CN102652735A - Porous silica nano particle loaded with medicaments with slight solubility and preparation method and application of particle - Google Patents
Porous silica nano particle loaded with medicaments with slight solubility and preparation method and application of particle Download PDFInfo
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- CN102652735A CN102652735A CN2011100523547A CN201110052354A CN102652735A CN 102652735 A CN102652735 A CN 102652735A CN 2011100523547 A CN2011100523547 A CN 2011100523547A CN 201110052354 A CN201110052354 A CN 201110052354A CN 102652735 A CN102652735 A CN 102652735A
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Abstract
The invention discloses a porous silica nano particle loaded with medicaments with slight solubility. The nano particle has a nano composite structure of inorganic mesoporous silica/organic micelle/the medicaments with slight solubility, and the medicaments with slight solubility are wrapped in the organic micelle in porous channels of the inorganic mesoporous silica. According to the preparation method, the medicaments with slight solubility are loaded in situ and in a single step, and the carrier synthesis and medicament load are performed simultaneously, thereby remarkably improving the loading of the medicaments with slight solubility and simplifying the medicament loading way, wherein the total loading rate of the medicaments is higher than 80%, and the loading quantity of the medicaments is not lower than 1mg/g; the prepared nano particle has good dispersibility and high suspension stability, the size of the particle is less than 500nm and is adjustable, and the aperture of the nano particle ranges from 2nm to 30nm and is adjustable; the nano particle has the characteristics of pH-responsive releasing medicaments without subsequent modification; the preparation process is simple and can be implemented in a scale; and the nano particle can be applied to the preparation of anti-inflammation or anti-cancer medicinal preparations and has wide application prospect in the field of biomedicine.
Description
Technical field
The present invention relates to a kind of porous silicon dioxide nano particle that is loaded with insoluble drug; Specifically; Relate to the porous silicon dioxide nano particle that is loaded with insoluble drug that a kind of pH of having response discharges medicinal property, belong to medicinal nano material technology field.
Background technology
A large amount of insoluble drugs usually have shortcomings such as toxicity height, body-internal-circulation time weak point because it is poorly soluble, cause its application to be very limited.The toxic and side effects, the raising bioavailability that reduce insoluble drug have great importance for new drug development.The water solublity that improves insoluble drug is the Critical policies that improves its drug effect, reduces its toxic and side effects.The present method that generally adopts is that insoluble drug is carried out organic micelle or liposome, yet there are some important shortcomings in this technology, is subject to bioerosion, the easy leakage of medicine etc. like carrier.Than traditional organic carrier (like liposome grain, micelle, dendritic macromolecule, Nano capsule, virus and gel nanoparticle); Inorganic porous silica supports has good heat stability and anti-biochemistry aggressivity; But also have controlled pore passage structure, high specific surface area and big pore volume, can load a large amount of medicines and have good medicament slow release behavior.Thereby, how to combine organic carrier and inorganic carrier, complementary its pluses and minuses, more efficient and safe drugs transmission system has important value for exploitation.
According to the pH value difference of diseased region and normal structure, make up the Nano medication transmission system and be used for realizing that at diseased region the pH response discharges medicine, be the toxic and side effects and an important channel of improving drug effect that reduces medicine.For antiinflammatory and anticancer; Make up a kind of pH response medicine delivery systme; Can be neutral or weakly alkaline normal structure and blood in do not discharge medicine fully, and only at tart Inflamed tissue and tumor locus response release medicine, be that people pursue but still unconsummated all the time.Current most of Nano medication transmission system can only discharge at external realization pH response medicine at most, and responsiveness is not high enough, the medicine leakage perhaps takes place under the condition of pH ≈ 7.4 easily.Therefore, how to realize the pH response medicine discharges to reach how to guarantee that under normal physiological condition, medicine not taking place reveals in the body, is the key that finally realizes pH responsive intelligent release medicine in the body.
Summary of the invention
The purpose of this invention is to provide the porous silicon dioxide nano particle that is loaded with insoluble drug that a kind of pH of having response discharges medicinal property; To overcome above-mentioned defective of the prior art; Realize the interior pH response medicine release of body and under normal physiological condition, medicine do not taking place revealing, for toxic and side effects and its drug effect of raising that reduces insoluble drug provides an important channel.
For realizing the foregoing invention purpose, the technical scheme that the present invention adopts is following:
The porous silicon dioxide nano particle that is loaded with insoluble drug provided by the invention; It is characterized in that: have inorganic mesoporous silicon dioxide/organic micelle/insoluble drug nano composite structure, the organic gel that described insoluble drug is wrapped in the porous channel of inorganic mesoporous silicon dioxide is intrafascicular.
Described insoluble drug can be slightly solubility antibiotic medicine (as: nystatin, cyclosporin, mitomycin, a rubidomycin etc.), also can be slightly solubility anticarcinogen (as: amycin, camptothecine, paclitaxel, cisplatin, carboplatin, 5-fluorouracil etc.).
The method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug of the present invention is characterized in that, comprises following concrete steps:
A) make insoluble drug in 10～100 ℃ of following water-soluble soluble surfactants; Wherein: insoluble drug and water soluble surfactant active's mol ratio is (1: 10000)～(1: 2), and water soluble surfactant active's concentration is controlled on its critical micelle concentration;
B) in system, add hydrolyst and esters of silicon acis, continue to stir 1～48 hour down at 10～100 ℃, centrifugal then, washing, drying; Wherein: the mol ratio of esters of silicon acis and hydrolyst is (1000: 1)～(1: 10), and the concentration of esters of silicon acis is 0.05～2mol/L.
Described water soluble surfactant active can be cationic, anionic or non-ionic water-soluble surfactant.
The preferred DTAB of described cation type water-soluble surfactant (DTAB), cetyl trimethyl ammonium bromide (CTAB), hexadecyltrimethylammonium chloride (CTAC) or perfluoro butyl sulfonic acid fluoride (FC-4).
Preferred dodecylbenzene sodium sulfonate of described anionic water soluble surfactant active (SDBS) or dodecyl sodium sulfate (SDS).
Described non-ionic water-soluble surfactant preferred, polyethers polyhydric alcohol P123; Triton X-100 (Triton X-100); Polyoxyethylenesorbitan sorbitan monooleate (Tween 80); Nonidet P40 (Nonidet P-40) or polyether surfactant (as: P105; P104; P103; P85; P84; P75; P65; P38; F127; F108; F98; F88; F87; F77; F68; F38; L122; L121; L101; L92; L81; L72; L65; L64; L63; L62; L61; L44; L43; L42; L35 or L31).
Described hydrolyst is to choose according to the anti-hydrolytic performance of insoluble drug, and its effect is to avoid medicine to be destroyed; If the medicine alkali resistance then can be used the basic hydrolysis catalyst, comprise sodium hydroxide, potassium hydroxide, ammonia, TPAOH and triethanolamine; If the medicine acid resistance then can be used the acidic hydrolysis catalyst, comprise hydrochloric acid, nitric acid, sulphuric acid, phosphoric acid and zirconium oxychloride; If medicine is neither acidproof not alkaline-resisting again, then can use nearly neutral hydrolyst, comprise phosphate or the acetate buffer solution of ammonium fluoride and pH=7.
Described esters of silicon acis can be selected methyl silicate, ethyl orthosilicate or positive silicic acid propyl ester for use, wherein preferred ethyl orthosilicate.
The mol ratio of described esters of silicon acis and hydrolyst is preferably (10: 1)～(1: 10).
Because of the porous silicon dioxide nano particle that is loaded with insoluble drug of the present invention's preparation has the characteristic of pH response release medicine, that is: medicine does not discharge basically under the physiological condition of pH ≈ 7.4; Under the acid condition of pH＜7, can discharge medicine by significance; And the stronger drug release of acidity is fast more; Therefore can be used in the preparation of antiinflammatory or anti-cancer drug preparation, with the drug effect that improves this type of insoluble drug, reduce its toxic and side effects, have broad application prospects at biomedicine field.
The advantage of the porous silicon dioxide nano particle that is loaded with insoluble drug of the present invention preparation is: 1) have good monodispersity and nanoscale controlled particle diameter (＜500nm); 2) in the process of synthesizing porous silicon dioxide, the insoluble drug original position is loaded in the hydrophobic cores of surfactant micella in porous duct; Synthetic nanoparticle has a kind of " inorganic mesoporous silicon dioxide/organic micelle/insoluble drug " nano composite structure can significantly improve the water solublity of insoluble drug; 3) have the characteristic that the pH response discharges medicine, that is: medicine does not discharge basically under the physiological condition of pH ≈ 7.4; Under the acid condition of pH＜7, can discharge medicine by significance, and the stronger drug release of acidity is fast more.
Compare with loading method behind the traditional medicine; The method that the present invention has adopted a step original position to load insoluble drug; Have following advantage: 1) the synthetic loading with medicine of carrier carried out simultaneously, can improve the loading of insoluble drug more significantly, and the overall charging ratio of medicine is more than 80%; Useful load is not less than 1mg/g, has simplified medicine and has loaded approach; 2) the nanoparticle good dispersion, suspension stability of preparation are high, and particle size is less than 500nm and scalable, and the aperture is scalable between 2～30nm; 3) need not follow-up modification and promptly have the characteristic that the pH response discharges medicine; 4) preparation technology is simple, but scale is implemented.
Surfactant described in the present invention is at " surfactant is complete works of " (Michael Ash, Irene Ash work; Wang Shengwu, Luo Huiping translates selected passages, Shanghai scientific and technical literature publishing house, 1988, ISBN number: 78051321
*/ all can find in TQ423).
Description of drawings
Fig. 1 is the porous silicon dioxide nano morphology of particles sketch map that is loaded with insoluble drug of the present invention, and among the figure: 1 is inorganic mesoporous silicon dioxide; 2 is organic micelle; 3 is insoluble drug.
Fig. 2 is the transmission electron microscope photo of the porous silicon dioxide nano particle that is loaded with insoluble drug (camptothecine) of embodiment 1 preparation.
Fig. 3 is the hydration particle size distribution figure that the porous silicon dioxide nano particle that is loaded with insoluble drug (camptothecine) of embodiment 1 preparation adopts the dynamic light scattering method to measure.
Fig. 4 is the vitro drug release curve chart of the porous silicon dioxide nano particle that is loaded with insoluble drug (camptothecine) under different pH value of embodiment 1 preparation.
Fig. 5 is the toxic action of the porous silicon dioxide nano particle that is loaded with insoluble drug (camptothecine) of embodiment 1 preparation to the MCF-7 breast cancer cell.
Fig. 6 is the toxic action of the porous silicon dioxide nano particle that is loaded with insoluble drug (camptothecine) of embodiment 1 preparation to MCF-7/ADR drug resistance breast cancer cell.
The practical implementation method
Below in conjunction with embodiment the present invention is done further in detail, intactly explains, but do not limit content of the present invention.
The porous silicon dioxide nano particle that is loaded with insoluble drug provided by the invention; Has inorganic mesoporous silicon dioxide/organic micelle/insoluble drug nano composite structure; Described insoluble drug 3 is wrapped in the organic micelle 2 in the porous channel of inorganic mesoporous silica 1, and its structural representation is seen shown in Figure 1.
Described insoluble drug can be slightly solubility antibiotic medicine (as: nystatin, cyclosporin, mitomycin, a rubidomycin etc.), also can be slightly solubility anticarcinogen (as: amycin, camptothecine, paclitaxel, cisplatin, carboplatin, 5-fluorouracil etc.).
Embodiment 1
0.5mmol CTAB and 0.5mmol camptothecine are added in the 50mL water together, and stirring is dissolved it fully under 80 ℃ of temperature, in system, adds the 4mmol ammonium fluoride then; Add the 4mmol ethyl orthosilicate after 30 minutes, it is centrifugal after 1 hour to continue stirring, with water washing three times.
Utilize the ultra-violet absorption spectrum appearance to detect the absorbance of mixed solution reaction front and back at the 368nm place; Calculate camptothecine drug level in the solution according to the Beer-Lambert law, calculate the medicine loading of porous silicon dioxide nano particle in conjunction with the output of porous silicon dioxide nano particle.
The medicine loading of the porous silicon dioxide nano particle that carries camptothecine that obtains is 1.5mg/g; Mean diameter is 100nm; Have narrow particle size distribution and good dispersibility, as shown in Figures 2 and 3: Fig. 2 can show the loose structure of this nanoparticle and good monodispersity intuitively; Fig. 3 can show that this nanoparticle has good monodispersity and suspension stability.
The porous silicon dioxide nano particle that is loaded with insoluble drug (camptothecine) that 60mg is above-mentioned is dispersed in 30mL pH=7.4 respectively; 6.5; In 5 and 4 the buffer solution; Under 37 ℃ of temperature, carry out the vitro drug release experiment, the drug release curve is as shown in Figure 4, can be known by Fig. 4: camptothecine cumulative release amount in 6 days in the buffer solution of pH=7.4 is no more than 2%; And in acidic buffer solution, significantly discharge, along with tart enhancing, drug release is fast more, and the drug accumulation burst size in the buffer solution of pH=4 in 6 days can reach 30%.This shows that the porous silicon dioxide nano particle that carries camptothecine of above-mentioned preparation has very strong pH sensitive drug release performance.
The above-mentioned porous silicon dioxide nano particle that carries camptothecine is carried out common cultivation with MCF-7 breast cancer cell and MCF-7/ADR mdr cell respectively, use CCK-8 test kit (commercially available obtaining) to detect the survival rate of cultivating cell after three days, like Fig. 5 and shown in Figure 6.After cultivating three days altogether, MCF-7 breast cancer cell and MCF-7/ADR drug resistance breast cancer cell all have lower cell survival rate, show that the porous silicon dioxide nano particle that carries camptothecine of preparation has anticancer and effect reverse multiple drug resistance of tumor property.
Embodiment 2
0.5mmol CTAB and 0.1mmol amycin are added in the 50mL water together, and stirring is dissolved it fully under 60 ℃ of temperature, in system, adds the 8mmol ammonium fluoride then; Add the 4mmol ethyl orthosilicate after 30 minutes, it is centrifugal after 2 hours to continue stirring, with water washing three times.
Learn through check and analysis: the medicine loading of the porous silicon dioxide nano particle that carries amycin of present embodiment preparation is 80mg/g; Mean diameter is 96nm; Have narrow particle size distribution and good dispersibility, and have very strong pH sensitive drug release performance.
0.17mmol P123 and 0.05mmol paclitaxel are added in the 80mL hydrochloric acid solution together; Under 35 ℃ of temperature, stirring dissolves it fully; In system, add 2mmol zirconium oxychloride and 10mmol methyl silicate then, it is centrifugal after 6 hours to continue stirring, with water washing three times.
Learn through check and analysis: the medicine loading of the porous silicon dioxide nano particle that carries paclitaxel of present embodiment preparation is 32mg/g; Mean diameter is 300nm; Have narrow particle size distribution and good dispersibility, and have very strong pH sensitive drug release performance.
1mmol CTAB and 0.04mmol nystatin are added in the PBS (0.15mol/L) of 100mL pH=7 together; Under 60 ℃ of temperature, stirring dissolves it fully; In system, add the 7mmol ethyl orthosilicate then, it is centrifugal after 2 hours to continue stirring, with water washing three times.
Learn through check and analysis: the medicine loading of the porous silicon dioxide nano particle that carries nystatin of present embodiment preparation is 20mg/g; Mean diameter is 60nm; Have narrow particle size distribution and good dispersibility, and have very strong pH sensitive drug release performance.
Should be noted that at last; Above embodiment is unrestricted the present invention in order to technical scheme of the present invention to be described only; Although with reference to preferred embodiment the present invention is specified, those of ordinary skill in the art should be appreciated that and can make amendment or be equal to replacement the technical scheme of invention; And not breaking away from the spirit and the scope of technical scheme of the present invention, it all should be encompassed in the claim scope of the present invention.
Claims (16)
1. porous silicon dioxide nano particle that is loaded with insoluble drug; It is characterized in that: have inorganic mesoporous silicon dioxide/organic micelle/insoluble drug nano composite structure, the organic gel that described insoluble drug is wrapped in the porous channel of inorganic mesoporous silicon dioxide is intrafascicular.
2. the porous silicon dioxide nano particle that is loaded with insoluble drug according to claim 1 is characterized in that: described insoluble drug is slightly solubility antibiotic medicine or slightly solubility anticarcinogen.
3. the porous silicon dioxide nano particle that is loaded with insoluble drug according to claim 2 is characterized in that: described slightly solubility antibiotic medicine is meant nystatin, cyclosporin, mitomycin or rubidomycin.
4. the porous silicon dioxide nano particle that is loaded with insoluble drug according to claim 2 is characterized in that: described slightly solubility anticarcinogen is meant amycin, camptothecine, paclitaxel, cisplatin, carboplatin or 5-fluorouracil.
5. the described method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug of claim 1 is characterized in that, comprises following concrete steps:
A) make insoluble drug in 10～100 ℃ of following water-soluble soluble surfactants; Wherein: insoluble drug and water soluble surfactant active's mol ratio is (1: 10000)～(1: 2), and water soluble surfactant active's concentration is controlled on its critical micelle concentration;
B) in system, add hydrolyst and esters of silicon acis, continue to stir 1～48 hour down at 10～100 ℃, centrifugal then, washing, drying; Wherein: the mol ratio of esters of silicon acis and hydrolyst is (1000: 1)～(1: 10), and the concentration of esters of silicon acis is 0.05～2mol/L.
6. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 5 is characterized in that: described water soluble surfactant active is cationic, anionic or non-ionic water-soluble surfactant.
7. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 6 is characterized in that: described cation type water-soluble surfactant is meant DTAB (DTAB), cetyl trimethyl ammonium bromide (CTAB), hexadecyltrimethylammonium chloride (CTAC) or perfluoro butyl sulfonic acid fluoride (FC-4).
8. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 6 is characterized in that: described anionic water soluble surfactant active is meant dodecylbenzene sodium sulfonate (SDBS) or dodecyl sodium sulfate (SDS).
9. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 6 is characterized in that: described nonionic surfactant is meant PPG P123, Triton X-100 (Triton X-100), polyoxyethylenesorbitan sorbitan monooleate (Tween 80), Nonidet P40 (Nonidet P-40) or polyether surfactant.
10. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 5; It is characterized in that; Described hydrolyst is to choose according to the anti-hydrolytic performance of insoluble drug: if the medicine alkali resistance is then used the basic hydrolysis catalyst; If the medicine acid resistance is then used the acidic hydrolysis catalyst; If medicine is neither acidproof not alkaline-resisting again, then use nearly neutral hydrolyst.
11. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 10 is characterized in that: described basic hydrolysis catalyst is meant sodium hydroxide, potassium hydroxide, ammonia, TPAOH or triethanolamine.
12. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 10 is characterized in that: described acidic hydrolysis catalyst is meant hydrochloric acid, nitric acid, sulphuric acid, phosphoric acid or zirconium oxychloride.
13. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 10 is characterized in that: described nearly neutral hydrolyst is meant the PBS of ammonium fluoride or pH=7 or the acetate buffer solution of pH=7.
14. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 5 is characterized in that: described esters of silicon acis is meant methyl silicate, ethyl orthosilicate or positive silicic acid propyl ester.
15. the method for preparing that is loaded with the porous silicon dioxide nano particle of insoluble drug according to claim 5 is characterized in that: the mol ratio of described esters of silicon acis and hydrolyst is (10: 1)～(1: 10).
16. the described application of porous silicon dioxide nano particle in antiinflammatory or anti-cancer drug preparation that is loaded with insoluble drug of claim 1.
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Cited By (9)
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| CN103169667A (en) * | 2013-01-17 | 2013-06-26 | 西安电子科技大学 | Preparation method of multifunctional meso-porous silicon nano preparation carrying gossypol derivative |
| CN103417975A (en) * | 2013-07-12 | 2013-12-04 | 四川大学 | Preparing method of corrosion type silicon dioxide xerogel drug sustained-release material |
| CN104127383A (en) * | 2014-06-25 | 2014-11-05 | 江苏大学 | Hollow silica nano sustained-release preparation loaded with capsicine, and preparation method thereof |
| CN104983687A (en) * | 2015-07-14 | 2015-10-21 | 西南大学 | Novel nano-drug with tumor treatment action and preparation method |
| CN105056233A (en) * | 2015-08-12 | 2015-11-18 | 苏州大学 | Multifunctional mesoporous silica nanoparticles having near-infrared photothermal and in-vivo fluorescence imaging characteristics as well as preparation method and application of mesoporous silica nanoparticles |
| CN105340919A (en) * | 2015-10-13 | 2016-02-24 | 兰州交通大学 | Camptothecin-avermectin silica nanoparticle, and preparation method and application thereof |
| CN107011969A (en) * | 2017-03-31 | 2017-08-04 | 河南大学 | Organic antioxidant silicon dioxide coating type composite and its preparation method and application |
| CN109568296A (en) * | 2018-12-20 | 2019-04-05 | 扬州大学 | Polyacid nano-functional material and its preparation method and application |
| CN109950014A (en) * | 2019-03-20 | 2019-06-28 | 浙江工业大学 | A kind of method that weak hydrolyzation system prepares magnetic mesoporous SiO 2 composite microsphere |
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| CN103169667B (en) * | 2013-01-17 | 2014-08-20 | 西安电子科技大学 | Preparation method of multifunctional meso-porous silicon nano preparation carrying gossypol derivative |
| CN103169667A (en) * | 2013-01-17 | 2013-06-26 | 西安电子科技大学 | Preparation method of multifunctional meso-porous silicon nano preparation carrying gossypol derivative |
| CN103417975B (en) * | 2013-07-12 | 2016-02-10 | 四川大学 | A kind of preparation method of corrosion type silicon dioxide xerogel drug sustained-release material |
| CN103417975A (en) * | 2013-07-12 | 2013-12-04 | 四川大学 | Preparing method of corrosion type silicon dioxide xerogel drug sustained-release material |
| CN104127383A (en) * | 2014-06-25 | 2014-11-05 | 江苏大学 | Hollow silica nano sustained-release preparation loaded with capsicine, and preparation method thereof |
| CN104127383B (en) * | 2014-06-25 | 2016-08-10 | 江苏大学 | A kind of hollow silica nano controlled-release preparation being loaded with capsaicin and preparation method thereof |
| CN104983687A (en) * | 2015-07-14 | 2015-10-21 | 西南大学 | Novel nano-drug with tumor treatment action and preparation method |
| CN105056233A (en) * | 2015-08-12 | 2015-11-18 | 苏州大学 | Multifunctional mesoporous silica nanoparticles having near-infrared photothermal and in-vivo fluorescence imaging characteristics as well as preparation method and application of mesoporous silica nanoparticles |
| CN105056233B (en) * | 2015-08-12 | 2018-03-13 | 苏州大学 | Multi-functional mesoporous silicon dioxide nano particle with near-infrared photo-thermal and internal fluorescence imaging characteristic and its preparation method and application |
| CN105340919A (en) * | 2015-10-13 | 2016-02-24 | 兰州交通大学 | Camptothecin-avermectin silica nanoparticle, and preparation method and application thereof |
| CN105340919B (en) * | 2015-10-13 | 2017-09-29 | 兰州交通大学 | A kind of camptothecine AVM Nano particles of silicon dioxide and its production and use |
| CN107011969A (en) * | 2017-03-31 | 2017-08-04 | 河南大学 | Organic antioxidant silicon dioxide coating type composite and its preparation method and application |
| CN107011969B (en) * | 2017-03-31 | 2020-09-29 | 河南大学 | Organic antioxidant-silicon dioxide coated composite material and preparation method and application thereof |
| CN109568296A (en) * | 2018-12-20 | 2019-04-05 | 扬州大学 | Polyacid nano-functional material and its preparation method and application |
| CN109950014A (en) * | 2019-03-20 | 2019-06-28 | 浙江工业大学 | A kind of method that weak hydrolyzation system prepares magnetic mesoporous SiO 2 composite microsphere |
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