CN110384686B - Preparation method of pH-responsive pentafluorouracil/mesoporous silica/pullulan oxide polysaccharide drug sustained-release system - Google Patents
Preparation method of pH-responsive pentafluorouracil/mesoporous silica/pullulan oxide polysaccharide drug sustained-release system Download PDFInfo
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Abstract
The invention relates to a preparation method of a five-fluorouracil/mesoporous silica/pullulan oxide drug sustained-release system with pH response. The method comprises the following steps: preparing pullulan oxide polysaccharide, preparing aminated mesoporous silica, preparing pentafluorouracil/aminated mesoporous silica, and preparing a pentafluorouracil/mesoporous silica/pullulan oxide polysaccharide drug sustained-release system. The invention has the beneficial effects that: the aminated mesoporous silica and the pullulan oxide are easy to have Schiff base reaction, and the pullulan has good film forming property, so that the aminated mesoporous silica loaded with the drug can be coated to block the pore channel of the aminated mesoporous silica, and the generated acylhydrazone bond has sensitivity to pH, so that the drug can be controlled to be released through the stimulation response of the pH. The drug sustained release system has simple preparation and good biocompatibility, and can be widely applied to the field of biological medicine.
Description
Technical Field
The invention relates to a preparation method of a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system with pH response, belonging to the field of biological medicine.
Technical Field
In the process of exploring the construction of a drug sustained-release system by taking a nano-carrier as a main material, mesoporous silica is often used for constructing a stimulus-responsive drug controlled-release system due to its characteristics of large specific surface area, pore volume, controllable pore size, easy surface functionalization and the like. Although mesoporous silica has been used in the field of drug sustained release, there are some disadvantages, such as premature or burst release of the drug, and therefore pullulan has been chosen to improve the above disadvantages. The pullulan is a neutral, biodegradable, non-toxic and non-immunogenic nonionic polysaccharide, and the pullulan and derivatives thereof can be used in a drug sustained release system due to the characteristics of good film forming property and easy modification of the pullulan.
The method comprises the first step of modifying pullulan, oxidizing hydroxyl on the surface of pullulan into aldehyde groups by utilizing sodium periodate, the second step of synthesizing aminated mesoporous silica, the third step of adding aminated mesoporous silica into a pentafluorouracil solution to obtain pentafluorouracil/aminated mesoporous silica, and the fourth step of adding pentafluorouracil/aminated mesoporous silica into a pullulan oxide solution. The acylhydrazone bond of the system has pH sensitivity, so that a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system with pH response is obtained, and the purpose of controlling and releasing the drug is achieved.
Disclosure of Invention
The invention aims to provide a preparation method of a five-fluorouracil/mesoporous silica/pullulan oxide drug sustained-release system with pH response.
The invention relates to a preparation method of a pH-responsive pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system, which comprises the following steps:
a. preparing oxidized pullulan polysaccharide: weighing a certain amount of pullulan polysaccharide, dissolving the pullulan polysaccharide in deionized water, adding a certain amount of sodium periodate, continuously stirring the solution for 24 hours under the condition of keeping out of the sun, then adding ethylene glycol, stirring for 1 hour, terminating the reaction, placing the product in a dialysis bag, purifying in the deionized water for 3 days, and carrying out freeze drying for 24 hours at-45 ℃ to obtain the pullulan oxide;
b. preparation of aminated mesoporous silica: weighing a certain amount of hexadecyl trimethyl ammonium bromide, adding the hexadecyl trimethyl ammonium bromide into a mixed solution of ammonia water, deionized water and ethanol, mechanically stirring the mixed solution for 30 minutes, then dropwise adding tetraethoxysilane and 3-aminopropyl triethoxysilane into the continuously stirred solution, reacting for 6 hours, centrifuging a sample, repeatedly washing the sample with the deionized water and absolute ethyl alcohol, drying the sample, placing the dried sample in a crucible, and calcining the sample in a muffle furnace at a certain temperature for a certain time to obtain aminated mesoporous silica;
c. Preparation of pentafluorouracil/aminated mesoporous silica: adding a certain amount of aminated mesoporous silica into 20mL of a certain-concentration pentafluorouracil solution, and magnetically stirring for 12 hours to obtain pentafluorouracil/aminated mesoporous silica;
d. preparing a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system: b, preparing the pullulan oxide prepared in the step a into a solution, adding the pentafluorouracil/aminated mesoporous silica prepared in the step c into the pullulan solution, magnetically stirring for a certain time, placing the obtained dispersion into a petri dish, and freeze-drying for 24 hours at-45 ℃ to obtain a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system;
e. the in-vitro release of the pentafluorouracil is carried out on a pentafluorouracil/mesoporous silica/pullulan oxide polysaccharide drug sustained-release system under different pH conditions: respectively preparing phosphate buffer solutions with pH values of 5.5, 6.8 and 7.4, placing 50mg of a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system into dialysis bags, respectively placing the dialysis bags into 50mL of phosphate buffer solutions with different pH values, carrying out in-vitro release of drugs by magnetic stirring at constant temperature of 37 ℃, carrying out accumulation of drug release for 720min, taking samples every 60min, taking 5mL of solution every time, measuring the absorbance of the pentafluorouracil, simultaneously supplementing 5mL of fresh phosphate buffer solution, measuring the absorbance of the pentafluorouracil at 265nm by using an ultraviolet-visible spectrophotometer, and calculating the cumulative percentage of drug release at different pH values according to the measured absorbance of the pentafluorouracil.
Further, in the step a, the mass of the pullulan added is 0.1-1 g, the mass of the sodium periodate added is 0.3-0.5 g, the volume of the glycol added is 0.5-1.5 mL, and the molecular cut-off of the dialysis bag is 3500.
Further, in the step b, the mass of the hexadecyl trimethyl ammonium bromide is 0.3-1.0 g, the volume of the ammonia water is 1.0-1.5 mL, the volume of the deionized water is 60-90 mL, the volume of the absolute ethyl alcohol is 40-70 mL, the volume of the ethyl orthosilicate is 0.5-1.5 mL, the volume of the 3-aminopropyl triethoxysilane is 0.4-0.8 mL, the calcination temperature is 500-560 ℃, and the calcination time is 5-8 h.
Furthermore, the mass of the aminated mesoporous silica added in the step c is 200-260 mg, and the concentration of the pentafluorouracil solution is 20-80 mug/mL.
Further, in the step d, the mass of the pentafluorouracil/aminated mesoporous silica is 80-150 mg, the volume of the pullulan oxide solution is 50mL, the concentration of the pullulan oxide solution is 5mg/mL, and the magnetic stirring time is 10-16 h.
The invention has the beneficial effects that: the aminated mesoporous silica and the pullulan oxide are easy to have Schiff base reaction, and the pullulan has good film forming property, so that the aminated mesoporous silica loaded with the drug can be coated to block the pore channel of the aminated mesoporous silica, and the generated acylhydrazone bond has sensitivity to pH, so that the drug can be controlled to be released through the stimulation response of the pH. The drug sustained release system has simple preparation and good biocompatibility, and can be widely applied to the field of biological medicine.
Drawings
The experiment is further described below with reference to the accompanying drawings.
FIG. 1 is a field emission scanning electron microscope image of a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained release system in example one;
FIG. 2 is a transmission electron microscope image of a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained release system in the first embodiment;
FIG. 3 is a transmission electron micrograph of the pentafluorouracil/aminated mesoporous silica of example one;
FIG. 4 is a Fourier transform infrared spectrum of a pullulan oxide, pentafluorouracil, aminated mesoporous silica, pentafluorouracil/mesoporous silica/pullulan oxide drug delivery system according to example one;
FIG. 5 is an X-ray powder diffraction pattern of aminated mesoporous silica, pentafluorouracil, and pentafluorouracil/aminated mesoporous silica of example one;
fig. 6 is a drug release profile of the drug sustained release system of pentafluorouracil/mesoporous silica/pullulan oxide under different pH conditions in example one.
Detailed Description
The invention will now be further illustrated by reference to specific examples, which are intended to be illustrative of the invention and are not intended to be a further limitation of the invention.
The first embodiment is as follows:
a preparation method of a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system with pH response comprises the following steps:
(1) weighing 1.0g of pullulan polysaccharide, dissolving in deionized water, adding 0.43g of sodium periodate, continuously stirring the solution for 24 hours under the condition of keeping out of the sun, then adding 1.0mL of glycol, stirring for 1 hour, placing the product in a dialysis bag with the molecular cut-off of 3500, then placing the product in deionized water, purifying for 3 days, and carrying out freeze drying for 24 hours at-45 ℃ to obtain oxidized pullulan polysaccharide;
(2) weighing 0.5g of hexadecyl trimethyl ammonium bromide, adding the hexadecyl trimethyl ammonium bromide into a mixed solution of 1.4mL of ammonia water, 90mL of deionized water and 70mL of ethanol, mechanically stirring the mixed solution for 30 minutes, then sequentially dropwise adding 0.8mL of ethyl orthosilicate and 0.4mL of 3-aminopropyltriethoxysilane into the continuously stirred solution, reacting for 6 hours, centrifuging a sample, repeatedly washing the sample with deionized water and absolute ethanol, drying, then placing the dried sample into a crucible, and calcining for 6 hours at 540 ℃ in a muffle furnace to obtain aminated mesoporous silica;
(3) adding 250mg of aminated mesoporous silica into 20mL of a pentafluorouracil solution with the concentration of 65 mug/mL, and magnetically stirring for 12 hours to obtain pentafluorouracil/aminated mesoporous silica;
(4) Dissolving the pullulan oxide prepared in the step (1) in deionized water to form a pullulan oxide solution with the volume of 50mL and the concentration of 5mg/mL, dispersing 100mg of the pentafluorouracil/aminated mesoporous silica prepared in the step (3) in the pullulan oxide solution, magnetically stirring for 12 hours, finally placing the dispersion in a watch glass, and freeze-drying for 24 hours at-45 ℃ to obtain the pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system;
(5) respectively preparing phosphate buffer solutions with pH values of 5.5, 6.8 and 7.4, placing 50mg of a pentafluorouracil/mesoporous silica/pullulan oxide drug slow-release system into a dialysis bag, respectively placing the dialysis bag into 50mL of phosphate buffer solutions with different pH values, carrying out in-vitro release by constant-temperature magnetic stirring at 37 ℃, carrying out accumulation of drug release for 720min, taking samples every 60min, taking 5mL of the solution every time, measuring the absorbance of the pentafluorouracil, simultaneously supplementing 5mL of fresh phosphate buffer solutions, measuring the absorbance of the pentafluorouracil at 265nm by using an ultraviolet visible spectrophotometer, and calculating the cumulative percentage of drug release at different pH values according to the measured absorbance of the pentafluorouracil.
Scanning electron microscope images and transmission electron microscope images of the wufluorouracil/mesoporous silica/pullulan oxide drug sustained-release system prepared in the first embodiment are shown in fig. 1 and fig. 2, and from fig. 1, it can be clearly seen that spherical mesoporous silica with regular morphology is coated with pullulan oxide, and from fig. 2, a core-shell structure of the wufluorouracil/mesoporous silica/pullulan oxide drug sustained-release system can be seen. The transmission electron micrograph of the pentafluorouracil/aminated mesoporous silica prepared in the first example is shown in fig. 3, and it can be seen from fig. 3 that the pentafluorouracil/aminated mesoporous silica has a spherical structure with a uniform particle size. The Fourier transform infrared spectrum of the sustained-release system of the drug containing the pentafluorouracil/mesoporous silica/pullulan oxide prepared in the first embodiment is shown in FIG. 4, and the pullulan oxide in FIG. 4 is at 1733cm-1The absorption peak is the characteristic peak of aldehyde group; pentafluorouracil at 1247cm-1The characteristic peak is the stretching vibration of C ═ O; aminated mesoporous silica is 1560cm-1The weak peak appeared here, due to the bending vibration of N-H, 1420cm-1The peak at (A) can be attributed to flexural vibration of the N-H bond or methylene C-H bond of the ammonium ion; pentafluorouracil/mesoporous silica/pullulan oxide drug sustained release agent The release system is at 3400cm-1The characteristic peak is caused by stretching vibration of-OH on the pullulan polysaccharide and is 1642cm-1The peak shows the characteristic peak of acylhydrazone bond, which indicates that the pullulan oxide polysaccharide and the aminated mesoporous silica have Schiff base reaction. 1247cm-1The characteristic peak is caused by the stretching vibration of C ═ O in the pentafluorouracil. The results fully show that the preparation of the sustained-release system of the pentafluorouracil/mesoporous silica/pullulan oxide polysaccharide medicament is successful. The X-ray powder diffraction pattern of the pentafluorouracil/aminated mesoporous silica prepared in the first example is shown in fig. 5, and a sharp absorption peak of pentafluorouracil at 28.5 ° 2 θ can be seen from the pattern; the aminated mesoporous silica has a very wide peak at a 2 theta of 10-30 degrees; the pentafluorouracil/aminated mesoporous silica has a strong absorption peak at a position of 28.5 degrees 2 theta, and belongs to the characteristic peak of pentafluorouracil, and the wide peak is mainly the characteristic peak of aminated mesoporous silica. In conclusion, the pentafluorouracil/aminated mesoporous silica is successfully prepared.
In example one, the drug release profile of the pentafluorouracil/mesoporous silica/pullulan oxide drug sustained release system under different pH conditions is shown in fig. 6. As can be seen from the figure, the cumulative release amount of the pentafluorouracil has obvious pH sensitivity, and the stronger the acidity, the greater the cumulative release amount in the same time, because the acidic condition is favorable for the hydrolysis of the acylhydrazone bond, thereby leading to the accelerated release of the drug, the drug release is basically balanced at 660min, and the cumulative release amounts of the drugs are 77.09%, 48.32% and 35.46% at pH 5.5, 6.8 and 7.4, respectively. The acidic condition is more beneficial to the release of the pentafluorouracil from a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system.
Claims (5)
1. A preparation method of a pH-responsive pentafluorouracil/mesoporous silica/pullulan oxide polysaccharide drug sustained-release system is characterized by comprising the following steps: the method comprises the following steps:
a. preparing oxidized pullulan polysaccharide: weighing a certain amount of pullulan polysaccharide, dissolving the pullulan polysaccharide in deionized water, adding a certain amount of sodium periodate, continuously stirring the solution for 24 hours under the condition of keeping out of the sun, then adding ethylene glycol, stirring for 1 hour, terminating the reaction, placing the product in a dialysis bag, purifying in the deionized water for 3 days, and carrying out freeze drying for 24 hours at-45 ℃ to obtain the pullulan oxide;
b. preparation of aminated mesoporous silica: weighing a certain amount of hexadecyl trimethyl ammonium bromide, adding the hexadecyl trimethyl ammonium bromide into a mixed solution of ammonia water, deionized water and ethanol, mechanically stirring the mixed solution for 30 minutes, then dropwise adding tetraethoxysilane and 3-aminopropyl triethoxysilane into the continuously stirred solution, reacting for 6 hours, centrifuging a sample, repeatedly washing the sample with the deionized water and absolute ethyl alcohol, drying the sample, placing the dried sample in a crucible, and calcining the sample in a muffle furnace at a certain temperature for a certain time to obtain aminated mesoporous silica;
c. preparation of pentafluorouracil/aminated mesoporous silica: weighing a certain amount of aminated mesoporous silica, adding the aminated mesoporous silica into 20mL of a certain-concentration pentafluorouracil solution, and magnetically stirring for 12 hours to obtain pentafluorouracil/aminated mesoporous silica;
d. Preparing a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system: b, preparing the pullulan oxide prepared in the step a into a solution, adding the pentafluorouracil/aminated mesoporous silica prepared in the step c into the pullulan solution, magnetically stirring for a certain time, placing the obtained dispersion into a watch glass, and freeze-drying for 24 hours at-45 ℃ to obtain a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system;
e. pH sensitivity of a pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system: respectively preparing phosphate buffer solutions with pH values of 5.5, 6.8 and 7.4, placing 50mg of the pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system prepared in the step d into a dialysis bag, respectively placing the dialysis bag into 50mL of phosphate buffer solutions with different pH values, carrying out in-vitro release of the drugs by magnetic stirring at constant temperature of 37 ℃, accumulating the drug release for 720min, taking samples every 60min, taking 5mL of the solution every time, measuring the absorbance of the pentafluorouracil, simultaneously supplementing 5mL of fresh phosphate buffer solution, measuring the absorbance of the pentafluorouracil at 265nm by using an ultraviolet visible spectrophotometer, and calculating the cumulative percentage of drug release at different pH values according to the measured absorbance of the pentafluorouracil.
2. The method for preparing the pH-responsive Pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system according to claim 1, wherein the pH-responsive Pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system comprises: in the step a, the mass of the pullulan added is 0.1-1 g, the mass of the sodium periodate added is 0.3-0.5 g, the volume of the glycol added is 0.5-1.5 mL, and the molecular cut-off of the dialysis bag is 3500.
3. The method for preparing the pH-responsive Pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system according to claim 1, wherein the pH-responsive Pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system comprises: in the step b, the mass of the hexadecyl trimethyl ammonium bromide is 0.3-1.0 g, the volume of ammonia water is 1.0-1.5 mL, the volume of deionized water is 60-90 mL, the volume of absolute ethyl alcohol is 40-70 mL, the volume of tetraethoxysilane is 0.5-1.5 mL, the volume of 3-aminopropyl triethoxysilane is 0.4-0.8 mL, the calcining temperature is 500-560 ℃, and the calcining time is 5-8 h.
4. The preparation method of the pH-responsive pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system according to claim 1, which is characterized in that: the mass of the aminated mesoporous silica added in the step c is 200-260 mg, and the concentration of the pentafluorouracil solution is 20-80 mug/mL.
5. The preparation method of the pH-responsive pentafluorouracil/mesoporous silica/pullulan oxide drug sustained-release system according to claim 1, which is characterized in that: in the step d, the mass of the pentafluorouracil/aminated mesoporous silica is 80-150 mg, the volume of the pullulan oxide solution is 50mL, the concentration of the pullulan oxide solution is 5mg/mL, and the magnetic stirring time is 10-16 h.
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| CN113018251B (en) * | 2021-03-03 | 2022-08-16 | 常州大学 | Dual-drug controlled release system with pH and glutathione dual responses and preparation method thereof |
| CN112978940B (en) * | 2021-04-22 | 2021-07-16 | 广州市点滴生物科技有限公司 | Organic sewage biological fermentation treating agent and preparation method thereof |
| CN113956370A (en) * | 2021-10-27 | 2022-01-21 | 梅州绿盛林业科技有限公司 | Dendrobium officinale polysaccharide purification method based on aminated dendritic nano mesoporous material |
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| CN1723904A (en) * | 2005-07-18 | 2006-01-25 | 天津大学 | pH sensing controlable nanometer particle carried with 5-Fu and its prepn. method |
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