CN114652686A - Preparation of heterojunction nano-particles loaded with romidepsin and having acoustic dynamic effect - Google Patents
Preparation of heterojunction nano-particles loaded with romidepsin and having acoustic dynamic effect Download PDFInfo
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- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/15—Depsipeptides; Derivatives thereof
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- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0028—Disruption, e.g. by heat or ultrasounds, sonophysical or sonochemical activation, e.g. thermosensitive or heat-sensitive liposomes, disruption of calculi with a medicinal preparation and ultrasounds
- A61K41/0033—Sonodynamic cancer therapy with sonochemically active agents or sonosensitizers, having their cytotoxic effects enhanced through application of ultrasounds
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- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0047—Sonopheresis, i.e. ultrasonically-enhanced transdermal delivery, electroporation of a pharmacologically active agent
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
- A61K9/0009—Galenical forms characterised by the drug release technique; Application systems commanded by energy involving or responsive to electricity, magnetism or acoustic waves; Galenical aspects of sonophoresis, iontophoresis, electroporation or electroosmosis
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
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Abstract
The invention discloses a preparation method of heterojunction nano-particles loaded with romidepsin and having an acoustic dynamic effect, which is a novel nano-particle material taking medicinal chemistry as a synthesis basis and is used for treating tumors by utilizing the unique excellent properties of the nano-particle material. The method specifically comprises the following steps: (1) preparing mesoporous titanium dioxide; (2) carbon nitride quantum dots (g-C)3N4QD) and preparing a titanium dioxide material; (3) the heterojunction nano-particles loaded with romidepsin and having an acoustic dynamic effect are prepared by uploading the romidepsin serving as an endogenous response small molecule drug; (4) The successful synthesis of the nano particles and the effect of the sonodynamic and chemotherapy synergistic treatment are verified through experiments. The finally obtained nanoparticle complex has good dispersibility, biocompatibility and tumor treatment effect, and has great application potential in the biomedical field and other social and economic fields.
Description
Technical Field
The invention relates to the field of chemical drugs, in particular to preparation and application of a heterojunction nano particle carrying romidepsin and having an acoustic dynamic effect.
Background
With the development of the nano biomedical field, more and more researchers are dedicated to research the application of nano materials in the minimally invasive and noninvasive treatment of cancer treatment, the method not only can accurately target cancer cells, but also has more accurate spatial and temporal resolution, and simultaneously can ensure the integrity of normal tissues and cells, greatly improve the treatment effect and reduce adverse effects. The sonodynamic cancer therapy is a novel noninvasive therapy mode, has good treatment effect on the aspect of tumor therapy, and can kill cancerated cells in tissues by exciting the sonosensitizer to generate toxic active oxygen through ultrasound. Wherein, the inorganic nano material as the sound sensitive agent has the characteristics of more stability, excellent physical and chemical properties and the like. And TiO 22Is the most studied inorganic sound-sensitive agent. To overcome TiO2Wide band gap induced electrons (e)-) -a cavity (h)+) Problem of fast complexation by modifying g-C on its surface3N4QDs form a direct Z-type heterojunction at the interface of the two materials, and the Z-type heterojunction formed can enhance charge separation to make g-C3N4Negative conduction band (C) of QDB) The potential is generated more1O2And TiO2Positive valence band (V)B) The potential generates more OH, thereby enhancing the therapeutic effect of the acoustic power. The two semiconductor materials are used for constructing a heterostructure, so that the inhibition of the rapid recombination of photon-generated carriers is also a technical means for enhancing photocatalytic hydrogen evolution and photodegrading organic dyes in the field of photoelectrocatalysis. However, the common synthesis methods are mostly high-temperature calcination, grinding and the like, which can affect the size, water solubility and dispersibility of the material, but the blood circulation of the nano material depends on the physicochemical properties, and the large-size nano material (> 200 nm) is easily filtered by spleen or cleared by a reticuloendothelial system, thereby affecting the anticancer treatment effect of the material in vivo.
Endogenous response prodrug-triggered tumor ablation has become oneA variety of hot research. Since the microenvironment of solid tumor tissue is significantly different from normal tissue. In particular, Glutathione (GSH) concentrations in the cytoplasm (2-10 mM) are significantly higher than extracellular (2-20. mu.M) and blood (1-2. mu.M), resulting in a large gradient of reduction potential between the extracellular and intracellular microenvironment. The redox-reactive nano-prodrug can reduce the toxic effect of chemotherapeutic drugs on normal tissues. Romdepsin (FK 228) is a small molecule prodrug possessing a reductive disulfide bond that can be activated by high concentrations of glutathione in solid tumors, producing metabolites containing free sulfhydryl groups. The metabolite is a potent histone deacetylase inhibitor, and the inhibition results in increased histone acetylation, which affects the cell cycle and leads to apoptosis. Through g-C3N4QD modified TiO2The prepared nano particles have uniform size and good dispersibility, and can generate active oxygen through ultrasonic drive to enhance the treatment effect of the acoustic power. Meanwhile, the compound can be used as a nano-carrier to enhance the permeation and retention effects of solid tumors, realize the effective delivery and controllable release of micromolecule chemotherapeutic drugs, namely romidepsin, and realize the synergistic anticancer curative effect of powerful sonodynamic combined chemotherapy.
Disclosure of Invention
Aiming at the problems that the existing drug delivery carrier for tumor treatment has single effect and poor treatment effect, the traditional photodynamic treatment has shallow tissue penetration depth and certain harm to normal tissues, and small-molecule chemotherapy drugs have poor targeting property, great toxic and side effects, rapid blood clearance and the like, the invention aims to synthesize a novel drug delivery platform which has high biocompatibility and long in-vivo circulation time and realizes the sonodynamic and chemotherapy synergistic treatment.
The technical scheme of the invention is as follows:
the preparation method of the heterojunction nano-particles loaded with romidepsin and having an acoustic power effect is characterized by comprising the following steps: comprises the following steps:
(1) preparing the mesoporous titanium dioxide nano particles: firstly, magnetically stirring a polyvinylpyrrolidone PVP K30 aqueous solution, absolute ethyl alcohol and hydrochloric acid at room temperature for 20 min to obtain a mixed dispersion liquid; followed byDropwise adding a titanium tetrafluoride aqueous solution into the dispersion liquid, and slowly stirring at room temperature for 1 h to obtain a mixed solution; transferring the mixed solution to a stainless steel high-pressure reaction kettle, raising the temperature to 180 ℃ by a program, keeping the temperature for 3 hours, and then lowering the temperature to room temperature by the program to obtain white suspended matters; the white mesoporous TiO is obtained by alternately centrifuging and washing ethanol and deionized water2Nano particles and then preparing into TiO2A solution;
(2) preparing carbon nitride quantum dots: firstly, grinding melamine into powder, heating the powder in a muffle furnace at 550 ℃ for 4 h, heating and cooling at the heating rate of 3 ℃/min to obtain light yellow blocky carbon nitride, grinding the light yellow blocky carbon nitride into powder and collecting the powder; dispersing powdered carbon nitride in ethanol, adding KOH solution, performing ultrasonic treatment for 10 min, transferring to a stainless steel high-pressure reaction kettle, keeping at 180 ℃ for 16 h, and cooling to room temperature to obtain a light yellow suspension; filtering the suspension through a filter with the pore size of 0.22 mu m, and performing running water dialysis in a dialysis bag 500 Da for three days to remove KOH and ethanol in the system to obtain light yellow g-C3N4A QD solution;
（3）TiO2@g-C3N4preparation of QD nanoparticles: firstly, a certain amount of TiO is taken2Solution with g-C3N4Mixing the QD solutions, carrying out ultrasonic treatment on the mixed solution for 10 min at room temperature, then transferring the mixed solution to a stainless steel high-pressure reaction kettle, and keeping the mixed solution at 110 ℃ for 1 h; then centrifugally washing by deionized water to remove excessive g-C3N4QD, obtaining TC nanoparticles, and preparing a TC solution;
（4）TiO2@g-C3N4preparation of QD/RMD nanoparticles: firstly, adding a certain amount of romidepsin solution into the TC solution, stirring for 24 hours at room temperature in a dark place, and centrifugally washing the obtained mixed solution through deionized water to obtain the TCR nano particles with the effect of the sonodynamic combined chemotherapy.
Further, the concentration of the polyvinylpyrrolidone aqueous solution in the step (1) is 50-100 mg/mL; the volume of the absolute ethyl alcohol in the step (1) is 20-30 mL; the concentration of the hydrochloric acid solution in the step (1) is 0.05-0.1 mol/L; the concentration of the titanium tetrafluoride solution in the step (1) is 4-5 mg/mL.
Further, the mass of the powdered carbon nitride in the step (2) is 20-30 mg; the volume of the ethanol in the step (2) is 20-30 mL; the concentration of KOH in the step (2) is 0.5-1 mol/L.
Further, TiO in the step (3)2And g-C3N4The mass ratio of QD is 2: 1-1: 2.
Further, the mass ratio of TC to romidepsin in the step (4) is 10: 1-1: 1.
Further, the rotation speed of the centrifugation in the steps (1), (3) and (4) is 8000 rpm, and the centrifugation time is 10 min.
The invention has the main advantages that:
aiming at the defects of the existing nano-carrier, the invention creatively prepares the acoustic power functional nano-drug delivery platform which realizes the synergistic treatment of a plurality of treatment methods and has better dispersibility and biocompatibility. In the present invention, by adding in TiO2Surface modification g-C3N4QD forms a direct Z-type heterojunction at the interface of the two materials, so that charges and cavities are effectively separated under the drive of ultrasound, the sonodynamic treatment effect is enhanced, and the nanoparticles have good dispersibility and stability. In addition, the loaded drug romidepsin realizes controllable release and effective delivery through the ultrasonic action, reduces the uptake of the romidepsin in normal tissues, thereby influencing cell proliferation and further inducing apoptosis. Finally obtaining the nano compound with the synergistic effect of the sonodynamic function and the chemotherapy.
Drawings
In order to make the purpose, technical scheme and beneficial effect of the invention more clear, the invention provides the following drawings:
fig. 1 is a schematic diagram of the synthesis of a hetero-junction nanoparticle (TCR) loaded with romidepsin having an acoustic dynamic effect according to embodiment 1 of the present invention.
Fig. 2 is a TEM image of a hetero-junction nanoparticle (TCR) loaded with romidepsin with acoustic dynamic effect in example 1 of the present invention.
Fig. 3 is a dynamic light scattering hydrated particle size distribution diagram (7 days) of the heterojunction nanoparticle (TCR) loaded with romidepsin with acoustic dynamic effect in different solutions according to example 1 of the present invention.
Fig. 4 is an infrared diagram of the heterojunction nanoparticles (TCR) loaded with romidepsin having acoustic dynamic effect in example 1 of the present invention.
FIG. 5 is a graph of the in vitro toxicity of Romidepsin loaded hetero-junction nanoparticles (TCR) in example 1 of the invention on 4T1 cancer cells for 24 h with and without sonication.
FIG. 6 is a graph showing the in vivo anti-tumor effect of the Romidepsin loaded heterojunction nanoparticles (TCR) in example 1 of the present invention.
FIG. 7 is a graph showing the conventional results of the acoustic dynamic effect of the hetero-junction nanoparticles (TCR) loaded with romidepsin in example 1 of the present invention in the blood of mice.
Detailed Description
The following examples are intended to illustrate the invention, but are not intended to limit the scope of the invention.
Example 1 preparation of Romidicin-loaded heterojunction nanoparticles with acoustic dynamic effect
The synthesis principle of the heterojunction nano-particle loaded with romidepsin with acoustic dynamic effect is shown in figure 1, and the synthesis method comprises the following synthesis steps:
(1) preparing the mesoporous titanium dioxide nano particles: firstly, 4 mL of polyvinylpyrrolidone PVP K30 aqueous solution (83.75 mg/mL), 27.6 mL of absolute ethyl alcohol and 0.1 mol/L of hydrochloric acid are magnetically stirred at room temperature for 20 min to obtain a mixed dispersion liquid; subsequently, 2.5 mL of titanium tetrafluoride aqueous solution (4.96 mg/mL) was added dropwise to the dispersion, and the mixture was stirred slowly at room temperature for 1 hour to obtain a mixed solution; transferring the mixed solution to a stainless steel high-pressure reaction kettle, raising the temperature to 180 ℃ by a program, keeping the temperature for 3 hours, and then lowering the temperature to room temperature by the program to obtain white suspended matters; the white mesoporous TiO is obtained by alternately centrifuging and washing ethanol and deionized water2Nano particles and then preparing into TiO2A solution;
(2) preparing the carbon nitride quantum dots: first, 6 g of melamine were groundGrinding into powder, heating in a muffle furnace at 550 ℃ for 4 h, heating at a heating rate of 3 ℃/min, cooling to obtain light yellow blocky carbon nitride, grinding into powder, and collecting; dispersing 30 mg of powdered carbon nitride in 30 mL of ethanol, adding 1 mol/L KOH solution, carrying out ultrasonic treatment for 10 min, transferring the mixture to a stainless steel high-pressure reaction kettle, keeping the mixture at 180 ℃ for 16 h, and cooling the mixture to room temperature to obtain a light yellow suspension; filtering the suspension through a filter with the pore size of 0.22 mu m, and performing running water dialysis in a dialysis bag 500 Da for three days to remove KOH and ethanol in the system to obtain light yellow g-C3N4A QD solution;
（3）TiO2@g-C3N4preparation of QD nanoparticles: first, 2.5 mL of TiO was taken2(4 mg/mL) with 1.66 mL g-C3N4QD (6 mg/mL) is mixed, the mixed solution is subjected to ultrasonic treatment for 10 min at room temperature, and then the mixed solution is transferred to a stainless steel high-pressure reaction kettle and is kept for 1 h at 110 ℃; then centrifugally washing by deionized water to remove excessive g-C3N4QD, obtaining TC nano particles, and preparing a TC solution;
（4）TiO2@g-C3N4preparation of QD/RMD nanoparticles: firstly, adding 200 mu L of romidepsin (2 mg/mL) into 4 mL of TC (0.5 mg/mL), stirring for 24 h at room temperature in a dark place, and centrifugally washing the obtained mixed solution through deionized water to obtain the TCR nano particles with the effect of the acoustic-dynamic combined chemotherapy.
The Transmission Electron Microscope (TEM) is shown in FIG. 2, and the TEM result shows that the diameter of the nanoparticle is about 116 nm. The particle size stability of the nanoparticle can be seen from the hydrated particle size diagram of the nanoparticle in different solution environments. FIG. 4 is an infrared spectrum analysis of different components, from which it can be seen that TC group 1340-1020 cm-1Is due to g-C3N4C-N heterocyclic stretching vibrations typical of QDs 1530 cm in the TCR set-1For a modification of the-CONH amide II band, 1740 cm-1Successful synthesis of the material was demonstrated for a telescopic vibration of C = O in the-COO-ester group. FIG. 5 is the in vitro toxicity profile of nanoparticles against 4T1 tumor cells for 24 h in the presence or absence of ultrasonic stimulation, respectively, from which it can be seen that the treatment is combined with the acoustic power and chemotherapyThe product has good killing effect on 4T1 tumor cells. FIG. 6 is a graph showing the tumor suppression effect of different treatments and different drugs in mice, from which it can be seen that the TCR group had significant tumor suppression effect under external ultrasound stimulation. Fig. 7 is a graph of the detection result of the biocompatibility of the TCR nanoparticles to the mouse, and it can be seen from the graph that there is no significant difference between the blood indexes at different time points and the blank group, which proves that the nanoparticles have higher biocompatibility and safety.
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, although the invention has been described in detail with reference to the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the scope of the invention as defined by the appended claims.
Claims (6)
1. The preparation method of the heterojunction nano-particle loaded with romidepsin and having the acoustic dynamic effect is characterized in that: comprises the following steps:
(1) preparing the mesoporous titanium dioxide nano particles: firstly, magnetically stirring a polyvinylpyrrolidone PVP K30 aqueous solution, absolute ethyl alcohol and hydrochloric acid at room temperature for 20 min to obtain a mixed dispersion liquid; then, dropwise adding a titanium tetrafluoride aqueous solution into the dispersion liquid, and slowly stirring at room temperature for 1 h to obtain a mixed solution; transferring the mixed solution to a stainless steel high-pressure reaction kettle, raising the temperature to 180 ℃ by a program, keeping the temperature for 3 hours, and then lowering the temperature to room temperature by the program to obtain white suspended matters; the white mesoporous TiO is obtained by alternately centrifuging and washing ethanol and deionized water2Nano particles and then preparing into TiO2A solution;
(2) preparing carbon nitride quantum dots: firstly, grinding melamine into powder, heating the powder in a muffle furnace at 550 ℃ for 4 h, heating and cooling at the heating rate of 3 ℃/min to obtain light yellow blocky carbon nitride, grinding the light yellow blocky carbon nitride into powder and collecting the powder; dispersing powdered carbon nitride in ethanol, adding KOH solution, ultrasonic treating for 10 min, transferring to stainless steel high-pressure reactor, maintaining at 180 deg.C for 16 hr, and cooling to room temperature to obtain light yellow suspensionLiquid; filtering the suspension through a filter with the pore size of 0.22 mu m, and performing running water dialysis in a dialysis bag 500 Da for three days to remove KOH and ethanol in the system to obtain light yellow g-C3N4A QD solution;
（3）TiO2@g-C3N4preparation of QD nanoparticles: firstly, a certain amount of TiO is taken2Solution with g-C3N4Mixing the QD solutions, carrying out ultrasonic treatment on the mixed solution for 10 min at room temperature, then transferring the mixed solution to a stainless steel high-pressure reaction kettle, and keeping the mixed solution at 110 ℃ for 1 h; then centrifugally washing by deionized water to remove excessive g-C3N4QD, obtaining TC nanoparticles, and preparing a TC solution;
（4）TiO2@g-C3N4preparation of QD/RMD nanoparticles: firstly, adding a certain amount of romidepsin solution into the TC solution, stirring for 24 hours at room temperature in a dark place, and centrifugally washing the obtained mixed solution through deionized water to obtain the TCR nano particles with the effect of the sonodynamic combined chemotherapy.
2. The preparation method of the Romidepsin loaded heterojunction nanoparticles with acoustic dynamic effect according to claim 1, wherein the preparation method comprises the following steps: the concentration of the polyvinylpyrrolidone aqueous solution in the step (1) is 50-100 mg/mL; the volume of the absolute ethyl alcohol in the step (1) is 20-30 mL; the concentration of the hydrochloric acid solution in the step (1) is 0.05-0.1 mol/L; the concentration of the titanium tetrafluoride solution in the step (1) is 4-5 mg/mL.
3. The preparation method of the Romidepsin supported heterojunction nanoparticles with acoustic dynamic effect according to claim 1, wherein the preparation method comprises the following steps: the mass of the powdered carbon nitride in the step (2) is 20-30 mg; the volume of the ethanol in the step (2) is 20-30 mL; the concentration of KOH in the step (2) is 0.5-1 mol/L.
4. The preparation method of the Romidepsin loaded heterojunction nanoparticles with acoustic dynamic effect according to claim 1, wherein the preparation method comprises the following steps: TiO in the step (3)2And g-C3N4The mass ratio of QD is 2: 1-1: 2.
5. The preparation method of the Romidepsin supported heterojunction nanoparticles with acoustic dynamic effect according to claim 1, wherein the preparation method comprises the following steps: the mass ratio of TC to romidepsin in the step (4) is 10: 1-1: 1.
6. The preparation method of the Romidepsin loaded heterojunction nanoparticles with acoustic dynamic effect according to claim 1, wherein the preparation method comprises the following steps: the rotation speed of centrifugation in the steps (1), (3) and (4) is 8000 rpm, and the centrifugation time is 10 min.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106492867A (en) * | 2016-09-27 | 2017-03-15 | 浙江大学 | g‑C3N4Quantum dot sensitized TiO2The preparation method of nanotube |
| CN112535731A (en) * | 2020-12-08 | 2021-03-23 | 上海市第六人民医院 | Preparation method of carbon dot/titanium carbide heterojunction acoustic sensitivity agent and application of acoustic sensitivity agent in acoustic dynamic cancer treatment |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106492867A (en) * | 2016-09-27 | 2017-03-15 | 浙江大学 | g‑C3N4Quantum dot sensitized TiO2The preparation method of nanotube |
| CN112535731A (en) * | 2020-12-08 | 2021-03-23 | 上海市第六人民医院 | Preparation method of carbon dot/titanium carbide heterojunction acoustic sensitivity agent and application of acoustic sensitivity agent in acoustic dynamic cancer treatment |
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