CN115403462B - Supermolecule succinic acid solvent, supermolecule modified elastin, and preparation methods and applications thereof - Google Patents
Supermolecule succinic acid solvent, supermolecule modified elastin, and preparation methods and applications thereof Download PDFInfo
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- 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
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- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
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Abstract
The invention relates to a supermolecule succinic acid solvent, supermolecule modified elastin, a preparation method and application thereof. The supermolecule modified elastin is obtained by encapsulating elastin with the supermolecule succinic acid solvent. The supermolecule succinic acid solvent has good skin penetration promoting effect, is safe and mild, can be used as a delivery carrier to smoothly deliver skin care active molecules with low transdermal delivery efficiency and low bioavailability to deep skin, and improves the bioavailability. The supermolecule modified elastin can overcome the problems of low percutaneous delivery efficiency and low bioavailability of elastin, smoothly deliver elastin to deep skin, improve bioavailability, has good biological safety and stability, and provides a simple and low-cost effective means for wide application of elastin in the cosmetic field.
Description
Technical Field
The invention belongs to the technical field of cosmetics, and relates to a supermolecule succinic acid solvent, supermolecule modified elastin and a preparation method and application thereof, in particular to a supermolecule succinic acid solvent and supermolecule modified elastin which active molecules can be delivered to deep layers of skin to play a role and can not stimulate the skin, and a preparation method and application thereof.
Background
Elastin is an important component of elastic fibers, which are mainly present in ligaments and vascular walls, accounting for only 2% of the total protein of the dermis, but can confer elasticity and tensile properties to tissues, playing a very important role in skin elasticity and softness. With aging of skin due to endogenous and exogenous aging, elastin is gradually decomposed, and its deficiency causes skin to loose, sagging and fine wrinkles. And the regeneration and the supplementation of the elastin can inhibit the skin aging process and prevent the aging problem. Therefore, the application of the elastin in the cosmetic field can achieve the effects of keeping the skin young, fine and elastic.
For example, CN114081858A discloses a face-refreshing and anti-aging mask and a preparation method thereof, the face-refreshing and anti-aging mask comprises the following raw material components: water, glycerol, butylene glycol, trehalose, hydroxyethyl urea, xylitol-based glucoside, dehydrated xylitol, aloe extract, gentian extract, propylene glycol, shea butter, lavender oil, hydrolyzed keratin, collagen, elastin, 1, 2-hexanediol, ammonium acryloyldimethyl taurate/VP copolymer, arginine, carbomer, disodium EDTA. The rejuvenation and anti-aging facial mask can effectively supplement water and preserve moisture, improve skin elasticity, keep skin compact, prevent skin from being dark, and further play a role in rejuvenating skin.
Although elastin has various excellent biological activities, it is difficult to be directly absorbed by the skin due to its own molecular weight, polarity, etc., so that it is difficult to exert its specific effects. Therefore, development of a delivery vehicle that can deliver elastin deep into the skin to exert its effect without adversely affecting the skin, such as irritation, is of great application value.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a supermolecule succinic acid solvent, supermolecule modified elastin and a preparation method and application thereof, in particular to a supermolecule succinic acid solvent, supermolecule modified elastin and a preparation method and application thereof, wherein the supermolecule succinic acid solvent and the supermolecule modified elastin can deliver active molecules to deep layers of skin to play a role without stimulating the skin.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a supramolecular succinic acid solvent obtained from the reaction of betaine and succinic acid.
The invention creatively develops an ionic liquid obtained by the reaction of betaine and succinic acid, namely the supermolecule succinic acid solvent, which has good skin penetration promoting effect, is safe and mild, can be used as a delivery carrier to smoothly deliver skin care active molecules with low transdermal delivery efficiency and low bioavailability to deep skin, and improves the bioavailability.
Preferably, the molar ratio of betaine to succinic acid is 1:6-6:1, for example, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, etc., and other specific values within the numerical range are selectable, and will not be described in detail herein.
In a second aspect, the present invention provides a method for preparing a supramolecular succinic acid solvent according to the first aspect, the method comprising: dissolving betaine and succinic acid in solvent respectively, dripping succinic acid solution into betaine solution under stirring, reacting, and removing solvent.
The preparation method of the supermolecule succinic acid solvent is simple and easy to operate, and is suitable for large-scale industrial production. When the product is prepared according to the following specific process parameters, the obtained product has more stable and more obvious penetration promoting effect.
Preferably, the reaction is carried out under the protection of an inert gas, including argon, helium or nitrogen.
Preferably, the reaction is carried out in a water bath at 20-80 ℃ (e.g., 20 ℃, 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃, 80 ℃ etc.) for 5-24 hours (e.g., 5 hours, 10 hours, 15 hours, 18 hours, 20 hours, 24 hours, etc.); other specific point values within the numerical range can be selected, and will not be described in detail herein.
Preferably, the solvent is removed by vacuum drying.
In a third aspect, the present invention provides the use of a supramolecular succinic acid solution according to the first aspect in the preparation of a permeation enhancing carrier.
In a fourth aspect, the present invention provides the use of a supramolecular succinic acid solution according to the first aspect for the preparation of a supramolecular modified active molecule comprising elastin and/or collagen.
In a fifth aspect, the present invention provides a supermolecule-modified elastin obtained from the supermolecule succinic acid solvent-entrapped elastin of the first aspect.
The supermolecule modified elastin can overcome the problems of low percutaneous delivery efficiency and low bioavailability of elastin, smoothly deliver elastin to deep skin, improve bioavailability, has good biological safety and stability, and provides a simple and low-cost effective means for wide application of elastin in the cosmetic field.
In a sixth aspect, the present invention provides a method for producing a supermolecule-modified elastin according to the fifth aspect, the method comprising: dripping elastin into supermolecule succinic acid solvent, and mixing.
Preferably, the mixing is performed at a stirring state of 15-40 ℃ (e.g., 15 ℃, 18 ℃, 20 ℃, 25 ℃, 30 ℃, 40 ℃ and the like) for 1-20 hours (e.g., 1 hour, 4 hours, 6 hours, 8 hours, 10 hours, 15 hours, 20 hours and the like); other specific point values within the numerical range can be selected, and will not be described in detail herein.
Preferably, the mixing is performed under an inert gas blanket, the inert gas including argon, helium or nitrogen.
In a seventh aspect, the present invention provides the use of a supramolecular succinic acid solvent according to the first aspect or a supramolecular modified elastin according to the fifth aspect in the preparation of a cosmetic.
Compared with the prior art, the invention has the following beneficial effects:
the invention creatively develops an ionic liquid obtained by the reaction of betaine and succinic acid, namely the supermolecule succinic acid solvent, which has good skin penetration promoting effect, is safe and mild, can be used as a delivery carrier to smoothly deliver skin care active molecules with low transdermal delivery efficiency and low bioavailability to deep skin, and improves the bioavailability. The supermolecule modified elastin can overcome the problems of low percutaneous delivery efficiency and low bioavailability of elastin, smoothly deliver elastin to deep skin, improve bioavailability, has good biosafety and stability, and provides a simple and low-cost effective means for wide application of elastin in the cosmetic field.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the supramolecular succinic acid solvent prepared in example 1.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The following related active molecular elastin and collagen are all purchased from Shenzhen Hemerocallis Biotechnology Inc.
Example 1
The present example provides a supermolecule succinic acid solvent and a supermolecule modified elastin, the preparation method is as follows:
(1) Weighing 0.01mol of betaine to be dissolved in water, weighing 0.01mol of succinic acid to be dissolved in water, uniformly mixing the succinic acid solution, transferring the mixture into a dropping funnel, dropwise adding the mixture into the betaine solution under the stirring state at 25 ℃, transferring the mixture into a water bath at 30 ℃ under the protection of nitrogen after the dropwise adding is finished, reacting for 24 hours, and vacuum drying for 12 hours after the reaction is finished to remove water to obtain the supermolecule succinic acid solvent. The nuclear magnetic hydrogen spectrum is shown in figure 1.
(2) Under the nitrogen atmosphere, dissolving the supermolecule succinic acid solvent in water, then dripping 0.01mg of elastin, stirring for 4 hours at 25 ℃, concentrating and drying for 6 hours, and obtaining the supermolecule modified elastin.
Example 2
The present example provides a supermolecule succinic acid solvent and a supermolecule modified elastin, the preparation method is as follows:
(1) Weighing 0.01mol of betaine to be dissolved in water, weighing 0.03mol of succinic acid to be dissolved in water, uniformly mixing the succinic acid solution, transferring the mixture into a dropping funnel, dropwise adding the mixture into the betaine solution under the stirring state at 25 ℃, transferring the mixture into a water bath at 40 ℃ under the protection of argon after the dropwise adding is finished, reacting for 18 hours, and vacuum drying for 24 hours after the reaction is finished to remove water to obtain the supermolecule succinic acid solvent.
(2) Under the argon atmosphere, dissolving the supermolecule succinic acid solvent in water, then dripping 0.01mg of elastin, stirring for 6 hours at 35 ℃, concentrating and drying for 6 hours, and obtaining the supermolecule modified elastin.
Example 3
The present example provides a supermolecule succinic acid solvent and a supermolecule modified elastin, the preparation method is as follows:
(1) Weighing 0.01mol of betaine to be dissolved in water, weighing 0.06mol of succinic acid to be dissolved in water, uniformly mixing the succinic acid solution, transferring the mixture into a dropping funnel, dropwise adding the mixture into the betaine solution under the stirring state at 25 ℃, transferring the mixture into a water bath at 50 ℃ under the protection of argon after the dropwise adding is finished, reacting for 12 hours, and vacuum drying for 24 hours after the reaction is finished to remove water to obtain the supermolecule succinic acid solvent.
(2) Under the argon atmosphere, dissolving the supermolecule succinic acid solvent in water, then dripping 0.01mg of elastin, stirring for 15h at 20 ℃, concentrating and drying for 6h, and obtaining the supermolecule modified elastin.
Example 4
The present example provides a supermolecule succinic acid solvent and a supermolecule modified elastin, the preparation method is as follows:
(1) Weighing 0.03mol of betaine to be dissolved in water, weighing 0.01mol of succinic acid to be dissolved in water, uniformly mixing the succinic acid solution, transferring the mixture into a dropping funnel, dropwise adding the mixture into the betaine solution under the stirring state at 25 ℃, transferring the mixture into a water bath at 60 ℃ under the protection of argon after the dropwise adding is finished, reacting for 5 hours, and vacuum drying for 24 hours after the reaction is finished to remove water to obtain the supermolecule succinic acid solvent.
(2) Under the argon atmosphere, dissolving the supermolecule succinic acid solvent in water, then dripping 0.01mg of elastin, stirring for 8 hours at 30 ℃, concentrating and drying for 6 hours, and obtaining the supermolecule modified elastin.
Example 5
The present example provides a supermolecule succinic acid solvent and a supermolecule modified elastin, the preparation method is as follows:
(1) Weighing 0.06mol of betaine to be dissolved in water, weighing 0.01mol of succinic acid to be dissolved in water, uniformly mixing the succinic acid solution, transferring the mixture into a dropping funnel, dropwise adding the mixture into the betaine solution under the stirring state at 25 ℃, transferring the mixture into a water bath at 20 ℃ under the protection of argon after the dropwise adding is finished, reacting for 24 hours, and vacuum drying for 24 hours after the reaction is finished to remove water to obtain the supermolecule succinic acid solvent.
(2) Under the argon atmosphere, dissolving the supermolecule succinic acid solvent in water, then dripping 0.01mg of elastin, stirring for 10 hours at 25 ℃, concentrating and drying for 6 hours, and obtaining the supermolecule modified elastin.
Example 6
This example provides a supramolecular succinic acid solvent and a supramolecular modified collagen, the preparation method differs from example 1 only in that 0.01mg of elastin is replaced by 0.01mg of collagen, all other conditions being maintained.
Comparative example 1
This comparative example provides a supramolecular glutamic acid solvent and a supramolecular modified elastin, the preparation method differs from example 1 only in that 0.01mol of succinic acid is replaced by 0.01mol of glutamic acid, the other conditions being kept unchanged.
Comparative example 2
This comparative example provides a supramolecular glycine solvent and a supramolecular modified elastin, the preparation process differs from example 1 only in that 0.01mol of succinic acid is replaced by 0.01mol of glycine, all other conditions being maintained.
Comparative example 3
This comparative example provides a pure supramolecular succinic acid solvent, prepared in the same manner as in example 1.
Comparative example 4
This comparative example provides a simple elastin monomer prepared in the same manner as in example 1.
Comparative example 5
This comparative example provides a simple collagen monomer prepared in the same manner as in example 1.
Test example 1
Biological safety evaluation:
the operation method comprises the following steps: after keratinocytes are treated by using samples to be tested with different concentrations, experimental operation is carried out according to a CCK-8 cell proliferation detection kit of Biyun Tian biotechnology Co., ltd, quantitative analysis is carried out by an enzyme-labeling instrument, and the cell vitality of each group is determined.
The test results are shown in table 1:
TABLE 1
| Group of | 0.1μg/mL | 50μg/mL | 200μg/mL | 800μg/mL |
| Example 1 | 99.83％ | 99.65％ | 97.63％ | 98.77％ |
| Example 2 | 98.87％ | 99.23％ | 97.89％ | 99.01％ |
| Example 3 | 98.93％ | 98.65％ | 98.93％ | 98.77％ |
| Example 4 | 98.97％ | 98.23％ | 99.29％ | 98.11％ |
| Example 5 | 97.87％ | 99.13％ | 97.89％ | 97.31％ |
| Example 6 | 99.93％ | 98.15％ | 98.93％ | 98.77％ |
| Comparative example 1 | 98.87％ | 99.73％ | 98.29％ | 98.01％ |
| Comparative example 2 | 97.93％ | 98.55％ | 96.93％ | 97.77％ |
| Comparative example 3 | 98.87％ | 99.27％ | 97.89％ | 98.61％ |
| Comparative example 4 | 98.93％ | 98.65％ | 98.93％ | 98.17％ |
As can be seen from the data in table 1: the supermolecule succinic acid solvent and the supermolecule modified elastin related by the invention have low cytotoxicity and high biological safety.
Test example 2
Skin penetration test:
the operation method comprises the following steps: the skin permeation performance of supermolecular elastin is evaluated by taking isolated mini-fragrant pig skin as a model, performing an in-vitro skin permeation experiment at 350r/min through a Franz diffusion cell at 32+ -0.1 ℃ and detecting the cumulative transdermal quantity (mug/cm < 2 >) of elastin or collagen at 24 h. The test results are shown in table 2:
TABLE 2
| Group of | Subcutaneous tissue | Stratum corneum layer |
| Example 1 | 68.57 | 13.32 |
| Example 2 | 62.57 | 10.46 |
| Example 3 | 59.21 | 11.89 |
| Example 4 | 59.78 | 13.21 |
| Example 5 | 56.12 | 10.78 |
| Example 6 | 51.39 | 9.87 |
| Comparative example 1 | 40.76 | 9.34 |
| Comparative example 2 | 37.21 | 8.89 |
| Comparative example 4 | 5.21 | 10.39 |
| Comparative example 5 | 3.21 | 8.87 |
As can be seen from the data in table 2: the supermolecule succinic acid solvent disclosed by the invention can greatly improve the percutaneous permeation of active molecules, wherein the retention of elastin in skin is obviously greater than that of elastin monomer, and the retention of collagen in skin is obviously greater than that of collagen monomer.
Test example 3
Evaluation test of collagen effect:
the operation method comprises the following steps: keratinocytes were treated with different samples to be tested (elastin concentration of 5000 ppm) for 24h, control groups were treated with PBS solution, experimental groups were treated with hydrogen peroxide solution (concentration 200. Mu.M) +each group of sample solutions, MMP-1 was detected according to the Metalloplasmin I (MMP-1) Elisa assay kit, and quantitative evaluation was performed using an enzyme-labeled instrument.
The test results are shown in table 3:
TABLE 3 Table 3
| Group of | Metal matrix enzyme I (% control) |
| Control group | 100 |
| Hydrogen peroxide | 145.1 |
| Example 1 | 117.2 |
| Example 2 | 118.9 |
| Example 3 | 121.3 |
| Example 4 | 120.02 |
| Example 5 | 124.9 |
| Comparative example 1 | 129.7 |
| Comparative example 2 | 122.65 |
| Comparative example 4 | 120.87 |
As can be seen from the data in table 3: compared with the comparative example, the supermolecule modified elastin has more excellent effects of inhibiting the metal matrix enzyme I, promoting the generation of collagen and resisting wrinkle.
The applicant states that the present invention is illustrated by the above examples as a supramolecular succinic acid solvent, a supramolecular modified elastin, and methods for preparing and using the same, but the present invention is not limited to, i.e. it is not meant that the present invention must be practiced in dependence upon the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the scope of the technical concept of the present invention, and all the simple modifications belong to the protection scope of the present invention.
In addition, the specific features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described further.
Claims (7)
1. The supermolecule modified elastin is characterized in that the supermolecule modified elastin is obtained by encapsulating elastin with a supermolecule succinic acid solvent;
the supermolecule succinic acid solvent is obtained by the reaction of betaine and succinic acid, and the preparation method comprises the following steps: respectively dissolving betaine and succinic acid in solvent, dripping succinic acid solution into betaine solution under stirring, reacting in water bath at 20-80deg.C under the protection of inert gas such as argon, helium or nitrogen for 5-24-h, and removing solvent.
2. The supermolecule modified elastin of claim 1, wherein the molar ratio of betaine to succinic acid is 1:6-6:1.
3. The supermolecule modified elastin of claim 1, wherein the solvent removal is vacuum drying.
4. A method for preparing a supermolecule-modified elastin according to any of claims 1-3, comprising: dripping elastin into supermolecule succinic acid solvent, and mixing.
5. The method for producing a supermolecule-modified elastin according to claim 4, wherein the mixing is carried out at 15 to 40℃under stirring for 1 to 20 h.
6. The method for producing a supermolecule-modified elastin according to claim 4, wherein the mixing is performed under the protection of an inert gas, the inert gas comprising argon, helium or nitrogen.
7. Use of the supermolecule-modified elastin according to any of claims 1-3 for the preparation of cosmetics.
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