodium cyanoborohydride (NaBH3CN) and sodium triacetoxyborohydride
  • reduced nicotine Commercially available compounds can be used for compounds such as amide adenine dinucleotide phosphate (NADPH), reduced nicotinamide adenine dinucleotide (NADH), reduced nicotinamide and Hantu ester.
  • NADPH amide adenine dinucleotide phosphate
  • NADH reduced nicotinamide adenine dinucleotide
  • Hantu ester any reduced compound can be obtained by reducing an oxidized compound by a general procedure.
  • an acid catalyst is an acid used for the purpose of protonating and activating a carbonyl group.
  • the acid catalyst is not particularly limited as long as it is a Bronsted acid, and for example, acetic acid, citric acid, formic acid, propionic acid, phosphoric acid and oxalic acid can be used. From the viewpoint of safety and convenience, acetic acid or phosphoric acid can be preferably used, although it is not particularly limited.
  • a nitrogen source is used to convert a carbonyl group into an imine.
  • a nitrogen source although not particularly limited, for example, ammonia or an ammonium salt can be used.
  • Ammonia and ammonium salts can restore carbonylated amino acids to their original amino acid structure.
  • Specific examples of nitrogen sources that can be used include aqueous ammonia, ammonium formate, ammonium acetate, ammonium carbonate, and ammonium hydrogen carbonate. Although it is not particularly limited from the viewpoint of ease of operation, ammonia water or ammonium acetate can be preferably used.
  • the present invention also provides a hair modification composition containing a reductive aminating agent containing a reducing agent, an acid catalyst and a nitrogen source, and a solvent.
  • the solvent used in the present invention includes, but is not particularly limited to, protic solvents, aprotic polar solvents and aprotic solvents.
  • Protic solvents include, for example, water, methanol, ethanol, 1-propanol, 2-propanol, propylene glycol, glycerin, butylene glycol and 1,3-BG.
  • Aprotic polar solvents include, for example, dimethylsulfoxide, dimethylformamide, acetonitrile, hexamethylphosphoramide, and the like.
  • Aprotic solvents include, for example, diethyl ether, chloroform, toluene, 1,4-dioxane and liquid hydrocarbons.
  • water, methanol, or ethanol can be preferably used in terms of reactivity and ease of handling.
  • water or ethanol can be preferably used.
  • the present invention also provides a method for reducing carbonylated proteins in hair, comprising reductively aminating hair with a reducing agent in a solvent in the presence of an acid catalyst and a nitrogen source.
  • hair can be treated with the agent or composition of the present invention as described above.
  • the reductive amination treatment of hair with a reducing agent involves preparing a composition containing a nitrogen source such as an aqueous ammonia solution and a reducing agent in a solvent containing an acid catalyst.
  • a method of treating the hair by, for example, can be used.
  • the present invention also provides an agent for improving water retention of hair containing a reductive aminating agent containing a reducing agent, an acid catalyst and a nitrogen source.
  • the present invention also provides a method of improving water retention of hair comprising reductively aminating hair with a reducing agent in a solvent in the presence of an acid catalyst and a nitrogen source.
  • improving the water holding capacity of hair means improving the water holding capacity of hair that has decreased due to aging. Including suppressing a decrease in water retention capacity.
  • the present invention also provides a hair curvature reducing agent containing a reductive aminating agent comprising a reducing agent, an acid catalyst and a nitrogen source.
  • the present invention also provides a method of reducing the curvature of hair comprising reductively aminating hair with a reducing agent in a solvent in the presence of an acid catalyst and a nitrogen source.
  • reducing the curvature of hair includes reducing the curvature of hair that has increased with age and suppressing the increase in curvature of hair with age.
  • the “curvature of hair” represents the degree of disorder of hair, and the higher the curvature, the greater the degree of disorder of hair.
  • agents and compositions of the present invention can contain any other ingredients in addition to the above-described ingredients, depending on the purpose of use, as long as they do not impair the effects of the present invention.
  • the agents and compositions of the present invention include anionic surfactants such as lauryl sulfate, polyoxyethylene lauryluther sulfate, laurylbenzenesulfonate and sodium lauroylmeth- ⁇ -alanine;
  • Amphoteric surfactants such as carboxymethyl-N-hydroxyethylimidazonium betaine, coconut fatty acid amidopropyl betaine and coconut alkyl N-carboxyethyl-N-hydroxyethylimidazolinium betaine sodium: cationized cellulose, polyacrylic acid and polymers such as poly(diallyldimethylammonium chloride); humectants such as sorbitol, inositol, glycerin, propylene glycol, butylene glycol
  • agent and composition of the present invention can be in any form, such as liquid, milky lotion, cream, gel, paste and foam, depending on the purpose of use.
  • the agents and compositions of the present invention can be in the form of hair cosmetics, for example.
  • Hair cosmetics include, for example, hair rinses, hair conditioners, hair treatments, leave-in treatments, hair packs, hair foams, hair waxes, pomades, hair gels, hair creams, hair sprays, hair mists, hair waters, hair liquids, hair oils, Hair tonic, hair lotion, hair color, perming agent, hair tonic and the like are included.
  • These hair cosmetics can be produced by conventionally known methods.
  • Subjects were selected from healthy Japanese women aged 40-60 who had not dyed or permed their hair for one week prior to the test. Only shampoo was used on the day before the test, and no hair styling agent or hair treatment was used on the day of the test. Hair samples were soaked in deionized water for 10 minutes to remove temporary hair shapes and to assess the intrinsic shape of hair.
  • Deuterium oxide 99.8% D was obtained from Kanto Kagaku Co., Ltd. (Tokyo, Japan).
  • the average curvature of the hair was measured using the method described in Non-Patent Document 5. Specifically, the hair fibers were soaked in water at 25° C. for 10 minutes to remove the temporary water set formed during drying of the hair fibers and caused by the exchange of hydrogen bonds. Next, the hair fiber was set in an image scanner (GT-X830, manufactured by Seiko Epson Corporation), a two-dimensional image of the hair shape was acquired, and the curvature of each curve from the hair root to the hair tip was analyzed. Since hair color has little effect on hair shape, shape measurements were performed indiscriminately on color-treated hair.
  • FIG. 3 shows an example of irregular shapes observed in white hair and dyed white hair.
  • the water behavior evaluation was performed using a method applying the water permeation measurement method described in Patent Document 3. Specifically, we sandwiched a smooth hair section using a rotating microtome between diamond cells developed in-house, and injected heavy water into the cell gap. The hair sections were evaluated serially using a Fourier transform infrared microscope (Thermo Fisher Scientific, Nicolet iN10). Water behavior was visualized and quantified by evaluating the OD stretching peak intensity at ⁇ 2500 cm ⁇ 1 indicative of heavy water in real time by line mapping measurements every 10 ⁇ m from the medulla to the cuticle.
  • FIG. 4 is a diagram showing measurement points for line mapping using an optical microscope image of untreated hair. In the measurement, the resolution was 8 cm -1 , the number of accumulations was 256, and the spectrum was obtained in the wavenumber range of 4000 to 650 cm -1 .
  • Figure 5 shows the behavior of black hair (diamond-shaped) and white hair (triangle) in the cortex from the same person of a Japanese woman in her 50s (OD stretching peak intensity at ⁇ 2500 cm -1 ; , followed by a drying step at 25°C and 50% RH for 4 hours).
  • This result indicates that white hair has a faster permeation rate of water from the outside than black hair.
  • white hair lost moisture one hour earlier than black hair.
  • the hair sample was immersed in 20 ⁇ M 5-FTSC/0.1 M MES-Na (pH 5.5) and incubated in the dark for 1 hour. After that, the hair was washed with PBS four times and observed under a fluorescence microscope. The resulting images were analyzed using ImageJ, and the fluorescence intensity per unit area of the hair sample was set as the degree of carbonylation.
  • Figure 6 shows the localization of carbonylated proteins in hair cross sections of each age group ((a) black hair in the 40s; (b) black hair in the 50s; (c) black hair in the 60s; (e) White hair in the 50's (f) Gray hair in the 60's As shown in Figure 6, an increase in carbonylated protein was observed with age, and white hair has more carbonylated protein than black hair. It has been shown.
  • FIG. 8 shows the localization of carbonylated proteins in a hair section of a Japanese woman in her 50s (Reagent: reductive amination treatment). Reductive amination treatment has been shown to reduce the amount of carbonylated proteins regardless of whether the hair is dark or white.
  • Figure 9 shows the water behavior of black hair (diamond shape), white hair (triangle) and reductively aminated gray hair (square) from the same person in the fifties Japanese woman in the cortex (at ⁇ 2500 cm -1 ). OD stretching peak strength; first 30 minutes under heavy water penetration conditions, then drying process at 25°C, 50% RH for 4 hours). The white hair treated with reductive amination had improved water retention capacity and showed water behavior equivalent to that of black hair.
  • 90% RH the mean curvature of 50's hair that had undergone reductive amination treatment was significantly reduced compared to hair that had not undergone reductive amination treatment.
  • FIG. 11 shows the level of introduction of amino groups in reductively aminated hair. As shown in Figure 11, it was found that the hair treated with PEMB had a higher level of amino group incorporation and more DBD-ED was introduced into the hair compared to the absence of PEMB (control). rice field. This result indicated that amino groups were introduced into the hair by the PEMB treatment.
  • FIG. 12 shows the effect of reducing carbonylated protein when using Hantu ester as a reducing agent.
  • Hantuester reduction-treated hair showed reduced amounts of carbonylated proteins.
  • FIG. 13 shows a comparison of the effect of reducing carbonylated protein by different solvents. The results showed that the amount of carbonylated proteins was reduced even in hair reduced using water or ethanol as a solvent.
  • the present invention can be suitably used for cosmetics and pharmaceuticals for modifying hair.

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Abstract

Le problème décrit par la présente invention concerne le changement de qualité des cheveux dû au vieillissement qui est un problèmes particulièrement chez les femmes de plus de 40 ans. Si la qualité des cheveux peut être efficacement améliorée, la qualité de vie (QOL) peut être davantage améliorée. Le but de la présente invention est de fournir un nouveau procédé et un nouvel agent permettant tous deux d'améliorer le changement de qualité des cheveux avec l'âge. La solution selon l'invention porte sur un agent de réduction des protéines carbonylées pour les cheveux, un agent d'amélioration de la capacité de rétention d'eau pour les cheveux, et un agent de réduction de la courbure des cheveux, dont chacun comprend un agent de réduction, un catalyseur acide, et un agent d'amination réductrice contenant une source d'azote.
PCT/JP2021/038092 2021-03-01 2021-10-14 Agent de réduction de protéine carbonylée pour les cheveux WO2022185599A1 (fr)

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Citations (4)

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Publication number Priority date Publication date Assignee Title
JP2004284988A (ja) * 2003-03-24 2004-10-14 Kose Corp 毛髪化粧料及び毛髪の蛋白質のカルボニル化を抑制する方法
JP2007291108A (ja) * 2006-04-25 2007-11-08 L'oreal Sa ケラチン繊維の成長を誘導及び／又は刺激するため、並びに／あるいはそれらの損失を予防するための薬剤としての４−アミノピペリジン誘導体の使用
JP2008508262A (ja) * 2004-07-30 2008-03-21 コリア リサーチ インスティテュートオフ゛ ケミカル テクノロシ゛ー 自己造形性パーマ剤と脱ロッド及び脱バンド型パーマ方法
JP2019001759A (ja) * 2017-06-19 2019-01-10 株式会社ミルボン 毛髪用組成物、及び毛髪処理方法

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JP2004284988A (ja) * 2003-03-24 2004-10-14 Kose Corp 毛髪化粧料及び毛髪の蛋白質のカルボニル化を抑制する方法
JP2008508262A (ja) * 2004-07-30 2008-03-21 コリア リサーチ インスティテュートオフ゛ ケミカル テクノロシ゛ー 自己造形性パーマ剤と脱ロッド及び脱バンド型パーマ方法
JP2007291108A (ja) * 2006-04-25 2007-11-08 L'oreal Sa ケラチン繊維の成長を誘導及び／又は刺激するため、並びに／あるいはそれらの損失を予防するための薬剤としての４−アミノピペリジン誘導体の使用
JP2019001759A (ja) * 2017-06-19 2019-01-10 株式会社ミルボン 毛髪用組成物、及び毛髪処理方法

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DATABASE GNPD MINTEL; December 2019 (2019-12-01), "XC-Hair Growth Serum", XP055963904, Database accession no. 7130589 *

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