CN113876741B - Preparation and application of wet-state adhesive oral gel patch - Google Patents
Preparation and application of wet-state adhesive oral gel patch Download PDFInfo
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
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- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
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Abstract
The invention discloses preparation and application of a wet-state adhesive oral gel patch, and belongs to the field of biological materials. The patch consists of double-layer hydrogel, wherein the bottom layer is poly-N-acryloyl-2-glycine hydrogel (PACG-gel) to provide a wet adhesion effect, the top layer is polymethacrylic anhydride modified gellan gum hydrogel (MeGG-gel) to provide mechanical properties and support materials, and meanwhile, the wet adhesion oral gel patch can control release of drugs, and gradually degrades in an oral environment to release the drugs, so that the purpose of treating oral ulcer is achieved. The oral gel patch provided by the invention has good wet adhesion and mechanical strength, can bear complex oral movement, solves the problems of weak adhesion, easy falling and damage, poor drug release effect and the like of the oral gel patch products on the market, and has wide application prospect in the field of biomedical polymers.
Description
Technical Field
The invention belongs to the field of biological materials, and relates to a preparation method of a wet-state adhesive oral gel patch, and application of the oral gel patch prepared by the preparation method in the fields of treatment of oral inflammation and wet-state environment adhesive materials.
Background
Glycine (Gly) is a natural product, has low market price, convenient and simple chemical synthesis, and has a melting point of about 233 ℃ (decomposition). The secondary structure of the protein is linked together by hydrogen bonds between C = O and N-H groups, with a unique natural hydrogen-bonded cluster structure. Poly (N-substituted glycine) (also called polypeptide), the main chain with N-substituted glycine, has excellent thermal processing performance, solubility, biocompatibility, gradually become biomedical and biotechnology research material.
Gellan gum (Gellan gum, GG) is a linear anionic heteropolysaccharide composed of glucuronic acid-glucose-rhamnose repeating units, and has biological properties such as good biocompatibility and drug-loading performance. Because GG is an anionic polysaccharide, with a certain amount of free carboxyl groups, both GG and viable cells are negatively charged at neutral pH. The strong negative charge on the polysaccharide surface provides a classical repulsion for a long time, which prevents rapid cell adhesion. It has been demonstrated that the Ming-Wei Lee et al design a novel gellan gum-based anti-mucosal membrane (GG-Cin membrane). The gellan gum has the capability of inhibiting cell migration, and can effectively inhibit inflammatory reaction of rats and formation of postoperative adhesion. The capacity of GG hydrogel in preventing postoperative adhesion is verified.
Canker sores are the most common health problem facing individuals worldwide. The process of oral ulcer healing involves a steady state and an initial phase of acute inflammation with increased release of invasive inflammation, vascular permeability, cytokines and proinflammatory mediators. Currently, treatments including cryotherapy do not solve this problem well. Due to the moist environment of the oral cavity and the diversity of activities (such as chewing, swallowing and the like), the oral gel patch products on the market have the problems of weak adhesion, easy falling and damage, poor drug release effect and the like, and the experience of patients is not good.
Based on the above analysis, the present application provides a wet-adherable gel patch that solves the above problems, the PACG-gel of the bottom layer provides strong wet-adhesion to adhere tightly to the oral tissue, and the megag-gel of the top layer has sufficient mechanical strength to withstand oral movements to avoid breakage of the patch. In addition, the wet adhesive gel patch has good drug release properties, and can meet the requirements of the oral gel patch.
Disclosure of Invention
In view of the above disadvantages, the present invention aims to improve the performance of the currently marketed oral patch, solve the problems that the oral patch is easy to fall off in the oral environment and the drug release effect is difficult to control, and provide a preparation method of a wet-state adhesive oral gel patch.
The invention is realized by the following means:
a wet-adherable oral gel patch comprises a bi-layer hydrogel with a bottom layer of poly-N-acryloyl-2-glycine hydrogel (PACG-gel) to provide wet adhesion effect and a top layer of polymethacrylic anhydride modified gellan gum hydrogel (MeGG-gel) to provide mechanical properties and support material. The oral gel patch has good wet adhesion and mechanical strength, can bear the complex movement of the oral cavity, and realizes the long-term firm adhesion and drug release of the gel patch in the oral environment.
Further, the preparation method of the wet-state adhesive oral gel patch is as follows:
(1) mixing 3-4g glycine (Gly) and 5-10mg K 2 CO 3 Dissolving in a mixed solution of a proper amount of water and diethyl ether, performing ice bath after the system is uniformly mixed, mixing 2-5mL of acryloyl chloride with 15-25mL of diethyl ether, then dropwise adding into the mixed system, reacting at normal temperature for 4h, adjusting the pH to 10-12, performing multiple extraction with ethyl acetate, adjusting the pH to 1-2, continuing performing multiple extraction with ethyl acetate until fine liquid drops appear in the mixed solution, and then performing rotary evaporation and vacuum drying to obtain N-acryloyl-2-glycine (ACG) for later use;
(2) dissolving 1-2g of Gellan Gum (GG) in a proper amount of deionized water, uniformly stirring at 80-90 ℃, cooling to 50-60 ℃, dropwise adding 2-8mL of methacrylic anhydride, adjusting the pH of the system to 8-9 with NaOH solution, continuously reacting for 6h, dialyzing the solution for 4 days, and freeze-drying to obtain methacrylic anhydride modified gellan gum (MeGG) and storing in a dark vacuum manner for later use;
(3) dissolving 1-2g of ACG, 0.05-0.1g of nano hydroxyapatite (HAp) and 0.05-0.1g of photoinitiator I2959 in a small amount of deionized water, maintaining the constant temperature of 50-60 ℃, and uniformly stirring the mixture in advance one night to obtain an ACG solution for later use;
(4) dissolving 0.5-1g MeGG and 0.3-0.4g photoinitiator I2959 in 30-40mL deionized water, maintaining the constant temperature of 50-60 ℃, stirring uniformly one night in advance, and adding a proper amount of CaCl the next day 2 Continuously stirring uniformly to obtain a MeCG solution for later use;
(5) respectively injecting the ACG solution and the MeGG solution into a mold, then carrying out illumination crosslinking under an ultraviolet lamp, taking out after gelling, and thus obtaining poly-N-acryloyl-2-glycine hydrogel (PACG-gel) and polymethacrylic anhydride modified gellan gum hydrogel (MeGG-gel).
The invention also discloses a wet adhesive oral gel patch prepared by the preparation method.
Further, the reaction equation of the preparation process of the wet-state adhesive oral gel patch is as follows:
the invention also discloses application of the wet-state adhesive oral gel patch in preparation of a medicament for treating oral ulcer.
The invention has the beneficial effects that:
the wet-state adhesive oral gel patch prepared by the invention has good wet-state adhesion and mechanical strength, can bear complex oral movement, can release the medicament in a controlled manner, and gradually degrades in the oral environment to release the medicament, thereby achieving the purpose of treating the oral ulcer. The oral gel patch provided by the invention solves the problems that the oral gel patch products on the market are not strong in adhesion, easy to fall off and damage, poor in drug release effect and the like, so that good wet adhesion and mechanical strength are obtained, the complex motion of the oral cavity can be borne, and the long-term firm adhesion and drug release of the gel patch in the oral cavity environment are realized. Has wide application prospect in the biomedical polymer field.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a nuclear magnetic hydrogen spectrum of ACG (left) and MeGG (right);
FIG. 2 is an infrared spectrum of ACG (left) and MeGG (right);
FIG. 3 is a cryo-scanning electron micrograph of PACG-gel (left) and MeGG-gel (right);
FIG. 4 is a graph of the rheological moduli of PACG-gel (left) and MeGG-gel (right);
FIG. 5 is a PACG-gel adhesion pull curve;
FIG. 6 is a peel stress curve of PACG-gel;
figure 7 is a graph of cumulative drug release concentration versus time for a drug-loaded oral gel patch.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
The present invention is further described with reference to specific examples, which are intended to be illustrative only and not limiting. If the experimental conditions not specified in the examples are specified, they are generally according to the conventional conditions, or according to the conditions recommended by the sales companies; the present invention is not particularly limited, and can be commercially obtained.
Example 1
In this embodiment, a method for synthesizing ACG and MeGG is provided, which includes the following steps:
mixing 3-4g glycine (Gly) and 5-10mg K 2 CO 3 Dissolving in the mixture of water and ether. After the system is uniformly mixed, 2-5mL of acryloyl chloride and 15-25mL of diethyl ether are mixed, then the mixture is dripped into the mixed system, the pH value is adjusted to 10-12 after the reaction is carried out for 4 hours at normal temperature, and ethyl acetate is used for multiple times of extraction. Adjusting the pH value to 1-2, continuously extracting with ethyl acetate for multiple times until the mixed solution generates fine droplets, and then carrying out rotary evaporation and vacuum drying to obtain the N-acryloyl-2-glycine (ACG).
Dissolving 1-2g Gellan Gum (GG) in appropriate amount of deionized water, and stirring at 80-90 deg.C. Cooling to 50-60 ℃, dropwise adding 2-8mL of methacrylic anhydride, and adjusting the pH of the system to 8-9 by using NaOH solution. The reaction was continued for 6h, after which the solution was dialyzed for 4 days and freeze-dried and stored under vacuum in the dark to give methacrylic anhydride-modified gellan gum (MeGG).
Fig. 1 is a nuclear magnetic hydrogen spectrum of the synthesized product, and each corresponding characteristic peak proves the successful synthesis of ACG and MeGG. FIG. 2 is an infrared spectrum of the synthesized product. 1550cm -1 The successful synthesis of ACG is proved by an amido bond characteristic peak, 1721cm -1 Characteristic peaks indicate successful synthesis of MeGG.
Example 2
In this embodiment, a method for preparing a PACG and MeGG gel patch is provided, which includes the following steps:
dissolving 1-2g of ACG, 0.05-0.1g of HAp and 0.05-0.1g of photoinitiator I2959 in a small amount of deionized water, and uniformly stirring the mixture in advance one night at 50-60 ℃ to obtain an ACG solution for later use.
0.5-1g of MeGG and 0.3-0.4g of photoinitiator I2959 are dissolved in 30-40mL of deionized water, and the mixture is stirred uniformly one night in advance while maintaining the temperature of 50-60 ℃. Adding appropriate amount of CaCl the next day 2 And continuously stirring uniformly to obtain a MeCG solution for later use.
Respectively injecting the ACG solution and the MeGG solution into a mold, then carrying out illumination crosslinking under an ultraviolet lamp, taking out after gelling, and thus obtaining poly-N-acryloyl-2-glycine hydrogel (PACG-gel) and polymethacrylic anhydride modified gellan gum hydrogel (MeGG-gel).
FIG. 3 is a cryo-scanning electron micrograph of PACG-gel and MeGG-gel. The PACG-gel section shows the structure of the seaweed, showing its potential adhesive properties. The section MeGG-gel shows a three-dimensional cross-linked structure and potential mechanical strength characteristics.
Example 3
In this example, a method for testing the rheological properties of the hydrogel prepared in example 2 is provided, which is as follows:
the PACG-gel and MeGG-gel prepared in example 2 were tested using a grit blasted surface probe of a rheometer. The modulus was measured at 29 samples in a constant strain 1% frequency sweep mode of 0.01-100Hz, maintaining a test temperature of 37 ℃.
FIG. 4 is a graph of the rheological moduli of PACG-gel and MeGG-gel. Both of them have higher storage modulus than loss modulus, indicating a certain elasticity. In addition, the storage modulus G '(0.4-1.2 kPa) and loss modulus G' (0.1-0.3 kPa) of PACG-gel are lower than those of MeGG-gel, which shows that the mechanical strength of PACG-gel is not high, the crosslinking degree is not high, and the PACG-gel is easier to deform along with tissues. The higher storage modulus G' (3-4 kPa) of MeGG-gel indicates that MeGG-gel has better mechanical strength and provides the function of supporting and protecting the gel patch.
Example 4
In this example, a method of testing the PACG-gel adhesion prepared in example 2 is provided, the testing method being as follows:
the PACG-gel prepared in example 2 was subjected to adhesion testing, setting the probe at a constant tensile speed of 10 μm/s, and its adhesion to break open to PACG-gel was tested by rheometer testing.
FIG. 5 is a graph of the adhesion tensile curve of PACG-gel. The maximum adhesion stress reaches 1.58N, and the stretching deformation is large, which shows that the gel patch can be tightly adhered and attached to tissues, and meets the requirement of adhesion of the gel patch in the oral cavity wet environment.
Example 5
In this embodiment, a method for testing a PACG-gel peeling stress is provided, which includes:
and (3) respectively adhering the pig tongues with proper sizes to two T-shaped clamps, placing the PACG-gel on the lower layer of the pig tongue, starting a texture instrument to compact for 10s, stretching to test, and recording the peeling stress when the PACG-gel is broken.
FIG. 6 is a peel stress curve of PACG-gel. The peel stress test on the pig tongue shows that the peel stress of PACG-gel is twice as strong as that of the commercial propolis oral patch product, which shows that the gel oral patch has strong adhesiveness on the surface of wet tissue, so that the gel oral patch can keep adhesion in the oral wet environment.
Example 6
In this embodiment, a method for preparing a drug-loaded oral gel double-layer patch (Dex-loaded PACG/MeGG-gel) and a drug-loaded oral gel single-layer patch (Dex-loaded PACG-gel) is provided, which includes the following steps:
1-2g of PACG, 0.05-0.1g of HAp, 0.5-1g of dexamethasone acetate (Dex) and 0.05-0.1g of photoinitiator I2959 are dissolved in a small amount of deionized water, and the mixture is kept at 50-60 ℃ and stirred uniformly one night in advance. 0.5-1g of MeGG and 0.3-0.4g of photoinitiator I2959 are dissolved in 30-40mL of deionized water, and the mixture is uniformly stirred in advance one night at 50-60 ℃. Adding appropriate amount of CaCl the next day 2 And continuously stirring the mixture evenly. Respectively injecting the PACG solution and the MeGG solution obtained by the method into a mould, then irradiating and crosslinking under an ultraviolet lamp, taking out a sample after gelling to respectively obtain a drug-loaded oral gel double-layer patch (Dex-loaded PACG/MeGG-gel) and a drug-loaded oral cavityGel monolayer patch (Dex-loaded PACG-gel).
Example 7
In this example, a method for testing the in vitro drug release test of the drug-loaded oral gel patch prepared in example 6 is provided, which comprises the following steps:
the Dex-loaded PACG/MeGG-gel and Dex-loaded PACG-gel prepared in example 6 were soaked in 10ml PBS solution, placed in a shaking table to shake and shake evenly (37 ℃), and absorbance at 242nm was tested by UV-vis at fixed time points (20 min, 40min, 60min, 80min, 100min, 120min, 4h, 6h, 12h, 1d, 2d, and 3 d), and then the actual concentration was calculated according to a standard release curve to obtain a cumulative drug release concentration-time diagram.
FIG. 7 is a graph showing the cumulative concentration-time of drug release of a drug-loaded oral gel patch, and the result shows that the burst release of the PACG-gel reaches 0.0158mg/mL within 40min, and the burst release of the PACG/MeGG-gel reaches 0.0284mg/mL within 40 min. Both can keep higher drug cumulative release concentration within 6h, which shows that the gel patch material has better drug burst release capacity and drug release effect.
The embodiments described above are intended to facilitate a person of ordinary skill in the art in understanding and using the invention. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (8)
1. A wet-adherent oral gel patch comprising:
a bottom layer of hydrogel; and
a top layer of hydrogel;
the bottom layer hydrogel is poly N-acryloyl-2-glycine hydrogel;
the top hydrogel is a polymethacrylic anhydride modified gellan gum hydrogel; wherein:
the wet-state adhesive oral gel patch is prepared by the following method:
(1) mixing 3-4g glycine (Gly) and 5-10mgK 2 CO 3 Dissolving in a mixed solution of a proper amount of water and diethyl ether, performing ice bath after the system is uniformly mixed, mixing 2-5mL of acryloyl chloride and 15-25mL of diethyl ether, then dropwise adding into the mixed system, reacting at normal temperature, adjusting the pH to 10-12, performing multiple extraction with ethyl acetate, adjusting the pH to 1-2, continuing performing multiple extraction with ethyl acetate, and performing rotary evaporation and vacuum drying to obtain N-acryloyl-2-glycine (ACG) for later use;
(2) dissolving 1-2g of Gellan Gum (GG) in a proper amount of deionized water, uniformly stirring at 80-90 ℃, cooling to 50-60 ℃, dropwise adding 2-8mL of methacrylic anhydride, adjusting the pH of the system to 8-9 with NaOH solution, continuously reacting for 6h, dialyzing and freeze-drying the solution, obtaining methacrylic anhydride modified gellan gum (MeGG), and storing in vacuum in a dark place for later use;
(3) dissolving 1-2g of ACG, 0.05-0.1g of nano hydroxyapatite (HAp) and 0.05-0.1g of photoinitiator I2959 in a small amount of deionized water, maintaining the constant temperature and uniformly stirring the mixture in advance one night to obtain an ACG solution for later use;
(4) dissolving 0.5-1g MeGG and 0.3-0.4g photoinitiator I2959 in 30-40mL deionized water, maintaining constant temperature, stirring uniformly one night ahead, adding appropriate amount of CaCl the next day 2 Continuously stirring uniformly to obtain a MeCG solution for later use;
(5) respectively injecting the ACG solution and the MeGG solution into a mold, then carrying out illumination crosslinking under an ultraviolet lamp, taking out after gelling, and thus obtaining poly-N-acryloyl-2-glycine hydrogel (PACG-gel) and polymethacrylic anhydride modified gellan gum hydrogel (MeGG-gel).
2. The wet-adhesive oral gel patch of claim 1, wherein:
the normal-temperature reaction time in the step (1) is 4 hours.
3. The wet-adherable oral gel patch of claim 1, wherein:
and (2) stopping extraction when fine liquid drops appear in the mixed solution at the end point of the multiple times of extraction of the ethyl acetate in the step (1).
4. The wet-adherable oral gel patch of claim 1, wherein:
the dialysis time of the solution in the step (2) is 4 days.
5. The wet-adhesive oral gel patch of claim 1, wherein:
and (3) keeping the temperature at 50-60 ℃ at constant temperature.
6. The wet-adhesive oral gel patch of claim 1, wherein:
and (4) keeping the temperature at 50-60 ℃ at constant temperature.
7. The wet-adherable oral gel patch according to any one of claims 1 to 6, which is prepared by the following reaction equation:
8. use of a wet-adherable oral gel patch according to any one of claims 1-6 for the preparation of a medicament for the treatment of canker sores.
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