CN115317405A - Application of multiple polyglutamic acid cross-linked polymer in skin repair - Google Patents
Application of multiple polyglutamic acid cross-linked polymer in skin repair Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/88—Polyamides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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Abstract
The invention belongs to the fields of biological high molecular materials, medical instruments and cosmetics, and particularly relates to an application of a polyglutamic acid cross-linked polymer in skin repair. The invention fully utilizes the advantages of polyglutamic acid with high molecular weight, medium molecular weight and low molecular weight and derivatives thereof, forms hydrogel polymer with 3D three-dimensional network structure through physical and chemical crosslinking, constructs the structure and components of extracellular matrix through simulation, is used for repairing damaged skin in an omnibearing and multi-level manner, deeply nourishes and accelerates the repair and reconstruction of skin tissue, enhances the barrier function of stratum corneum, effectively reduces the evaporation of water in the skin, improves the rough and dry state of the skin, and can be widely used for repairing the skin tissue.
Description
Technical Field
The invention belongs to the fields of biological high molecular materials, medical instruments and cosmetics, and particularly relates to an application of a polyglutamic acid cross-linked polymer in skin repair.
Background
The skin is the largest organ of the human body, is the main channel for maintaining the exchange of substances between the body and the outside, and is easily damaged by the influence of the external environment. The skin tissue mainly comprises an epidermal layer, a dermal layer and a subcutaneous tissue, is an organ with the largest specific area of an organism and is used for feeding back an external physical stimulation signal; transferring and exchanging nutrient substances and sweat wastes generated by organism, regulating organism immunoreaction, resisting or avoiding bacterial/fungal infection and foreign body invasion, etc. Therefore, it is a key scientific problem to be solved at present how to explore skin regeneration and remodeling from the level of molecules, cells and tissues and organs.
The hydrogel is used as a 3D three-dimensional network structure wet soft polymer scaffold constructed by hydrophilic natural or synthetic high molecular materials, and is widely applied to the fields of cosmetics, cell culture and skin tissue engineering due to good physicochemical properties. The cross-linking mode of the hydrogel support is reasonably regulated, the physical and chemical properties and biochemical clues of the hydrogel support can be accurately designed, the structure and the composition which are highly similar to those of natural extracellular matrix can be simulated and constructed, the regeneration process of the tissue is reasonably regulated, the specific structure and the function of the tissue are further simulated, and the skin tissue repair is promoted.
Because the polyglutamic acid is different from common polyamino acid, the gamma-amido bond which is difficult to be identified by the protease can resist the degradation of the protease in vivo, and because the polyglutamic acid is difficult to initiate the immune reaction of the human body and can not induce the strengthening response; can obviously inhibit the activity of tyrosinase, thereby inhibiting the generation of skin melanin and achieving the effect of whitening; in addition, polyglutamic acid also has the effect of inhibiting the activity of hyaluronidase, and can eliminate or slow down pathological skin diseases such as skin water deficiency and wrinkles caused by the degradation of hyaluronic acid in skin connective tissue due to the activation of hyaluronidase. Therefore, the polyglutamic acid can simulate the components of the extracellular matrix, promote the repair of damaged tissues of skin, has the advantages of moisture retention, wrinkle removal, water retention and the like, and has wide market prospects in the fields of cosmetics and biomedicine.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides an application of a polyglutamic acid cross-linked polymer in skin repair. Aiming at improving the deep moisture retention of skin tissues, increasing the skin elasticity, repairing damaged cells, recruiting endogenous cells, promoting the transdermal absorption of the skin tissues and accelerating the repair and regeneration of the damaged tissues by the polyglutamic acid cross-linked polymer prepared by esterification reaction cross-linking.
In order to achieve the purpose, the invention adopts the following technical scheme:
(1) Performing ring-opening polymerization reaction on polyglutamic acid and derivatives thereof with different molecular weights and epoxy ether in a chemical cross-linking agent structure under an acidic condition to form a multiple polyglutamic acid cross-linked polymer;
(2) The polyglutamic acid cross-linked polymer in the step (1) is used as a skin repairing agent for evaluating the repairing effect of skin, and the specific evaluation methods include but are not limited to moisturizing performance, antioxidant performance, biocompatibility and blood compatibility.
Preferably, the moisture retention performance evaluation in the step (2): placing the polyglutamic acid cross-linked polymer in the step (1) in a fixed container containing a drying agent to measure the mass of the polyglutamic acid cross-linked polymer at different time points, and then utilizing a formula: the moisturizing performance of the polyglutamic acid-crosslinked polymer was calculated from the mass of the crosslinked polymer at various times/initial mass of the crosslinked polymer × 100%.
Preferably, the antioxidant performance evaluation in step (2) includes, but is not limited to, DPPH radical, superoxide anion radical, hydroxyl radical scavenging and total antioxidant capacity measurement.
Preferably, the biocompatibility in step (2) includes, but is not limited to, cell proliferation test and cell phototoxicity test.
Preferably, the cells for biocompatibility in step (2) include but are not limited to at least one of mouse fibroblasts, 3T3 fibroblasts, and B16 mouse melanoma cells, and the cell proliferation assay includes but is not limited to at least one of MTT method, CCK-8 method, flow cytometry, and dead-live staining photography.
Preferably, the cytotoxicity test of the polyglutamic acid cross-linked polymer in the application of skin repair in step (2) includes, but is not limited to, at least one of the effects of the polyglutamic acid cross-linked polymer on the repair of phototoxic cells, and the effects of the polyglutamic acid cross-linked polymer on the content of neutral active oxygen, nitric oxide, melanin, collagen, malondialdehyde, superoxide dismutase and the like of the phototoxic cells.
Preferably, the blood compatibility test of step (2): after incubation of mammalian red blood cell suspension and the polyglutamic acid cross-linked polymer, hemolytic behavior is observed, then centrifugation is carried out, and the hemolysis rate of the supernatant is calculated by testing the absorbance of the supernatant.
The invention also provides the application of the polyglutamic acid cross-linked polymer prepared by the method in skin repair, and the potential and the advantage of the polyglutamic acid cross-linked polymer in skin repair are proved by further evaluating the moisturizing performance, the oxidation resistance, the biocompatibility and the blood compatibility of the polyglutamic acid cross-linked polymer.
Compared with the prior art, the invention has the beneficial effects that:
the invention utilizes the physicochemical advantages of polyglutamic acid with different molecular weights and derivatives thereof to construct a multiple polyglutamic acid cross-linked polymer, so that the multiple polyglutamic acid cross-linked polymer has very important application prospect in skin repair. The invention fully excavates the protection mechanism of polyglutamic acid and derivatives thereof with different molecular weights on skin tissues (for example, the polyglutamic acid with high molecular weight can form a relatively compact gel protection layer on the surface of skin to resist the degradation of related biological enzymes, so as to achieve the purpose of long-acting moisture preservation, the polyglutamic acid with medium molecular weight has the effects of moisture preservation and lubrication, the polyglutamic acid with low molecular weight can increase the elasticity of skin, remove oxygen radicals, promote the proliferation and differentiation of endogenous cells and soften the horny layer of skin, the polyglutamic acid with ultralow molecular weight can promote the absorption of organisms, achieve the effects of deep moisture preservation and activating growth factors in the organisms, improve the deep moisture preservation of the skin tissues, increase the elasticity of skin, repair damaged cells, recruit endogenous cells, promote the transdermal absorption of the skin tissues and accelerate the repair and regeneration of the damaged tissues.
Drawings
FIG. 1 is a graph showing the moisturizing properties of the polyglutamic acid crosslinked polymer of the present invention.
FIG. 2 is a graph showing the antioxidant ability of the polyglutamic acid crosslinked polymer of the present invention.
FIG. 3 shows the results of CCK-8 test of the polyglutamic acid crosslinked polymer of the present invention.
FIG. 4 is a reactive oxygen species test in cytotoxic cells of the polyglutamic acid crosslinked polymer of the present invention.
FIG. 5 shows a melanin test in cytotoxic cells of the polyglutamic acid crosslinked polymer of the present invention.
FIG. 6 is a result of testing the blood compatibility of the polyglutamic acid crosslinked polymer of the present invention.
Detailed Description
The invention will be better understood and further elucidated with reference to the following examples and the accompanying drawings. However, the description of the embodiments is only for illustrating the present invention and not for limiting the claims of the present invention.
Example 1
(1) Performing ring-opening polymerization reaction on polyglutamic acid and derivatives thereof with different molecular weights and epoxy ether in a chemical cross-linking agent structure under an acidic condition to form a multiple polyglutamic acid cross-linked polymer;
(2) The polyglutamic acid cross-linked polymer in the step (1) is used as a skin repairing agent for evaluating the repairing effect of skin, and is mainly evaluated through moisturizing performance, oxidation resistance, biocompatibility and blood compatibility.
(3) Placing the multiple polyglutamic acid cross-linked polymer in the step (2) into a fixed container containing a drying agent to measure the mass of the multiple polyglutamic acid cross-linked polymer at different time points, and then utilizing a formula: the moisturizing performance of the polyglutamic acid crosslinked polymer was calculated from the mass of the crosslinked polymer at different times/initial mass of the crosslinked polymer × 100%.
(4) DPPH free radical scavenging assay for polyglutamic acid-crosslinked polymers: and (3) immersing the polyglutamic acid cross-linked polymer into a 0.2mM ethanol solution of DPPH, carrying out light-shielding reaction for 2 hours, measuring the absorbance of the polyglutamic acid cross-linked polymer at the wavelength of 517nm, and calculating the antioxidant performance of the polyglutamic acid cross-linked polymer by taking deionized water with the same volume as a control group.
(5) Evaluation of biocompatibility of the polyglutamic acid-crosslinked polymer: inoculating mouse fibroblast to the surface of the polyglutamic acid cross-linked polymer, respectively culturing for 1, 2 and 3 days, adding a CCK-8 solution, placing in a carbon dioxide incubator, incubating for 2 hours, measuring absorbance at a wavelength of 450nm, and evaluating cell proliferation performance by taking a DMEM cell culture medium as a control group.
(6) Evaluation of biocompatibility of the polyglutamic acid-crosslinked polymer: after incubating the 2% red blood cell suspension with the multiple polyglutamic acid cross-linked polymer for 3 hours, observing hemolysis behavior, then centrifuging by using a centrifuge of 3000rad/min, taking supernatant, testing absorbance at 575nm, and calculating hemolysis rate.
Example 2
(1) Performing ring-opening polymerization reaction on polyglutamic acid and derivatives thereof with different molecular weights and epoxy ether in a chemical cross-linking agent structure under an acidic condition to form a multiple polyglutamic acid cross-linked polymer;
(2) The polyglutamic acid cross-linked polymer in the step (1) is used as a skin repairing agent for evaluating the repairing effect of skin, and is mainly evaluated through antioxidant performance and biocompatibility.
(3) Hydroxyl radical scavenging test for polyglutamic acid-crosslinked polymers: the polyglutamic acid cross-linked polymer is immersed into 9mM ferrous sulfate and 9mM salicylic acid ethanol solution to be completely mixed, 8.8mM hydrogen peroxide solution is added, the mixture is placed in an incubator at 37 ℃ for incubation for 15 minutes, then the absorbance of the mixture is measured at the wavelength of 510nm, and then the anti-oxidation performance of the mixture is calculated by taking equal volume of deionized water as a control group.
(4) Evaluation of cytotoxicity of multiple polyglutamic acid crosslinked polymers: co-culturing mouse fibroblasts and polyglutamic acid cross-linked polymer, transferring the mouse fibroblasts and the polyglutamic acid cross-linked polymer to a carbon dioxide incubator for incubation for 24 hours after ultraviolet irradiation is carried out for 30 minutes, and observing the survival state of the cells by using a fluorescence inverted microscope after the mouse fibroblasts and the polyglutamic acid cross-linked polymer are incubated in the carbon dioxide incubator for 30 minutes after AO/EB dye liquor is used for dyeing.
Example 3
(1) Performing ring-opening polymerization reaction on polyglutamic acid and derivatives thereof with different molecular weights and epoxy ether in a chemical cross-linking agent structure under an acidic condition to form a multiple polyglutamic acid cross-linked polymer;
(2) The polyglutamic acid cross-linked polymer in the step (1) is used as a skin repairing agent for evaluating the repairing effect of skin, and is mainly evaluated through antioxidant performance and biocompatibility.
(3) Superoxide anion radical scavenging test for polyglutamic acid-crosslinked polymers: immersing the polyglutamic acid cross-linked polymer into a Tris-HCl buffer solution for complete mixing, standing for 30 minutes, adding a 60mM pyrogallol solution, quickly shaking up, measuring the absorbance of the pyrogallol solution at the wavelength of 325nm, and then using the HCl solution with the same volume as the pyrogallol solution as a control group to calculate the antioxidant performance of the polyglutamic acid cross-linked polymer.
(4) Active oxygen assay in cytotoxic cells of polyglutamic acid-crosslinked polymers: co-culturing mouse fibroblasts and polyglutamic acid cross-linked polymer, transferring the mouse fibroblasts and the polyglutamic acid cross-linked polymer to a carbon dioxide incubator for incubation for 24 hours after ultraviolet irradiation is carried out for 30 minutes, adding a DCFH-DA fluorescent probe solution, incubating the mouse fibroblasts and the polyglutamic acid cross-linked polymer in the carbon dioxide incubator for 30 minutes, detecting the mouse fibroblasts and the polyglutamic acid cross-linked polymer by using a fluorescence spectrophotometer, and evaluating the active oxygen content in the cells.
Example 4
(1) Performing ring-opening polymerization reaction on polyglutamic acid and derivatives thereof with different molecular weights and epoxy ether in a chemical cross-linking agent structure under an acidic condition to form a multiple polyglutamic acid cross-linked polymer;
(2) The polyglutamic acid cross-linked polymer in the step (1) is used as a skin repair agent for evaluating the repair effect of skin, and is mainly evaluated through biocompatibility.
(3) Active oxygen assay in cytotoxic cells of polyglutamic acid-crosslinked polymers: co-culturing B16 mouse primary melanoma cells and polyglutamic acid cross-linked polymer, transferring the cells to a carbon dioxide incubator for incubation for 24 hours after ultraviolet irradiation is carried out for 30 minutes, removing supernate, adding a sodium hydroxide solution of DMSO to lyse the cells, dissolving melanin in water bath at 80 ℃, centrifuging at 10000rad/min, measuring absorbance at wavelengths of 405nm and 570nm respectively, and evaluating the melanin content in the cells.
In conclusion, the invention provides a multiple polyglutamic acid cross-linked polymer, which enables the multiple polyglutamic acid cross-linked polymer to be applied to skin repair. The invention fully excavates the protection mechanism of different molecular weight polyglutamic acid and derivatives thereof on skin tissues, improves the deep moisture retention of the skin tissues, increases the skin elasticity, repairs damaged cells, recruits endogenous cells, promotes the skin absorption of the skin tissues, and accelerates the repair and regeneration of the damaged tissues.
Claims (8)
1. The application of the polyglutamic acid cross-linked polymer in skin repair is characterized by comprising the following steps:
(1) Performing ring-opening polymerization reaction on polyglutamic acid and derivatives thereof with different molecular weights and epoxy ether in a chemical cross-linking agent structure under an acidic condition to form a multiple polyglutamic acid cross-linked polymer;
(2) The polyglutamic acid cross-linked polymer in the step (1) is used as a skin repairing agent for evaluating the repairing effect of skin, and the specific evaluation methods include but are not limited to moisturizing performance, antioxidant performance, biocompatibility and blood compatibility.
2. The use of the polyglutamic acid crosslinked polymer of claim 1, wherein the moisturizing performance evaluation of step (2): placing the polyglutamic acid cross-linked polymer in the step (1) in a fixed container containing a drying agent to measure the mass of the polyglutamic acid cross-linked polymer at different time points, and then utilizing a formula: the moisturizing performance of the polyglutamic acid-crosslinked polymer was calculated from the mass of the crosslinked polymer at various times/initial mass of the crosslinked polymer × 100%.
3. The use of the polyglutamic acid crosslinked polymer of claim 1, wherein the antioxidant property assessment of step (2) includes but is not limited to DPPH free radical, superoxide anion free radical, hydroxyl radical scavenging and total antioxidant capacity determination.
4. The use of the polyglutamic acid crosslinked polymer of claim 1, wherein the biocompatibility in step (2) includes but is not limited to cell proliferation test and cytotoxicity test.
5. The use of the polyglutamic acid crosslinked polymer of claim 4 for skin repair is performed by using cells for biocompatibility including but not limited to at least one of mouse fibroblasts, 3T3 fibroblasts and B16 mouse melanoma cells, and cell proliferation assay including but not limited to at least one of MTT method, CCK-8 method, flow cytometry and dead-live staining photography.
6. The cytotoxicity test of the polyglutamic acid cross-linked polymer for use in skin repair according to claim 4 comprises, but is not limited to, at least one of the effects of the polyglutamic acid cross-linked polymer on the repair of phototoxic cells, and the effects of the polyglutamic acid cross-linked polymer on the content of active oxygen, nitric oxide, melanin, collagen, malondialdehyde, superoxide dismutase and the like in the phototoxic cells.
7. The use of the polyglutamic acid crosslinked polymer according to claim 1 for skin repair, wherein the blood compatibility test of step (2): after a mammalian red blood cell suspension is incubated with the polyglutamic acid cross-linked polymer, the hemolysis behavior is observed, then the centrifugation treatment is carried out, and the hemolysis rate is calculated by testing the absorbance of a supernatant fluid.
8. The use of the poly (glutamic acid) -crosslinked polymer according to any one of claims 1 to 7 for skin repair.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1803124A (en) * | 2005-01-12 | 2006-07-19 | 东海生物科技股份有限公司 | Gama-poly glutamic acid, gama-poly glutamic acid salt and use of hydrogel thereof |
| WO2007034795A1 (en) * | 2005-09-20 | 2007-03-29 | Genolac Bl Corporation | Ϝ-polyglutamic acid crosslinked product and method for producing same |
| CN105342882A (en) * | 2015-10-27 | 2016-02-24 | 山东省药学科学院 | Multi-efficiency compound moisturizing essence and application method thereof |
| CN112341640A (en) * | 2020-11-06 | 2021-02-09 | 南京工业大学 | Bio-based self-repairing hydrogel and preparation method and application thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1803124A (en) * | 2005-01-12 | 2006-07-19 | 东海生物科技股份有限公司 | Gama-poly glutamic acid, gama-poly glutamic acid salt and use of hydrogel thereof |
| WO2007034795A1 (en) * | 2005-09-20 | 2007-03-29 | Genolac Bl Corporation | Ϝ-polyglutamic acid crosslinked product and method for producing same |
| CN105342882A (en) * | 2015-10-27 | 2016-02-24 | 山东省药学科学院 | Multi-efficiency compound moisturizing essence and application method thereof |
| CN112341640A (en) * | 2020-11-06 | 2021-02-09 | 南京工业大学 | Bio-based self-repairing hydrogel and preparation method and application thereof |
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