CN110201163B - Hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticle - Google Patents
Hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticle Download PDFInfo
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Abstract
The invention discloses a drug-loaded mesoporous titanium dioxide nanoparticle modified by hyaluronic acid and polydopamine. The drug-loaded mesoporous titanium dioxide nanoparticles modified by hyaluronic acid and polydopamine disclosed by the invention can be used for aggregating the nanoparticles at a tumor part through the active targeting property of hyaluronic acid and increasing the selectivity of a preparation, so that the toxic and side effects of the preparation are reduced. On the other hand, the mesoporous titanium dioxide can generate singlet oxygen under the ultrasonic condition, simultaneously, the polydopamine can convert light energy into heat energy under the irradiation of near-infrared laser, and the combined application of acoustic kinetic treatment, photothermal treatment and chemotherapy can be realized along with the release of the medicine.
Description
Technical Field
The invention relates to the field of medical drugs, in particular to a drug-loaded mesoporous titanium dioxide nanoparticle modified by hyaluronic acid and polydopamine.
Background
At present, the clinical cancer treatment modes mainly comprise surgical treatment, chemotherapy, radiotherapy, targeted drug therapy and the like, but the treatment modes mostly have the defects of large surgical trauma, high toxic and side effects, incomplete treatment, strong drug resistance and the like. Therefore, the development of cancer treatment with specific killing and high safety and efficiency is a scientific problem and development direction of the current cancer treatment. With the development and perfection of nanotechnology and materials, multifunctional nanocomposites are bringing new hopes for precise localization, early diagnosis and combined therapy of tumors.
The application of nano-drugs is developed from carrying traditional drugs for chemotherapy to photothermal therapy, photodynamic therapy, sonodynamic therapy, magnetothermal therapy, gene therapy, immunotherapy and the like. The application of the nano material in the medical field provides a wider platform for researching and treating human diseases.
Sonodynamic Therapy (SDT) is a therapeutic method that uses Ultrasound (US) to excite sonosensitizers to generate Reactive Oxygen Species (ROS) to destroy organelles and induce apoptosis. Because the sonosensitizer has no toxicity and can kill cells only when being excited by ultrasound, compared with the traditional tumor treatment modes such as radiotherapy, chemotherapy and the like, the sonosensitizer has smaller toxic and side effects and good tissue permeability of ultrasound, so that the sonodynamic therapy has better clinical application prospect.
Titanium dioxide (TiO)2) As a novel sonodynamic therapeutic sonosensitizer, the compound has the characteristics of low price, stable chemical property, low toxicity and the like. The surface of the material can be subjected to various modifications, so that various active groups are introduced to improve the performance of the material. The mesoporous titanium dioxide nano particle (MTN) is TiO with rich pore channels2And (3) nanoparticles. On one hand, the MTN has large specific surface area and strong drug loading capacity, and can overcome the problems of easy agglomeration, short drug action time and the like when the drug is used alone; on the other hand, titanium dioxide forms a hole-electron pair under Ultrasonic (US) excitation, and the hole and the electron are separated under an electric field and react with surrounding water and dissolved oxygen to generate Reactive Oxygen Species (ROS) which are extremely strong in oxidizing property, and the ROS can destroy the structures of biological macromolecules (such as DNA and the like) in tumor cells, so that the tumor cells are effectively killed, and the titanium dioxide can be used as acoustic dynamic therapy (SDT).
Photothermal therapy (PTT), a novel tumor treatment technology, has received much attention in recent years due to its high tumor-eliminating ability and extremely low damage to normal tissues. Over the past decade, many inorganic photothermal conversion materials, especially gold and carbon nanomaterials, have been reported to be widely used in the study of photothermal therapy. With the development of nanotechnology and nanomaterials, the types and properties of photothermal reagents are also continuously improved. With the incentive for superior therapeutic effects of photothermal therapy, people are increasingly concerned about the possibility of the development of clinical applications. Some novel organic photothermal conversion agents have been developed rapidly in recent years because they can overcome the non-biodegradable characteristic of inorganic materials.
Polydopamine (PDA) is used as a high-efficiency photothermal conversion material, and has strong adhesion and good biocompatibility. The PDA-coated surface can be easily modified with various other polymer molecules or biomolecules, and by combining PDA with other materials, photothermal therapy combined with other therapeutic methods can be obtained, thereby improving the therapeutic effect.
Hyaluronic Acid (HA), an acidic mucopolysaccharide, is a major component of the extracellular matrix, HAs a structure comprising repeating units of D-glucuronic acid and N-acetylglucosamine, HAs good water solubility and biocompatibility, and is biodegradable. Hyaluronic acid also has affinity to a CD44 receptor, and a hyaluronic acid-based carrier can be accumulated in a plurality of malignant tumor cells (such as breast cancer, lung cancer, colorectal cancer and the like) with high expression of a CD44 receptor at a high concentration.
The drug-loaded mesoporous titanium dioxide nanoparticles modified by hyaluronic acid and polydopamine prepared by the invention can reach tumor parts through the active targeting property of hyaluronic acid, so that the selectivity of the preparation is increased. On the other hand, the mesoporous titanium dioxide can generate active oxygen under the ultrasonic condition, and simultaneously, the polydopamine can convert light energy into heat energy under the irradiation of near-infrared laser, so that the combined application of acoustic dynamic treatment, photothermal treatment and chemotherapy can be realized.
Disclosure of Invention
The invention aims to realize the combined application of multifunctional treatment and improve the defects of poor selectivity, high toxicity and the like of a monotherapy. The nano-particles take docetaxel as a chemotherapeutic drug and mesoporous titanium dioxide as a carrier, the surface of the nano-particles is modified with polydopamine and hyaluronic acid, the biocompatibility is improved while the therapeutic function of the nano-particles is increased, the nano-particles are selectively gathered at a tumor target area through the active targeting property of the hyaluronic acid, the chemotherapeutic drug is gradually released while the acoustodynamic therapy and the photothermal therapy are realized, and the therapeutic effect is remarkably enhanced through the combined application of a plurality of therapeutic modes.
The purpose of the invention can be realized by the following technical scheme:
step 1: taking a certain amount of glacial acetic acid, adding a small amount of tetrabutyl titanate while stirring, then adding a proper amount of water, continuously stirring for 10min, carrying out prehydrolysis on a titanium precursor, transferring the obtained mixture to a hydrothermal reaction kettle, reacting for 12h at 150 ℃, carrying out solvent heat treatment, centrifuging the mixture, washing the precipitate for 3 times by using water, and drying to obtain the mesoporous titanium dioxide.
Step 2: weighing a proper amount of medicine and the mesoporous titanium dioxide obtained in the step 1, dissolving the medicine with dichloromethane, treating the solution for 10min under the water bath ultrasonic condition, and then removing the dichloromethane through reduced pressure rotary evaporation to obtain the medicine-carrying mesoporous titanium dioxide.
And step 3: dispersing the drug-loaded mesoporous titanium dioxide prepared in the step 2 by using a proper amount of trihydroxymethyl aminomethane hydrochloride buffer solution, then adding a certain amount of dopamine hydrochloride and hyaluronic acid, and quickly stirring for 8 hours in the dark. And then centrifuging, and washing the precipitate for 3 times by using water to obtain the hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles.
The mesoporous titanium dioxide nanoparticles are prepared by prehydrolysis and solvent heat treatment of the titanium precursor, the medicine-carrying mesoporous titanium dioxide nanoparticles modified by hyaluronic acid and polydopamine are further successfully prepared, and the method has the advantages of simple process, good biocompatibility and high specific combination.
The invention has the advantages that: the invention selects the mesoporous titanium dioxide with large specific surface area, proper grain diameter and easy surface modification as the carrier. The compound has higher stability, can not only load a large amount of drugs (the drug loading is up to 38 percent) to improve the dispersion stability of hydrophobic drugs in water, but also can be used as a sonosensitizer to realize sonodynamic treatment. In addition, as the surface of the hyaluronic acid-dopamine composite is easy to modify, the hyaluronic acid and the polydopamine are modified on the surface of the hyaluronic acid-dopamine composite by electrostatic adsorption, so that the biocompatibility is improved, and more treatment functions are increased: (1) the hyaluronic acid can be highly specifically combined with malignant tumor cells highly expressed by CD44, so that an active targeting function is realized. (2) The polydopamine can be used as a photothermal conversion material to realize photothermal treatment.
Drawings
FIG. 1 is an appearance diagram of hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
FIG. 2 is a transmission electron microscope image of hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
FIG. 3 is a particle size distribution diagram of hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
FIG. 4 is a diagram of in vitro photothermal effect of hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
FIG. 5 is a diagram of in vitro generation of active oxygen by hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
FIG. 6 is a cytotoxicity test chart of drug-loaded mesoporous titanium dioxide nanoparticles modified by hyaluronic acid and polydopamine
FIG. 7 is a fluorescence microscope picture of cell uptake of hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
Detailed Description
The present invention will be described in detail below with reference to the embodiments shown in the drawings, but the present invention is not limited to the embodiments.
Example 1
1. Preparation of mesoporous titanium dioxide nanoparticles
1mL of tetrabutyl titanate was slowly dropped into 15mL of glacial acetic acid under stirring at room temperature, followed by addition of 0.5mL of distilled water to initiate hydrolysis of tetrabutyl titanate, followed by increasing the stirring speed as appropriate, the mixture was continuously stirred at room temperature for 10min, and then transferred to a hydrothermal reaction tank to be reacted at 150 ℃ for 12 h. And (3) collecting the precipitate through centrifugation, washing the precipitate for 3 times by using water, and drying to obtain the mesoporous titanium dioxide (MTN).
2. Preparation of hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
10mg of MTN and 20mg of docetaxel were weighed, dissolved in 1ml of dichloromethane, sonicated in a water bath for 10min, and then dichloromethane was rapidly removed by evaporation under reduced pressure. Adding 5ml of trihydroxymethyl aminomethane hydrochloride buffer solution (10 mmol. L-1, pH8.5), performing ultrasonic dispersion in water bath, adding dopamine hydrochloride and hyaluronic acid each 10mg, and rapidly stirring in dark for 8 h. And (3) collecting the precipitate through centrifugation, and washing the precipitate with water for 3 times to obtain the hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles.
The appearance of the prepared hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles is shown in figure 1; the drug-loaded mesoporous titanium dioxide nanoparticle suspension modified by hyaluronic acid and polydopamine is released by a certain multiple, and the shape of the suspension is observed by a transmission electron microscope, as shown in figure 2, the drug-loaded mesoporous titanium dioxide nanoparticle modified by hyaluronic acid and polydopamine has uniform particle size and is in a shuttle shape. The particle size is measured by a laser particle size analyzer, the particle size distribution result is shown in figure 3, the particle size of the drug-loaded mesoporous titanium dioxide nano-particles modified by hyaluronic acid and polydopamine is smaller, and the average particle size is less than 200 nm.
Example 2
1. In-vitro photothermal effect research of hyaluronic acid and polydopamine-coated drug-loaded mesoporous titanium dioxide nanoparticles
The power density is 2.5W/cm2Irradiating the drug-loaded mesoporous titanium dioxide nanoparticle suspension (1mL) which is placed in a quartz cell and is wrapped by hyaluronic acid and polydopamine and has the concentration of 1000ug/mL by using laser of 808nm, measuring the temperature of the suspension once every 30 seconds, and measuring the time for 10 minutes. The result is shown in fig. 4, the temperature of the drug-loaded mesoporous titanium dioxide nanoparticles coated by hyaluronic acid and polydopamine gradually rises along with the prolonging of the laser irradiation time, which indicates that the drug-loaded mesoporous titanium dioxide nanoparticles coated by hyaluronic acid and polydopamine have good photo-thermal conversion performance.
2. Detection of active oxygen generated in vitro by hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
Treating hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles and 1, 3-diphenyl isobenzofuran (DPBF) for different time under the excitation of ultrasound (1.5W), and then detecting the absorbance value of the DPBF at 455nm by using an ultraviolet-visible spectrophotometer. The result is shown in fig. 5, after the hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles and DPBF are subjected to ultrasonic treatment, the absorbance value of the DPBF at 455nm is obviously reduced, and the reduction is more obvious along with the extension of the ultrasonic time, which indicates that the amount of generated active oxygen is also gradually increased. The result shows that the hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles can generate active oxygen under the ultrasonic condition.
3. Cytotoxicity research of hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
The cytotoxicity of the hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles on human lung cancer cells A549 is detected by adopting an MTT method. Taking A549 cells in a logarithmic growth phase,the cell density was adjusted to 6X 10 by DMEM medium containing 10% fetal bovine serum4One/ml of the cells were inoculated into a 96-well plate at 100. mu.l/well with 5% CO at 37 ℃2The culture was carried out overnight in an incubator. Blank group is culture medium without drug; the control group is A549 cell sap normally cultured without drugs; the experimental group is culture solution containing docetaxel with different concentrations (2.5 mug/ml, 5 mug/ml, 10 mug/ml and 20 mug/ml) and hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles. Taking out the 96-well plate, removing the old culture medium, adding preparations with different concentrations according to a grouping design, repeating the wells for 6 times, and continuously culturing for 24 h. Then, serum-free medium containing MTT (1mg/ml) was added again, and the cells were incubated for 4 hours in the absence of light. The culture was terminated, the supernatant was discarded, 150. mu.l of DMSO solution was added to each well, the mixture was shaken for 10min to dissolve formazan sufficiently, and the light absorption was measured at 490nm using a microplate reader. As shown in fig. 6, the results show that, compared with docetaxel, the cell inhibition rate of the drug-loaded mesoporous titanium dioxide nanoparticle modified by hyaluronic acid and polydopamine is obviously improved. The result shows that the hyaluronic acid can be specifically bound with a CD44 receptor on the surface of the A549 cell, the uptake of the cell to the medicine is obviously increased, and the anti-tumor efficiency of the medicine is improved.
4. Cell uptake fluorescence microscope observation of hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles
Fat-soluble fluorescent dye coumarin-6 is used as a fluorescent probe, and a laser scanning confocal microscope is adopted to detect the fluorescence expression quantity. For receptor competition tests, an experimental group is coumarin-6 labeled hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles diluted by a serum-free DMEM medium, a control group is free hyaluronic acid pretreated for 2 hours to serve as a receptor blocking agent, and then the equivalent amount of coumarin-6 labeled hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticles are added. A549 cells in logarithmic growth phase were collected, digested with 0.25% trypsin, centrifuged at 5X 10/well5The cells were inoculated in 6-well plates at 37 ℃ with 5% CO2Incubate for 12 h. Treating the above two groups respectively, culturing in incubator for 0.5 hr, removing culture solution, washing with fresh PBS for 3 times, and adding more than 4%The cells were fixed by paraformaldehyde, and then the uptake of both groups of cells was observed under a fluorescent microscope. The result is shown in fig. 7, the fluorescence intensity of the experimental group (group a) is significantly stronger than that of the control group (group B), which indicates that the addition of free sodium hyaluronate as a receptor blocker can significantly reduce the uptake of coumarin-6 labeled nanoparticles by a549 cell. The hyaluronic acid serving as a targeting factor is further proved to have good affinity with the A549 cells highly expressed by the CD44, and the hyaluronic acid can effectively mediate the drug to enter the cells, so that the treatment effect of the drug is improved.
Claims (3)
1. A medicine-carrying mesoporous titanium dioxide nanoparticle modified by hyaluronic acid and polydopamine is characterized by comprising hyaluronic acid, polydopamine, mesoporous titanium dioxide nanoparticles and an anti-tumor medicine;
wherein the weight ratio of the polydopamine to the hyaluronic acid is 5:1-1:5, the weight ratio of the antitumor drug to the mesoporous titanium dioxide nanoparticles is 2:1-1:50, and the weight ratio of the polydopamine to the mesoporous titanium dioxide nanoparticles is 3:1-1: 30;
the preparation method comprises the following steps:
(1) taking a certain amount of glacial acetic acid, adding a proper amount of tetrabutyl titanate while stirring, then adding a proper amount of water, continuously stirring for 10min, then transferring the obtained mixture to a hydrothermal reaction kettle, reacting for 12h at 150 ℃, carrying out solvent heat treatment, centrifuging the mixture, washing the precipitate for 3 times by using water, and drying to obtain mesoporous titanium dioxide nanoparticles;
(2) weighing a proper amount of an anti-tumor drug and the mesoporous titanium dioxide nanoparticles obtained in the step (1), dissolving the anti-tumor drug and the mesoporous titanium dioxide nanoparticles with dichloromethane, treating the solution for 10min under the condition of water bath ultrasound, and then removing the dichloromethane by reduced pressure rotary evaporation to obtain drug-loaded mesoporous titanium dioxide nanoparticles;
(3) dispersing the drug-loaded mesoporous titanium dioxide nanoparticles prepared in the step (2) by using a proper amount of trihydroxymethyl aminomethane hydrochloride buffer solution, then adding a certain amount of dopamine hydrochloride and hyaluronic acid, quickly stirring for 8 hours in the dark, then centrifuging, and washing the precipitate for 3 times by using water to obtain the drug-loaded mesoporous titanium dioxide nanoparticles modified by hyaluronic acid and polydopamine.
2. The hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticle according to claim 1, wherein: the average grain diameter of the nanoparticles is 100nm-500 nm.
3. The hyaluronic acid and polydopamine modified drug-loaded mesoporous titanium dioxide nanoparticle according to claim 1, wherein: the antitumor drug is one or a mixture of more than two of docetaxel, paclitaxel, camptothecin, hydroxycamptothecin, curcumin and honokiol.
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