KR101715590B1 - 11- 1 Anti-aging cosmetic composition or skin external composition comprising compound of 11-hydroxysteroid dehydrogenase type 1 inhibitor - Google Patents
11- 1 Anti-aging cosmetic composition or skin external composition comprising compound of 11-hydroxysteroid dehydrogenase type 1 inhibitor Download PDFInfo
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- KR101715590B1 KR101715590B1 KR1020150157476A KR20150157476A KR101715590B1 KR 101715590 B1 KR101715590 B1 KR 101715590B1 KR 1020150157476 A KR1020150157476 A KR 1020150157476A KR 20150157476 A KR20150157476 A KR 20150157476A KR 101715590 B1 KR101715590 B1 KR 101715590B1
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
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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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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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
- A61Q19/08—Anti-ageing preparations
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Abstract
Description
The present invention relates to a cosmetic composition comprising a compound inhibiting the activity of 11? -
The main areas of interest in functional cosmetic technology are products that delay skin aging and help to improve wrinkles, products that protect the skin from ultraviolet rays and the external environment, and products that help to whiten skin.
In order to develop a wrinkle-improving cosmetic for delaying aging of the skin, development of a functional raw material capable of exhibiting physiological efficacy in the skin should be preceded.
In general, wrinkles and skin elasticity, aging, and dry skin appear on aged skin, mostly due to changes in substrate proteins in the dermis. Since the dermis plays a role in supporting the strength and shape of the skin in the skin, when the morphological change occurs in this part when the aging proceeds, it plays a decisive role in the generation of wrinkles and skin wrinkles. Matrix metalloproteinases (MMPs) are typical enzymes that decompose these matrix proteins, and they are important factors in promoting skin aging by remarkably decomposing collagen and other matrix proteins in the skin. do.
Physical stimuli from the outside cause a physiological stress response in the human body by stress hormones such as the brain and corticotrophin-releasing hormone (CRH), glucocorticoids, and epinephrine. Skin is the main sensory organ that senses stress from external stimulus sources. Typical stimulus sources are ultraviolet rays, and skin frequently exposed to ultraviolet light causes early skin aging. In addition, ultraviolet light activates stress hormones repeatedly and damages the skin. This results in severe skin adverse effects, such as disruption of dermal fibroblast tissue, just as overdose of steroids on the skin. Ultraviolet stimulation is known to be the main cause of glucocorticoids activity in human skin such as cortisol. In addition, UV-stimulation increases the expression of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1), which is an enzyme in human body activating cortisol. The increase in the activity and expression of 11? -HSD1 by ultraviolet rays is closely related to skin aging, and thus has been attracting attention as a new target for inhibiting skin aging.
According to Tiganescu, 11β-hydroxysteroid dehydrogease type 1 (hereinafter referred to as 11β-HSD1), a stress hormone regulatory enzyme, plays a significant role in skin aging. That is, the activity and expression of ll [beta] -HSDl increases with progress of skin aging (Tiganescu A et al, 2011; 131, 30-36), and the activity and expression of ll [beta] -HSDl is markedly increased, (Tiganescue et al, 2013; 123 (7): 30513060). In addition, when applying inhibitors of ll [beta] -HSDl, or making aged mice lacking the ll [beta] -HSDl gene, it was also found that the recovery of skin wounds was promoted and there was little change in dermal aging (Tiganescua et al, 2013 ; 123 (7): 30513060). Thus, it has been suggested that the control of 11 [beta] -HSD1 can inhibit or improve skin aging. 11β-HSD1 enzyme is an enzyme that converts inactive stress hormone into active stress hormone, and various mental stress as internal factors, and ultraviolet rays, pollutants and chemicals as external factors increase the activity and expression. In particular, the increase in the activity and expression of 11? -HSD1 by ultraviolet light is closely related to skin aging.
In the meantime, vitamin C, α-tocopherol, retinol and derivatives thereof have been used in cosmetics and medicines for improving wrinkles. However, when they are formulated in the formulations, they have a disadvantage that they are not removed or chemical stability is poor have.
The inventors of the present invention have made extensive efforts to overcome the problems of the prior art. As a result, the present inventors have found that the role of 11? -HSD1 activated by ultraviolet light is related to photoaging, Compounds that effectively inhibit activity were selected by in silico.
Protein-based navigation speed virtual drug with an active framework (Receptor-Oriented Pharamcophore based in silico High-Throughput Screening, in Silico HTS) analyzes the interaction of proteins and materials to express them in chemical properties feature is similar to one of the new chemical Is one of the computational chemistry methods for the development of new materials having a structure. The Pharmacophore is the arrangement of the chemical conditions that are essential for the efficacy of the material using three-dimensional coordinates. In particular, the definition of active skeleton is very important for the binding of one protein to protein and its activity, which can be defined through known experimental data or sufficient structural analysis. The interaction between the protein and the material can be defined through the formation of hydrogen bonding (hydrophobic bonding) and hydrophobic (lipophilic) environments, and these become the chemical conditions for the active framework. Hydrogen bonding is expressed as a feature of the hydrogen bonding (HBA) and the hydrogen bonding accepting (HBD), and the hydrophobic environment is represented as a feature of (Lipo). It is defined in map form.
In the present invention, the compound of formula (1) (trimethyl- [2- (2-oxo-5H-furan-3-yl) ethyl] BLAHcarbaldehyde selected by in silico suppresses photoaging through increased expression of 11? -HSD1 and MMPs, Thereby confirming the possibility of prevention or improvement of aging, thereby completing the present invention.
It is a primary object of the present invention to provide a cosmetic composition or a composition for external application for skin comprising as an active ingredient a compound of formula (I) inhibiting the activity of 11? -
Still another object of the present invention is to provide a cosmetic composition for preventing skin aging or composition for external application for skin comprising a compound of formula (I) inhibiting the activity of the 11? -
In the present invention, a three-dimensional structure of 11β-
According to one aspect of the present invention, there is provided a compound of formula (1), which inhibits the activity of 11? -Hydroxysteroid dehydrogenase type 1 (trimethyl- [2- (2-oxo -5H-furan-3-yl) ethyl] BLAHcarbaldehyde) as an active ingredient.
[Chemical Formula 1]
In the experimental examples of the present invention, it was proved that the compound of the formula (1) effectively inhibits the expression of 11? -Hydroxysteroid dehydrogenase type 1 (11? -HSD1) and MMPs and restores collagen production, thereby preventing or improving skin aging.
In the example of the present invention, compounds capable of binding to the active site of ll [beta] -HSDl were selected in a hypothetical new drug search for ll [beta] -HSDl (Fig. 1) HSD1 can be competitively bound to the active site of HSD1 to inhibit the activity of ll [beta] -HSDl.
In the present invention, the compound is contained in an amount of 0.01 to 10% by weight based on the total weight of the composition. If the amount is less than 0.01% by weight, the effect of inhibiting photoaging may be insignificant. On the contrary, if it exceeds 10% by weight, it may be undesirable from the viewpoint of economy.
In the present invention, the compound is characterized by exhibiting an inhibitory effect on the expression of 11? -Hydroxysteroid dehydrogenase type 1 (11? -HSD1).
According to the experimental example of the present invention, it was confirmed that the compound inhibits 11β-HSD1 overexpressed by ultraviolet light, and it was confirmed that the compound suppresses the production of cortisol, a stress hormone. As a result, the
In the present invention, the compound is characterized by inhibiting the expression of Matrix metalloproteinases (MMPs) and restoring collagen production.
According to the experimental example of the present invention, the compound of the present invention can prevent or improve skin aging by effectively inhibiting the expression of MMPs.
In the present invention, the skin aging prevention cosmetic composition is preferably characterized in that the skin aging is photoaging.
The term " photoaging " of the present invention is a phenomenon caused by external environmental factors. Ultraviolet rays are the most typical factor. Ultraviolet light leads to activation of proteolytic enzymes, chain breakage of substrate proteins and damage of biocomponents such as abnormal cross-linking, and the repetition of such mechanisms causes apparent skin aging. That is, unlike the endogenous aging caused by the genetic elements regardless of the external environment, the present invention provides a cosmetic composition for preventing or improving skin aging caused by photoaging caused by ultraviolet rays, .
In the present invention, the composition may be used as a skin lotion, a skin softener, a skin toner, an astringent, a lotion, a milk lotion, a moisturizing lotion, a nutrition lotion, a massage cream, a nutritional cream, a moisturizer cream, a hand cream, A cosmetic lotion, an essence, a pack, a soap, a cleansing foam, a cleansing lotion, a cleansing cream, a body lotion and a body cleanser.
According to another aspect of the present invention, there is provided a composition for preventing or ameliorating skin aging comprising, as an active ingredient, a compound (trimethyl- [2- (2-oxo-5H-furan- 3- yl) ethyl] BLAHcarbaldehyde The present invention provides a composition for external application for skin comprising:
[Chemical Formula 1]
The composition for external skin application for preventing or improving skin aging containing the above-mentioned compound as an active ingredient is as described in the cosmetic composition for preventing or improving skin aging which contains the compound as an active ingredient.
In the present invention, the composition for external application for skin may be prepared in any formulations conventionally produced in the art, and examples thereof include emulsion, cream, lotion, pack, foundation, lotion, essence and hair cosmetic . Specifically, the present invention relates to a skin lotion, a skin softener, a skin toner, an astringent, a lotion, a milk lotion, a moisturizing lotion, a nutrition lotion, a massage cream, a nutritive cream, a moisturizing cream, a hand cream, a foundation, Foams, cleansing lotions, cleansing creams, body lotions and body cleansers.
The composition of the present invention may contain other adjuvants in addition to the carrier, for example, preservatives, antioxidants, stabilizers, solubilizers, vitamins, pigments and perfumes.
In the present invention, each of the above compositions may be formulated in the form of powders, granules, tablets, capsules, suspensions, emulsions, external preparations such as syrups and aerosols, and sterilized injection solutions according to a conventional method. Creams, gels, patches, sprays, ointments, alerts, lotions, liniments, pastes or cataplasms.
Examples of carriers, excipients and diluents that can be contained in the composition include lactose, dextrose, sucrose, oligosaccharide, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, Cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil. In the case of formulation, a diluent or excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, or a surfactant is usually used. Solid formulations for oral administration include tablets, pills, powders, granules, capsules and the like, which may contain at least one excipient such as starch, calcium carbonate, Sucrose, lactose, gelatin and the like. In addition to simple excipients, lubricants such as magnesium stearate talc are also used. Examples of the liquid preparation for oral use include suspensions, solutions, emulsions, and syrups. In addition to water and liquid paraffin, simple diluents commonly used, various excipients such as wetting agents, sweeteners, fragrances, preservatives and the like may be included . Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories. Examples of the suspending agent include propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like. Examples of the suppository base include witepsol, macrogol, tween 61, cacao butter, laurin, glycerogelatin and the like.
As described above, the compound of the present invention (trimethyl- [2- (2-oxo-5H-furan-3-yl) ethyl] BLAHcarbaldehyde) inhibits the expression of 11? -HSD1 and MMPs overexpressed by ultraviolet light Thereby preventing or preventing or improving skin aging.
Figure 1 is a three-dimensional structure of ll [beta] -HSDl.
Figure 2 shows two active framework maps that bind to ll [beta] -HSDl.
Fig. 3 shows the results of Experimental Example 1 in which the effect on the expression of ll [beta] -HSD1 in treating human fibroblasts with the compound of
4 shows the results of Experimental Example 1 in which the effect on the expression of cortisol in human fibroblasts treated with the compound of
FIG. 5 shows the results of Experimental Example 2 in which the effect on the expression of MMP-1 messenger RNA in human fibroblasts treated with the compound of
Fig. 6 shows the results of Experimental Example 2 in which the effect on the expression of MMP-3 messenger RNA in human fibroblasts treated with the compound of
FIG. 7 shows the results of Experimental Example 2 in which the effect on the expression of MMP-1 protein in human fibroblasts treated with the compound of
Hereinafter, the present invention will be described in more detail with reference to Examples. These embodiments are only for illustrating the present invention, and thus the scope of the present invention is not construed as being limited by these embodiments.
Example 1: extraction of the compound of formula (1)
The hypothetical new drug search for 11β-HSD1 (FIG. 1) determined the active site in which the material binds in the three-dimensional structure of the known 11β-HSD1 and 5 Å around it to determine the active skeleton map for this region One map was defined to contain 5-6 elements, and finally two active skeleton maps were completed (Fig. 2). A compound library was searched using this active skeleton map, and a substance which is considered to be a candidate for 11β-HSD1 inhibitory activity was selected. The compound library has been able to search for multiple conformations of three-dimensional structures to include all chemically possible conformers. In the case of the compound library, a focused library containing about 300 compounds was constructed in consideration of the characteristics of the cosmetic material in order to meet the object of the present invention.
(Trimethyl- [2- (2-oxo-5H-furan-3-yl) ethyl] BLAHcarbaldehyde, which is predicted to ultimately inhibit 11? -HSD1 activity through the above- ) Were selected.
Experimental Example 1: Stress Inhibitory Effect of Compound of
After one inoculation of human fibroblasts in order to verify the messenger RNA expression inhibitory effects of 11β-HSD1 leading to UVB of compounds of formula (I) in fibroblasts at a density of 4
In order to confirm the UVB-induced cortisol inhibitory effect of the compound of formula (1), human fibroblasts were inoculated in a 6-well cell culture dish at a density of 4 × 10 5 , and cultured in a 5% CO 2 incubator at 37 ° C. for 24 hours Lt; / RTI > UVB was irradiated at 15 mJ, followed by addition of the compound of formula (1), followed by further incubation for 24 hours, and the medium was recovered. The recovered medium was centrifuged at 12,000 rpm for 10 minutes to remove impurities and assayed using a cortisol ELISA kit (R & D system, USA).
As a result, as shown in Figs. 3 and 4, the expression of 11? -HSD1 and cortisol was inhibited depending on the concentration of the compound of
Experimental Example 2: Collagenase inhibitory activity of the compound of
Human fibroblasts were cultured in the same manner as described in Experimental Example 1 to confirm the inhibitory effect of UVB-induced MMP-1 of the compound of
In order to confirm the UVB-induced inhibition of MMP-1 protein expression of the compound of formula (1) in human fibroblasts, human fibroblasts were inoculated in a 6-well cell culture dish at a density of 4 × 10 5 , % CO 2 incubator for 24 hours. UVB was irradiated at 15 mJ, followed by addition of the compound of formula (1), followed by further incubation for 24 hours, and the medium was recovered. The recovered medium was centrifuged at 12,000 rpm for 10 minutes to remove impurities and assayed using an enzyme-linked immunosorbent assay (MMP-1 ELISA) kit (ID Labs, Canada).
As a result, as shown in Figs. 5 to 7, the inhibitory effect of MMPs on the compound of
Formulation Example 1: Preparation of Toner
The toner preparation containing Example 1 was prepared in a conventional manner according to the compositional components and composition ratios shown in Table 3 below.
Formulation Example 2: Preparation of lotion agent
Lotion preparations containing Example 1 were prepared in a conventional manner according to the compositional components and composition ratios shown in Table 4 below.
Formulation Example 3: Preparation of cream agent
The creams containing Example 1 were prepared in a customary manner according to the compositional components and composition ratios shown in Table 5 below.
Claims (7)
[Chemical Formula 1]
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Application Number | Priority Date | Filing Date | Title |
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KR1020150157476A KR101715590B1 (en) | 2015-11-10 | 2015-11-10 | 11- 1 Anti-aging cosmetic composition or skin external composition comprising compound of 11-hydroxysteroid dehydrogenase type 1 inhibitor |
PCT/KR2016/010533 WO2017082534A1 (en) | 2015-11-10 | 2016-09-21 | SKIN ANTI-AGING COSMETIC COMPOSITION OR EXTERNAL USE SKIN PREPARATION COMPOSITION, BOTH OF WHICH CONTAIN COMPOUND INHIBITING ACTIVITY OF 11β-HYDROXYSTEROID DEHYDROGENASE TYPE 1 |
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KR1020150157476A KR101715590B1 (en) | 2015-11-10 | 2015-11-10 | 11- 1 Anti-aging cosmetic composition or skin external composition comprising compound of 11-hydroxysteroid dehydrogenase type 1 inhibitor |
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WO (1) | WO2017082534A1 (en) |
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- 2016-09-21 WO PCT/KR2016/010533 patent/WO2017082534A1/en active Application Filing
Non-Patent Citations (3)
Title |
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C.ALAGESABOOPATHI, Andrographis SPP.: A Source of Bitter Compounds For Medicinal Use, Ancient Science of Life Vol. No XIX (3&4) January, February, March, April 2000, pages 164-168 |
C.ALAGESABOOPATHI, Andrographis SPP.: A Source of Bitter Compounds For Medicinal Use, Ancient Science of Life Vol. No XIX (3&4) January, February, March, April 2000, pages 164-168 * |
Jiyoung You et al, The Antiaging Properties of Andrographis paniculata by Activation Epidermal Cell Stemness, Molecules 2015, 20, pages 17557-17569 * |
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