A supramolecular myristoyl pentapeptide-4, its preparation method and application

Abstract

This invention discloses a supramolecular myristoyl pentapeptide-4, its preparation method, and its application. The method includes the following steps: under an inert atmosphere, L-carnitine taurine ionic liquid is placed in a water bath; myristoyl pentapeptide-4 is added to the L-carnitine taurine ionic liquid to obtain a mixed solution; the mixed solution is ultrasonically stirred, homogenized, and dialyzed to obtain supramolecular myristoyl pentapeptide-4. This invention uses L-carnitine taurine ionic liquid as a carrier to combine with myristoyl pentapeptide-4 for supramolecular modification, resulting in supramolecular myristoyl pentapeptide-4. This not only improves skin permeability but also ensures that the original hair-care and skin-nourishing effects of L-carnitine and taurine are further enhanced, improving the hair-repairing, breakage-preventing, and skin-nourishing effects of myristoyl pentapeptide-4, significantly increasing its bioavailability and enhancing its application effects.

Description

Technical Field

[0001] This invention relates to the field of cosmetic compound technology, and in particular to a supramolecular myristoyl pentapeptide-4, its preparation method and application. Background Technology

[0002] Myristoyl pentapeptide-4 is a complex polypeptide that effectively stimulates the synthesis of hair keratin by activating keratin genes, thereby promoting eyelash growth and making hair thicker and stronger. Clinical trials have shown that using a care product containing 10% eyelash peptide solution, applied to the eyelash area once a day, resulted in 71% eyelash growth and thickening after six weeks. In addition, myristoyl pentapeptide-4 also has skin-nourishing effects. Myristoyl pentapeptide-4 consists of a long-chain fatty acyl myristic acid linked to pentapeptide-4, which can prevent peptide degradation, alter the hydrophilic-lipophilic balance of peptide compounds, enhance peptide surface activity, and aid in emulsification. However, its permeability is reduced, and more peptides remain on the skin surface. Therefore, it is necessary to select an ionic liquid with penetration-enhancing capabilities to form a supramolecular structure with myristoyl pentapeptide-4 to increase its permeability and allow it to fully exert its efficacy.

[0003] Therefore, existing technologies still need to be improved and developed. Summary of the Invention

[0004] In view of the shortcomings of the prior art, the purpose of this invention is to provide a supramolecular myristoyl pentapeptide-4, its preparation method and application, in order to solve the problem of low transdermal penetration efficiency of myristoyl pentapeptide-4 in the prior art.

[0005] The technical solution adopted by the present invention to solve the above-mentioned technical problems is as follows:

[0006] A method for preparing supramolecular myristoyl pentapeptide-4, comprising the following steps:

[0007] Under an inert atmosphere, L-carnitine taurine ionic liquid was placed in a water bath at a preset temperature. Myristoyl pentapeptide-4 was added to the L-carnitine taurine ionic liquid to obtain a mixed solution. The mixed solution was then subjected to ultrasonic stirring, homogenization, and dialysis to obtain the supramolecular myristoyl pentapeptide-4.

[0008] The method for preparing supramolecular myristoyl pentapeptide-4, wherein the mass ratio of the L-carnitine taurine ionic liquid to the myristoyl pentapeptide-4 is (5:1) to (1:5).

[0009] The method for preparing supramolecular myristoyl pentapeptide-4, wherein the inert gas is nitrogen or argon.

[0010] The method for preparing supramolecular myristoyl pentapeptide-4, wherein the preset temperature is 25~35℃.

[0011] The method for preparing supramolecular myristoyl pentapeptide-4, wherein the stirring speed is 500~700 rad / min and the stirring time is 16~24 h.

[0012] The method for preparing supramolecular myristoyl pentapeptide-4 includes the following steps: the frequency of the ultrasound is 20-40 kHz, the power of the ultrasound is 800-2000 W, the duration of the ultrasound is 4-12 h, the interval is 1-5 s, and the duration of the ultrasound is 2-10 s.

[0013] The method for preparing supramolecular myristoyl pentapeptide-4 includes a homogenization pressure of 10-80 MPa, a homogenization flow rate of 30-60 L / h, and a homogenization cycle of 1-3 times.

[0014] The method for preparing supramolecular myristoyl pentapeptide-4 includes the following steps: dialysis is performed using a cellulose dialysis bag with a molecular weight of 1000; the dialysis time is 2-6 hours; and the number of dialysis cycles is 1-3.

[0015] A supramolecular myristoyl pentapeptide-4, wherein it is prepared by the preparation method described in the above-described scheme of the present invention.

[0016] The application of supramolecular myristoyl pentapeptide-4 as described in the above-described scheme of the present invention in the preparation of cosmetics.

[0017] Beneficial Effects: This invention discloses a supramolecular myristoyl pentapeptide-4, its preparation method, and its applications. To address the problem of poor peptide permeability, this invention uses L-carnitine taurine ionic liquid as a carrier to combine with myristoyl pentapeptide-4 for supramolecular modification, resulting in supramolecular myristoyl pentapeptide-4. After supramolecular formation, the permeability of myristoyl pentapeptide-4 is improved, thereby better exerting its efficacy. Myristoyl pentapeptide-4 consists of a long-chain fatty acyl myristic acid linked to pentapeptide-4. While this alters the hydrophilic-lipophilic balance of the peptide compound and enhances its surface activity, it also reduces permeability, causing more peptides to remain on the skin surface. L-carnitine taurine ionic liquid is combined with myristoyl pentapeptide-4 for supramolecular modification. The amino group in L-carnitine and the hydroxyl group in taurine attract each other and bind through ionic bonds to form L-carnitine taurine ionic liquid. The amino group in this ionic liquid attracts the carboxyl group in myristoyl pentapeptide-4, causing hydrogen displacement and forming supramolecular myristoyl pentapeptide-4. L-carnitine taurine ionic liquid can enhance transdermal transcellular and decellular transport, bypass the stratum corneum (SC) barrier, and disrupt cell integrity. It works by opening tight junctions within the SC, mainly by enhancing fluidization within the myristoyl pentapeptide-4 region to promote paracellular transport, thereby improving the transdermal penetration ability of myristoyl pentapeptide-4. Therefore, the supramolecular myristoyl pentapeptide-4 prepared by the method of this invention can improve skin permeability, and further enhance the hair repair, breakage prevention and skin nourishing effects of myristoyl pentapeptide-4 on the basis of the original hair care and skin nourishing effects of L-carnitine and taurine, greatly improving its bioavailability and enhancing its application effect. Attached Figure Description

[0018] Figure 1 This is a flowchart of a preferred embodiment of a method for preparing supramolecular myristoyl pentapeptide-4 provided by the present invention.

[0019] Figure 2 The hydrogen nuclear magnetic resonance spectrum of the L-carnitine taurine ionic liquid in Example 1 of this invention.

[0020] Figure 3 This is the two-dimensional NMR (NOESY) spectrum of supramolecular myristoyl pentapeptide-4 in Example 1 of the present invention.

[0021] Figure 4 This is a statistical analysis of transdermal permeation of samples from embodiments of the present invention at different time points.

[0022] Figure 5 The results are from the cuticle test in Example 1 of this invention.

[0023] Figure 6 This is a comparative graphic analysis of the combing characteristics of the hair shaft after using the test sample and the control sample.

[0024] Figure 7 A graphical analysis of the hair bundle fracture load after using the test sample and the control sample. Detailed Implementation

[0025] To enable those skilled in the art to better understand the present invention, the technical solutions of the present invention will be clearly and completely described below with reference to the accompanying drawings of the embodiments. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0026] It will be understood by those skilled in the art that, unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. It should also be understood that terms such as those defined in general dictionaries should be understood to have the same meaning as in the context of the prior art, and should not be interpreted in an idealized or overly formal sense unless specifically defined as herein.

[0027] Myristoyl pentapeptide-4 is a pentapeptide-4 with a long-chain fatty acyl myristic acid attached to it. This can prevent peptide degradation, change the hydrophilic-lipophilic balance of peptide compounds, enhance the surface activity of peptides, and help with emulsification. However, its permeability is reduced and more peptides remain on the skin surface. Therefore, it is urgent to select an ionic liquid with the ability to promote penetration to form a supramolecular structure with myristoyl pentapeptide-4 to solve the problem of poor peptide permeability.

[0028] Based on this, the present invention provides a method for preparing supramolecular myristoyl pentapeptide-4, see [link to method]. Figure 1 It includes the following steps:

[0029] S10. Under an inert atmosphere, place the L-carnitine taurine ionic liquid in a water bath at a preset temperature, and add myristoyl pentapeptide-4 to the L-carnitine taurine ionic liquid to obtain a mixed solution.

[0030] S20. The mixed solution is ultrasonically stirred, homogenized, and dialyzed to obtain the supramolecular myristoyl pentapeptide-4.

[0031] Specifically, myristoyl pentapeptide-4 can stimulate hair keratin synthesis by activating keratin genes, thereby promoting eyelash growth, making hair thicker and stronger, and also nourishing the skin. L-carnitine and taurine are also commonly used in hair care and nourishing products. L-carnitine can enhance cellular energy, upregulate the expression of major components of the extracellular matrix, and increase skin tension and elasticity, thus it is often used in hair care and skin care. Taurine can increase the production of IGF-1 growth factor, which can act on the human hair cycle, thereby prolonging the growth phase and producing thick and strong hair. Therefore, taurine has the ability to repair damaged hair, increase the production of hair growth factors, and promote hair growth.

[0032] Myristoyl pentapeptide-4 is a pentapeptide-4 with a long-chain fatty acyl myristic acid attached. While this alters the hydrophilic-lipophilic balance of the peptide compound and enhances its surface activity, it also reduces its permeability, causing more peptides to remain on the skin surface. After supramolecular modification by combining L-carnitine taurine ionic liquid with myristoyl pentapeptide-4 to form a supramolecular structure, the tight junctions within the stratum corneum are opened under the action of the L-carnitine taurine ionic liquid, thereby promoting the paracellular transport of myristoyl pentapeptide-4 and improving its transdermal penetration ability. Therefore, the supramolecular myristoyl pentapeptide-4 prepared by the method of this invention can improve skin permeability, further enhancing its hair repair, breakage prevention, and skin nourishing effects on top of the original hair care and skin nourishing effects of L-carnitine and taurine, greatly improving its bioavailability and enhancing its application effect.

[0033] Optionally, the mass ratio of the L-carnitine taurine ionic liquid to the myristoyl pentapeptide-4 is (5:1) to (1:5). Controlling the mass ratio of the L-carnitine taurine ionic liquid to the myristoyl pentapeptide-4 within this range can enable the L-carnitine taurine ionic liquid and the myristoyl pentapeptide-4 to have a synergistic effect, achieving optimal effects in hair care, skin nourishment, hair repair, and breakage prevention.

[0034] Optionally, the inert gas is nitrogen or argon, which can prevent the formation of byproducts.

[0035] Optionally, the preset temperature is 25~35℃; the stirring speed is 500~700 rad / min, and the stirring time is 16~24h; the ultrasonic frequency is 20~40kHz, the ultrasonic power is 800~2000W, the ultrasonic time is 4~12h, and the interval is 1~5s every 2~10s. Under the above conditions, the reaction between L-carnitine taurine ionic liquid and myristoyl pentapeptide-4 is more complete, and supramolecular myristoyl pentapeptide-4 can be synthesized better.

[0036] Optionally, the homogenization pressure is 10-80 MPa, the homogenization flow rate is 30-60 L / h, and the homogenization is performed 1-3 times; the dialysis uses a cellulose dialysis bag with a molecular weight of 1000, the dialysis time is 2-6 h, and the dialysis is performed 1-3 times. Homogenization under the above conditions can increase the reaction rate and the yield of supramolecular myristoyl pentapeptide-4. Dialysis under the above conditions can achieve product separation and purification. The molecular weight of supramolecular myristoyl pentapeptide-4 is greater than 1000, while the molecular weights of myristoyl pentapeptide-4, L-carnitine, and taurine are all less than 1000. Therefore, substances that do not form supramolecular myristoyl pentapeptide-4 can be dialyzed to the outside of the dialysis bag, while only supramolecular myristoyl pentapeptide-4 remains inside the dialysis bag, so that supramolecular myristoyl pentapeptide-4 achieves a high purity, thereby maximizing the efficacy of supramolecular myristoyl pentapeptide-4 in hair care and skin nourishment.

[0037] The present invention also provides a supramolecular myristoyl pentapeptide-4, which is prepared by the preparation method described in the above-described scheme of the present invention.

[0038] This invention also provides the application of supramolecular myristoyl pentapeptide-4 as described above in the preparation of cosmetics such as water, lotion, serum, cream, lotion, and aqueous solution.

[0039] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are merely some embodiments of the present invention, not all embodiments, and are intended only to illustrate the present invention and not to limit it. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without creative effort are within the scope of protection of the present invention.

[0040] Example 1

[0041] Under nitrogen atmosphere, 3g of L-carnitine taurine ionic liquid was placed in a 25°C water bath. 1g of myristoyl pentapeptide-4 was added to the L-carnitine taurine ionic liquid to obtain a mixed solution. The mixed solution was then subjected to ultrasonic stirring and homogenization at a stirring rate of 700 rad / min for 18 h, an ultrasonic frequency of 30 kHz, an ultrasonic power of 1000 W, an ultrasonic time of 6 h, an interval of 5 s every 2 s, a homogenization pressure of 50 MPa, a homogenization flow rate of 40 L / h, and three homogenization cycles. After 18 h of reaction, dialysis was performed using a cellulose dialysis bag with a molecular weight of 1000 for 6 h and three dialysis cycles to obtain supramolecular myristoyl pentapeptide-4.

[0042] The L-carnitine taurine ionic liquid in Example 1 was characterized by one-dimensional 1H-NMR spectroscopy. D₂O was used as the test solvent in the experiment, and the results are as follows. Figure 2 The data are as follows: H1 NMR (700 MHz, D2O) δ 4.86 –4.81 (m, 1H), 3.69 (dd, J = 8.8, 4.2 Hz, 4H), 3.52 (dd, J = 8.9, 4.3 Hz, 2H), 3.51 – 3.48 (m, 9H), 2.70 (qd, J =15.4, 6.7 Hz, 2H). The 1H NMR spectrum indicates that L-carnitine and taurine exist in a 1:1 molecular ratio in the L-carnitine taurine ionic liquid.

[0043] The supramolecular myristoyl pentapeptide-4 prepared in Example 1 was characterized by two-dimensional nuclear magnetic resonance (NOESY) spectroscopy, with DMSO used as the test solvent. Figure 3 The two-dimensional NMR NOESY spectrum of supramolecular myristoyl pentapeptide-4 clearly shows correlation points between the L-carnitine taurine ionic liquid and myristoyl pentapeptide-4 at (H1 3.2 ppm, H2 2.1 ppm) and (H1 2.1 ppm, H2 3.2 ppm). The correlation points (cross-peaks) in the NOESY spectrum indicate that the protons of the two groups are spatially close, suggesting an interaction between the L-carnitine taurine ionic liquid and myristoyl pentapeptide-4, indicating the presence of hydrogen bonds, thus forming supramolecular myristoyl pentapeptide-4.

[0044] Comparative Example 1

[0045] A supramolecular myristoyl pentapeptide-4 (2) is provided, which differs from the preparation process in Example 1 in that the mass of the L-carnitine taurine ionic liquid is 5g.

[0046] Comparative Example 2

[0047] A supramolecular myristoyl pentapeptide-4 (3) is provided, which differs from the preparation process in Example 1 in that the mass of the L-carnitine taurine ionic liquid is 1g and the mass of the myristoyl pentapeptide-4 is 5g.

[0048] Comparative Example 3

[0049] A supramolecular myristoyl pentapeptide-4 (4) is provided, which differs from the preparation process in Example 1 in that the mass of the L-carnitine taurine ionic liquid is 7g and the mass of the myristoyl pentapeptide-4 is 1g.

[0050] Comparative Example 4

[0051] A supramolecular myristoyl pentapeptide-4 (5) is provided, which differs from the preparation process in Example 1 in that the mass of the L-carnitine taurine ionic liquid is 1g and the mass of the myristoyl pentapeptide-4 is 7g.

[0052] Test Example 1

[0053] Two solutions, one at 4% and the other at 1%, were prepared with the same myristoyl pentapeptide-4 content. These solutions served as the experimental and control groups, respectively. The transdermal efficacy of these solutions was then tested using the following method:

[0054] I. Use skin from the back of a piglet, carefully peel off the subcutaneous fat layer and connective tissue, rinse it clean with physiological saline, and place it in physiological saline for later use.

[0055] II. Transdermal experiments were conducted using the Franz cell method. The exposed skin area in the diffusion cell of the Franz diffusion apparatus was 1.13 cm². 2 The volume of the receiving chamber is 15 mL.

[0056] III. Take 1 mL of the experimental group and control group prepared above and place them on the exposed skin surface in the diffusion cell as the test drug solution. Add 15 mL of physiological saline receiving solution to the receiving cell and place it in a constant temperature water bath at 37±1℃ with a stirring speed of 300 rad / min.

[0057] IV. Subcutaneous sample collection: 1 mL of receiving fluid was collected at 2, 4, 8, 16 and 24 h. Immediately after sampling, 1 mL of receiving fluid was added to the receiving chamber, and the sample was collected at 24 h.

[0058] V. After filtration through a 0.22 μm microporous membrane, the sample was detected by high-performance liquid chromatography (HPLC).

[0059] The formula for calculating the permeability per unit volume is as follows: (1)

[0060] (1)

[0061] Where: P: permeation volume per unit volume; V: volume of receiving liquid in the receiving chamber, 15 mL; V0: volume of each sample taken, 1.0 mL; Ci: drug concentration in the receiving liquid during the first to n-1 samplings; Cn: sample concentration measured at the nth sampling point.

[0062] The results are as follows Figure 4As shown, after 24 h of percutaneous infiltration, the permeation volume per unit volume of the supramolecular myristoyl pentapeptide-4 experimental group and the supramolecular myristoyl pentapeptide-4 control group were 0.18 and 0.07 μg / mL, respectively, based on the content of myristoyl pentapeptide-4. The permeation volume per unit volume of myristoyl pentapeptide-4 in the supramolecular myristoyl pentapeptide-4 experimental group was 2.57 times that of the supramolecular myristoyl pentapeptide-4 control group. The results indicate that the percutaneous infiltration capacity of supramolecular myristoyl pentapeptide-4 is superior to that of myristoyl pentapeptide-4, suggesting that L-carnitine taurine ionic liquid has a permeation-promoting effect on myristoyl pentapeptide-4.

[0063] The supramolecular myristoyl pentapeptide-4 (2), supramolecular myristoyl pentapeptide-4 (3), supramolecular myristoyl pentapeptide-4 (4), and supramolecular myristoyl pentapeptide-4 (5) prepared in Comparative Examples 1 to 4 were subjected to transdermal efficacy tests according to the above method, and compared with the supramolecular myristoyl pentapeptide-4 prepared in Example 1. The test results are shown in Table 1:

[0064] Table 1. Statistics on Penetration Effect

[0065]

[0066] As shown in Table 1, the permeation per unit volume of supramolecular myristoyl pentapeptide-4 and supramolecular myristoyl pentapeptide-4 (2)~(5) were 0.18, 0.16, 0.14, 0.08, and 0.07 μg / mL, respectively. The permeation per unit volume was higher when the mass ratio of L-carnitine taurine ionic liquid to myristoyl pentapeptide-4 was within (5:1)~(1:5), and lower when the mass ratio was outside (5:1)~(1:5). Therefore, using a mass ratio of (5:1)~(1:5) to prepare supramolecular myristoyl pentapeptide-4 can effectively improve the transdermal permeation capacity of myristoyl pentapeptide-4.

[0067] Test Example 2

[0068] Two solutions, both containing the same amount of myristoyl pentapeptide-4, were prepared: a 4% solution and a 1% solution. Following the guidelines of the group standard T / SHFCA (Guidelines for Cosmetic Stability), the effect of L-carnitine taurine ionic liquid on improving the stability of myristoyl pentapeptide-4 was investigated under different temperature conditions, including freezing (-20℃), refrigeration (5℃), high temperature (45℃), light exposure, and thermal cycling. The results are shown in Table 2: Compared with myristoyl pentapeptide-4, supramolecular myristoyl pentapeptide-4 has a longer half-life and more stable physicochemical properties.

[0069] Table 2. Statistical results of stability of myristoyl pentapeptide-4 and supramolecular myristoyl pentapeptide-4

[0070]

[0071] Test Example 3

[0072] Two solutions, one containing the same amount of myristoyl pentapeptide-4 (4% and 1%), were prepared and used as the experimental and control groups, respectively, for a closed patch test on human skin to verify the safety of the samples. According to the "Cosmetic Safety Technical Specifications (2015 Edition)," qualified patch testing equipment was selected. Using a closed patch test method, 0.020 g to 0.025 g of the test substance was placed in the testing equipment, and a hypoallergenic adhesive tape was applied to the flexor side of the subject's forearm. After 24 hours, the test substance was removed, and skin reactions were observed at 0.5, 24, and 48 hours after removal. The results were recorded according to the skin reaction grading standards in Table 3 of the "Cosmetic Safety Technical Specifications (2015 Edition)" to detect potential adverse reactions of the cosmetic product on human skin. The results are shown in Table 4: The results of the closed patch test on human skin of the supramolecular myristoyl pentapeptide-4 control group and the supramolecular myristoyl pentapeptide-4 experimental group showed that 0 cases of adverse reactions occurred in 31 people, indicating that the sample is safe and non-irritating.

[0073] Table 3. Grading Criteria for Skin Reactions in Occlusive Patch Tests

[0074]

[0075] Table 4 Summary of Cosmetic Human Skin Patch Test Results

[0076]

[0077] Test Example 4

[0078] Two solutions, one containing the same amount of myristoyl pentapeptide-4 (4% and 1%), were prepared and used as the experimental and control groups, respectively, for a human skin patch test to verify the safety of the samples. Following the guidelines in Chapter 6, Toxicological Test Methods: 4 Skin Irritation / Corrosion Tests of the Cosmetic Safety Technical Specifications (2015 Edition), approximately 24 hours before the test, the hair on both sides of the spine on the back of the test animal was shaved without damaging the epidermis. The shaved area was approximately 3cm × 3cm on both the left and right sides. 0.5mL of the sample was applied to the shaved skin on the left side (2.5cm × 2.5cm), with the other side serving as a control. The sample was applied once daily for 14 consecutive days. Starting from the second day, the hair was shaved before each application, and any residual test substance was removed with warm water. Local skin reactions were observed and scored 1 hour later. The results are shown in Tables 5 and 6: Myristoyl pentapeptide-4 solution and supramolecular myristoyl pentapeptide-4 had an average score of 0 per animal per day in multiple skin irritation tests on Hartley guinea pigs. According to the skin irritation intensity classification of the skin irritation test in the "Cosmetic Safety Technical Specifications" (2015 edition), it is considered non-irritating.

[0079] Table 5 Results of repeated skin irritation tests with myristoyl pentapeptide-4 solution

[0080]

[0081] Table 6 Results of repeated skin irritation tests on supramolecular myristoyl pentapeptide-4

[0082]

[0083] Test Example 5

[0084] A 4% supramolecular myristoyl pentapeptide-4 solution and a 1% supramolecular myristoyl pentapeptide-4 solution were prepared, with the same content of myristoyl pentapeptide-4 in both solutions. These solutions were used as the supramolecular myristoyl pentapeptide-4 sample group and the supramolecular myristoyl pentapeptide-4 control group, respectively, to test the hair repair and breakage prevention efficacy.

[0085] 1. Repairs damaged hair cuticles

[0086] Based on laboratory methods, the condition of hair cuticles before and after using supramolecular myristoyl pentapeptide-4 sample group and supramolecular myristoyl pentapeptide-4 control group was observed by electron microscopy. Before-and-after comparison and parallel comparison were used to evaluate the efficacy of the samples in repairing hair cuticles.

[0087] The results are as follows Figure 5As shown: Before treatment, the hair strands exhibited significant cuticle opening and closing, with some cuticle loss. After treatment with the supramolecular myristoyl pentapeptide-4 control group, some individual hair strands still showed significant cuticle opening and closing, with some cuticle loss. After treatment with the supramolecular myristoyl pentapeptide-4 sample group, the degree of cuticle opening and closing decreased, and no cuticle loss occurred. The cuticle condition after treatment with the supramolecular myristoyl pentapeptide-4 sample group was better than that after treatment with the supramolecular myristoyl pentapeptide-4 control group, indicating that supramolecular myristoyl pentapeptide-4 has the effect of repairing damaged hair cuticles, and its effect is superior to that of myristoyl pentapeptide-4.

[0088] 2. Improves the combability of dry hair

[0089] Based on laboratory methods, a single-center experiment was conducted. Dry combability tests were performed on hair strands treated with supramolecular myristoyl pentapeptide-4 and a control group, with parallel controls, to evaluate the effectiveness of the test samples in improving the dry combability of hair strands.

[0090] The results are shown in Table 7 and Figure 6 As shown, the combing ability of the hair shaft decreased by 24.7% after treatment with supramolecular myristoyl pentapeptide-4, which was significantly lower than that of the control group. Lower combing ability indicates better hair shaft combability, meaning that supramolecular myristoyl pentapeptide-4 can significantly improve hair shaft combability, and its effect is superior to that of myristoyl pentapeptide-4.

[0091] Table 7 Results of the Analytical Testing

[0092]

[0093] Note: "ns" means p>0.05; "*" means p≤0.05; "**" means 0.001≤p<0.01; "***" means p<0.001.

[0094] 3. Prevents hair breakage

[0095] Based on laboratory methods, the breaking strength of hair was measured in parallel with and after treatment with supramolecular myristoyl pentapeptide-4 in both the sample group and the control group to evaluate the product's efficacy in improving hair strength. The results are shown in Table 8. Figure 7 As shown, the breakage load of a single hair increased by 36.45% after treatment with supramolecular myristoyl pentapeptide-4, which was significantly higher than that of the control group. A higher breakage load indicates a better anti-breakage effect of the tested sample, meaning that supramolecular myristoyl pentapeptide-4 has anti-breakage efficacy, and its effect is superior to that of myristoyl pentapeptide-4.

[0096] Table 8. Descriptive statistics of fracture load test results (unit: gmf)

[0097]

[0098] Note: "ns" means p>0.05; "*" means p≤0.05; "**" means 0.001≤p<0.01; "***" means p<0.001.

[0099] Based on data analysis of its effects on repairing damaged hair cuticles, improving hair combability, and preventing breakage, supramolecular myristoyl pentapeptide-4, obtained by supramolecular modification with L-carnitine taurine ionic liquid, showed superior repair and breakage prevention effects compared to myristoyl pentapeptide-4. This indicates that L-carnitine taurine ionic liquid can effectively promote the hair repair and breakage prevention effects of myristoyl pentapeptide-4.

[0100] Test Example 6

[0101] The mixture of supramolecular myristoyl pentapeptide-4, myristoyl pentapeptide-4 and imidazole ionic liquid with myristoyl pentapeptide-4 was prepared into essences with contents of 4%, 1% and 4% respectively. The contents of myristoyl pentapeptide-4 in the three were the same, and they were used as supramolecular myristoyl pentapeptide-4 sample group, supramolecular myristoyl pentapeptide-4 control group (1) and supramolecular myristoyl pentapeptide-4 control group (2) to test the nourishing efficacy.

[0102] In each group, 31 subjects used supramolecular myristoyl pentapeptide-4 sample group, supramolecular myristoyl pentapeptide-4 control group (1) and supramolecular myristoyl pentapeptide-4 control group (2) for 4 consecutive weeks. Skin moisture content, skin gloss and skin roughness Ra value were measured at 0 weeks, 2 weeks and 4 weeks before using the sample to evaluate the nourishing effect of the sample.

[0103] 1. Skin moisture content test

[0104] The statistical analysis results of skin moisture content in the sample group and the control group are shown in Table 9.

[0105] Table 9. Statistical analysis results of skin moisture content before and after use in the experimental and control groups.

[0106]

[0107] Note: “ns” indicates no statistical difference, P≥0.05; 0.01<P<0.05 indicates a significant difference (“*”); P<0.01 indicates a highly significant difference (“**”).

[0108] After 2 and 4 weeks of continuous use of the supramolecular myristoyl pentapeptide-4 sample group, compared with week 0, the subjects' skin moisture content increased by 30.56% and 36.33%, respectively, and the results were statistically significant. After 2 and 4 weeks of continuous use of the supramolecular myristoyl pentapeptide-4 control group (1), compared with week 0, the subjects' skin moisture content increased by 22.26% and 28.28%, respectively, and the results were statistically significant. After 2 and 4 weeks of continuous use of the supramolecular myristoyl pentapeptide-4 control group (2), compared with week 0, the subjects' skin moisture content increased by 25.34% and 32.27%, respectively, and the results were statistically significant. This indicates that supramolecular myristoyl pentapeptide-4 can significantly increase skin moisture content, and its effect is superior to that of myristoyl pentapeptide-4, as well as superior to the delivery effect of other ionic liquids on myristoyl pentapeptide-4.

[0109] 2. Skin Glossiness Test

[0110] The statistical analysis results of skin gloss of supramolecular myristoyl pentapeptide-4 sample group, supramolecular myristoyl pentapeptide-4 control group (1) and supramolecular myristoyl pentapeptide-4 control group (2) are shown in Table 10.

[0111] Table 10 Statistical analysis results of skin glossiness before and after use in the experimental and control groups.

[0112]

[0113] Note: “ns” indicates no statistical difference, P≥0.05; 0.01<P<0.05 indicates a significant difference (“*”); P<0.01 indicates a highly significant difference (“**”).

[0114] After 2 and 4 weeks of continuous use of the supramolecular myristoyl pentapeptide-4 sample group, compared with week 0, the subjects' skin glossiness increased by 14.02% and 28.28%, respectively, and the results were statistically significant. After 2 and 4 weeks of continuous use of the supramolecular myristoyl pentapeptide-4 control group (1), compared with week 0, the subjects' skin glossiness increased by 12.06% and 19.65%, respectively, and the results were statistically significant. After 2 and 4 weeks of continuous use of the supramolecular myristoyl pentapeptide-4 control group (2), compared with week 0, the subjects' skin glossiness increased by 12.67% and 22.51%, respectively, and the results were statistically significant. This indicates that supramolecular myristoyl pentapeptide-4 can significantly improve skin glossiness, and the effect is better than that of myristoyl pentapeptide-4, and also better than the delivery effect of other ionic liquids on myristoyl pentapeptide-4.

[0115] 3. Skin roughness Ra value test

[0116] The statistical analysis results of skin roughness Ra values ​​of supramolecular myristoyl pentapeptide-4 sample group, supramolecular myristoyl pentapeptide-4 control group (1) and supramolecular myristoyl pentapeptide-4 control group (2) are shown in Table 11.

[0117] Table 11 Statistical analysis results of skin roughness Ra values ​​before and after use in the experimental and control groups.

[0118]

[0119] Note: “ns” indicates no statistical difference, P≥0.05; 0.01<P<0.05 indicates a significant difference (“*”); P<0.01 indicates a highly significant difference (“**”).

[0120] After 2 and 4 weeks of continuous use of the supramolecular myristoyl pentapeptide-4 sample group, compared with week 0, the Ra value of the subjects' skin roughness decreased by 10.59% and 17.48%, respectively, and the results were statistically significant. After 2 and 4 weeks of continuous use of the supramolecular myristoyl pentapeptide-4 control group (1), compared with week 0, the Ra value of the subjects' skin roughness decreased by 7.69% and 12.37%, respectively, and the results were statistically significant. After 2 and 4 weeks of continuous use of the supramolecular myristoyl pentapeptide-4 control group (2), compared with week 0, the Ra value of the subjects' skin roughness decreased by 8.45% and 13.68%, respectively, and the results were statistically significant. This indicates that supramolecular myristoyl pentapeptide-4 can significantly improve skin roughness, and the effect is better than that of myristoyl pentapeptide-4, and also better than the delivery effect of other ionic liquids on myristoyl pentapeptide-4.

[0121] Based on the analysis of skin moisture content, skin luster, and skin roughness Ra value data, the supramolecular myristoyl pentapeptide-4 obtained by supramolecular modification with L-carnitine taurine ionic liquid showed a better skin nourishing effect than other ionic liquids on the delivery of myristoyl pentapeptide-4. This indicates that L-carnitine taurine ionic liquid can effectively promote the skin nourishing effect of myristoyl pentapeptide-4, and that carnitine taurine ionic liquid has a synergistic effect on myristoyl pentapeptide-4.

[0122] In summary, this invention discloses a supramolecular myristoyl pentapeptide-4, its preparation method, and its application. The method includes the following steps: under an inert atmosphere, L-carnitine taurine ionic liquid is placed in a water bath at a preset temperature; myristoyl pentapeptide-4 is added to the L-carnitine taurine ionic liquid to obtain a mixed solution; the mixed solution is then ultrasonically stirred, homogenized, and dialyzed to obtain the supramolecular myristoyl pentapeptide-4. This invention uses L-carnitine taurine ionic liquid as a carrier to combine with myristoyl pentapeptide-4 for supramolecular modification, resulting in supramolecular myristoyl pentapeptide-4. Myristoyl pentapeptide-4 consists of a long-chain fatty acyl myristic acid linked to the pentapeptide-4. While this alters the hydrophilic-lipophilic balance of the peptide compound and enhances its surface activity, it also reduces its permeability, causing more peptides to remain on the skin surface. After supramolecular modification by combining L-carnitine taurine ionic liquid with myristoyl pentapeptide-4 to form a supramolecular structure, the tight junctions within the stratum corneum are opened under the action of the L-carnitine taurine ionic liquid, thereby promoting the paracellular transport of myristoyl pentapeptide-4 and enhancing its transdermal penetration ability. Therefore, the supramolecular myristoyl pentapeptide-4 prepared by the method of this invention can improve skin permeability, further enhancing its hair repair, breakage prevention, and skin nourishing effects on top of the original hair care and skin nourishing effects of L-carnitine and taurine, greatly improving its bioavailability and enhancing its application efficacy.

[0123] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and not to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that they can still modify the technical solutions described in the foregoing embodiments, or make equivalent substitutions for some of the technical features; and these modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A method for preparing supramolecular myristoyl pentapeptide-4, characterized in that, Including the following steps: Under an inert atmosphere, L-carnitine taurine ionic liquid was placed in a water bath at a preset temperature, and myristoyl pentapeptide-4 was added to the L-carnitine taurine ionic liquid to obtain a mixed solution. The mixed solution was subjected to ultrasonic stirring, homogenization, and dialysis to obtain the supramolecular myristoyl pentapeptide-4; The mass ratio of the L-carnitine taurine ionic liquid to the myristoyl pentapeptide-4 is (5:1) to (1:5).

2. The method for preparing supramolecular myristoyl pentapeptide-4 according to claim 1, characterized in that, The inert gas is nitrogen or argon.

3. The method for preparing supramolecular myristoyl pentapeptide-4 according to claim 1, characterized in that, The preset temperature is 25~35℃.

4. The method for preparing supramolecular myristoyl pentapeptide-4 according to claim 1, characterized in that, The stirring speed is 500~700 rad / min, and the stirring time is 16~24 h.

5. The method for preparing supramolecular myristoyl pentapeptide-4 according to claim 1, characterized in that, The frequency of the ultrasound is 20~40kHz, the power of the ultrasound is 800~2000W, the duration of the ultrasound is 4~12h, the interval is 1~5s, and the ultrasound duration is 2~10s.

6. The method for preparing supramolecular myristoyl pentapeptide-4 according to claim 1, characterized in that, The homogenization pressure is 10~80MPa, the homogenization flow rate is 30~60 L / h, and the homogenization is performed 1~3 times.

7. The method for preparing supramolecular myristoyl pentapeptide-4 according to claim 1, characterized in that, The dialysis is performed using a cellulose dialysis bag with a molecular weight of 1000. The dialysis time is 2-6 hours, and the number of dialysis sessions is 1-3.

8. A supramolecular myristoyl pentapeptide-4, characterized in that, It is prepared by the preparation method described in any one of claims 1 to 7.

9. The use of supramolecular myristoyl pentapeptide-4 as described in claim 8 in the preparation of cosmetics.

Images