CN114057830B - Oligopeptide-1 derivatives, preparation method and application thereof - Google Patents
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Abstract
The invention discloses an oligopeptide-1 derivative, a preparation method and application thereof, and relates to the technical field of polypeptide derivative synthesis. The oligopeptide-1 derivative is an oligopeptide-1 amidated derivative; the chemical substances for derivatization in the oligopeptide-1 derivatives comprise L-alanine-7-amino-4-methylcoumarin or 5-aminoarundoin. The oligopeptide-1 derivative is prepared by amidation reaction of carboxyl in oligopeptide-1 structure and amino in L-alanine-7-amino-4-methylcoumarin or 5-aminoarundoin structure. The oligopeptide-1 derivative prepared by the invention has more excellent antioxidant activity, the anti-ultraviolet effect is obviously improved, the expression and activity of MMP (matrix metalloproteinase) increased by UV (ultraviolet) are further reduced, wrinkles are effectively improved, and the skin is prevented from aging; meanwhile, the collagen protein has excellent collagen activity promoting and transdermal absorption performances.
Description
Technical Field
The invention belongs to the technical field of polypeptide derivative synthesis, and particularly relates to an oligopeptide-1 derivative, and a preparation method and application thereof.
Background
Oligopeptide-1 is tripeptide-1 of GHK sequence, is an active polypeptide containing three amino acids, and has an amino acid sequence of H-Gly-His-Lys-OH. GHK-Cu is used for promoting wound healing and improving skin elasticity for the first time in medicine, and a part of recent researches consider that fine lines can be improved; PAL-GHK has the function of lip plumping, is used in the production of lipstick, makes the lips look plump and soft and bright after being used, and is also a necessary raw material of safe breast plumping products.
Tripeptide-1 is effective in preventing and reducing wrinkles, and makes skin younger, smoother and more elastic. Relevant experimental studies show that 5 ppm of tripeptide-1 and 0.05% of vitamin A are active in promoting the synthesis of collagen and glycosaminoglycan, but can avoid the generation of irritation and side reactions, which makes tripeptide-1 have great advantages and potential in wrinkle-removing and skin-care. Therefore, the tripeptide-1 structure is modified by a chemical modification method, and the finding of the tripeptide-1 derivative with more excellent and abundant effects is of great significance. However, few reports on tripeptide-1 derivatives are available.
Disclosure of Invention
The invention aims to provide an oligopeptide-1 derivative, a preparation method and application thereof, wherein the oligopeptide-1 derivative has more excellent antioxidant activity, the anti-ultraviolet effect is obviously improved, the expression and activity of MMP (metal matrix metalloproteinase) increased by UV (ultraviolet) are further reduced, wrinkles are effectively improved, and skin aging is prevented; meanwhile, the collagen protein has excellent collagen activity promoting and transdermal absorption performances.
The technical scheme adopted by the invention for realizing the purpose is as follows:
an oligopeptide-1 derivative which is an oligopeptide-1 amidated derivative;
the chemical substances for derivatization in the oligopeptide-1 derivatives comprise L-alanine-7-amino-4-methylcoumarin or 5-aminoarundoin. The oligopeptide-1 derivative is prepared by chemically modifying oligopeptide-1 by adopting L-alanine-7-amino-4-methylcoumarin or 5-aminoarundoin and performing amidation reaction, so that the biological activity of the derivative can be effectively enhanced, the antioxidant activity of the derivative is remarkably enhanced, superoxide anion free radicals are effectively eliminated, and cells are protected from oxidative damage; the collagen protein has more excellent effect of inhibiting the activity of MMP-2 induced by ultraviolet rays, the anti-ultraviolet effect is obviously improved, the expression and activity of MMP increased due to UV can be further reduced, and the synthesis of collagen reduced due to UV can be increased; the collagen is effective in improving wrinkle and preventing skin aging.
The chemical structure of the oligopeptide-1 derivative is shown as formula I:
I。
the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 with the L-alanine-7-amino-4-methylcoumarin has more excellent collagen generation promoting activity, and can be used for increasing the thickness of skin, tightening the skin and increasing the elasticity; and under the condition that the oligopeptide-1 derivative prepared by 5-aminoarundoin modified oligopeptide-1 exists at the same time, the collagen activity is promoted to have obvious gain effect.
It should be noted that the chemical structure of the oligopeptide-1 derivative can also be shown as formula II:
II。
the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 with 5-aminoarundoin has better transdermal absorption performance, better exerts the biological activity through the skin and improves the skin state; and the transdermal absorption performance of the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 by the L-alanine-7-amino-4-methylcoumarin has an effect of gaining under the condition of coexistence.
The preparation method of the oligopeptide-1 derivative comprises the following steps: the oligopeptide-1 derivative is prepared by amidation reaction of carboxyl in an oligopeptide-1 structure and amino in an L-alanine-7-amino-4-methylcoumarin or 5-aminoarundoin structure.
Specifically, the preparation method of the oligopeptide-1 derivative comprises the following steps:
dissolving oligopeptide-1 in a tetrahydrofuran/water (v/v, 1: 1-2) mixed solution, adding CDI under the condition of ice-water bath, uniformly mixing, slowly dropwise adding the mixture into a tetrahydrofuran solution containing L-alanine-7-amino-4-methylcoumarin and triethylamine, and reacting for 3-5 h at 30-40 ℃ after dropwise adding; concentrating under reduced pressure, adding a 2-4 volume times of water/ethyl acetate (v/v, 1: 2-3) mixed solution, adding hydrochloric acid to adjust the pH to 2-3, washing an organic phase with brine, adding anhydrous sodium sulfate to dry, filtering, and drying in vacuum to obtain an oligopeptide-1 derivative;
or the like, or, alternatively,
dissolving oligopeptide-1 in a tetrahydrofuran/water (v/v, 1: 1-2) mixed solution, adding CDI under the condition of ice-water bath, uniformly mixing, slowly dropwise adding the mixture into a tetrahydrofuran solution containing 5-aminoarundoin and triethylamine, and reacting for 3-5 h at 30-40 ℃ after dropwise adding; concentrating under reduced pressure, adding a 2-4 volume times of water/ethyl acetate (v/v, 1: 2-3) mixed solution, adding hydrochloric acid to adjust the pH to 2-3, washing an organic phase with brine, adding anhydrous sodium sulfate to dry, filtering, and drying in vacuum to obtain the oligopeptide-1 derivative.
The solid-to-liquid ratio of the oligopeptide-1 to the tetrahydrofuran/water mixed solution is 1 g: 8-12 mL; the mass ratio of the oligopeptide-1 to the CDI is 1: 0.4-0.6; the molar ratio of the oligopeptide-1 to the L-alanine-7-amino-4-methylcoumarin is 1: 1-1.5; the mass ratio of triethylamine to CDI is 1: 1-1.5; the solid-liquid ratio of the L-alanine-7-amino-4-methylcoumarin to the tetrahydrofuran is 1 g: 10-15 mL.
The molar ratio of oligopeptide-1 to 5-aminoarundoin is 1: 1-1.5; the mass ratio of triethylamine to CDI is 1: 1-1.5; the solid-to-liquid ratio of the 5-aminoarundoin to the tetrahydrofuran is 1 g: 10-15 mL.
A cosmetic composition comprises the oligopeptide-1 derivative.
The amount of the oligopeptide-1 derivative added in the cosmetic composition is 0.01 to 0.5 wt%.
Preferably, the addition amount of the oligopeptide-1 derivative shown in the formula I is 0.01-0.5 wt%.
Preferably, the addition amount of the oligopeptide-1 derivative shown in the formula II is 0.01-0.5 wt%.
The invention also discloses application of the oligopeptide-1 derivatives shown in the formula I and/or the formula II in enhancing the antioxidant and wrinkle-removing effects of cosmetics.
The invention also discloses the application of the oligopeptide-1 derivatives in preparing antioxidant cosmetics.
The invention also discloses the application of the oligopeptide-1 derivative in preparing cosmetics for fading wrinkles.
Compared with the prior art, the invention has the following beneficial effects:
the invention adopts L-alanine-7-amino-4-methylcoumarin or 5-aminoarundoin to chemically modify oligopeptide-1, and the oligopeptide-1 derivative is prepared through amidation reaction, so that the antioxidant activity is obviously enhanced, and superoxide anions can be effectively removed; and has more excellent efficacy of inhibiting ultraviolet-induced MMP-2 activity, obviously improves the anti-ultraviolet effect, can increase collagen synthesis reduced due to UV, and improves wrinkles. Meanwhile, the oligopeptide-1 derivative disclosed as formula I has more excellent collagen generation promoting activity, and has an obvious collagen promoting effect when being compounded with the oligopeptide-1 derivative disclosed as formula II. In addition, the oligopeptide-1 derivative shown in the formula II prepared by the invention has better transdermal absorption performance, and can be compounded with the oligopeptide-1 derivative shown in the formula I to play a role in enhancing the transdermal absorption performance.
Therefore, the oligopeptide-1 derivative and the preparation method and application thereof are provided, the oligopeptide-1 derivative has more excellent antioxidant activity, the anti-ultraviolet effect is obviously improved, the expression and activity of MMP (metal matrix metalloproteinase) increased by UV (ultraviolet) are further reduced, wrinkles are effectively improved, and the skin is prevented from aging; meanwhile, the collagen protein has excellent collagen activity promoting and transdermal absorption performances.
Drawings
FIG. 1 is a graph showing the results of an overall relative permeation test of a transdermal agent in example 5 of the present invention;
FIG. 2 shows the results of UV-induced MMP-2 activity assay in example 6 of the present invention.
Detailed Description
The technical solution of the present invention is further described in detail below with reference to the following detailed description and the accompanying drawings:
example 1:
preparation of oligopeptide-1 derivatives:
dissolving oligopeptide-1 in a tetrahydrofuran/water (v/v, 1: 1.4) mixed solution, wherein the solid-to-liquid ratio is 1 g: 10 mL; adding CDI (the mass ratio of oligopeptide-1 to CDI is 1: 0.52) under the condition of ice-water bath, uniformly mixing, slowly dropwise adding into a tetrahydrofuran solution containing L-alanine-7-amino-4-methylcoumarin (the molar ratio of oligopeptide-1 to L-alanine-7-amino-4-methylcoumarin is 1: 1.3) and triethylamine (the mass ratio of oligopeptide-1 to CDI is 1: 1.2), wherein the solid-to-liquid ratio of L-alanine-7-amino-4-methylcoumarin to tetrahydrofuran is 1 g: 13 mL; after the dropwise addition is finished, reacting for 4 hours at 35 ℃; concentrating under reduced pressure, adding 3 times volume of water/ethyl acetate (v/v, 1: 2.5) mixed solution, adding hydrochloric acid to adjust pH to 2.4, washing organic phase with brine, adding anhydrous sodium sulfate, drying, filtering, and vacuum drying to obtain oligopeptide-1 derivative with chemical structure shown in the following.
1H NMR (400 MHz, CDCl3), δppm: 8.82 (s, 1H, IMI-H), 7.78 (s, 1H, IMI-H), 7.94、7.71、7.60 (3H, Ph-H), 6.32 (s, 1H, C=CH), 5.04、4.80、4.62 (3H, -CH), 3.26、3.01 (m, 2H, IMI-CH2), 3.61 (s, 2H, O=C-CH2), 2.77 (t, 2H, N-CH2), 2.49、1.56 (6H, -CH3), 1.84、1.63、1.32 (6H, -CH2)。HRMS (ESI): Calcd for C27H36N8O6, m/z [M+H]+, 568.31。
Example 2:
the oligopeptide-1 derivatives were prepared differently from example 1: 5-aminoarundoin is adopted to replace L-alanine-7-amino-4-methylcoumarin. The chemical structure is as follows:
1H NMR (400 MHz, CDCl3), δppm: 8.85 (s, 1H, IMI-H), 7.72 (s, 1H, IMI-H), 7.68、7.41 (3H, Ph-H), 7.24 (s, 1H, Pyr-H), 5.08、4.67 (2H, -CH), 3.66 (s, 2H, O=C-CH2), 3.21、3.04 (m, 2H, IMI-CH2), 3.17 (s, 2H, Pyr-CH2), 2.71 (t, 2H, N-CH2), 2.28 (s, 6H, -CH3), 1.92、1.60、1.35 (6H, -CH2)。HRMS (ESI): Calcd for C25H37N9O3, m/z [M+H]+, 511.32。
example 3:
cytotoxicity test
Human keratinocytes (HaCaT cells) were cultured at 1X 106The strain is cultured in a density division manner, and after 24 hours, the strain is replaced by a culture medium without FBS to continue the starvation treatment for 24 hours. Following treatment with the addition of biologically active substance, a final concentration of 30 mM, panel M1: oligopeptide-1 derivatives prepared in example 1; experimental group M2: oligopeptide-1 derivatives prepared in example 2; experimental group M3: the oligopeptide-1 derivative prepared in example 1 and the oligopeptide-1 derivative prepared in example 2 (the mass ratio of the two is 1: 0.8) are added to form a final concentration of 100 mug/mL; experimental group M4: oligopeptide-1. After 24 hours of treatment, the medium was removed, 40. mu.L/well of 5 mg/mL MTT was added thereto, the medium was removed after 4 hours of incubation, 200. mu.L of DMSO was added thereto in an amount of 1 mL, and after 12 minutes of shaking, the absorbance at 540 nm was measured using a spectrophotometer. The absorbance intensity after treatment with the solvent in which the biologically active substance is dissolved is used as a control and is expressed as a percentage. Cell viability was calculated according to the following formula:
cell viability% = (absorbance of bioactive substance-treated group/absorbance of control group) × 100%
The test results are shown in table 1:
TABLE 1 cytotoxicity test results
As can be seen from the data in Table 1, the oligopeptide-1 derivatives prepared by the invention have no toxicity to cells.
Example 4:
antioxidant activity and collagen production promoting activity test
Taking human skin into fiberCells (HSF) were incubated at 37 ℃ with 5% CO2Under the conditions, the culture was carried out in DMEM medium containing 10% fetal bovine serum, 100U/mL penicillin and 100. mu.g/mL streptomycin.
Taking HSF cells in logarithmic growth phase, digesting with trypsin for passage, stopping digestion with culture medium, and performing cell culture at 2 × 105The density of individual cells/well was seeded in 6-well plates and incubated at 37 ℃ with 5% CO2Culturing for 24 h under the condition, and enabling the culture to grow adherently. Then removing the original culture medium and changing the culture medium; adding bioactive substances, setting blank control group D1: a complete culture medium; positive control group D2: complete medium containing 15% vitamin C and 1% vitamin E; experimental group M1: oligopeptide-1 derivative prepared in example 1 at a final concentration of 100. mu.g/mL; experimental group M2: oligopeptide-1 derivative prepared in example 2 at a final concentration of 100. mu.g/mL; experimental group M3: the oligopeptide-1 derivative prepared in example 1 and the oligopeptide-1 derivative prepared in example 2 (the mass ratio of the two is 1: 0.8) are added to form a final concentration of 100 mug/mL; experimental group M4: oligopeptide-1, final concentration 100. mu.g/mL. After 72 h of action of the biologically active substance, the relevant activity of the cells of each group was determined according to the instructions of each kit.
I. Determination of antioxidant Activity
SOD is an intracellular antioxidase, can effectively remove superoxide anion free radicals, and can protect cells from oxidative damage. SOD activity was detected by WST-1 cell proliferation assay kit (purchased from Nanjing institute of bioengineering).
Analysis of results
The test results are shown in table 2:
TABLE 2 SOD content test results
As can be seen from the data in Table 2, the SOD content of the bioactive substances in groups M1 and M2 is obviously higher than that in groups D1 and M4 and higher than that in group D2, which indicates that the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 by adopting L-alanine-7-amino-4-methylcoumarin or 5-aminoarundoine has more excellent antioxidant effect and the antioxidant property is better than that of a positive control group. The effect of the M3 group is obviously better than that of the M1 group and the M2 group, which shows that the antioxidant activity is better by compounding the oligopeptide-1 derivatives shown in the formula I and the formula II.
Determination of collagen content
By measuring the level of hydroxyproline in the cells, the collagen content can be assessed. The hydroxyproline content is determined by adopting an enzyme digestion method.
Analysis of results
The test results are shown in table 3:
TABLE 3 hydroxyproline content test results
The data in table 3 show that the hydroxyproline content after the treatment of the bioactive substances in the group M1 is obviously higher than that in the groups D1 and M4 and higher than that in the group D2, which indicates that the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 by using L-alanine-7-amino-4-methylcoumarin has more excellent collagen generation promoting activity, and can increase the skin thickness, tighten the skin and increase the elasticity; and the activity performance is better than that of a positive control group. The hydroxyproline content after the treatment of the M2 group bioactive substances is equivalent to that of the M4 group, which shows that the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 by using 5-aminoarundoin does not have negative influence on the collagen generation promoting activity of the oligopeptide-1 derivative. The effect of the M3 group is obviously better than that of the M1 group and the M2 group, which shows that the compound use of the oligopeptide-1 derivatives shown in the formula I and the formula II has the synergistic enhancement effect and better collagen generation promoting activity, and the existence of the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 with 5-aminoarundoin is shown, so that the collagen generation promoting activity of the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 with L-alanine-7-amino-4-methylcoumarin has the gain effect.
Example 5:
transdermal absorption Performance test
SD rats (sourced from Shanghai Si Laike laboratory animals, Inc.) were dehaired on the abdomen, and intact abdominal skin tissues were taken and placed in 0.9% physiological saline for use.
Experiment grouping
Experimental group M1: oligopeptide-1 derivatives prepared in example 1; experimental group M2: oligopeptide-1 derivatives prepared in example 2; experimental group M3: the oligopeptide-1 derivative prepared in example 1 and the oligopeptide-1 derivative prepared in example 2 (the mass ratio of the two is 1: 0.8); experimental group M4: oligopeptide-1.
Preparing a transdermal substance: collecting 15 μ g oligopeptide-1 or its derivative, and adding 500 μ L physiological saline to obtain transdermal substance.
Transdermal drug delivery
The lower groove of the transdermal groove is filled with normal saline and is put into a magnetic stirrer, the intact rat abdominal skin tissue prepared before is well fixed between the upper groove and the lower groove of the transdermal groove, and the transdermal substance is added into the upper groove. Then placing in a Franz transdermal diffusion instrument, keeping the temperature at 37 ℃ and performing at 300 rpm, and taking 200 mu L of collecting liquid from the opening of a lower groove of a transdermal groove after 16 h; then, the oligopeptide-1 or the derivative thereof is quantitatively detected. And (3) determining the content of the oligopeptide-1 or the derivative thereof in the collected liquid: and (3) taking the collection liquid, measuring the absorbance at the corresponding wavelength, and then calculating the concentration of the oligopeptide-1 or the derivative thereof of the measured point sample according to the standard curve so as to further calculate the integral relative permeation quantity of the transdermal substance.
Analysis of results
The test results are shown in fig. 1. From the analysis in the figure, the overall relative permeation amount of the transdermal substance after the sample treatment of the group M1 is equivalent to that of the group M4, which shows that the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 by using the L-alanine-7-amino-4-methylcoumarin has no negative influence on the transdermal absorption performance. The overall relative permeability of the transdermal substance treated by the M2 group of samples is obviously better than that of the M4 group of samples, which indicates that the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 by using 5-aminoarundoin has better transdermal absorption performance. The effect of the M3 group is obviously better than that of the M1 group and the M2 group, which shows that the transdermal absorption activity is better when the oligopeptide-1 derivatives shown in the formula I and the formula II are compounded, and the existence of the oligopeptide-1 derivatives prepared by modifying the oligopeptide-1 with L-alanine-7-amino-4-methylcoumarin shows that the transdermal absorption activity of the oligopeptide-1 derivatives prepared by modifying the oligopeptide-1 with 5-aminoarundoine has a gain effect.
Example 6:
determination of anti-ultraviolet Activity
To evaluate the effect of derivative samples on UV-induced MMP-2 activity in UV-irradiated human skin fibroblasts, this test was performed using gelatinase spectroscopy. MMP-2 is a proteolytic enzyme that increases when ultraviolet or oxidative stress is applied to fibroblasts. A sample of 100. mu.M final concentration of fibroblasts was taken, oxidative stress was induced by ultraviolet rays, and the activity of MMP-2 was measured in the supernatant. Wherein, setting blank control group N1: no sample was added and no uv irradiation was performed; uv control group N2: no sample was added; experimental group M1: oligopeptide-1 derivatives prepared in example 1; experimental group M2: oligopeptide-1 derivatives prepared in example 2; experimental group M3: the oligopeptide-1 derivative prepared in example 1 and the oligopeptide-1 derivative prepared in example 2 (the mass ratio of the two is 1: 0.8); experimental group M4: oligopeptide-1.
Analysis of results
The test results are shown in fig. 2. From the analysis in the figure, the MMP-2 activity after the sample treatment of the M1 and M2 groups is obviously lower than that of the D2 and M4 groups, which shows that the oligopeptide-1 derivative prepared by modifying the oligopeptide-1 by adopting L-alanine-7-amino-4-methylcoumarin or 5-aminoarundoin has more excellent efficacy of inhibiting the ultraviolet-induced MMP-2 activity, the anti-ultraviolet effect is obviously improved, the expression and activity of MMP increased due to UV can be further reduced, and the collagen synthesis reduced due to UV can be increased; the collagen is effective in improving wrinkle and preventing skin aging. The effect of the M3 group is obviously better than that of the M1 group and the M2 group, and is equivalent to that of the D1 group, which shows that the oligopeptide-1 derivatives shown in the formula I and the formula II are compounded for use, have a synergistic enhancement effect, have better efficacy of inhibiting ultraviolet-induced MMP-2 activity, and are equivalent to the MMP-2 activity of normal cells.
Conventional techniques in the above embodiments are known to those skilled in the art, and therefore, will not be described in detail herein.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
Claims (6)
1. An oligopeptide-1 derivative, the chemical structure of which is shown in formula I or formula II:
I；
II。
2. a method for preparing the oligopeptide-1 derivative of claim 1, which comprises: the oligopeptide-1 derivative is prepared by amidation reaction of carboxyl in a GHK-1 structure and amino in an L-alanine-7-amino-4-methylcoumarin or 5-aminoarundoin structure.
3. A cosmetic composition comprising the oligopeptide-1 derivative of claim 1.
4. The cosmetic composition of claim 3, wherein: the addition amount of the oligopeptide-1 derivative is 0.01-0.5 wt%.
5. Use of the oligopeptide-1 derivative according to claim 1 in the preparation of cosmetics for antioxidation.
6. Use of the oligopeptide-1 derivative according to claim 1 for the preparation of cosmetics for lightening wrinkles.
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Address after: 518000 floor 5, building 206 plant (Building B, Hengyu Center), No. 19, Dengliang Road, Dengliang community, Nanshan street, Nanshan District, Shenzhen, Guangdong Province Patentee after: Shenzhen Branch of Zhejiang Peptide Biology Co.,Ltd. Address before: 518000 floor 5, building 206 plant (Building B, Hengyu Center), No. 19, Dengliang Road, Dengliang community, Nanshan street, Nanshan District, Shenzhen, Guangdong Province Patentee before: Zhejiang Pai peptide biology Co.,Ltd. Shenzhen Branch |