CN115770224A - Acrylic acid microsphere carrying paclitaxel medicine and preparation method thereof - Google Patents
Acrylic acid microsphere carrying paclitaxel medicine and preparation method thereof Download PDFInfo
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Abstract
The invention relates to an acrylic microsphere carrying paclitaxel drugs and a preparation method thereof, belongs to the technical field of preparation of embolization microspheres, and is used for solving the problem that the existing embolization microspheres can not carry paclitaxel drugs. The preparation method comprises the following steps: the method comprises the following steps: the method comprises the following steps: preparing an aqueous phase mixture; the water phase mixture comprises polyvinyl alcohol aqueous solution, acrylic acid, an initiator and a cross-linking agent; step two: preparing an oil phase mixture; the oil phase mixture comprises liquid paraffin and an emulsifier; step three: adding the water phase mixture obtained in the step one into the oil phase mixture obtained in the step two under the protection of nitrogen, stirring and heating to 50-55 ℃, adding a catalyst after 10min, carrying out polymerization reaction for 4-6 h, repeatedly washing the product obtained by the reaction with a surfactant to obtain microspheres, and freeze-drying the microspheres to obtain blank microspheres; step four: and (4) immersing the blank microspheres obtained in the step three into a paclitaxel buffer solution, stirring for loading the medicine, and naturally drying to obtain the acrylic microspheres carrying the paclitaxel medicine.
Description
Technical Field
The invention relates to the technical field of preparation of embolism microspheres, in particular to an acrylic microsphere carrying paclitaxel drugs and a preparation method thereof.
Background
Benign Prostatic Hyperplasia (BPH) is a common disease in middle-aged and elderly men, with the incidence of more than 50% in men over 50 years old and 90% in men over 80 years old. Prostatic hyperplasia often causes obstruction of bladder, dysuria and other lower urinary tract obstruction symptoms, finally causes bladder and kidney damage, and becomes one of important diseases affecting the health of middle-aged and old men. Current methods of treating BPH include medical, surgical, and minimally invasive treatments, but all have limitations. The basic principle of the super-selective prostatic artery embolization is that the prostatic volume is reduced by ischemia and necrosis of prostatic tissues caused by super-selective embolization of prostatic arteries, so that embolization materials are the most important.
At present, a plurality of embolism materials are applied to blood vessels, such as gelatin sponge, polyvinyl alcohol particles, acrylic acid material particles, various drug-loaded microspheres, glue and the like, and the materials for PAE (post Effect of antibiotics) mainly comprise the polyvinyl alcohol particles and the acrylic acid material particles, but the drug-loaded microspheres have no application report. In addition, because taxol can inhibit vascular smooth muscle cells and endothelial cells at the same time, taxol drug-coated devices have been widely used for prevention and treatment of vascular restenosis after interventional therapy, but taxol has poor water solubility and high drug toxicity, so that there is a challenge in preparing microspheres that can carry taxol drugs and can be slowly released.
Disclosure of Invention
In view of the above analysis, the embodiments of the present invention are directed to providing an acrylic microsphere carrying paclitaxel and a preparation method thereof, so as to solve the problem that the existing embolic microsphere cannot carry paclitaxel.
In one aspect, the invention provides a preparation method of acrylic microspheres carrying paclitaxel drugs, which comprises the following steps:
the method comprises the following steps: preparing an aqueous phase mixture;
the water phase mixture comprises polyvinyl alcohol aqueous solution, acrylic acid, an initiator and a cross-linking agent;
step two: preparing an oil phase mixture;
the oil phase mixture comprises liquid paraffin and an emulsifier;
step three: polymerizing to obtain blank microspheres;
adding the water phase mixture obtained in the step one into the oil phase mixture obtained in the step two under the protection of nitrogen, stirring and heating to 50-55 ℃, adding a catalyst after 10min, carrying out polymerization reaction for 4-6 h, repeatedly washing a product obtained by the reaction with a surfactant to obtain microspheres, and freeze-drying the microspheres to obtain blank microspheres;
step four: loading paclitaxel drug on the blank microspheres;
and (4) immersing the blank microspheres obtained in the step three into a paclitaxel buffer solution, stirring for loading the medicine, and naturally drying to obtain the acrylic microspheres carrying the paclitaxel medicine.
Further, the weight ratio of the polyvinyl alcohol aqueous solution, acrylic acid, initiator and crosslinking agent is 35.
Further, the mass fraction of the polyvinyl alcohol aqueous solution is 10% -20%.
Further, the initiator is one of persulfates.
Further, the cross-linking agent is one of acrylamide compounds.
Further, the weight ratio of the liquid paraffin to the emulsifier is 200;
the emulsifier is one of hydrophilic surfactants.
Further, in the third step, the weight ratio of the catalyst to the emulsifier is 1;
the catalyst is tetramethylethylenediamine;
the mass ratio of the water-phase mixture to the oil-phase cyclic compound is 1.
Further, in the fourth step, the paclitaxel buffer solution is a paclitaxel-ethanol solution with a concentration of 50mg/mL;
the mass ratio of the blank microspheres to the paclitaxel buffer solution is 0-30.
On the other hand, the invention provides an acrylic acid microsphere carrying paclitaxel medicine, which is prepared by adopting the preparation method.
Further, the acrylic microspheres carrying paclitaxel drugs can be applied to interventional therapy products.
Compared with the prior art, the invention can realize at least one of the following beneficial effects:
(1) The preparation method is simple and convenient and easy to operate, the obtained blank microspheres have regular spheres, uniform dispersion and good biocompatibility and stability, have rich cellular structures on the surfaces and inside, and have strong drug loading capacity and good slow release effect;
(2) The preparation method of the invention takes safe and nontoxic polyvinyl alcohol as a raw material, and is safer compared with the conventional preparation method; the microsphere is synthesized by a pure chemical process, the process operation is simple and convenient, the synthesis time of the microsphere is shortened, and the production efficiency is improved;
(3) The acrylic acid microsphere carrying the paclitaxel medicament has the following drug loading: 380 plus or minus 21ug of paclitaxel/mg microspheres; encapsulation efficiency: 10% ± 1.2%; the experimental verification of cytotoxicity and blood compatibility both meet the standard; the in vivo release experiment proves that the paclitaxel can be detected in blood within 4 days after embolism, and the in vitro release experiment proves that the accumulative drug release reaches 46% in 7 days;
(4) The acrylic acid microsphere carrying the paclitaxel medicament is a medicament-carrying microsphere which can be used for intravascular interventional therapy, has better embolization effect and small toxic and side effects of the paclitaxel sustained-release medicament, and can well inhibit vascular endothelial cells and smooth muscle cells so as to improve clinical curative effect.
In the invention, the technical schemes can be combined with each other to realize more preferable combination schemes. Additional features and advantages of the invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. The objectives and other advantages of the invention will be realized and attained by the structure particularly pointed out in the written description and drawings.
Drawings
The drawings, in which like reference numerals refer to like parts throughout, are for the purpose of illustrating particular embodiments only and are not to be considered limiting of the invention.
FIG. 1 is an electron micrograph of blank acrylic microspheres prepared in an embodiment;
FIG. 2 is an electron micrograph of a cross-section of a blank acrylic microsphere prepared in an embodiment;
fig. 3 is an electron micrograph of acrylic microspheres loaded with paclitaxel drug prepared in the embodiment.
Detailed Description
The preferred embodiments of the present invention will now be described in detail with reference to the accompanying drawings, which form a part hereof, and which together with the embodiments of the invention serve to explain the principles of the invention and not to limit its scope.
In the description of the embodiments of the present invention, it should be noted that, unless otherwise explicitly specified or limited, the term "connected" should be interpreted broadly, and may be, for example, a fixed connection, a detachable connection, or an integral connection, which may be a mechanical connection, an electrical connection, which may be a direct connection, or an indirect connection via an intermediate medium. The specific meanings of the above terms in the present invention can be understood according to specific situations by those of ordinary skill in the art.
The terms "top," "bottom," "at 8230; \8230above," "below," and "at 8230; \8230above," and "above" are used throughout to describe relative positions of components with respect to the device, such as the relative positions of the top and bottom substrates inside the device. It will be appreciated that the devices are multifunctional, regardless of their orientation in space.
The general working surface of the invention can be a plane or a curved surface, can be inclined or horizontal. For convenience of explanation, the embodiments of the present invention are placed on a horizontal plane and used on the horizontal plane, and are defined as "high and low" and "up and down".
Because the polyvinyl alcohol material is not suitable for carrying the medicament, the medicament carrying microspheres DC-Beads and HeaPashere of foreign commodities are high in price and do not have the capability of carrying the paclitaxel medicament, and the invention aims to develop the paclitaxel medicament carrying acrylic microspheres which can improve the clinical effect and reduce the toxic and side effects of the medicament.
The invention discloses a preparation method of acrylic acid microspheres carrying paclitaxel drugs, which comprises the following steps:
the method comprises the following steps: preparing an aqueous phase mixture;
the aqueous phase mixture comprises a polyvinyl alcohol aqueous solution, acrylic acid, an initiator and a crosslinking agent.
In the first step, the weight ratio of the polyvinyl alcohol aqueous solution, acrylic acid, initiator and crosslinking agent is 35.
The mass fraction of the polyvinyl alcohol aqueous solution is 10% -20%, and preferably the mass fraction of the polyvinyl alcohol aqueous solution is 15%.
The initiator is one of persulfates. Preferably, the initiator is ammonium persulfate or potassium persulfate, and the initiator can release free radicals in a low-temperature environment, so that the initiation efficiency is high, and the reaction time is reduced.
The cross-linking agent is one of acrylamide compounds. Preferably, the cross-linking agent is N, N' -methylene bisacrylamide, and the cross-linking agent can enable polyvinyl alcohol and acrylic acid to be cross-linked to form a network structure, so that the product structure is firm, and the microspheres are not easy to break in an aqueous solution.
Step two: preparing an oil phase mixture;
the oil phase mixture comprises liquid paraffin and an emulsifier.
In the second step, the weight ratio of the liquid paraffin to the emulsifier is 200.
The emulsifier is one of hydrophilic surfactants. Preferably, the emulsifier is Span-80, and the emulsifier can enable the oil phase and the water phase to form a good emulsion, so that the reaction is more sufficient, and the generated microsphere is more uniform and has a smoother surface.
Step three: polymerizing to obtain blank microspheres;
and (2) under the protection of nitrogen, adding the water phase mixture obtained in the first step into the oil phase mixture obtained in the second step, stirring and heating to 50-55 ℃ (preferably 55 ℃), adding a catalyst after 10min, carrying out polymerization reaction for 4-6 h (preferably 4 h), repeatedly washing a product obtained by the reaction with a surfactant (preferably an anionic surfactant) to obtain microspheres, and freeze-drying the microspheres to obtain blank microspheres (namely blank acrylic microspheres).
In the third step, the weight of the catalyst and the emulsifier is 1. The catalyst is tetramethylethylenediamine, and the catalyst can accelerate catalytic reaction in the reaction, so that the product has firmer structure and higher stability. Stirring at the rotating speed of 400-500r/min. The mass ratio of the water-phase mixture to the oil-phase cyclic compound is 1.
And in the third step, after the water phase mixture and the oil phase mixture are mixed, pre-crosslinking is carried out for 10min at the rotating speed of 400 to 500r/min and at the temperature of 50 to 55 ℃, and then a catalyst is added, so that the reaction is more complete.
In the third step, the microspheres are continuously freeze-dried for about 6 hours at the temperature of-40 ℃ to obtain blank microspheres.
Step four: loading paclitaxel drug on the blank microspheres;
and (4) immersing the blank microspheres obtained in the step three into a paclitaxel buffer solution, stirring for drug loading, and naturally drying to obtain the acrylic microspheres carrying paclitaxel drugs.
In the fourth step, the paclitaxel buffer solution is paclitaxel-ethanol solution, the concentration of which is 50mg/mL, experiments prove that the loading efficiency is highest under the concentration, specifically, 10g of blank acrylic microspheres are immersed into paclitaxel-ethanol solutions with the concentrations of 10mg/mL, 20mg/mL, 30mg/mL, 40mg/mL and 50mg/mL respectively for stirring, and the acrylic microspheres carrying paclitaxel drugs are obtained after natural drying. It is concluded that 50mg/ml paclitaxel-ethanol solution is the maximum solubility of paclitaxel, and the increase of the concentration of paclitaxel-ethanol solution can shorten the drug loading time and increase the encapsulation efficiency. The ethanol in the paclitaxel-ethanol solution is absolute ethanol, so that the paclitaxel medicament can be quickly dissolved in the ethanol, and the ethanol has the advantages of no toxic or side effect and quick volatilization. The mass ratio of the blank microspheres to the paclitaxel buffer solution is 0-30 (0-30 does not include 0, and the range of other positions includes two ends; preferably 30.
The invention also discloses an acrylic acid microsphere carrying paclitaxel drugs, which is prepared by adopting the preparation method and can be applied to interventional therapy products. The particle size distribution of the acrylic microspheres carrying the paclitaxel medicament is within the range of 10 to 500 mu m.
[ EXAMPLES one ]
A preparation method of acrylic microspheres carrying paclitaxel drugs comprises the following steps:
(1) Stirring 3.5ml of 10% polyvinyl alcohol aqueous solution, 1g of acrylic acid, 0.4g of ammonium persulfate and 0.1g of N, N' -methylene-bisacrylamide to prepare an aqueous phase mixture, and eliminating bubbles in the solution by using ultrasound;
(2) Adding 0.1g of Span-80 into 20ml of liquid paraffin to prepare an oil phase mixture;
(3) And (3) adding the water phase mixture obtained in the step (1) into the oil phase mixture obtained in the step (2) under the protection of nitrogen, heating to 55 ℃ at the rotating speed of 200r/min, adding 0.1ml of tetramethylethylenediamine after 10min, carrying out polymerization reaction for 4h, repeatedly cleaning microspheres by using a surfactant after the reaction is finished, and freeze-drying to obtain the blank acrylic microspheres. The obtained blank acrylic acid microspheres have irregular spheres, adhesive surfaces and uneven dispersion, and the particle size of the microspheres is distributed in the range of 10-700 um;
(4) And (4) taking 10g of the blank acrylic acid microspheres obtained in the step (3), immersing the blank acrylic acid microspheres into a paclitaxel-ethanol solution with the concentration of 30mg/ml, stirring, and naturally drying to obtain the acrylic acid microspheres carrying paclitaxel drugs. The drug loading and encapsulation efficiency of the microspheres were calculated by measuring the concentration of paclitaxel solution at a wavelength of 230nm using high performance liquid chromatography, drug loading: 150 +/-11 ug paclitaxel/mg microspheres; encapsulation efficiency: 7% + -1.5%.
[ EXAMPLE II ]
A preparation method of acrylic microspheres carrying paclitaxel drugs comprises the following steps:
(1) Stirring 3.5ml of 15% polyvinyl alcohol aqueous solution, 1g of acrylic acid, 0.4g of ammonium persulfate and 0.1g of N, N' -methylene-bisacrylamide to prepare an aqueous phase mixture, and eliminating bubbles in the solution by using ultrasound;
(2) Adding 0.1g Span-80 into 20ml liquid paraffin to obtain oil phase mixture;
(3) And (3) adding the water phase mixture obtained in the step (1) into the oil phase mixture obtained in the step (2) under the protection of nitrogen, heating to 55 ℃ at the rotating speed of 300r/min, adding 0.1ml of tetramethylethylenediamine after 10min, carrying out polymerization reaction for 3h, repeatedly cleaning microspheres by using a surfactant after the reaction is finished, and freeze-drying to obtain the blank acrylic acid microspheres. The obtained blank acrylic microspheres have regular spheres, adhesive surfaces and uniform dispersion, and the particle size of the microspheres is distributed in the range of 10-500 um;
(4) And (4) immersing 10g of the blank acrylic microspheres obtained in the step (3) into a paclitaxel-ethanol solution with the concentration of 40mg/ml, stirring, and naturally drying to obtain the acrylic microspheres carrying paclitaxel drugs. The drug loading and encapsulation efficiency of the microspheres were calculated by detecting the concentration of paclitaxel solution at a wavelength of 230nm using high performance liquid chromatography, drug loading: 235 plus or minus 14ug of paclitaxel/mg microspheres; the encapsulation efficiency is as follows: 8.1% + -1.1%.
[ EXAMPLE III ]
A preparation method of acrylic microspheres carrying paclitaxel drugs comprises the following steps:
(1) Stirring 3.5ml of 20% polyvinyl alcohol aqueous solution, 1g of acrylic acid, 0.4g of ammonium persulfate and 0.1g of N, N' -methylene-bisacrylamide to prepare an aqueous phase mixture, and eliminating bubbles in the solution by using ultrasound;
(2) Adding 0.1g of Span-80 into 20ml of liquid paraffin to prepare an oil phase mixture;
(3) And (3) adding the water phase mixture obtained in the step (1) into the oil phase mixture obtained in the step (2) under the protection of nitrogen, heating to 50 ℃ at the rotating speed of 400r/min, adding 0.1ml of tetramethylethylenediamine after 10min, carrying out polymerization reaction for 4h, repeatedly cleaning microspheres by using a surfactant after the reaction is finished, and freeze-drying to obtain the blank acrylic microspheres. The obtained blank acrylic acid microspheres have regular spheres, smooth surfaces, partial adhesion and uniform dispersion, and the particle size of the microspheres is in the range of 40-500 um;
(4) And (4) taking 10g of the blank acrylic acid microspheres obtained in the step (3), immersing the blank acrylic acid microspheres into a paclitaxel-ethanol solution with the concentration of 50mg/ml, stirring, and naturally drying to obtain the acrylic acid microspheres carrying paclitaxel drugs. The drug loading and encapsulation efficiency of the microspheres were calculated by detecting the concentration of paclitaxel solution at a wavelength of 230nm using high performance liquid chromatography, drug loading: 307 +/-16 ug paclitaxel/mg microspheres; the encapsulation efficiency is as follows: 9.2% + -1.3%.
[ EXAMPLE IV ]
A preparation method of acrylic acid microspheres carrying paclitaxel drugs comprises the following steps:
(1) Stirring 3.5ml of 15% polyvinyl alcohol aqueous solution, 1g of acrylic acid, 0.4g of potassium persulfate and 0.1g of N, N' -methylenebisacrylamide to prepare an aqueous phase mixture, and eliminating bubbles in the solution by using ultrasound;
(2) Adding 0.1g Span-80 into 20ml liquid paraffin to obtain oil phase mixture;
(3) And (3) under the protection of nitrogen, adding the water phase mixture obtained in the step (1) into the oil phase mixture obtained in the step (2), heating to 55 ℃ at the rotating speed of 500r/min, adding 0.1ml of tetramethylethylenediamine after 10min, carrying out polymerization reaction for 6h, repeatedly cleaning microspheres by using a surfactant after the reaction is finished, and freeze-drying to obtain the blank acrylic microspheres. The obtained blank acrylic acid microspheres have regular spheres, smooth and non-adhesive surfaces and uniform dispersion, and the particle size of the microspheres is distributed in the range of 10-500 um; as shown in fig. 1, the blank microspheres are seen to have a surface rich cellular structure. As shown in fig. 2, the section of the blank microsphere can see the honeycomb structure with abundant interior;
(4) And (4) immersing 10g of the blank acrylic microspheres obtained in the step (3) into a paclitaxel-ethanol solution with the concentration of 50mg/ml, stirring, and naturally drying to obtain the acrylic microspheres carrying paclitaxel drugs. The drug loading and encapsulation efficiency of the microspheres were calculated by measuring the concentration of paclitaxel solution at a wavelength of 230nm using high performance liquid chromatography, drug loading: 380 plus or minus 21ug of paclitaxel/mg microspheres; encapsulation efficiency: 10% + -1.2%. As shown in fig. 3, the microspheres are loaded with paclitaxel drug.
The invention is summarized by different examples: along with the increase of the concentration of the polyvinyl alcohol solution, the particle size of the prepared microspheres is slightly increased and part of the microspheres are adhered; after the stirring speed is increased, the particle size of the microspheres is reduced and the dispersity is improved; the polymerization reaction time is prolonged, and the balling rate is improved; the increase of the concentration of the paclitaxel-ethanol solution can shorten the drug loading time and improve the encapsulation efficiency.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention.
Claims (10)
1. A preparation method of acrylic microspheres carrying paclitaxel drugs comprises the following steps:
the method comprises the following steps: preparing an aqueous phase mixture;
the water phase mixture comprises polyvinyl alcohol aqueous solution, acrylic acid, an initiator and a cross-linking agent;
step two: preparing an oil phase mixture;
the oil phase mixture comprises liquid paraffin and an emulsifier;
step three: polymerizing to obtain blank microspheres;
adding the water phase mixture obtained in the step one into the oil phase mixture obtained in the step two under the protection of nitrogen, stirring and heating to 50-55 ℃, adding a catalyst after 10min, carrying out polymerization reaction for 4-6 h, repeatedly washing the product obtained by the reaction with a surfactant to obtain microspheres, and freeze-drying the microspheres to obtain blank microspheres;
step four: loading paclitaxel drug on the blank microspheres;
and (4) immersing the blank microspheres obtained in the step three into a paclitaxel buffer solution, stirring for drug loading, and naturally drying to obtain the acrylic microspheres carrying paclitaxel drugs.
2. The production method according to claim 1, wherein the weight ratio of the aqueous polyvinyl alcohol solution, acrylic acid, initiator and crosslinking agent is 35.
3. The preparation method according to claim 1, wherein the mass fraction of the polyvinyl alcohol aqueous solution is 10-20%.
4. The method according to claim 1, wherein the initiator is one of persulfates.
5. The method according to claim 1, wherein the crosslinking agent is one of acrylamide compounds.
6. The method according to claim 1, wherein the weight ratio of the liquid paraffin to the emulsifier is 200;
the emulsifier is one of hydrophilic surfactants.
7. The preparation method according to claim 1, wherein in the third step, the weight ratio of the catalyst to the emulsifier is 1;
the catalyst is tetramethyl ethylenediamine;
the mass ratio of the water-phase mixture to the oil-phase cyclic compound is 1.
8. The method according to claim 1, wherein in the fourth step, the paclitaxel buffer solution is paclitaxel-ethanol solution with a concentration of 50mg/mL;
the mass ratio of the blank microspheres to the paclitaxel buffer solution is 0-30.
9. Acrylic microspheres carrying a paclitaxel drug, characterized in that they are obtained by the process according to any one of claims 1 to 8.
10. The acrylic microsphere carrying paclitaxel drugs according to claim 9, which can be applied in interventional therapy products.
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