CN110384686A - A kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system preparation method with pH response - Google Patents
A kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system preparation method with pH response Download PDFInfo
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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Abstract
The present invention relates to a kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system preparation methods with pH response.The following steps are included: preparation pullulan oxide, prepares amidized mesoporous silicon oxide, prepares 5-Fluorouracil/amidized mesoporous silicon oxide, prepare 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system.The beneficial effects of the present invention are: amidized mesoporous silicon oxide and pullulan oxide are easy to happen schiff base reaction, and pulullan polysaccharide has good film forming, therefore cladding can be carried out to the amidized mesoporous silicon oxide for having loaded drug to block its duct, since the acylhydrazone key of generation has sensibility to pH, the control that drug can be carried out by the stimuli responsive of pH discharges.The drug sustained release system prepares simple, good biocompatibility, can be widely applied to biomedicine field.
Description
Technical field
The present invention relates to a kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drugs with pH response
The preparation method of slow-released system, belongs to biomedicine field.
Technical background
During exploring the building drug sustained release system using nano-carrier as material of main part, mesoporous silicon oxide is because of it
With big specific surface area and duct volume, the pore size that can regulate and control, especially it is easy to carry out the characteristics such as surface functionalization,
It is commonly used for constructing stimuli responsive type controlled release drug delivery system.Although mesoporous silicon oxide has been used for medicament slow release field,
But there is also some disadvantages, such as drug to discharge or be released too early, therefore we select pulullan polysaccharide come on improving
State disadvantage.Pulullan polysaccharide is a kind of neutral, biodegradable, nontoxic, non-immunogenicity nonionic polysaccharide, due to Propiram
Polysaccharide has preferable film forming and easily modified feature, therefore pulullan polysaccharide and its derivative can be used for medicament slow release
In system.
The first step of the invention is modified to pulullan polysaccharide, and the hydroxyl quilt on its surface is made using sodium periodate oxidation
It is oxidized to aldehyde radical, second step is the mesoporous silicon oxide of synthesizing amino, and third step is to add amidized mesoporous silicon oxide
Enter into 5-Fluorouracil solution, obtain 5-Fluorouracil/amidized mesoporous silicon oxide, the 4th step is that five fluorine urine is phonetic
Pyridine/amidized mesoporous silicon oxide is added in pullulan oxide solution, due to the aldehyde on pullulan oxide chain
The amino of base and amidized meso-porous titanium dioxide silicon face occur schiff base reaction generate acylhydrazone key, and pulullan polysaccharide have compared with
Good film forming feature, so as to be coated on meso-porous titanium dioxide silicon face and block its duct.The system has due to acylhydrazone key
There is pH sensibility, therefore has obtained a kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide medicine with pH response
Object slow-released system, to achieve the purpose that drug controlled release.
Summary of the invention
The purpose of the present invention is to provide a kind of 5-Fluorouracil/general Shandongs of mesoporous silicon oxide/oxidation with pH response
The preparation method of blue polysaccharide medicine slow-released system.
A kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug with pH response of the present invention
The preparation method of slow-released system, comprising the following steps:
A, it prepares pullulan oxide: weighing a certain amount of pulullan polysaccharide and be dissolved in deionized water, be added certain
The sodium metaperiodate of amount continuously stirs the solution for 24 hours under the conditions of being protected from light, and terminates reaction after then adding ethylene glycol stirring 1h,
Place the product in being put into deionized water to purify 3 days after bag filter, general Shandong is aoxidized by freeze-drying to obtain the final product for 24 hours at -45 DEG C
Blue polysaccharide；
B, it prepares amidized mesoporous silicon oxide: weighing a certain amount of cetyl trimethylammonium bromide, be added to ammonia
In the mixed solution of water, deionized water and ethyl alcohol, by mixed solution mechanical stirring 30 minutes, then by ethyl orthosilicate and 3- ammonia
Propyl-triethoxysilicane is successively added dropwise in the solution continuously stirred, reaction 6 hours after, sample is centrifuged and spend from
Sub- water and dehydrated alcohol are dry after washing repeatedly, then the sample after drying is placed in crucible, in Muffle furnace under certain temperature
Certain time is calcined to get amidized mesoporous silicon oxide；
C, it prepares 5-Fluorouracil/amidized mesoporous silicon oxide: taking a certain amount of amidized mesoporous silicon oxide,
It is added in the certain density 5-Fluorouracil solution of 20mL, magnetic agitation 12h is to get 5-Fluorouracil/amidized mesoporous
Silica；
D, it prepares 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system: is prepared by step a
Pullulan oxide wiring solution-forming, 5-Fluorouracil/amidized mesoporous silicon oxide prepared by step c is added to general
In the orchid polysaccharide solution of Shandong, obtained dispersion liquid is placed in surface plate by the magnetic agitation regular hour, and is freezed at -45 DEG C
Drying is for 24 hours to get 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system；
E, by 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system in different pH conditions
The lower release in vitro for carrying out 5-Fluorouracil: the phosphate buffer solution that pH is 5.5,6.8 and 7.4 is prepared respectively, takes 50mg five
Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system is placed in bag filter, and bag filter is set respectively
In the phosphate buffer solution of the 50mL of different pH, 37 DEG C of magnetic agitations of constant temperature carry out the release in vitro of drug, drug release
It is accumulative to carry out 720min, a sample is taken every 60min, 5mL solution is taken out every time, measures the absorbance of 5-Fluorouracil, simultaneously
The fresh phosphate buffer solution of 5mL is supplemented, the absorbance of 5-Fluorouracil is using ultraviolet-uisible spectrophotometer at 265nm
Measurement, according to the absorbance of the 5-Fluorouracil of measurement, to calculate the drug release cumulative percentage in different pH value.
Further, the quality that pulullan polysaccharide is added in step a is 0.1~1g, and the quality that sodium metaperiodate is added is 0.3
~0.5g, the volume that ethylene glycol is added is 0.5~1.5mL, and the molecule interception of bag filter is 3500.
Further, the quality of cetyl trimethylammonium bromide is 0.3~1.0g in step b, and the volume of ammonium hydroxide is 1.0
~1.5mL, the volume of deionized water are 60~90mL, and the volume of dehydrated alcohol is 40~70mL, and the volume of ethyl orthosilicate is
0.4~0.8mL of volume of 0.5~1.5mL, 3- aminopropyl triethoxysilane, calcination temperature are 500~560 DEG C, calcination time
It is 5~8h.
Further, the quality for the amidized mesoporous silicon oxide being added in step c is 200~260mg, and five fluorine urine is phonetic
The concentration of pyridine solution is 20~80 μ g/mL.
Further, 5-Fluorouracil/amidized mesoporous silicon oxide quality is 80~150mg in step d, oxidation
It is 5mg/mL that the volume of pulullan polysaccharide solution, which is 50mL, concentration, and the time of magnetic agitation is 10~16h.
The beneficial effects of the present invention are: amidized mesoporous silicon oxide and pullulan oxide are easy to happen schiff bases
Reaction, and pulullan polysaccharide has good film forming, therefore can be to the amidized mesoporous silicon oxide for having loaded drug
Cladding is carried out to block its duct, since the acylhydrazone key of generation has sensibility to pH, can be rung by the stimulation of pH
It should carry out the control release of drug.The drug sustained release system prepares simple, good biocompatibility, can be widely applied to biological medicine
Field.
Detailed description of the invention
This experiment is further illustrated with reference to the accompanying drawing.
Fig. 1 is 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system field in embodiment one
Emit scanning electron microscope (SEM) photograph；
Fig. 2 is that 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system is saturating in embodiment one
Penetrate electron microscope；
Fig. 3 is 5-Fluorouracil/amidized mesoporous silicon oxide transmission electron microscope picture in embodiment one；
Fig. 4 is pullulan oxide in embodiment one, 5-Fluorouracil, amidized mesoporous silicon oxide, five fluorine urine
Pyrimidine/mesoporous silicon oxide/pullulan oxide drug sustained release system Fourier transform infrared spectroscopy figure；
Fig. 5 is amidized mesoporous silicon oxide, 5-Fluorouracil and 5-Fluorouracil/amidized in embodiment one
The X-ray powder diffraction figure of mesoporous silicon oxide；
Fig. 6 is 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug under condition of different pH in embodiment one
The drug release patterns figure of slow-released system.
Specific embodiment
Presently in connection with specific embodiment, the present invention will be further described, following embodiment be intended to illustrate invention rather than
Limitation of the invention further.
Embodiment one:
A kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system with pH response
Preparation method, comprising the following steps:
(1) pulullan polysaccharide for weighing 1.0g is dissolved in deionized water, and the sodium metaperiodate of 0.43g is added, by the solution
It is continuously stirred under the conditions of being protected from light for 24 hours, then adds 1.0mL ethylene glycol and stir 1h, be 3500 place the product in molecule interception
Bag filter after be put into deionized water and purify 3 days, by freeze-drying for 24 hours up to pullulan oxide at -45 DEG C；
(2) cetyl trimethylammonium bromide for weighing 0.5g is added to 1.4mL ammonium hydroxide, 90mL deionized water and 70mL
In the mixed solution of ethyl alcohol, by mixed solution mechanical stirring 30 minutes, then by 0.8mL ethyl orthosilicate and 0.4mL3- ammonia third
Ethyl triethoxy silicane alkane is successively added dropwise in the solution continuously stirred, reacts 6 hours, sample is centrifuged and uses deionized water
It is dry after being washed repeatedly with dehydrated alcohol, then the sample after drying is placed in crucible, 6h is calcined at 540 DEG C in Muffle furnace,
Up to amidized mesoporous silicon oxide；
(3) the amidized mesoporous silicon oxide of 250mg is taken, it is molten to be added to the 5-Fluorouracil that 20mL concentration is 65 μ g/mL
In liquid, 5-Fluorouracil/amidized mesoporous silicon oxide is arrived after magnetic agitation 12h；
(4) pullulan oxide prepared by step (1) is dissolved in deionized water, forming volume is 50mL, and concentration is
The pullulan oxide solution of 5mg/mL, 5-Fluorouracil/amidized meso-porous titanium dioxide prepared by 100mg step (3)
Silicon is distributed in the pullulan oxide solution, which is finally placed in surface plate by magnetic agitation 12h, and -45
It is freeze-dried at DEG C for 24 hours to get 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system；
(5) phosphate buffer solution that pH is 5.5,6.8 and 7.4 is prepared respectively, takes 50mg 5-Fluorouracil/mesoporous dioxy
SiClx/pullulan oxide drug sustained release system is placed in bag filter, and bag filter is respectively placed in the 50mL's of different pH
In phosphate buffer solution, 37 DEG C of magnetic agitations of constant temperature carry out the release in vitro of drug, and drug release is accumulative to carry out 720min, often
A sample is taken every 60min, 5mL solution is taken out every time, measures the absorbance of 5-Fluorouracil, while supplementing the fresh phosphoric acid of 5mL
The absorbance of salt buffer solution, 5-Fluorouracil is measured at 265nm using ultraviolet-uisible spectrophotometer, according to the five of measurement
The absorbance of fluorouracil, to calculate the drug release cumulative percentage in different pH value.
5-Fluorouracil/mesoporous silicon oxide/pullulan oxide the drug sustained release system prepared in embodiment one
Scanning electron microscope (SEM) photograph and transmission electron microscope picture are as depicted in figs. 1 and 2, we can be clearly seen that from Fig. 1, the ball-type of regular appearance
Mesoporous silicon oxide is oxidized pulullan polysaccharide cladding, it can be seen that 5-Fluorouracil/mesoporous silicon oxide/oxidation from Fig. 2
The core-shell structure of pulullan polysaccharide drug sustained release system.The 5-Fluorouracil prepared in embodiment one/amidized mesoporous dioxy
The transmission electron microscope picture of SiClx is as shown in figure 3,5-Fluorouracil/amidized mesoporous silicon oxide is in grain as can see from Figure 3
The uniform spherical structure of diameter.5-Fluorouracil/mesoporous silicon oxide/pullulan oxide the drug prepared in embodiment one is slow
The Fourier transform infrared spectroscopy figure of release system is as shown in figure 4, pullulan oxide is in 1733cm in Fig. 4-1The absorption peak at place
For the characteristic peak of aldehyde radical；5-Fluorouracil is in 1247cm-1The characteristic peak at place is the stretching vibration of C=O；Amidized mesoporous dioxy
SiClx is in 1560cm-1Locate the weak peak occurred, is the bending vibration due to N-H, 1420cm-1The peak at place is attributable to ammonium ion
The bending vibration of N-H key or methylene c h bond；5-Fluorouracil/mesoporous silicon oxide/pullulan oxide medicament slow release system
System is in 3400cm-1The characteristic peak at place is due to caused by the stretching vibration of-OH on pulullan polysaccharide, in 1642cm-1Place occurs
The characteristic peak of acylhydrazone key illustrates that schiff base reaction has occurred in pullulan oxide and amidized mesoporous silicon oxide.
1247cm-1The characteristic peak at place is as caused by the stretching vibration of C=O in 5-Fluorouracil.Result above absolutely proves that five fluorine urine is phonetic
The successful preparation of pyridine/mesoporous silicon oxide/pullulan oxide drug sustained release system.The five fluorine urine prepared in embodiment one is phonetic
Pyridine/amidized mesoporous silicon oxide X-ray powder diffraction figure is as shown in figure 5,5-Fluorouracil is 2 as we can see from the figure
θ is a sharp absorption peak occur at 28.5o；Amidized mesoporous silicon oxide 2 θ be 10~30 ° at have one very
Wide peak；5-Fluorouracil/amidized mesoporous silicon oxide is to have a strong absorption peak at 28.5o in 2 θ, belongs to five fluorine
The characteristic peak of uracil, and the broad peak occurred is mainly the characteristic peak of amidized mesoporous silicon oxide.In conclusion five fluorine are urinated
Pyrimidine/amidized mesoporous silicon oxide is successfully prepared.
5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug is slow under different pH condition in embodiment one
The drug release patterns figure of release system is as shown in Figure 6.It can be seen from the figure that the cumulative release amount of 5-Fluorouracil has obviously
PH sensibility, it is acid stronger, at the same time in cumulative release amount it is bigger, this is because acid condition is conducive to acylhydrazone key
Hydrolysis, so as to cause the accelerated release in vitro of drug, drug release basically reaches balance when 660min, and the cumulative release amount of drug is in pH
5.5,6.8 and 7.4 when respectively 77.09%, 48.32% and 35.46%.Illustrate acid condition be more advantageous to 5-Fluorouracil from
Release in 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system.
Claims (5)
1. a kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system system with pH response
Preparation Method, it is characterised in that: steps are as follows:
A, it prepares pullulan oxide: weighing a certain amount of pulullan polysaccharide and be dissolved in deionized water, be added a certain amount of
Sodium metaperiodate continuously stirs the solution for 24 hours under the conditions of being protected from light, and terminates reaction after then adding ethylene glycol stirring 1h, will produce
Object is placed in after bag filter to be put into deionized water and purify 3 days, more up to oxidation Propiram for 24 hours by freeze-drying at -45 DEG C
Sugar；
B, it prepares amidized mesoporous silicon oxide: weighing a certain amount of cetyl trimethylammonium bromide, be added to ammonium hydroxide, go
In the mixed solution of ionized water and ethyl alcohol, by mixed solution mechanical stirring 30 minutes, then by ethyl orthosilicate and 3- aminopropyl
Triethoxysilane is successively added dropwise in the solution continuously stirred, after reaction 6 hours, sample is centrifuged and uses deionized water
It is dry after being washed repeatedly with dehydrated alcohol, then the sample after drying is placed in crucible, it is calcined under certain temperature in Muffle furnace
Certain time is to get amidized mesoporous silicon oxide；
C, it prepares 5-Fluorouracil/amidized mesoporous silicon oxide: weighing a certain amount of amidized mesoporous silicon oxide, add
Enter into the certain density 5-Fluorouracil solution of 20mL, magnetic agitation 12h is to get 5-Fluorouracil/amidized mesoporous two
Silica；
D, 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system: oxygen prepared by step a is prepared
Change pulullan polysaccharide wiring solution-forming, 5-Fluorouracil/amidized mesoporous silicon oxide prepared by step c is added to Propiram
In polysaccharide solution, obtained dispersion liquid is placed in surface plate by magnetic agitation certain time, and is freeze-dried at -45 DEG C
For 24 hours to get 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system；
E, 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide drug sustained release system pH sensibility: pH is prepared respectively
For 5.5,6.8 and 7.4 phosphate buffer solution, the 5-Fluorouracil/mesoporous silicon oxide/oxidation for taking 50mg step d to prepare
Pulullan polysaccharide drug sustained release system is placed in bag filter, and bag filter is respectively placed in the phosphate-buffered of the 50mL of different pH
In solution, 37 DEG C of magnetic agitations of constant temperature carry out the release in vitro of drug, and drug release is accumulative to carry out 720min, take every 60min
Sample takes out 5mL solution every time, measures the absorbance of 5-Fluorouracil, while it is molten to supplement the fresh phosphate-buffered of 5mL
The absorbance of liquid, 5-Fluorouracil is measured at 265nm using ultraviolet-uisible spectrophotometer, according to the 5-Fluorouracil of measurement
Absorbance, to calculate the drug release cumulative percentage in different pH value.
2. a kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide with pH response according to claim 1
High iodine is added it is characterized in that: the quality that pulullan polysaccharide is added in step a is 0.1~1g in the preparation method of drug sustained release system
The quality of sour sodium is 0.3~0.5g, and the volume that ethylene glycol is added is 0.5~1.5mL, and the molecule interception of bag filter is 3500.
3. a kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide with pH response according to claim 1
The preparation method of drug sustained release system, it is characterized in that: in the step b quality of cetyl trimethylammonium bromide be 0.3~
1.0g, the volume of ammonium hydroxide are 1.0~1.5mL, and the volume of deionized water is 60~90mL, the volume of dehydrated alcohol is 40~
70mL, the volume of ethyl orthosilicate are 0.5~1.5mL, 0.4~0.8mL of volume of 3- aminopropyl triethoxysilane, calcining temperature
Degree is 500~560 DEG C, and calcination time is 5~8h.
4. a kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide with pH response according to claim 1
The preparation method of drug sustained release system, it is characterized in that: the quality for the amidized mesoporous silicon oxide being added in the step c is
200~260mg, the concentration of 5-Fluorouracil solution are 20~80 μ g/mL.
5. a kind of 5-Fluorouracil/mesoporous silicon oxide/pullulan oxide with pH response according to claim 1
The preparation method of drug sustained release system, it is characterized in that: 5-Fluorouracil/amidized mesoporous silicon oxide in the step d
Quality is 80~150mg, and it is 5mg/mL that the volume of pullulan oxide solution, which is 50mL, concentration, and the time of magnetic agitation is
10~16h.
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| CN112978940A (en) * | 2021-04-22 | 2021-06-18 | 广州市点滴生物科技有限公司 | Organic sewage biological fermentation treating agent 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 |
| CN115300514A (en) * | 2022-08-09 | 2022-11-08 | 常州大学 | Dual-response drug controlled release system with dual-drug sequential delivery function and preparation method and application thereof |
| CN115300514B (en) * | 2022-08-09 | 2024-05-24 | 常州大学 | Double-response drug controlled release system with double-drug sequential delivery function and preparation method and application thereof |
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