CN112367968B - Cosmetic composition for removing or adsorbing fine dust comprising peptide complex as active ingredient - Google Patents
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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
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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Abstract
The present invention relates to a cosmetic composition for removing or adsorbing fine dust, which comprises a fatty acid-amino acid complex or a fatty acid oligopeptide complex as an active ingredient, and which is free from skin toxicity and excellent in fine dust removal effect, and thus can be usefully used as a composition for preventing or treating various diseases caused by fine dust.
Description
Technical Field
The present invention relates to a cosmetic composition for removing or adsorbing fine dust, which comprises a peptide complex as an active ingredient.
Background
The dust particles (particulate matter, PM) are Nitrate (NO) 3 - ) Ammonium (NH) 4 + ) Sulfate (SO) 4 2- ) The atmospheric pollutants such as plasma components, carbon compounds and metal compounds are particulate matters having a diameter of 10 μm or less and drifting in the atmosphere for a long time. If the particle diameter of the fine dust is less than 10 μm, it is denoted as PM10, and if the particle diameter is less than 2.5 μm, it is denoted as PM2.5, and it is called ultra fine dust or ultra fine dust. Most of the ultra-fine dust is generated by human factors such as dust drifting in an automobile exhaust gas, an industrial process, a road, and the like.
When exposed to fine dust for a long period of time, immunity is drastically reduced, and thus respiratory diseases such as cold, asthma, and tracheitis may be caused, and various diseases such as cardiovascular diseases, skin diseases, and eye diseases may be caused. Dust particles are reported to worsen respiratory diseases such as asthma and to cause a decrease in lung function, and in particular, ultra dust particles are extremely fine so as not to be filtered through nasal mucosa but to directly penetrate into alveoli, thereby increasing the prevalence and early mortality of pulmonary diseases. Also, the fine dust can invade not only into the body through the nose and mouth but also into the body through the skin. Since the fine dust is about 20 times larger than the size of the hair pores, it is difficult to remove the fine dust by easily penetrating into the pores, and there is a possibility that the skin immunity is lowered due to the increase of inflammatory cytokines and in-vivo active oxygen caused by the absorbed fine dust, thereby further accelerating skin aging phenomena such as acne, wrinkle formation, skin dryness and pigmentation. Specifically, the dust can trigger inflammatory reactions to cause damage to skin barriers, thereby deteriorating atopic dermatitis, generating active oxygen (reactive oxygen species) in mitochondria to reduce collagen synthesis, and increasing collagen degradation to trigger skin aging. Further, polynuclear aromatic hydrocarbons (polynuclear aromatic hydrocarbon, PAH) attached to fine dust proliferate melanocytes to increase facial pigmentation spots, and particularly, asians are darker than white, so that there is a high possibility that pigmentation spots are increased due to fine dust, and dermatitis, burning, and itching of humans having sensitive skin can be increased. In the case of prolonged exposure to fine dust, the skin will lose its function of protecting the body from pressure factors due to irrecoverable skin damage, and serious diseases such as skin cancer may also be caused.
Recently, as the danger and hazard of fine dust become serious, attention for development of products for preventing fine dust is gradually increased, sales of cosmetics, health functional foods, air cleaners, masks, etc. related to fine dust are rapidly increased, and particularly development of cosmetic compositions capable of removing fine dust or remarkably preventing adsorption of fine dust is continuously underway. Representative materials among highly functional biological materials that meet this trend are peptide materials. The peptide has physiological activity in vivo or in skin according to the arrangement and structure of amino acid sequences in the peptide, and thus can be applied to the development of biological materials in various ways, and can also be applied to the development of quasi-therapeutic products for improving wrinkles, whitening, allergic skin and improving various skin diseases, and thus has excellent industrial value as cosmetic and pharmaceutical materials.
On the other hand, "cosmetic composition for adsorbing and removing fine dust comprising coral tree and bangla rubber tree resin extracts as an active ingredient" is disclosed in korean patent No. 1723941, and "cosmetic composition for removing heavy metals or fine dust comprising chrysanthemum flower extracts as an active ingredient" is disclosed in korean patent No. 1850313, but the cosmetic composition for removing or adsorbing fine dust comprising peptide complexes as an active ingredient of the present invention is not disclosed.
Disclosure of Invention
Technical problem
The present invention has been made in view of the above-described circumstances, and has been accomplished by the present inventors, based on the finding that the above-described complex can reduce cytotoxicity caused by fine dust and remove fine dust by aggregating with the fine dust, by developing a fatty acid-amino acid complex and a fatty acid oligopeptide complex by binding a saturated fatty acid or an unsaturated fatty acid to the N-terminal, C-terminal or side chain of an amino acid or oligopeptide.
Solution to the problem
In order to solve the above problems, the present invention provides a cosmetic composition for removing or adsorbing fine dust, comprising a complex of amino acids or oligopeptides with fatty acids bound at the N-terminal, C-terminal or side chain thereof as an active ingredient.
ADVANTAGEOUS EFFECTS OF INVENTION
The peptide complex of the present invention has excellent effects of protecting cells from fine dust and removing fine dust by agglomerating or binding with fine dust, and thus, the composition comprising the peptide complex of the present invention can be used as a cosmetic or pharmaceutical composition for preventing and treating various diseases caused by exposure to fine dust.
Drawings
Fig. 1 is a schematic diagram showing a method of binding fatty acids at the N-terminus (a), C-terminus (B) or side chain (C) of an oligopeptide.
Fig. 2 to 4 are results of analyzing peptide complexes purified by high performance liquid chromatography (High Performance Liquid Chromatography, HPLC) (table 5-division 9).
FIGS. 5 to 15 show the results of confirming the cell viability after simultaneously treating keratinocytes with ultra-fine dust (diesel exhaust particles: fine dust having a diameter of 2.5 μm or less, PM 2.5) and the peptide complex of the present invention. N.c. (negative control group): 0.2% dimethyl sulfoxide (DMSO, dimethyl sulfoxide)/darbert k modified eagle medium (DMEM, dulbecco's Modified Eagle Medium), p.c. (positive control group): 10% dimethyl sulfoxide/Dalbek's modified eagle's medium treatment.
FIG. 16 is a graph showing cytotoxicity of a solution containing ultrafine dust in a human lung cancer epithelial cell line (A549) treated at a concentration.
FIG. 17 is a graph showing the results of confirming cell viability after A549 cells were simultaneously treated with ultra-fine dust and after oligopeptide-bound complex of saturated fatty acids. The information of the chart X-axis sample is the same as in table 10 below.
FIG. 18 is a photograph of SDS-PAGE gel using silver staining (silver staining) to analyze the agglutination effect of peptide complexes and ultra dust.
Fig. 19 is a graph showing particle removal efficiency of a general mask (HIP's) and a fine dust mask (KF 84) sold in the market using a dust collection (particle removal) efficiency evaluation system.
Fig. 20 and 21 are graphs showing the ultra-fine dust particle removal efficiency of a general mask not sprayed with any substance, a general mask sprayed with purified water, and a general mask sprayed with 250ppm of fatty acid oligopeptide complex (diluted with distilled water) using the dust collection (particle removal) efficiency evaluation system.
Detailed Description
To achieve the object of the present invention, the present invention provides a cosmetic composition for removing or adsorbing fine dust, which comprises a complex of amino acids or oligopeptides with fatty acids bonded at the N-terminal, C-terminal or side chain thereof as an active ingredient.
In the present invention, the term "fine dust" refers to dust having a diameter of 10 μm or less, and the term "ultra fine dust" refers to dust having a diameter of 2.5 μm or less, and may include yellow sand, car exhaust gas, factory soot, combustion gas in daily life, heavy metals, but is not limited thereto.
In the present invention, the term "dust adsorption" may be removal by adsorbing fine substances remaining in pores or the like in the skin. The adsorption force to the fine dust is improved by the treatment of the cosmetic composition based on the fatty acid, the amino acid complex or the fatty acid and oligopeptide complex, thereby the skin is low stimulated, and the skin inflammation, skin allergy and the like which may occur when the fine dust remains can be solved.
In the present invention, the terms "N-terminal and C-terminal" refer to amino groups (-NH) in the amino acid sequence of a peptide 2 ) The term "side chain" refers to a carbon chain branching from a straight chain carbon atom, wherein the carbon atoms are regularly linked, or an aliphatic carbon chain linked on the ring of a cyclic compound, and having a carboxyl group (-COOH) on the other side.
In the cosmetic composition for removing or adsorbing fine dust according to the present invention, the above amino acid may be selected from the group consisting of Alanine (Alanine, a), cysteine (Cysteine, C), aspartic acid (D), glutamic acid (Glutamic acid, E), phenylalanine (phenylllanine, F), glycine (Glycine, G), histidine (Histidine, H), isoleucine (Isoleucine, I), lysine (Lysine, K), leucine (Leucine, L), methionine (Methionine, M), asparagine (aspargine, N), pyrrolysine (O), proline (P), glutamine (Q), arginine (R), serine (S), threonine (T), selenocysteine (U), valine (V), tryptophan (W), and Tyrosine (Y), preferably, but not limited thereto, glycine (G), glutamic acid (E), or Lysine (K). The above amino acids may include, but are not limited to, D-form amino acids and L-form amino acids.
Also, in the cosmetic composition for removing or adsorbing fine dust according to the present invention, the oligopeptide is a peptide formed of 2 or more amino acids, and preferably may be one selected from the group consisting of AAPV (sequence 1), AAP (sequence 2), AA (sequence 3), GHK (sequence 4), GH (sequence 5), KTTKS (sequence 6), KTTK (sequence 7), KTT (sequence 8), KT (sequence 9), EEMQRR (sequence 10), EEMQR (sequence 11), EEMQ (sequence 12), EEM (sequence 13), EE (sequence 14), KKKKKKKKK (sequence 15), KKKKK (sequence 16), KKK (sequence 17), KK (sequence 18), GPO (sequence 19), GP (sequence 20), GQPR (sequence 21), GQP (sequence 22), GQ (sequence 23), TTKS (sequence 24), TKS (sequence 25), TK (sequence 26), RRRRRRRRR (sequence 27), RRR (sequence 28), RRR (sequence 29) and LLWIALRKK (sequence 30), but is not limited thereto. The amino acid of the oligopeptide may be D-form amino acid or L-form amino acid, and the amino acid PO of the sequence 19 may be O-hydroxyproline (O-hydroxyproline), but is not limited thereto.
In the cosmetic composition for removing or adsorbing fine dust according to the present invention, the above fatty acid may be a saturated fatty acid or an unsaturated fatty acid, but is not limited thereto.
The saturated fatty acid of the present invention may be selected from Caproic acid (Caproic acid, C6: 0), octanoic acid (Capric acid, C8: 0), pelargonic acid (Pelargonic acid, C9: 0), decanoic acid (Capric acid, C10:0), undecanoic acid (Undecyclic acid, C11:0), lauric acid (Lauric acid, C12:0), myristic acid (Myricic acid, C14:0), pentadecanoic acid (Pentadecylic acid, C15:0), palmitic acid (Palmic acid, C16:0), margaric acid (Margaric acid, C17:0), stearic acid (Stearic acid, C18:0), nonadecanoic acid (Nonadic acid, C19:0), arachic acid (Arachidic acid, C20:0), heneicosanic acid (Heneicosylic acid, C21:0), behenic acid (Behenic acid, C22:0), tricosaic acid (Tricosyl acid, C23:0), tetracosanoic acid (Lignoic acid, C24:0), pentacosanoic acid (Pentacosylic acid, C25:0), cerotic acid (Cerotic acid, C26:0), heptacosoic acid (C26:0), montanic acid (C34:0), montanic acid (Gecosyl acid, pycyrniobic acid, pc 0), icosanic acid (Cocosyl acid, C35:0), icosanic acid (Cocosyl acid, C22:0), tricosanoic acid (Cocosyl acid, C35:0), icosanic acid (Cocosyl acid, C35:0, pc 35:0), icosanic acid (Cocosyl acid, pc 0, pc 35:0) and the group of the acid (Cocosyl acid, pxacosyl acid, pc 0, pcosyl 0, pc 0, pcosyl) and the acid (Pcosyl) 0, pcosyl 0) and acid (Pcosyl) and 3P 0), preferably, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, behenic acid or lignoceric acid may be used, but is not limited thereto.
The unsaturated fatty acid may be selected from Palmitoleic acid (C16: 1), oleic acid (Oleic acid, C18: 1), elaidic acid (Elaidic acid, C18: 1), petroselinic acid (Petroselinic acid, C18:1), iso-Oleic acid (Vaccenic acid, C18:1), tricosanoic acid (Gondoic acid, C20:1), erucic acid (Ericic acid, C22:1), nervonic acid (Nervonic acid, C24:1), linoleic acid (Linolenic acid, C18:2), linolenic acid (cis-Linolenic acid, C18:3), punicic acid (Punicic acid, C18:3), eleostearic acid (Eleostetic acid, C18:3), stearidonic acid (stearidonic acid, C18:4), arachidonic acid (Arachidonic acid, C20:4), eicosapentaenoic acid (Eicosapentaenoic acid, C20:5), menhadic acid (Docosapentaenoic acid, C22:5), adrenonic acid (C22:4), docosahexaenoic acid (Docosahexaenoic acid:6, ricinoleic acid (Ric acid, C18:3), oleic acid, linolenic acid, palmitoleic acid, linolenic acid, oleic acid, linolenic acid, and the group of these acids being preferred examples, and the preferred examples.
The cosmetic composition for removing or adsorbing fine dust of the present invention is a complex of fatty acid and amino acid or a complex of fatty acid and oligopeptide in which fatty acid is bound to N-terminal, C-terminal or side chain of amino acid or oligopeptide, and the complex of fatty acid and amino acid may be formed by binding oleic acid as unsaturated fatty acid to glycine (G), glutamic acid (E) or lysine (K), but is not limited thereto, the complex of the fatty acid and the oligopeptide may be formed by bonding one N-terminal, C-terminal or side chain of the oligopeptide formed from the amino acid sequences of sequence 1, sequence 4, sequence 6, sequence 7, sequence 8, sequence 10, sequence 11, sequence 15, sequence 16, sequence 17, sequence 19, sequence 21, sequence 27, sequence 28, sequence 29 and sequence 30 to one saturated fatty acid selected from the group consisting of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, behenic acid and lignoceric acid or one or more unsaturated fatty acid selected from the group consisting of oleic acid, linoleic acid, palmitoleic acid, elaidic acid, petroselinic acid, isooleic acid, behenic acid, sinapic acid, nervonic acid, linolenic acid, punicic acid, eleostearic acid, menhadic acid and ricinoleic acid, but is not limited thereto.
Preferably, in the cosmetic composition for removing or adsorbing fine dust according to the present invention, the complex of the side chain-bound fatty acid of the oligopeptide may be, but not limited to, a ninth Lysine (K) in the oligopeptide (LLWIALRKK, L-form amino acid; llwialrkk, D-form amino acid) amino acid sequence of the sequence 30, a fourth Lysine in the oligopeptide amino acid sequences of the sequence 6 (KTTKS) and the sequence 7 (kttkk), and a fifth Lysine-bound fatty acid in the oligopeptide amino acid sequence of the sequence 16 (KKKKK).
Also, the peptide complex of the present invention may be one in which an amino group (-NH) is bonded to the N-terminus or the C-terminus 2 ) Or carboxyl (-COOH) group, specifically, NH 2 -amino acid-fatty acid-COOH, NH 2 -oligopeptide-fatty acid-COOH, COOH-amino acid-fatty acid-NH 2 COOH-oligopeptide-fatty acid-NH 2 、NH 2 -fatty acid-amino acid-COOH, NH 2 -fatty acid oligomer peptide-COOH, COOH-fatty acid-amino acid-NH 2 COOH-fatty acid oligomer peptide-NH 2 Morphology, but is not limited thereto.
The complex of the amino acid or oligopeptide and the saturated fatty acid or unsaturated fatty acid combined at the N-terminal, the C-terminal or the side chain has no toxicity to normal skin, can reduce cytotoxicity caused by tiny dust, and has the effect of removing ultra-tiny dust particles (dust trapping).
Specifically, the present invention decanoic acid and sequence 6, sequence 7, sequence 15, sequence 16, sequence 27, sequence 28 or sequence 29 oligopeptide combined complexes, palmitic acid and sequence 4, sequence 6, sequence 7, sequence 15, sequence 16, sequence 27, sequence 28, sequence 29 or sequence 30 oligopeptide combined complexes, oleic acid and sequence 1, sequence 4, sequence 6, sequence 7, sequence 8, sequence 11, sequence 15, sequence 16, sequence 21, sequence 27, sequence 28 or sequence 30 oligopeptide combined complexes, linoleic acid and sequence 10, sequence 16, sequence 27, sequence 28 or sequence 30 oligopeptide combined complexes, octanoic acid and sequence 15, 16, 27 or 28, a complex of lauric acid with an oligopeptide of sequence 4, sequence 15, sequence 16, sequence 17, sequence 27 or sequence 28, a complex of myristic acid with an oligopeptide of sequence 10, sequence 15, sequence 16, sequence 27 or sequence 28, a complex of heptadecanoic acid with an oligopeptide of sequence 15, sequence 16, sequence 27, sequence 28 or sequence 30, a complex of stearic acid with an oligopeptide of sequence 15, sequence 16, sequence 27, sequence 28 or sequence 30, a complex of behenic acid with an oligopeptide of sequence 15, sequence 16, sequence 19, sequence 27, sequence 28 or sequence 30, a complex of behenic acid with an oligopeptide of sequence 15, sequence 16, sequence 27, sequence 28 or sequence 30, a complex of lignoceric acid with an oligopeptide of sequence 1, sequence 15, sequence 21 or sequence 27, a complex of elaidic acid with an oligopeptide of sequence 6, sequence 15, sequence 16, sequence 19 or sequence 27, a complex of elaidic acid with an oligopeptide of sequence 15, sequence 16, sequence 19 or sequence 27, a complex of petroceric acid with a sequence 6, sequence 16, sequence 30 The reduced amount of binding of the binding agent to the oligopeptide of sequence 27 or sequence 30, the binding agent to the oligopeptide of sequence 15, sequence 27 or sequence 28, the binding agent to the oligopeptide of sequence 6, sequence 15, sequence 27, sequence 28 or sequence 30, the binding agent to the oligopeptide of sequence 4, sequence 6, sequence 15, sequence 16, sequence 27, sequence 28 or sequence 30, the binding agent to the oligopeptide of linolenic acid, the binding agent to the oligopeptide of sequence 15, sequence 16, sequence 27, sequence 28 or sequence 30, the binding agent to the oligopeptide of sequence 6, 15, 16 or sequence 27, the binding agent to the oligopeptide of sequence 15, sequence 27 or sequence 30, the binding agent to the oligopeptide of oleic acid, the binding agent to the oligopeptide of sequence 1, sequence 15, sequence 16 or sequence 29, or the binding agent to the oligopeptide of oleic acid is reduced, and the increased (ultra-high dust-binding agent) can be achieved.
Preferably, the cosmetic composition for removing or adsorbing fine dust of the present invention is one or more dosage forms selected from the group consisting of solutions, suspensions, emulsions, pastes, gels, creams, skin-care lotions, powders, soaps, surfactant-containing cleansers, oils, foundation liquids, wax foundation liquids and sprays, more preferably, may be one dosage form selected from the group consisting of skin ointments, creams, softening emulsions, nourishing emulsions, facial masks, essences, hair tonics, shampoos, hair conditioners, hair care essences, hair treatment ointments, gels, skin emulsions, skin softeners, skin lotions, astringents, skin lotions, moisturizing emulsions, nourishing emulsions, massage creams, nutrition creams, eye creams, foundation creams, nutrition, sun-protection creams, soaps, cleansing foams, cleansing emulsions, cleansing essences, skin lotions and cleansing emulsions, but not limited thereto. The composition of these individual dosage forms may contain appropriate various bases and additives for formulation of the dosage forms thereof, the types and amounts of which may be selected by one of ordinary skill in the art to which the present invention pertains.
In the case where the dosage form of the present invention is a paste, cream or gel, as the carrier component, animal fiber, vegetable fiber, wax, paraffin, starch, tragacanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, zinc acid or the like can be used.
In the case where the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, polyamide powder, and particularly in the case of a spray, a propellant such as chlorofluorocarbon, propane/butane dimethyl ether may be additionally used as a carrier component.
In the case where the dosage form of the present invention is a solution or emulsion, as the carrier component, a solvent, an emulsifier, for example, water, ethanol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butanediol oil, glycerin aliphatic ester, polyethylene glycol, a fatty acid ester of sorbitan are used.
In the case where the dosage form of the present invention is a suspension, as the carrier component, liquid diluents such as water, ethanol and propylene glycol, suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar or tragacanth, and the like can be used.
In the case where the formulation of the present invention is a surfactant-containing detergent, as the carrier component, fatty alcohol sulfate, fatty alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyl taurate, sarcosinate, fatty acid amide ether sulfate, alkyl amino betaine, fatty alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, linolenine derivative, ethoxylated glycerin fatty acid ester can be used.
The present invention will be described in detail with reference to examples. The following examples are merely illustrative examples of the present invention, and the content of the present invention is not limited to the following examples.
Example 1: preparation of peptide complexes
Amino acid starting materials for complex synthesis were purchased from GLS (GL biochemi, shanghai), fatty acids from TCI (TCI chemicals, india) and Sigma (Sigma Aldrich, U.S. Pat. No. (Table 1)), dimethylformamide (DMF), diisopropylethylamine (DIEA), dichloromethane (DCM), piperidine (piperidine) from (Daejungchem, korea).
TABLE 1
Fatty acid purchase information
1-1 resin expansion (sweilling)
The synthesis of peptides having carboxyl groups (-COOH) at the end of the complex using a solid phase (solid-phase) synthesis reactor equipped with a filtration membrane was carried out using 2-chlorotrichloroethylene resin 2-Chlorotritylchloride resin; bead Tech, korea) bound with peptide bond (-CONH) at the end of the complex 2 ) The terminal peptide was prepared using a starting resin for polypeptide synthesis (Rink amide resin; GLS, china). The resin was allowed to swell for 20 minutes using dichloromethane and dimethylformamide to prepare for synthesis.
1-2 amino acid loading (loading)
The synthesis using trichlorochloroethylene resin involves a first loading of amino acids into the resin. The solvent was removed by filtration through a membrane under reduced pressure. After 3 to 5 equivalents of amino acid are completely dissolved in dimethylformamide, the resulting solution is added to a trichlorochloroethylene resin, and diisopropylethylamine in consideration of density is added in an amount corresponding to 3 to 5 equivalents of the trichlorochloroethylene resin. Thereafter, the reaction was carried out for 5 hours or more at a temperature of 24℃to 32℃using a reactor.
1-3 deprotection of resin fluorenylmethoxycarbonyl chloride
The synthetic process using the above-mentioned chlorotrifluoroethylene resin or RINK amide resin includes a deprotection reaction process in fluorenylmethoxycarbonyl chloride (Fmoc, fluorenylmethyloxycarbonyl chloride). In the deprotection of the fluorenylmethoxycarbonyl chloride resin, the solvent was removed through a filtration membrane under reduced pressure, and after washing for 5 minutes by adding 20% (v/v) piperidine in dimethylformamide, washing was performed again for 10 minutes. The reaction mixture was filtered and removed under reduced pressure, and washed with dichloromethane or Dimethylformamide (DMF) for 5 minutes or more.
1-4 fatty acid-amino acid Complex and fatty acid oligopeptide Complex Synthesis
After 3 to 5 equivalents of amino acid are completely dissolved in dimethylformamide, the solvent-removed RINK amide resin is put in. As a coupling agent (coupling reagent), 2M hydroxybenzotriazole/diisopropylcarbodiimide (HOBt/DIC) was added in an amount in accordance with the amino acid equivalent and RINK amide resin. Then, the reaction is carried out for more than 5 hours at the temperature of 24-32 ℃. When the reaction was completed, after the solvent was removed by a filtration membrane under reduced pressure, it was washed 6 times with clean dimethylformamide for 5 minutes. After the completion of the washing, the amino acids were coupled in sequence by the same methods as the above amino acid binding method, respectively. Then, 3 equivalents of 2M hydroxybenzotriazole/diisopropylcarbodiimide were added to the resin in a peptide-synthesized state in an amount corresponding to the amino acid equivalent and the resin amount. Then, the reaction is carried out for more than 5 hours at the temperature of 24-32 ℃ by using a reactor.
1-5 separation (Cleavage)
After the reaction was completed, the solvent was removed through the filtration membrane under reduced pressure, and then washed 2 times by clean dimethylformamide for 2 minutes and 2 times by dichloromethane for two minutes, and then the solvent was removed through the filtration membrane under reduced pressure. With 70% (v/v) trichloroacetic acid/29% (v/v) dichloromethane/1% (v/v) H 2 O solution, the dried peptide complex resin was subjected to 4 hours of separation.
1-6 recrystallization (Crystal)
For the solvent that completed the isolation, diethyl ether (ethyl ether) was used to recrystallize and extract the crude product. Specific synthesis procedures are shown in table 2 below.
TABLE 2
The peptide complex Synthesis procedure of the present invention
* Resin substitution rate: -Rink amide MBHA resin (substitution rate: 0.54 mmole/g) -Chlorotrityl chloride resin (substitution rate: 1.25 mmole/g) amino acids: 3-10 eq coupling agent: diisopropylcarbodiimide, hydroxybenzotriazole, dimethylformamide coupling time: 6 hours coupleJoint temperature: 24-32 ℃ separation: 70% trichloroacetic acid/29% dichloromethane/1%H 2 O,4 hours, 5% trichloroacetic acid/95% dichloromethane 5 min extraction: diethyl ether
1-7 Synthesis of the product
Novel complexes were developed by solid phase peptide synthesis (Solid Phase Peptide Synthesis, SPPS) in which fatty acids having 6 to 24 carbon atoms (Table 3) were bound to glycine (G), glutamic acid (E), lysine (K) or oligopeptides of sequences 1 to 30 as amino acids. Specifically, an amino group (NH) present at the N-terminus of an amino acid or oligopeptide may be bonded 2 ) And carboxyl group (COOH) of fatty acid (FIG. 1A), glycol is applied as a crosslinking agent (linker) to bind carboxyl group of fatty acid to carboxyl group present at C-terminal of amino acid or oligopeptide (FIG. 1B), and carboxyl group of fatty acid can be bound to side chain of lysine (K) present in oligopeptide (FIG. 1C).
Finally, the complex of the synthesized amino acid or oligopeptide and fatty acid is presented in tables 4 and 10 below, in Table 10, uppercase for L-amino acid and lowercase for D-amino acid. The complex in which fatty acid is bonded to the N-terminus of amino acid or oligopeptide is described in the order of fatty acid-peptide, the complex in which fatty acid is bonded to the C-terminus of amino acid or oligopeptide is described in the order of peptide-fatty acid, the complex in which fatty acid is bonded to the side chain of oligopeptide is indicated by underline (_) after the amino acid to which the side chain of fatty acid is bonded is indicated by brackets, and the complex in which fatty acid is bonded to the side chain is indicated by brackets.
TABLE 3 Table 3
Fatty acid species
TABLE 4 Table 4
Synthetic fatty acid amino acid complexes and fatty acid oligopeptide complex species
TABLE 5
Synthetic fatty acid oligopeptide complex species
TABLE 6
Synthetic fatty acid oligopeptide complex species
TABLE 7
Synthetic fatty acid oligopeptide complex species
TABLE 8
Synthetic fatty acid oligopeptide complex species
TABLE 9
Synthetic fatty acid oligopeptide complex species
Table 10
Synthetic fatty acid oligopeptide complex species
Example 2: complex purification
The crude complex product synthesized in example 1 above was dissolved in distilled water to which 10% (v/v) acetonitrile (acetonitrile) was added, and then purified by High Performance Liquid Chromatography (HPLC) under gradient (gradient) conditions (fig. 2 to 4), and freeze-dried to obtain the objective complex. The conditions of high performance liquid chromatography and the conditions of separation gradient are shown in tables 11 and 12 below. Further, the molecular weight of the purified complex crude product was measured by MALDI-TOF-MASS, the molecular weight measurement method is shown in Table 13, and the molecular weight measurement results are shown in tables 14 to 23.
TABLE 11
High performance liquid chromatography conditions
Table 12
Gradient conditions
| Time (minutes) | H 2 0(％) | Acetonitrile (acetonitrile) (%) |
| 0～12 | 89→77 | 11→23 |
| 12～13 | 77→5 | 23→95 |
| 13～18 | 5→5 | 95→95 |
| 18～19 | 5→89 | 95→11 |
| 19～27 | 89→99 | 11→11 |
TABLE 13
Molecular weight measuring method
TABLE 14
Molecular weight confirmation
K side chain: the ninth K amino acid (underlined) of the oligopeptide (LLWIALRKK ) in sequence 30 binds to a fatty acid.
TABLE 15
Molecular weight confirmation
Table 16
Molecular weight confirmation
TABLE 17
Molecular weight confirmation
TABLE 18
Molecular weight confirmation
TABLE 19
Molecular weight confirmation
Table 20
Molecular weight confirmation
Table 21
Molecular weight confirmation
Table 22
Molecular weight confirmation
Table 23
Molecular weight confirmation
Example 3: analysis of cytotoxicity of ultra dust in human keratinocytes (HaCat)
In order to confirm cytotoxicity of the fatty acid-amino acid complex and the fatty acid oligomer peptide (sequences 1 to 30) complex, the cell number reached 2×10 4 Means of individual/ml the cells were cultured for 16 to 20 hours after dilution in darburg's modified eagle's medium (10% fetal bovine serum) and 100 μl inoculation into 6-well dishes until the cells were attached to the plate surface. The medium was removed and each complex material was diluted to a 10 μm concentration by Darburg's Modified Eagle's Medium (DMEM) and treated in cells at 100 μl and then at 37 ℃ with 5% co 2 After culturing in the incubator for 24 hours, the medium was removed again. The solution of thiazole blue (5 mg/ml in Phosphate Buffer (PBS)) reagent diluted 10-fold was inoculated with 100. Mu.l of the modified eagle's medium to darber's disease and after 3 to 4 hours of reaction, the thiazole blue reagent was removed, and after 30 minutes of reaction in an incubator with 100. Mu.l of inoculated dimethyl sulfoxide (DMSO, dimethyl sulfoxide), the cell viability in the modified eagle's medium treated group, the 0.2% dimethyl sulfoxide/modified eagle's medium treated group (negative control group), the 10% dimethyl sulfoxide/modified eagle's medium treated group (positive control group) and the group treating the amino acids or the complexes of oligopeptides and fatty acids disclosed in the above tables 4 to 10 was analyzed by measuring absorbance (540 nm).
As a result, when the cell viability in the group treated with the complex was at a level of 100±4% similar to that in the negative control group, compared with the negative control group having a cell viability of 100%, the cell viability was 8 to 25% in the positive control group for cytotoxicity (retention results are not revealed). Thus, the complexes of the present invention incorporating fatty acids at the N-terminus, C-terminus or side chains of amino acids or oligopeptides are not toxic to skin cells.
Example 4: cytoprotective effect on ultra-fine dust amino acid or oligopeptide and fatty acid complexes (human keratinocytes)
To confirm whether the fatty acid-amino acid complex and fatty acid oligomer peptide (sequences 1 to 30) complexes can reduce the cytotoxicity increased by the ultrafine dust, the ultrafine dust (diesel exhaust particles, diesel exhaust particles, DEP) and complex treatment in keratinocytes (HaCaT cells) from human skin was performed, and cytotoxicity was analyzed by thiazole blue analysis. The diesel exhaust particles (fine dust having a diameter of 2.5 μm or less, PM 2.5) were purchased from national academy of environmental sciences (National Institute for Environmental studies, japan), and 4JB type 1 2740cc4 cylinder direct injection diesel engine (Isuzu auto co., japan) was operated under a load condition of 1500rpm and a torque condition of 10 (10 kg/ml) and collected by a glass fiber filter.
To achieve a cell number of 2X 10 4 The cells were diluted in Dalberg's modified eagle's medium (10% fetal bovine serum) and inoculated in 100. Mu.l to a 96-well dish, and cultured for 16 to 20 hours until the cells were attached to the plate surface. After completion of the culture, the medium was taken out, and 100. Mu.l of each well was inoculated with a solution of 10 μm complex and ultrafine dust at a concentration of 50. Mu.g/ml, at 37℃and 5% CO 2 After culturing in the incubator for 24 hours, the medium was removed again. Thereafter, the cell viability was confirmed by the thiazole blue assay in the same manner as in example 3.
As a result, a significant increase in cell viability was confirmed in the group in which the ultrafine dust alone and the complex in which the amino acid or oligopeptide was bound to the fatty acid were simultaneously treated, as compared with the group in which the ultrafine dust alone was treated (fig. 5 to 15).
Thus, the complex of the present invention, in which an amino acid or oligopeptide is combined with a fatty acid, can effectively protect skin cells by agglomerating ultra dust.
Example 5: analysis of cytotoxicity of ultra dust in lung cancer epithelial cells (A549)
Cytotoxicity was analyzed by thiazole blue assay after ultra dust treatment in human lung cancer epithelial cell line (a 549). Thiazole blue assay was performed in the same manner as in example 3 above, with ultrafine dust at concentrations of 50. Mu.g/ml, 60. Mu.g/m, 70. Mu.g/ml, 80. Mu.g/ml, 90. Mu.g/ml, 100. Mu.g/ml, 110. Mu.g/ml, 120. Mu.g/ml and 200. Mu.g/ml being treated in cultured lung cancer epithelial cells.
As a result, the higher the treatment concentration of ultra-fine dust was, the lower the cell viability was, and in particular, only about 20% of cells survived in the 200. Mu.g/ml fine dust treatment group at the highest concentration (FIG. 16).
Example 6: analysis of the cytoprotective Effect of peptide and fatty acid complexes on ultra dust (lung cancer epithelial cells)
To confirm whether the fatty acid oligomer peptide (saturated fatty acid bound to the amino acid sequence side chain of sequence 30) complex can reduce cytotoxicity due to ultrafine dust, cytotoxicity was analyzed by thiazole blue assay. The thiazole blue assay was performed by the same method as example 3 above.
As a result, the cell viability was increased in the group treated with the fatty acid oligopeptide complex, in particular, the cell viability was significantly increased in the peptide complex binding the remaining C8 to C16 saturated fatty acids other than the C6 saturated fatty acid, compared to the group treated with the ultrafine dust alone (about 40%), wherein the complex (P4, P11, P18, P25) exhibited cell viability of 70% or more in combination with Capric acid (Capric acid, C10), thereby confirming the reduction of cytotoxicity to ultrafine dust (fig. 17).
Example 7: analysis of aggregation Effect of fatty acid oligopeptide Complex and ultra dust Using silver staining (silver staining) method
The amounts of the ultrafine dust and fatty acid oligomer peptide complex P11 (decanoic acid bound to the side chain of the amino acid sequence of sequence 30) which did not aggregate with ultrafine dust were confirmed by silver staining, were simultaneously treated in a 20% SDS-PAGE gel.
After treatment of the ultra-fine dust alone at a concentration of 100. Mu.g/ml or of the P11 complex simultaneously with a concentration of 10. Mu.m, 50. Mu.m, 100. Mu.m, in a modified eagle's medium of Dalberk, at 37℃with 5% CO 2 The culture was carried out in an incubator for 24 hours, and the supernatant was prepared by centrifugation at 10000Xg for 1 hour. Thereafter, 15. Mu.l of the top liquid was loaded into a 20% SDS-PAGE gel and subjected to electrophoresis. Silver staining procedure using ELPIS biotechnological kit (PeptiGel) TM ELPISBIOTECH, EBA-1053) is performed as follows. The gel after electrophoresis was reacted with a solution of 30% ethanol and 10% acetic acid for 1 hour to be solidified, and washing was performed 2 times with distilled water. Thereafter, the gel was put in the solution A for 1 minute and washed 2 times with distilled water, and the gel was put in the solution B2 containing formaldehyde for 20 to 30 minutes. Finally, by distilled waterAfter washing 2 times at 1 minute, the gel was put in solution C and the reaction was stopped using a fixative solution after waiting for the occurrence of bands.
As a result, the band intensity was slightly reduced in the group in which the ultrafine dust and the complex P11 were simultaneously treated, as compared with the group in which the complex P11 was treated alone, and it was confirmed that the ultrafine dust and the fatty acid oligopeptide complex were aggregated, and the amount of peptide present in the supernatant was reduced (fig. 18). Thus, the complex of the oligopeptide-bound fatty acid of the present invention is aggregated with the ultrafine dust, whereby the ultrafine dust can be removed.
Example 8: analysis of dust trapping (particle removal) efficiency of fatty acid oligopeptide Complex by comparison of micronic particle permeation amount of mask
In order to confirm whether or not the fatty acid oligopeptide complex adsorbs moving ultra fine dust to improve the filtering efficiency of the mask, the dust trapping (particle removal) efficiency was analyzed, and the evaluation method and calculation formula of the dust trapping efficiency are shown in table 24 below.
Table 24
Dust trapping (particle removal) efficiency evaluation and calculation
As a result of measuring the particle removal efficiency (%) of the mask by quantifying the amount of 50nm to 300nm size dust particles in the air passing through a general mask (HIP's) and a dust mask (KF 84), the dust mask has a particle removal (dust trapping) efficiency of about 89 to 100% for 50 to 300nm size dust particles, whereas the general mask has a particle removal efficiency of about 39 to 57% for 50 to 300nm size dust particles (fig. 19).
Further, as a result of measuring the removal (split-into-trap) efficiency (%) of mask particles by measuring the amount of fine dust particles having a size of 50 to 300nm in the air after once spraying a distilled water or a 250ppm solution of a fatty acid oligopeptide complex (distilled water dilution) onto a general mask, the dust trapping efficiency of masks for treating a fatty acid-peptide complex (Palmitic acid-KTTKS, palmitic acid-rrrrrrr, palmitic acid-KKKKK, capric acid-RRRRR, capric acid-RRRRRRRRR) was increased compared with a general mask not sprayed with any substance and a general mask sprayed with distilled water, and in particular, the particle removal efficiency of a fatty acid-peptide complex was excellent as the fine dust particle size was smaller (fig. 20 and 21).
Sequence listing
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Claims (1)
1. Use of a cosmetic composition for removing or adsorbing fine dust, characterized in that the cosmetic composition comprises a complex of fatty acids bound at the N-terminal, C-terminal or side chain of an oligopeptide as an active ingredient;
wherein the oligopeptide is one selected from the group consisting of amino acid sequences of sequences 4, 6-8, 10-11, 15-17, 19, 21, 27 to 30;
the fatty acid is saturated fatty acid or unsaturated fatty acid;
the saturated fatty acid is one selected from the group consisting of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, behenic acid and lignoceric acid;
the unsaturated fatty acid is one selected from the group consisting of palmitoleic acid, oleic acid, elaidic acid, petroselinic acid, isooleic acid, megaly acid, sinapic acid, nervonic acid, linoleic acid, linolenic acid, punicic acid, eleostearic acid, menhaden acid and ricinoleic acid.
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| KR20180078889 | 2018-07-06 | ||
| KR10-2018-0078889 | 2018-07-06 | ||
| PCT/KR2019/008330 WO2020009548A1 (en) | 2018-07-06 | 2019-07-05 | Cosmetic composition for removing or adsorbing particulate matter containing peptide complex as active ingredient |
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| KR102378053B1 (en) * | 2020-12-24 | 2022-03-25 | 주식회사 조에바이오 | Composition for protecting the skin against harmful substance, light and stress |
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| CN106999401A (en) * | 2014-12-16 | 2017-08-01 | 赛德玛公司 | Peptide compounds, the purposes for including their compositions and the compound, particularly cosmetics |
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| EP1132451A1 (en) * | 1996-02-15 | 2001-09-12 | MERCK PATENT GmbH | Choleristic flakes |
| KR20040062602A (en) * | 2001-10-30 | 2004-07-07 | 펜타팜아게 | Dermopharmaceutically and cosmetically active oligopeptides |
| KR100699429B1 (en) * | 2005-12-26 | 2007-03-28 | 주식회사 화진화장품 | Fabrication method for skin fuctional peptide combined oleic acid |
| CN101991513B (en) * | 2009-08-12 | 2013-06-12 | 陈励 | Raw material for production of cosmetics and medicament for personal care |
| ES2358829B1 (en) * | 2009-10-23 | 2012-06-25 | Lipotec, S.A. | USEFUL PEPTIDES IN THE TREATMENT AND / OR CARE OF SKIN, MUCOSES AND / OR HAIR AND ITS USE IN COSMETIC OR PHARMACEUTICAL COMPOSITIONS. |
| JP6382111B2 (en) * | 2012-03-01 | 2018-08-29 | ノヴォ ノルディスク アー／エス | N-terminal modified oligopeptide and use thereof |
| KR101437237B1 (en) | 2012-12-10 | 2014-10-30 | 미원상사주식회사 | Anti-aging tetrapeptide and cosmetic composition containing the same |
| KR101622382B1 (en) * | 2013-02-27 | 2016-05-19 | (주)내츄럴엔도텍 | Transdermal Penetration Enhancer and Their Uses |
| JP2016088929A (en) | 2014-10-30 | 2016-05-23 | 日光ケミカルズ株式会社 | Pollution preventing agent, and pollution preventing cosmetic or pollution preventing skin external preparation including the same |
| KR101723941B1 (en) * | 2016-02-26 | 2017-04-06 | (주)진셀팜 | Cosmetic composition for adsorbing and removing fine dust containing resin extracts of ardisia pusilla and bengal fig as active ingredient |
| JP6718728B2 (en) | 2016-04-06 | 2020-07-08 | キユーピー株式会社 | Anti-pollution agent and external skin composition for anti-pollution |
| KR101809209B1 (en) * | 2016-05-31 | 2017-12-15 | 주식회사 올리패스코스메슈티컬즈 | Cosmetic composition for improving the health of scalp and manufacturing method thereof |
| KR101849280B1 (en) * | 2016-08-17 | 2018-04-17 | (주)진셀팜 | Peptide for adsorbing and removing fine dust, and uses thereof |
| KR101886347B1 (en) * | 2016-08-17 | 2018-08-09 | (주)진셀팜 | Peptide for adsorbing and removing fine dust, and uses thereof |
| KR101850313B1 (en) * | 2016-08-18 | 2018-04-20 | (주)진셀팜 | Cosmetic compositon for removing heavy metal or fine dust containing extracts of chrysanthemum |
| KR101715599B1 (en) * | 2016-10-04 | 2017-03-13 | (주)셀트리온 | Tripeptide combined with fatty acid and anti-wrinkle cosmetic composition comprising the same |
| KR101786913B1 (en) * | 2017-02-24 | 2017-10-17 | 주식회사 삼양사 | Cosmetic composition for enhancing skin permeation of active ingredient |
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| CN103314005A (en) * | 2011-03-25 | 2013-09-18 | 利普泰股份公司 | Peptides useful in the treatment and/or care of the skin and/or mucous membranes and their use in cosmetic or pharmaceutical compositions |
| CN106999401A (en) * | 2014-12-16 | 2017-08-01 | 赛德玛公司 | Peptide compounds, the purposes for including their compositions and the compound, particularly cosmetics |
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