CN115715745B - Oil-control acne-removing gel based on 3-hydroxy medium-chain fatty acid slow release, preparation method and application - Google Patents
Oil-control acne-removing gel based on 3-hydroxy medium-chain fatty acid slow release, preparation method and application Download PDFInfo
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- 206010000496 acne Diseases 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 230000000694 effects Effects 0.000 claims abstract description 32
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims abstract description 21
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Abstract
The invention provides an oil control acne removal gel based on 3-hydroxy medium chain fatty acid slow release, a preparation method and application thereof, wherein 3-hydroxy medium chain fatty acid is loaded in hydrogel formed by chitosan and oxidized hyaluronic acid, and the 3-hydroxy medium chain fatty acid can be slowly and stably released after the gel is applied to skin due to weak interaction of ionic bonds between the 3-hydroxy medium chain fatty acid and the chitosan, so that the activity of 5 alpha-reductase is inhibited, and a good oil control effect is generated together with the hyaluronic acid with a moisturizing effect; meanwhile, the 3-hydroxyl medium chain fatty acid and chitosan also synergistically inhibit propionibacteria, and the gel layer can absorb acne secretion, so that the acne-removing gel has an outstanding acne-removing effect. The oil-control acne-removing gel patch is composed of natural products or derivatives thereof, is transparent and moist, has good skin compatibility, is not easy to be allergic, has remarkable oil-control acne-removing effect, and can be used in daily chemicals and medicine related fields such as facial skin care, beauty treatment, acne prevention and the like.
Description
Technical Field
The invention belongs to the technical field of biological materials and daily chemicals, and relates to a multifunctional gel patch for external use on a human body.
Background
Hydroxyl-containing organic acids have been widely used for skin care. For example, short chain alpha hydroxy fatty acids, including glycolic acid, citric acid, malic acid, tartaric acid, lactic acid, and the like, exfoliate the surface layer and regulate the stratum corneum and improve acne. However, short-chain hydroxy fatty acids are difficult to penetrate into deep layers of skin due to their water solubility and acidity, and are liable to cause adverse reactions such as skin swelling, burn and itching, so they should be carefully used.
In recent years, 10-hydroxydecanoic acid and 10-hydroxy-2-decenoic acid (royal jelly acid) have been found to have antibacterial, whitening, ultraviolet radiation resistance and the like, and thus have been used in high-end skin care products (CN 111111494303a, JP 3693754B 2). Compared with short-chain and high-activity alpha hydroxy fatty acid, the 10-hydroxy dec (ene) acid has longer carbon chain, so that the 10-hydroxy dec (ene) acid has weaker acid and hydrophilicity, and the hydroxy group and the carboxyl group are furthest located, so that the effect is very mild, and skin irritation is not easy to generate. However, 10-hydroxydecanoic acid is mainly derived from castor oil, has complex hydrolysis and purification processes and is easy to mix into ricin; the royal jelly acid is mainly extracted from the royal jelly, and the source of the royal jelly acid is very limited, so that the price is high.
3-hydroxy medium chain fatty acids are widely found in bacterially secreted glycolipids and polyhydroxyalkanoates (Applied Microbiology and Biotechnology,2000, 53:167-172), and are available by hydrolysis and the like, and are more widely available. According to the chemical structure of different hydroxy fatty acids, it is presumed that the relative positions of hydroxy groups and carboxyl groups, the carbon chain length and the number of carbon-carbon double bonds can affect the biological activity of the hydroxy fatty acids, however, the effect of the 3-hydroxy medium chain fatty acid on the skin has not been reported yet, and the advantages and disadvantages of the 3-hydroxy medium chain fatty acid compared with 10-hydroxy decanoic acid are not clear.
Disclosure of Invention
Aiming at overcoming the defects of the prior art, the invention provides an oil-control acne-removing gel based on 3-hydroxy medium-chain fatty acid, a preparation method and application thereof.
The technical scheme adopted by the invention is as follows:
the preparation method of the oil-control acne-removing gel based on 3-hydroxy medium chain fatty acid slow release comprises the following steps:
(1) Dissolving 1-5 parts by weight of 3-hydroxy medium chain fatty acid and 1-10 parts by weight of oxidized hyaluronic acid in a first part by weight of water and adjusting the pH to 7 to obtain a first solution;
(2) Dissolving 1-5 parts by weight of chitosan in a second part by weight of 0.1wt% acetic acid aqueous solution, and adjusting the pH to 5 to obtain a second solution;
(3) Mixing the first solution and the second solution to obtain an oil-control acne-removing gel; wherein the sum of the first and second parts by weight is 80-97 parts by weight.
Wherein aldehyde groups in the oxidized hyaluronic acid and amine groups of the chitosan are subjected to Schiff base reaction to generate jelly-like gel, and the gel is suitable for skin surface application; and the 3-hydroxy medium chain fatty acid with negative charges and the chitosan with positive charges form an ionic bond, so that the gel can load the 3-hydroxy medium chain fatty acid and play a role in slow release. Because 3-hydroxy medium chain fatty acid has physiological effect of inhibiting 5 alpha-reductase (participating in testosterone metabolism in vivo and causing seborrheic alopecia with high activity), and hyaluronic acid has moisturizing effect, the two effects together play a role in reducing facial skin fat secretion; in addition, the 3-hydroxy medium chain fatty acid has strong bactericidal effect, and can effectively kill propionibacterium causing acne, thereby inhibiting acne for a long time.
Further, in the above step, the adjustment of the pH may be performed by adding sodium hydroxide, hydrochloric acid, acetic acid or the like.
Further, the 3-hydroxy medium chain fatty acid refers to a 3-hydroxy fatty acid with 5-14 carbon atoms and 0-2 carbon-carbon double bonds, and further has a chemical structural formula as follows:
wherein n=5-11, m=10-24.
Further, the oxidized hyaluronic acid is prepared by the following method: dissolving 1-10 parts by weight of hyaluronic acid in 100 parts by weight of water, adding 0.5-2 times by weight of sodium periodate, adjusting the pH to 6, reacting for 3 hours at room temperature, adding glycol to terminate the reaction, dialyzing and freeze-drying to obtain oxidized hyaluronic acid.
The oil-control acne-removing gel prepared by the preparation method is characterized in that ionic bonds are formed between 3-hydroxyl medium-chain fatty acid and chitosan with positive charges and are loaded on jelly-like gel generated by the reaction of oxidized hyaluronic acid and chitosan.
Use of the oil-control acne-removing gel, comprising:
as oil control and/or acne removal medicine;
can be used as acne preventing and treating medicine.
Further, the oil control acne removal gel realizes oil control by inhibiting the activity of 5 alpha-reductase; the oil-control acne-removing gel realizes acne removal and acne prevention by killing propionibacteria.
The beneficial effects of the invention are as follows: the oil-control acne-removing gel containing 3-hydroxy medium chain fatty acid prepared by the invention has multiple effects and innovativeness. First, the inhibition rate of 3-hydroxy medium chain fatty acid to 5α -reductase and the bactericidal effect to propionibacterium are significantly better than those of 10-hydroxydecanoic acid and 10-hydroxy-2-decenoic acid, which may be related to the closer hydroxy position to the carboxyl group, and thus the higher bioactivity. Secondly, the slow release of the 3-hydroxyl medium-chain fatty acid is realized by utilizing the charge attraction effect of the chitosan and the 3-hydroxyl medium-chain fatty acid, and the 3-hydroxyl medium-chain fatty acid can be slowly and stably released after the gel is applied to the skin, so that the activity of 5 alpha-reductase is inhibited, and a good oil control effect is generated together with the hyaluronic acid with a moisturizing effect, so that the oil control and sterilization effects can be exerted for a long time. And thirdly, the invention skillfully designs the synergistic oil control effect of the 3-hydroxyl medium-chain fatty acid and the hyaluronic acid and the synergistic sterilization effect of the 3-hydroxyl medium-chain fatty acid and the chitosan, and the gel layer can absorb acne secretion, so that the acne-removing gel has outstanding acne-removing effect. Compared with 3-hydroxy medium chain fatty acid, the gel product has the synergistic characteristic of functions; finally, the product of the invention adopts natural polymer chitosan and hyaluronic acid as raw materials, and the 3-hydroxyl medium-chain fatty acid is derived from microorganism metabolic products, thereby conforming to the development concept of green and healthy daily chemicals. The invention has the advantages of transparency, moisture, good skin compatibility, difficult allergy, remarkable oil control and acne removal effects, and can be used in daily chemical and medicine related fields such as facial skin care, beauty treatment, acne prevention and treatment, and the like.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's knowledge.
Example 1: preparation of oxidized hyaluronic acid
Dissolving 10g of hyaluronic acid in 100ml of water, adding 10g of sodium periodate, adding sodium hydroxide or hydrochloric acid to adjust the pH to 6, stirring at room temperature for 3 hours, adding 5ml of glycol to terminate the reaction, dialyzing by using a dialysis bag with the molecular weight cutoff of 600Da, and freeze-drying to obtain 9.4g of oxidized hyaluronic acid. The aldehyde group content was determined by titration with hydroxylamine hydrochloride, and the degree of oxidation was found to be 32%.
Example 2: preparation of oil-control acne-removing gel based on 3-hydroxy medium-chain fatty acid
Different 3-hydroxy medium chain fatty acids and oxidized hyaluronic acid are dissolved in water together, sodium hydroxide or acetic acid is added to adjust the pH to 7, and the mixture is stirred until the mixture is clear and transparent. Chitosan was dissolved in 0.1wt% aqueous acetic acid, stirred to clear and transparent, and then added with sodium hydroxide or acetic acid to adjust the pH to 5. Subsequently, the above two solutions were mixed and stirred well to form a jelly-like gel. The composition formula is shown in table 1.
TABLE 1 formulation of oil control acne-removing gel
Example 3: determination of the Release Properties of 3-hydroxy Medium-chain fatty acids
The four gels of example 2, numbered 3# -6#, were each applied to 1g of the surface of pig skin (from freshly killed pig belly skin) and placed in a 37 ℃ incubator for 2-24 hours, the gel was scraped off, the residual 3-hydroxy medium chain fatty acid was extracted with ethyl acetate, the concentration of the 3-hydroxy medium chain fatty acid was determined by HPLC-differential refractometry, and the released 3-hydroxy medium chain fatty acid content was calculated. The results are shown in Table 2. It can be seen that as the carbon chain length increases, the release rate of 3-hydroxy medium chain fatty acids increases, possibly in relation to its increased hydrophobicity leading to increased skin penetration and thus faster release into the pigskin layer.
TABLE 2 3 time-dependent release rate of hydroxy medium chain fatty acids
Example 4: antibacterial effect test of gel
7 250mL Erlenmeyer flasks were prepared, 0.75g of the four gels numbered 3-6 # in example 2 were added to 4 of the flasks, equal amounts of the gels containing 10-hydroxydecanoic acid and 10-hydroxy-2-decenoic acid were added to 2 of the flasks as test control groups (7 # and 8 #), 1 flask was not added as blank control group, and then 70mL of 0.03mol/L PBS buffer was added to each flask. 5mL of propionibacterium acnes (Propionibacterium acnes, ATCC 11827) bacterial liquid is added into each flask, the final gel concentration is 10g/L, the bottle stopper is covered, the flask is placed on a constant temperature oscillator, 1mL of the flask is respectively sampled after the flask is oscillated for 12h and 24h at the speed of 150r/min under the condition of 24 ℃, 1mL of the flask is respectively sucked after the flask is diluted to a proper multiple by a 10-fold dilution method, the flask is respectively transferred into a sterilized plate, the flask is poured into a nutrient agar culture medium and is cultured for 24h at the temperature of 37 ℃, then the colony count on the plate is counted, and the dilution multiple is multiplied to obtain the viable bacteria concentration in different flasks, and the bacteriostasis rate is calculated according to the following formula:
wherein:
antibacterial Rate of Y-sample
W t Blank control burnConcentration of viable bacteria in bottle
Q t Concentration of viable bacteria in sample flask
The results of the sterilization rate after 12h and 24h are shown in Table 3, and the 3-hydroxy medium chain fatty acid has excellent sterilization effect and synergistic sterilization effect with chitosan.
TABLE 3 antibacterial effect test of oil control and acne removal gel based on 3-hydroxy medium chain fatty acid
Example 5: determination of inhibition of 5 alpha-reductase by gel
10 male rats are taken, 5-alpha reductase is extracted from the prostate tissues of the male rats by centrifugation and other modes, different reagents are sequentially added according to the method shown in table 4, the four gels with the number of 3# -6# in the example 2 are used as test control groups (7 # and 8 #) for reaction at 37 ℃ for 30min, 2mL of dichloromethane is added after the reaction is finished to stop the reaction, 1min is oscillated after the reaction is stopped, 5000RPM/min is centrifuged for 10min, the upper water phase is removed, about 1.0mL of organic phase is removed, the organic phase is evaporated to dryness, dissolved in 1.0mL of methanol after evaporation, and the testosterone peak area is measured at the wavelength of 245nm by liquid chromatography for three times in parallel.
TABLE 4 reagent compositions of different reaction tubes (unit: mL)
The inhibition was calculated using the following formula:
the results are shown in Table 5 below, which shows that 3-hydroxy-containing medium chain fatty acids have better inhibition of 5α -reductase than the control group of 10-hydroxydecanoic acid and 10-hydroxy-2-decenoic acid. In addition, the shorter the carbon chain, the better the inhibitory effect of the 3-hydroxy medium chain fatty acid, indicating higher bioactivity at this time.
TABLE 5 inhibition test of 5α -reductase of oil control and acne removal gel based on 3-hydroxy medium chain fatty acid
Example 6: determination of facial oil control effect of gel application
The oil control effect is measured on the oil control rate of the forehead oil outlet through gel. Testing ambient temperature: 20-22 ℃, relative humidity: 40% -60%. The tested parts of 21 male subjects aged 18-25 years are recruited, cleaned by an alkaline soap-based cleaning product, and the tested parts are dried by a chipless water-absorbing dry tissue after being washed clean by clean water. Subjects were divided into 7 groups of 3 persons each, and 7 groups of samples in table 6 were tested separately. Dividing the forehead of a subject into two areas of 3cm multiplied by 3cm, respectively measuring the oil amount on the skin surface of a sample smearing area and a control area within 3min after cleaning, then smearing 0.1mL of sample on each area for one time, quantitatively sampling by a syringe, and uniformly smearing the sample in a specified area by using a latex finger stall. And measuring at different positions in the sample smearing area and the control area respectively every two hours to obtain the skin surface grease amount of each area, and counting the average value of the skin surface grease amounts of the sample smearing area and the control area of each group.
The results are shown in Table 6 below, and the gel oil output of the 3-hydroxy medium chain fatty acid is lower compared to the blank (average skin surface oil amount of all subjects in the control area), and the 3-hydroxy medium chain fatty acid has better oil control effect.
TABLE 6 oil control effect test of oil control acne-removing gel based on 3-hydroxy medium chain fatty acid
Example 7: gel applied skin corrosiveness test
The skin corrosiveness test of gel application was performed according to the national standard GB/T27830-2011. The prepared three-dimensional human skin model (constructed according to the method described in published papers of the inventor, meng, Q; shen, C, experimental Dermatology,2018.10, 27:1098-1103) was used to prepare a gel No. 3-6 at 50mg/cm 2 The amount of (C) was uniformly applied to the surface of a skin model, after further incubation in an incubator of 37℃and 5% carbon dioxide for 24 hours, the gel on the skin surface was gently scraped off, and the skin sample was placed in a solution of 0.3mg/ml of thiazolium blue (MTT), after incubation for 3 hours, the blue reduction product was extracted with hydrochloric acid-isopropanol, and absorbance was measured at 570 nm.
The skin model without gel was used as a negative control, the activity was set to 100%, and the OD value of the remaining samples was expressed as a percentage of the cell relative activity compared to the negative control. The results are shown in Table 7 below. It can be seen that none of the gel samples exhibited skin corrosiveness.
TABLE 7 skin corrosiveness test of oil control and acne removal gels based on 3-hydroxy medium chain fatty acids
Example 8: questionnaire method for testing acne removing effect of oil control acne removing gel
30 volunteers were recruited according to the daily chemical society standard T/TDCA 004-2021, the ages were 18-35, and both men and women had a certain amount of acne on the facial skin, and no allergic disease or cosmetic allergy history. Subjects were divided into three groups of 10 persons each, and samples numbered 3#,7# and 9# were issued, respectively. The first visit required the subject to sign a written informed consent and evaluate and record facial acne conditions. The subjects were asked to apply the samples each time a day, in an amount to cover the acne and surrounding skin. After one week of continuous use, the laboratory was returned to evaluate again the facial acne condition of each group, and subjects were subjected to a questionnaire to count the acne improvement.
TABLE 8 acne treatment efficacy test of oil control and acne treatment gel based on 3-hydroxy medium chain fatty acid
From the above table, all three samples have acne removing effect, wherein the 3# sample has the best acne improving effect, and compared with the 9# sample of 3-hydroxy medium chain fatty acid, the gel product has the synergistic characteristic of functions, and the 7# sample (containing 10-hydroxy decanoic acid) has weaker effect.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary or exhaustive of all embodiments. And obvious variations or modifications thereof are contemplated as falling within the scope of the present invention.
Claims (4)
1. The preparation method of the oil-control acne-removing gel based on 3-hydroxy medium-chain fatty acid slow release is characterized by comprising the following steps of:
(1) Dissolving 1-5 parts by weight of 3-hydroxy medium chain fatty acid and 1-10 parts by weight of oxidized hyaluronic acid in a first part by weight of water and adjusting the pH to 7 to obtain a first solution; the 3-hydroxy medium chain fatty acid is 3-hydroxydecanoic acid, 3-hydroxyoctanoic acid, 3-hydroxy lauric acid, 3-hydroxytetradecanoic acid or 3-hydroxydec-8-enoic acid;
(2) Dissolving 1-5 parts by weight of chitosan in a second part by weight of 0.1wt% acetic acid aqueous solution, and adjusting the pH to 5 to obtain a second solution;
(3) Mixing the first solution and the second solution to obtain an oil-control acne-removing gel; wherein the sum of the first weight part and the second weight part is 80-97 weight parts;
the oxidized hyaluronic acid is prepared by the following method: dissolving 1-10 parts by weight of hyaluronic acid in 100 parts by weight of water, adding 0.5-2 times by weight of sodium periodate, adjusting the pH to 6, reacting for 3 hours at room temperature, adding glycol to terminate the reaction, dialyzing and freeze-drying to obtain oxidized hyaluronic acid.
2. The oil-control acne-removing gel prepared by the preparation method of claim 1, wherein the 3-hydroxy medium chain fatty acid is loaded on jelly-like gel generated by the reaction of oxidized hyaluronic acid and chitosan through forming an ionic bond with positively charged chitosan.
3. Use of the oil-controlling acne-removing gel according to claim 2 for preparing an oil-controlling and/or acne-removing medicament and preparing an acne-controlling medicament.
4. The use according to claim 3, wherein the oil control and acne removal gel achieves oil control by inhibiting the activity of 5α -reductase; the oil-control acne-removing gel realizes acne removal and acne prevention by killing propionibacteria.
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