CN102266268A - Composition for inhibiting melanin generation and application thereof - Google Patents
Composition for inhibiting melanin generation and application thereof Download PDFInfo
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- CN102266268A CN102266268A CN 201010198426 CN201010198426A CN102266268A CN 102266268 A CN102266268 A CN 102266268A CN 201010198426 CN201010198426 CN 201010198426 CN 201010198426 A CN201010198426 A CN 201010198426A CN 102266268 A CN102266268 A CN 102266268A
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Abstract
The invention provides a composition for inhibiting melanin generation and promoting skin whitening, which comprises a compound shown as the following general formula :
wherein R is1Is a C2 to C10 alkylene group or a halogen substituted alkylene group; r2、R3Each independently hydrogen, a five or six membered heterocyclic or cyclic group, C1 to C6 amidoalkyl, C1 to C6 hydroxyalkyl, or C1 to C6 carboxyalkyl, or R2、R3The nitrogen atoms to which they are attached together form a five or six membered heterocyclic group containing an oxygen atom. The invention also provides a method for inhibiting melanin generation and promoting skin whitening by using the composition.
Description
Technical field
The invention relates to a kind of melanin that suppresses and generate compositions and the application thereof that promotes skin-whitening, particularly by the tryrosinase that suppresses in the melanocyte, to suppress compositions and the application thereof that melanin generated and promoted skin-whitening.
Background technology
Melanin (melanin) is constantly to be made by the melanosome (melanosome) in the melanocyte (melanocyte) to produce in human body, and melanocyte is distributed in tissues such as eyes, hair, brain and skin.
Melanocyte at skin is the basal layer of position in epidermal tissue.Can be surrounded by 30～40 horn cells (keratinocyte) around the melanocyte, form so-called " epidermal area melanin unit " (epidermal melanin unit).Though melanocyte has only accounted for the space of small part at this layer tissue, it is playing the part of important function on skin.
Melanocyte can continue to make the black corpusculum, and manufactured melanosome can be secreted to contiguous on every side horn cell via the tree-shaped axon ends of melanocyte.The black corpusculum be the position in the Cytoplasm of melanocyte, be a kind of spherical or oval-shaped born of the same parents' device with film, can protect free radical (free radical) pair cell that discharges in the cell antagonism melanin generative process to produce the oxidisability injury.
Melanic formation is in the presence of tyrosine (tyrosine) in the black corpusculum, and elder generation is through the catalysis of tryrosinase (tyrosinase), what form under the catalysis of a succession of enzyme.The black that forms have two kinds, and a kind of is the eumelanin (eumelanin) of brownish black, and a kind of is the phaeomelanin (phaeomelanin) of yellowish-brown.And tryrosinase is a kind of copper bearing enzyme, is the rate-determing step that melanin forms.
At present being subjected to sure whitening composition is vitamin C, hydroquinone (hydroquinone), Arbutin (arbutin), kojic acid (kojic acid) etc., and these compositions all have tyrosinase inhibitory activity, probably can cause cytopathy to poison under the life-time service.The compositions of the restraint of tyrosinase of a novelty is developed in our expectation.
Summary of the invention
The object of the present invention is to provide a kind of compositions that melanin produced and then promoted skin-whitening that suppresses.Compositions of the present invention comprises a kind of composition of novelty, this novel ingredients is the chemical compound of a small-molecular weight and tool bio-compatibility, in addition, this novel ingredients also has tryrosinase (Tyrosinase) and suppresses active effect, and the melanin that therefore can suppress B16 melanoma (melanoma) and human melanocyte generates.
Another purpose of the present invention provides a kind of melanin that suppresses and produces the method that promotes skin-whitening.
The chemical compound that another purpose of the present invention provides described novel ingredients is used to suppress the purposes that melanin produces.
For reaching above-mentioned purpose, the invention provides a kind of compositions that melanin produces that suppresses, it is characterized in that comprising the chemical compound shown in following general formula (I):
R wherein
1Stretching alkyl (alkylene, alkylene) or stretching alkyl for C2 to C10 through what halogen replaced; R
2, R
3Independent separately is hydrogen, five or hexavalent heterocycle or cyclic group, C1 to C6 amido alkyl, C1 to C6 hydroxy alkyl or C1 to C6 carboxyalkyl, perhaps R
2, R
3Common five or the hexa-member heterocycle group that contains oxygen atom that form of coupled nitrogen-atoms.
Preferably, the chemical compound shown in the described general formula (I) is the chemical compound shown in the following structural formula (I-a) to (I-e):
(I-a): N-(2-acetamido)-2-amido ethyl sulfonic acid [N-(2-Acetamido)-2-aminoethanesulfonic acid abbreviates ACES as]
(I-b): 3-(N-morpholinyl) propane sulfonic acid [3-(N-Morpholino) propanesulfonic acid abbreviates MOPS as]:
(I-c): N, two (2-the ethoxy)-2-amido ethyl sulfonic acids of N-[(N, N-bis (2-hydroxyethyl)-2-aminoethanesulfonic acid) is called for short BES]
(I-d): 2-(N-cyclohexylamino) ethyl sulfonic acid [2-(N-Cyclohexylamino) ethanesulfonicacid is called for short CHES]
(I-e): 2-(N-morpholinyl) ethyl sulfonic acid [2-(N-Morpholino) ethanesulfonic acid is called for short MES]
Preferably, described compositions of the present invention further comprises acceptable excipient on the skin care.Excipient can be accepted on the skin care of the present invention and deionized water, polyhydric alcohol, hydrophilic high molecular material or its mixture can be.This hydrophilic high molecular material comprises Polyethylene Glycol (PEG; Polyethyleneglycol, Polyethylene Glycol), polyvinyl alcohol (PVA; PolyvinylAlcohol), starch, modified starch, xanthan gum, carrageenan, gelatin, chitosan, pectin, propolis, melon glue, locust bean gum, alginate jelly, collagen protein, cellulose derivative, modified cellulose polymer, arabic gum galactan, Konjac glucomannan, fish bone glue, Guar gum, microbial polymer, glucosan, agar, carrageenin, alginic acid polymer or its mixture.This polyhydric alcohol comprises, but is not limited to propylene glycol, glycerol, Sorbitol, butanediol, hexanediol, ethyoxyl glucose, 1,2-hexanediol, hexanetriol or dipropylene glycol.
Preferably, the content of the chemical compound shown in the described general formula (I) is 0.01～99.99wt%, more preferably is 0.1～80wt%.
Preferably, the content of acceptable excipient is 0.01～99.99wt% on the described skin care.
Preferably, the chemical compound of described general formula (I) has the active function of restraint of tyrosinase.
Preferably, described compositions is to be added in commercially available cosmetics or the skin care products.
The present invention also provides a kind of method that melanin produces that suppresses, and it comprises described compositions and contact skin with effective dose.
Preferably, said composition is after being added in commercially available cosmetics or the skin care products, to contact with human skin again.
The present invention provides a kind of again general formula (I) chemical compound is used to suppress the purposes that melanin produces.For example, described purposes is the purposes that general formula (I) chemical compound is used for preparing the compositions that suppresses the melanin generation.
The compositions that inhibition melanin provided by the present invention produces can be the form of skin preparations for extenal use such as common cosmetics, skin care products, pharmaceuticals, for example whitening agent, wetting agent, antioxidant, oiliness composition, UV absorbent, surfactant, tackifier, alcohols, powder composition, colouring matter, water composition, aqueous solution, various skin-nourishing agent etc.Other composition of above kenel is that its prescription that is suitable for is respectively arranged according to its purposes, and those skilled in the art is when can implement the compositions that inhibition melanin of the present invention produces in proper range.
The compositions that inhibition melanin of the present invention produces is to utilize a kind of novel ingredients with restraint of tyrosinase generation to reach to suppress the effect that melanin generates, it is sneaked in commercially available skin care products or the cosmetics, can improve the white-skinned face function of skin care products or cosmetics.
Description of drawings
Fig. 1 shows the ability of the embodiment of the invention 1 at restraint of tyrosinase.
Fig. 2 shows the observed result of mouse melanocyte under 400 times of microscopes through handling in 72 hours.
Fig. 3 shows that ACES and MOPS suppress the B16-F1 cell and produce melanic experimental result.
Fig. 4 shows that ACES and MOPS suppress the B16-F1 cell and discharge melanic experimental result.
Fig. 5 shows that embodiment of the invention 2-1 and 2-2 suppress the experimental result that melanin produces at human melanocyte.
Fig. 6 shows VISIA
TMThe numeral skin analyzer carries out the result that melanin is analyzed.
Fig. 7 shows VISIA
TMThe result that the numeral skin analyzer carries out the skin speckle component analysis.
The specific embodiment
As previously mentioned, the compositions that inhibition melanin provided by the present invention produces, it comprises the chemical compound shown in general formula (I):
R wherein
1Stretching alkyl or stretching alkyl for C2 to C10 through what halogen replaced; R
2, R
3Independent separately is hydrogen, five or hexavalent heterocycle or cyclic group, C1 to C6 amido alkyl, C1 to C6 hydroxy alkyl or C1 to C6 carboxyalkyl, perhaps R
2, R
3Common five or the hexa-member heterocycle group that contains oxygen atom that form of coupled nitrogen-atoms.
The specific embodiment of the method that inhibition melanin of the present invention produces comprises: the chemical compound shown in the general formula (I) is scattered on the skin care in the acceptable excipient, it is contacted with human body skin again.Further, can be added into compositions of the present invention in commercially available cosmetics or the skin care products after, again with contact skin.
Among the present invention on the used skin care acceptable excipient mainly be to be used for making compositions preparation of the present invention to be shaped, it comprises the habitual excipient in this area, comprise but be not limited to deionized water, polyhydric alcohol, hydrophilic high molecular material or its mixture, and this hydrophilic high molecular material comprises Polyethylene Glycol (PEG; Polyethyleneglycol, Polyethylene Glycol), polyvinyl alcohol (PVA; Polyvinyl Alcohol), starch, modified starch, xanthan gum, carrageenan, gelatin, chitosan, pectin, propolis, melon glue, locust bean gum, alginate jelly, collagen protein, cellulose derivative, modified cellulose polymer, arabic gum galactan, Konjac glucomannan, fish bone glue, Guar gum, microbial polymer, glucosan, agar, carrageenin, alginic acid polymer or its mixture, but be not limited to this.This polyhydric alcohol comprises, but is not limited to propylene glycol, glycerol, Sorbitol, butanediol, hexanediol, ethyoxyl glucose, 1,2-hexanediol, hexanetriol or dipropylene glycol.
The compositions that inhibition melanin of the present invention produces can further comprise the material of one or more skin beneficiatings, as radical scavenger, antioxidant, antiinflammatory, anti-sensitizer, anti-acne agents, skin texture improving agent, antimicrobial, brighten composition or the like; And one or more auxiliary elements, as antiseptic, surfactant, thickening agent, mix the beautifying nourishing composition that changes the colour of skin and/or improve skin condition that has that obtains with water.
Because compositions of the present invention mainly is to come restraint of tyrosinase to produce with the chemical compound shown in the general formula (I) as novel ingredients, generates to suppress melanin, and reach the effect of whitening.Therefore, when will be understood that, also the chemical compound of general formula (I) can be added in commercially available cosmetics or the skin care products after, again with contact skin.
Therefore, the present invention also provides a kind of purposes that general formula (I) chemical compound is used to suppress the melanin generation.
Technical characterictic of the present invention specifically is described in the invention description, and all other material and prescription belong to known skill, and those skilled in the art is when implementing the present invention easily.Below will be by mode illustration feature of the present invention and the advantage of embodiment.
Embodiment 1: use tyrosinase inhibitor restraint of tyrosinase of the present invention to generate melanin
Experimental technique:
The experimental technique of present embodiment is to add 90 μ L 0.1U tryrosinase solution in the test well of 96 porose discs, and add the serial dilution solution (experimental group) or the blank group of 50 μ L determinands, wherein this determinand is MOPS, SB-12 (3-(N, N-dimethyl dodecyl ammonium) propane sulfonate (N-Dodecyl-N, N-dimethyl-3-ammonio-1-propanesulfonate)), ACES or Tris-HCl, and be respectively the blank assay of experimental group and matched group with 0.1M phosphate buffer (Phosphate Buffer) and substance dissolves solvent.This test is minimum carries out three repetitions.Test panel is placed 37 ℃, 400rpm evenly mixed 5 minutes.Test panel is inserted in the machine, carry out the 492nm wave band and absorb test, carrying out twice data test and getting its meansigma methods is background value.Take out test panel, in each well, add 60 μ L 1mM L-Dopa solution respectively, and placed 37 ℃ of hybrid reactions (400rpm) 15 minutes.Test panel carries out the 492nm wave band again and absorbs test, and carrying out twice data test and getting its meansigma methods is test value, after the background correction value, calculates the inhibition degree, and the result of gained as shown in Figure 1.
Experimental result:
Fig. 1 shows that embodiment 1 generates the melanin experimental result at restraint of tyrosinase, and the data among the figure are calculated and got with following formula:
Suppression ratio=(1-experimental group OD value)/(control group OD value) * 100%
Result among the figure shows, when relative concentration increases, represents that promptly this test substances has restraint of tyrosinase and produces melanic effect.This result confirms chemical compound used in the present invention compared to the blank group, has restraint of tyrosinase and generates melanic effect.
Embodiment 2: cell melanin inhibition test
Present embodiment is tyrosinase inhibitor of the present invention to be used for melanocyte suppress melanic generation.The employed cell strain of present embodiment is mouse melanocyte (B16-F1, Mousemelanoma; ATCC CRL-6323) and human melanocyte (HEM, Human epidermalmelanocytes).List the condition of culture of mouse melanocyte and human melanocyte in the present embodiment in table 1 and the table 2 respectively, table 3 item is listed the additive that each embodiment and comparative example adds.Mouse melanocyte and human melanocyte are cultivated according to the condition of table 1～table 3, after 72 hours, this cell and cell culture fluid of handling 72 hours is collected, destroy cell through the ultrasound concussion again, to measure melanin, the result of gained such as Fig. 3 are to shown in Figure 5.
Table 1 mouse melanocyte condition of culture
| Cell strain | B16-F1 |
| Culture medium | DMEM+10wt％FBS+1wt％P/S |
| Condition of culture | 37℃，5％CO 2 |
| Growthform | Epithelial cell shape (Epithelial-like) |
| Culture medium is changed | Per 2 to 3 days |
| Freezing culture medium | 93wt% culture medium+7wt%DMSO |
| Successive transfer culture | 0.05wt% trypsin solution (trypsin-EDTA); 37 ℃, 3 minutes |
● P/S system expression penicillin (Penicillin)/streptomycin (Streptomycin).
The human melanocyte condition of culture of table 2
| Cell strain | HEM |
| Culture medium | Melanocyte culture medium and successive transfer culture reagent cover group (Melanocyte growth medium and subculture reagent kit) |
| Condition of culture | 37℃，5％CO 2 |
| Growthform | Fibroblast shape (Fibroblast-like) |
| Culture medium is changed | Per 2 to 3 days |
| Freezing culture medium | 93wt% culture medium+7wt%DMSO |
| Successive transfer culture | 0.05wt% trypsin solution (trypsin-EDTA); 37 ℃, 3 minutes |
Table 3 makes an addition to the material of culture medium
| Embodiment 2-1 | ACES (being dissolved in cell culture fluid, pH=6.5-7.5,200 μ g/mL) |
| Embodiment 2-2 | MOPS (being dissolved in cell culture fluid, pH=6.5-7.5,200 μ g/mL) |
| Comparative example 1 | Do not add any product (blank group) |
Fig. 2 shows the observed result of mouse melanocyte under 400 times of microscopes through handling in 72 hours, and wherein picture A is the blank group, and picture B is the situation that is added with ACES in the culture medium, and picture C is the situation that is added with MOPS in the culture medium.Can be known by the result of Fig. 2 and to learn that the present invention adds chemical compound of the present invention in culture medium, it has the melanocyte of inhibition really and produces melanic effect.Find to produce melanin by the B16-F1 cell experiment when ACES and MOPS can significantly suppress the mouse melanoma cell at concentration 200 μ g/ml.
Fig. 3 shows that ACES and MOPS suppress the B16-F1 cell and produce melanic experimental result.Result by Fig. 3 shows, finds that ACES and MOPS suppress B16-F1 cell generation melanin ability and be respectively 35.0% and 41.7%.Fig. 4 shows that ACES and MOPS suppress the B16-F1 cell and discharge melanic experimental result.The result of Fig. 4 shows that ACES and MOPS suppress B16-F1 cell release melanin ability and be respectively 38.9% and 42.3%.Fig. 5 shows that embodiment 2-1 and 2-2 suppress melanocyte at human melanocyte and produce melanic experimental result.If suppression ratio increases, represent that then this test substances has the effect of the melanin generation that suppresses human melanocyte.Result by Fig. 5 shows, uses MOPS and ACES can increase suppression ratio, and this promptly confirms chemical compound used in the present invention compared to the blank group, and the melanin that can effectively suppress human melanocyte generates.Show all significantly restraint of tyrosinase generations of ACES of the present invention as can be known and MOPS chemical compound by the result, confirm that chemical compound of the present invention has the melanocyte of inhibition and generates melanic effect.More than test is to measure the cell survival rate cytoactive with MTTassay (3-[4,5-dimethylthiahiazo-2-y 1]-2,4-diphenytetrazolium bromide).
Embodiment 3: use the test of whitening of the human skin of tyrosinase inhibitor of the present invention
Present embodiment is with tyrosinase inhibitor of the present invention, is applied to skin care with the skin-whitening dosage form of colloidal attitude, suppresses the effect of melanic generation with Da Meibai.Table 4 is listed the prescription composition that each embodiment and comparative example adds, and wherein GT-700 and cyclic amino acid (Ectoin) are all commercially available cosmetic material.GT-700 (the PEG-240/HDI copolymer is two-decyl tetradecyl alchohol polyethers-20 ether [PEG-240/HDI Copolymer Bis-Decyltetradeceth-20 Ether]; Available from KALINENTERPRISE CO., LTD.) be a kind of viscosity control agent.
Table 4, make an addition to the material of prescription
10 experimenters are collected in this test, and duration of test was 8 weeks, carried out the test of whitening of skin.Embodiment 3 (containing MOPS) is applied in left face and right face respectively with comparative example 2 (not containing MOPS), and use once every day sooner or later.In the 0th, 2,4,6,8 weeks are respectively with VISIA
TMThe numeral skin analyzer carries out the skin complexion analysis.Utilization multiple spectrum image science and technology is carried out the analysis that face whitens, the result of gained such as Figure 6 and Figure 7 from melanin and skin speckle amount etc.
Fig. 6 shows VISIA
TMThe numeral skin analyzer carries out the result that melanin is analyzed, and Fig. 7 then shows VISIA
TMThe result that the numeral skin analyzer carries out the skin speckle component analysis.The gained result shows, can find that after using for the 2nd week the melanin of embodiment 3 and skin speckle amount significantly reduce than comparative example 2, and may persist to during 8 weeks.The prescription that this demonstration comprises general formula of the present invention (I) chemical compound can effectively reduce the melanin generation, that is the effect of the certain Pear Power of tyrosinase inhibitor of the present invention (being the chemical compound of general formula (I)).
In sum, the compositions that inhibition melanin provided by the present invention produces, be to comprise a kind of novel ingredients that restraint of tyrosinase produces that has, utilize this characteristic to reach and suppress the effect that melanin generates, it is applied in skin care products or the cosmetics, can provides that consumer is a kind of to be different from traditional whitening product.
Other implements aspect
All features that are exposed in present disclosure can make combination in any way.The disclosed feature of this description can be used, and feature identical, equal or similar purpose replaces.Therefore, except the place is emphasized in special statement, the disclosed embodiment who is characterized as in series of equivalent or the similar features of this description.
In addition; content according to the exposure of this description; those of ordinary skill in the art can be easily according to basic feature of the present invention; in not breaking away from spirit of the present invention and scope; do appropriate change and modification at different usings method and situation; therefore, other enforcement aspect also is contained in protection scope of the present invention.
Claims (11)
1. one kind is suppressed the compositions that melanin produces, and it is characterized in that comprising the chemical compound shown in following general formula (I):
R wherein
1Stretching alkyl or stretching alkyl for C2 to C10 through what halogen replaced; R
2, R
3Independent separately is hydrogen, five or hexavalent heterocycle or cyclic group, C1 to C6 amido alkyl, C1 to C6 hydroxy alkyl or C1 to C6 carboxyalkyl, perhaps R
2, R
3Common five or the hexa-member heterocycle group that contains oxygen atom that form of coupled nitrogen-atoms.
2. compositions as claimed in claim 1, the chemical compound shown in the wherein said general formula (I) is following structure
Chemical compound shown in the formula (I-a) to (I-e):
3. compositions as claimed in claim 1, it further comprises acceptable excipient on the skin care.
4. compositions as claimed in claim 3, acceptable excipient is deionized water, polyhydric alcohol, hydrophilic high molecular material or its mixture on the wherein said skin care.
5. compositions as claimed in claim 3, the content of the chemical compound shown in the wherein said general formula (I) is 0.01～99.99wt%.
6. compositions as claimed in claim 3, the content of acceptable excipient is 0.01～99.99wt% on the wherein said skin care.
7. compositions as claimed in claim 1, the chemical compound of wherein said general formula (I) has the active function of restraint of tyrosinase.
8. compositions as claimed in claim 1, it is to be added in commercially available cosmetics or the skin care products.
9. one kind is suppressed the method that melanin produces, its comprise with effective dose as claim 1～8 each described compositions and contact skin.
10. method as claimed in claim 9, it is after being added into described compositions in commercially available cosmetics or the skin care products, to contact with human skin again.
11. purposes that general formula (I) chemical compound is used to suppress the melanin generation:
R wherein
1Stretching alkyl or stretching alkyl for C2 to C10 through what halogen replaced; R
2, R
3Independent separately is hydrogen, five or hexavalent heterocycle or cyclic group, C1 to C6 amido alkyl, C1 to C6 hydroxy alkyl or C1 to C6 carboxyalkyl, perhaps R
2, R
3Common five or the hexa-member heterocycle group that contains oxygen atom that form of coupled nitrogen-atoms.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6303656B1 (en) * | 1998-09-09 | 2001-10-16 | L'oreal | Composition comprising urea, and its uses in the field of cosmetics and/or dermatology |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6303656B1 (en) * | 1998-09-09 | 2001-10-16 | L'oreal | Composition comprising urea, and its uses in the field of cosmetics and/or dermatology |
Non-Patent Citations (1)
| Title |
|---|
| 《中国生化药物杂志》 19991231 赵荧 等 《牛磺酸对酪氨酸酶的抑制作用》 13-14页 1－11 第20卷, 第1期 * |
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Application publication date: 20111207 |