WO2005018598A1 - 一重項酸素消去剤、及びそれを用いた組成物 - Google Patents
一重項酸素消去剤、及びそれを用いた組成物 Download PDFInfo
- Publication number
- WO2005018598A1 WO2005018598A1 PCT/JP2004/012315 JP2004012315W WO2005018598A1 WO 2005018598 A1 WO2005018598 A1 WO 2005018598A1 JP 2004012315 W JP2004012315 W JP 2004012315W WO 2005018598 A1 WO2005018598 A1 WO 2005018598A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- singlet oxygen
- oxygen scavenger
- skin
- inhibitor
- platinum
- Prior art date
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 55
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Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- 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
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Definitions
- the present invention relates to a novel singlet oxygen scavenger, and a composition containing the same as an active ingredient.
- ESR is effective in detecting radical species such as superoxide / hydroxy radical, but cannot detect singlet oxygen that is not a radical species.
- the lifetime of singlet oxygen in water is as short as about 4 ⁇ s, and detection methods having both sensitivity and specificity are limited (for example, Japanese Patent Application Laid-Open No. 7-159325). Therefore, those that have been reported as reactions involving active oxygen species in a broad sense and those that have been reported as agents that are effective in capturing active oxygen species have been examined in terms of their detection methods. Most are not clear about oxygen.
- each reactive oxygen species exhibits a specific reactivity.
- superoxide dihydroxy radicals readily react with proteins and cause their fragmentation.
- singlet oxygen forms a crosslink in the protein and polymerizes the protein. It shows a unique reactivity that is completely different from
- the present invention provides a singlet oxygen scavenger comprising a colloidal solution of a platinum group metal to solve the above problems.
- 1 is the singlet oxygen erasing constant 0 X 1 0 8 ⁇ - ⁇ s the singlet oxygen quencher is one of 1 or more;.
- the platinum group metal, the single platinum or mouth Jiumu The singlet oxygen scavenger, which is a colloidal solution of a single metal species; the singlet oxygen scavenger, which is a platinum colloidal solution or a rhodium colloidal solution;
- a singlet oxygen scavenger containing a water-soluble polymer; the platinum group metal and the water-soluble polymer The singlet oxygen scavenger having a mass ratio of 1:40 to 1: 100 with respect to a molecule; and the singlet oxygen, wherein the water-soluble polymer is poly (1-butyl-12-pyrrolidone).
- the singlet oxygen scavenger of the present invention or a composition containing the same as an active ingredient can be used to suppress various reactions involving singlet oxygen. It can be used as an oxidation inhibitor, an enzyme inactivation inhibitor, a lipid peroxidation inhibitor, a cell aging inhibitor or a dye fading inhibitor.
- composition containing the singlet oxygen scavenger as an active ingredient a composition containing the singlet oxygen scavenger as an active ingredient; a skin external preparation containing the singlet oxygen scavenger as an active ingredient
- the present invention it is possible to provide a singlet oxygen scavenger that maintains good singlet oxygen scavenging ability for a long period of time. Further, according to the present invention, it is possible to provide a singlet oxygen scavenger and a composition capable of suppressing various reactions caused by singlet oxygen. Further, according to the present invention, by applying to the skin, it is possible to prevent aging of the skin, blackening of the skin, damage to the skin, etc., which may be caused by a reaction involving singlet oxygen. Term oxygen scavengers and compositions can be provided. BEST MODE FOR CARRYING OUT THE INVENTION
- the singlet oxygen scavenger of the present invention comprises a colloidal solution of a platinum group metal.
- the platinum group metal is a general term for transition metals composed of ruthenium, osmium, rhodium, iridium, palladium, and platinum. Of these, rhodium and platinum are preferred.
- the colloid liquid means a state in which particles of these platinum group metals are dispersed in a liquid phase. It may be a kind of colloid solution selected from platinum group metals, or a colloid solution of two or more kinds of metals. Among them, a colloid solution of a single metal species is preferable. Lloyd or rhodium colloid is preferred.
- the colloidal liquid of platinum group metal refers to a liquid in which particles of platinum group metal are dispersed in a liquid phase. In order to obtain a stable colloidal state, it is preferable that the platinum group metal particles have a large specific surface area and excellent surface reactivity.
- the particle size of the platinum group metal particles is not particularly limited, but is preferably 50 nm or less, more preferably 2 O nm or less, further preferably 10 nm or less, and particularly preferably about 1 to 6 nm.
- the average particle size of the colloid particles can be determined by observing the particles with a transmission electron microscope.
- the main component of the liquid phase in which the particles of the platinum group metal are dispersed is preferably water.
- An organic solvent may be contained as long as the colloid state is not destabilized.
- the organic solvent include alcohols such as methanol and ethyl alcohol; and polyhydric alcohols such as glycerin, diglycerin, 1,3-butylene glycol, and dipropylene glycol.
- metal particles for example, JP-B-57-43125, JP-B-59-120249, and JP-A-9-1225317, JP-A-10-176207, JP-A-2001-79382, JP-A-201-122723, etc.
- a chemical method called a precipitation method or a metal salt reduction reaction method or a physical method called a combustion method can be used.
- a combustion method As the singlet oxygen scavenger of the present invention, particles prepared by any method may be used, but it is preferable to use metal particles prepared by a metal salt reduction reaction method in terms of ease of production and quality. .
- an aqueous solution or an organic solvent solution of a water-soluble or organic solvent-soluble metal salt or metal complex is prepared, and after adding a water-soluble polymer to this solution, the pH is adjusted as necessary. By heating and refluxing under an inert atmosphere, metal particles can be obtained by reduction.
- the kind of the water-soluble or organic solvent-soluble salt of the metal is not particularly limited. For example, acetate, chloride, sulfate, nitrate, sulfonate, or phosphate can be used. May be used.
- the type of the water-soluble polymer used in the metal salt reduction reaction method is not particularly limited, for example, , Polyvinylpyrrolidone, polyvinyl alcohol, polyacrylic acid, cyclodextrin, aminopectin, methylcellulose and the like can be used, and two or more of these may be used in combination.
- poly (vinylpyrrolidone) can be used, and more preferably, poly (1-butyl-12-pyrrolidone) can be used.
- the concentration ratio of the platinum group metal to the water-soluble polymer (preferably poly (1-butyl-1-pyrrolidone)) as a unit chemical formula amount is preferably 1:40 to 1: 200.
- surfactants for example, anionic, cationic, amphoteric, nonionic or lipophilic surfactants, in place of or together with the water-soluble polymer. is there.
- alcohol ethyl alcohol, n-propyl alcohol, n-butyl alcohol, n-amyl alcohol, ethylene glycol, or the like is used.
- these water-soluble polymers and surfactants contribute to the stabilization of the colloid state as a protective colloid agent.
- the method for preparing the metal particles is not limited to the method described above.
- the metal particles generated in the liquid phase by the metal salt reduction reaction method may be used for preparing a singlet oxygen scavenger without being separated from the liquid phase as it is.
- metal particles are formed in a liquid phase by a metal salt reduction reaction method, and an appropriate purification step (for example, a step of distilling off the organic solvent used in the metal salt reduction reaction step under reduced pressure) as required.
- an appropriate purification step for example, a step of distilling off the organic solvent used in the metal salt reduction reaction step under reduced pressure
- a singlet oxygen scavenger consisting of a stable colloid solution can be prepared by adding an arbitrary amount of water or by removing an arbitrary amount of water.
- Surfactants and dispersants that contribute to the stabilization of the colloidal state may be added if desired.
- the method for preparing the singlet oxygen scavenger of the present invention is not limited to this.
- the concentration of the platinum group metal in the colloidal liquid as the mother liquor used in the preparation of the final product is not particularly limited as long as the stability of the colloidal state is not impaired. In general, the stability is maintained at about 1 nmol / L to 1 mmo 1 L, but the stability of the colloidal state is different for each metal and is not limited to this range. Of the platinum group metal in the final product composition The preferred range of the concentration will be described later.
- Singlet oxygen quencher of the present invention is preferably at singlet oxygen erasing constant 1. 0 X 10 8 M- 1 s one 1 or more, 1. OX 10 9 M one 1 s-1 or more of And more preferably 1.0 X 10 1 Q M- 1 s- 1 or more.
- a singlet oxygen scavenger is added at various concentrations (Cq) to a system in which singlet oxygen is arbitrarily generated and emission accompanying the transition of singlet oxygen is observed, and the emission intensity ( I) was measured, and the ratio (Io) / (I) to the luminescence intensity (Io) without addition was calculated.
- ⁇ is the lifetime of singlet oxygen and is a constant that varies depending on the solvent of the system.
- the concentration C q is the concentration of the metal, and the unit is mo 1 / L.
- an experimental system used for calculating the singlet oxygen extinction constant and a luminescence detecting device those described in Japanese Patent No. 3356517 can be used.
- the singlet oxygen scavenger of the present invention is not oxidized during use and does not lose its effect, the singlet oxygen scavenging ability can be maintained for a long time.
- the singlet oxygen scavenger of the present invention can be used in applications that suppress reactions caused or promoted by the presence of singlet oxygen.
- singlet oxygen is known to crosslink collagen which is a constituent of the dermis (J. Soc. Cosmet. Chem. Japan. Vol. 28, No. 2 1994, p. 163-171). Collagen cross-linking reduces the elasticity and flexibility of the skin and contributes to aging of the skin.
- the singlet oxygen scavenger of the present invention can be used as a collagen crosslinking inhibitor.
- singlet oxygen is frequently generated on the skin surface by UV-A irradiation, and is involved in the non-enzymatic immediate darkening caused by the oxidation of dopa, and in the peroxidation of skin surface lipids. Is known to be involved (Journal of the Japanese Society of Perfumery Science vol.19 No. l 1995, p. 1-6). Therefore, by applying the singlet oxygen scavenger of the present invention to the skin, it can be used as an inhibitor for suppressing the peroxidation of the skin lipids of the immediate black skin of the skin.
- the singlet oxygen quencher of the present invention is used as an immediate darkening inhibitor, is greater than dopa singlet oxygen erasing constant of singlet oxygen quencher, i.e., 6. 8 X 1 0 8 M one It is more preferably 1 s- 1 or more.
- singlet oxygen is known to cause or promote inactivation of a number of enzymes responsible for in vivo reactions. Therefore, the singlet oxygen scavenger of the present invention can be used as an enzyme inactivation inhibitor.
- the singlet oxygen scavenging constant of the singlet oxygen scavenger must be larger than that of the enzyme. Is more preferred.
- singlet oxygen causes or promotes fading or discoloration of pigments such as plant extracts incorporated in cosmetics and foods.
- the presence of singlet oxygen may cause or accelerate the decomposition of a medicinal agent incorporated in skin cosmetics and the like.
- the singlet oxygen scavenger of the present invention is blended, not only the singlet oxygen scavenging ability and the above-mentioned effects accompanying the singlet oxygen scavenger are obtained, but also the effect of suppressing the decomposition of other agents that are blended together is obtained.
- the singlet oxygen scavenger of the present invention can be used as a dye fading inhibitor, and can be used not only for fading but also as a preservative for other medicinal agents.
- the composition containing the singlet oxygen scavenger of the present invention as an active ingredient can be used for various purposes such as pharmaceuticals, quasi-drugs, cosmetics, and foods.
- Singlet oxygen is constantly in contact with oxygen and is present on skin surfaces that are exposed to ultraviolet light, so
- the composition containing the singlet oxygen scavenger of the invention is more useful as an external preparation for skin.
- the reaction suppressed by the elimination of singlet oxygen is a reaction that contributes to aging of the skin, darkening of the skin, and damage to the skin.
- the agent and a composition containing the same as an active ingredient are particularly useful as a skin cosmetic for preventing skin aging, whitening, and beautiful skin.
- An external preparation for skin is prepared by mixing the singlet oxygen scavenger of the present invention alone or together with one or more known external pharmaceutical additives or skin cosmetic additives according to a conventional method. be able to.
- the amount of the singlet oxygen scavenger of the present invention depends on the dosage form of the external preparation, the purpose of use, etc., and also depends on the singlet oxygen scavenging ability of the singlet oxygen scavenger.
- the concentration of the platinum group metal In the final composition is preferably 0.1 Ol / mo 1 ⁇ ⁇ 50 // 11101 / L, more preferably 1 nmo1 / L ⁇ : ⁇ 1 / L. Within this range, the colloid liquid can be stably compounded, and excellent drug efficacy can be exhibited.
- the singlet oxygen scavenger of the present invention can be used alone as a skin external preparation, or a skin external preparation can be prepared by mixing it with one or more additives.
- Additives that are added as needed include water (purified water, hot spring water, deep water, etc.), alcohol, oils, surfactants, which are commonly used in the preparation of skin cosmetics and external medicines.
- Metal soaps gelling agents, powders, alcohols, water-soluble polymers, film-forming agents, resins, UV protection agents, clathrate compounds, antibacterial agents, fragrances, deodorants, salts, ⁇ regulators, fresheners , Animal / microbial extract, plant extract, blood circulation enhancer, astringent, antiseborrheic, whitening, anti-inflammatory, active oxygen scavenger other than singlet oxygen scavenger of the present invention, cell activator Humectants, chelating agents, keratolytic agents, enzymes, hormones, vitamins and the like.
- Preparation of the external preparation for skin can be performed according to a conventional method, and the amount of the additive can be determined according to a conventional method within a range not to impair the effects of the present invention.
- the form of the external preparation for skin is not limited, and forms belonging to skin cosmetics such as milky lotions, creams, lotions, cosmetic liquids, packs, facial cleansers, makeup cosmetics, etc .; shiambu, hair treatment, hair styling , Hair restoration, hair restoration, etc. forms related to hair cosmetics; and dispersions, ointments, aerosols, patches, cataplasms, External medicines such as liniment and the like.
- skin cosmetics such as milky lotions, creams, lotions, cosmetic liquids, packs, facial cleansers, makeup cosmetics, etc .
- shiambu hair treatment, hair styling , Hair restoration, hair restoration, etc. forms related to hair cosmetics
- dispersions, ointments, aerosols, patches, cataplasms, External medicines such as liniment and the like.
- Poly (1-1vinyl-2-pyrrolidone) (0.147 g, manufactured by Wako Pure Chemical Industries, Ltd.) was placed in a 10 OmL two-necked eggplant-shaped flask connected with a water condenser cooling tube and a three-way cock, and distilled water (23 mL) was used. Dissolved. The solution was stirred for 10 minutes, chloroplatinic acid (H 2 P t C 1 6 ⁇ 6H 2 0, manufactured by Wako Pure Chemical Industries, Ltd.) 1. 66 X 10- 2 M solutions were dissolved in distilled water (2 mL) Was added and the mixture was further stirred for 30 minutes.
- the inside of the reaction system was replaced with nitrogen, and 25 mL of special grade ethanol was added, and the mixture was refluxed at 100 ° C for 2 hours while maintaining the nitrogen atmosphere.
- the UV of the reaction solution was measured, and the disappearance of the platinum ion peak and the saturation of the peak due to the scattering of the metal solid were confirmed, and the reduction reaction was terminated.
- the organic solvent was distilled off under reduced pressure to prepare a platinum colloid solution (average particle size: 2.4 ⁇ 0, ⁇ nm).
- the platinum concentration of the obtained platinum colloid solution was 1 mm 0 1 ZL.
- the singlet oxygen detector an apparatus described in Japanese Patent No. 3356517 (the details are described in column 0026 of the same publication) was used.
- a 200 aqueous solution of Rose Bengal was circulated in the flow cell at a rate of 2 OmL / min.
- Rhodium colloid solution 2.4 X 10 10 M— 1 s- 1
- component (12) The following components (8) to (9) were added to component (12), and after swelling, component (10) was added, mixed, heated and maintained at 70 ° C to prepare an aqueous phase.
- component (1) to (6) were heated and mixed at 70 ° C., added to the aqueous phase, and emulsified.
- the emulsion was cooled to room temperature, and the following components (7), (11) and (13) were added and mixed uniformly to obtain an emulsion.
- Rhodium colloid liquid (rhodium concentration 1 At mo 1 / L) 50
- the prepared lotion and milky lotion were constant without discoloration, discoloration, and sediment, and were applicable to the skin. Industrial applications
- the singlet oxygen scavenger of the present invention or a composition containing the same as an active ingredient has singlet oxygen scavenging ability, reactions involving singlet oxygen, in particular, singlet oxygen-related aging of the skin It is useful for suppressing various reactions that contribute to immediate blackening, skin damage, and the like.
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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CN2004800240527A CN1838935B (zh) | 2003-08-22 | 2004-08-20 | 单线态氧消除剂及使用它的组合物 |
EP04772271A EP1661548A4 (en) | 2003-08-22 | 2004-08-20 | MEANS FOR ELIMINATION OF SINGLET OXYGEN AND THIS USE METHOD |
JP2005513367A JP4763460B2 (ja) | 2003-08-22 | 2004-08-20 | 一重項酸素消去剤、及びそれを用いた組成物 |
US10/568,875 US7588747B2 (en) | 2003-08-22 | 2004-08-20 | Singlet oxygen quencher and composition using the same |
HK07101591.4A HK1094428A1 (en) | 2003-08-22 | 2007-02-09 | Agent for eliminating singlet oxygen and composition using the same |
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JP2003-298188 | 2003-08-22 | ||
JP2003298188 | 2003-08-22 |
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WO2005018598A1 true WO2005018598A1 (ja) | 2005-03-03 |
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PCT/JP2004/012315 WO2005018598A1 (ja) | 2003-08-22 | 2004-08-20 | 一重項酸素消去剤、及びそれを用いた組成物 |
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US (1) | US7588747B2 (ja) |
EP (1) | EP1661548A4 (ja) |
JP (1) | JP4763460B2 (ja) |
KR (1) | KR20070030158A (ja) |
CN (1) | CN1838935B (ja) |
HK (1) | HK1094428A1 (ja) |
TW (1) | TWI329022B (ja) |
WO (1) | WO2005018598A1 (ja) |
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Also Published As
Publication number | Publication date |
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JP4763460B2 (ja) | 2011-08-31 |
HK1094428A1 (en) | 2007-03-30 |
TWI329022B (en) | 2010-08-21 |
US7588747B2 (en) | 2009-09-15 |
CN1838935A (zh) | 2006-09-27 |
JPWO2005018598A1 (ja) | 2006-10-12 |
TW200513265A (en) | 2005-04-16 |
EP1661548A4 (en) | 2010-05-19 |
KR20070030158A (ko) | 2007-03-15 |
CN1838935B (zh) | 2011-05-04 |
EP1661548A1 (en) | 2006-05-31 |
US20070090153A1 (en) | 2007-04-26 |
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