CN111184689A - Self-assembled nano micelle, preparation method and application thereof - Google Patents
Self-assembled nano micelle, preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a self-assembled nano micelle loaded with near-infrared II region fluorescent micromolecule HBP and chemotherapeutic drug taxol molecules, which is obtained by wrapping HBP and taxol molecules by poloxamer. The self-assembled nano micelle provided by the invention not only can efficiently wrap HBP and paclitaxel molecules, but also can red-shift an absorption peak of HBP to a near-infrared II region in a J-type aggregation mode, so that the nano micelle obtains good photo-thermal conversion capability and photo-acoustic contrast capability in the near-infrared II region, and has a good inhibition effect on tumor growth. After tail vein injection, the compound preparation can be efficiently enriched at a tumor part, can realize efficient near-infrared II-region photothermal and chemotherapy combined treatment under the condition of lower optical power, and has no tumor recurrence within 60 days. Also has more stable photo-thermal conversion efficiency.
Description
Technical Field
The invention belongs to the technical field of nano-micelle, and particularly relates to a self-assembled nano-micelle, a preparation method and an application thereof.
Background
With the recent research on cancer treatment, we have found that the traditional treatment methods including, but not limited to, chemotherapy, surgery, etc. are difficult to achieve complete treatment of tumors due to their own drawbacks. Therefore, the development of a treatment means with high curative effect and low toxicity has very important significance.
Photothermal therapy is a novel tumor treatment means for killing tumor cells by irradiating a tumor part with near-infrared laser to increase the temperature. However, limited by the insufficient penetration depth of the near-infrared I-region laser (750-950 nm), photothermal therapy based on the near-infrared I-region has certain limitations in treating large tumors and deep tissue tumors. In recent years, many studies show that near-infrared region II laser (1000-1700 nm) has weaker light scattering, light reflection and the like in biological tissues than traditional near-infrared region I laser, so that the biological tissue penetration depth is better. Therefore, the method has better application potential in the aspects of biological imaging, tumor photothermal therapy and the like. Besides the near-infrared II-region laser is used for improving the curative effect of tumor photothermal therapy, the photothermal therapy and other therapeutic means (such as chemotherapy and radiotherapy) are organically integrated, so that the curative effect of tumor therapy can also be effectively improved.
Disclosure of Invention
In view of the above, the present invention provides a self-assembled nano-micelle, a preparation method thereof and an application thereof, wherein the self-assembled nano-micelle has a good inhibition effect on tumor growth.
The invention provides a self-assembled nano micelle, which is obtained by wrapping HBP and paclitaxel molecules by using poloxamer;
the HBP has a structural formula shown in formula (I):
preferably, the mass ratio of HBP to paclitaxel is 1:4.5 to 5.5.
Preferably, the mass ratio of HBP to poloxamer is 1:5.5 to 6.5.
Preferably, the particle size of the self-assembled nano micelle is 15-30 nm.
The invention provides a preparation method of the self-assembled nano micelle in the technical scheme, which comprises the following steps:
mixing HBP with a structure shown in a formula (I) and paclitaxel, and dissolving in an organic solvent to obtain a mixed solution;
and mixing the mixed solution with a poloxamer aqueous solution, and stirring to obtain the self-assembled nano micelle.
Preferably, the organic solvent is selected from dichloromethane.
Preferably, the poloxamer aqueous solution is prepared by the following method:
and dissolving 8-12% of poloxamer by mass in a 3mol/L sodium chloride aqueous solution to obtain the poloxamer aqueous solution.
The invention provides an application of the self-assembled nano-micelle in the technical scheme in preparing a medicine for treating tumor by combining photothermal therapy and chemotherapy.
The invention provides a self-assembled nano micelle, which is obtained by wrapping HBP and paclitaxel molecules by using poloxamer. The self-assembled nano micelle provided by the invention not only can efficiently wrap HBP and paclitaxel molecules, but also can red-shift an absorption peak of HBP to a near-infrared II region in a J-type aggregation mode, so that the nano micelle obtains good photo-thermal conversion capability and photo-acoustic contrast capability in the near-infrared II region, and has a good inhibition effect on tumor growth. Can be efficiently enriched at the tumor part after tail vein injection, and can realize efficient near-infrared II-region photothermal and chemotherapy combined treatment under the condition of lower optical power. Also has more stable photo-thermal conversion efficiency. The experimental results show that: the HBP/PTX micelle can be used for photothermal therapy under 1064nm laser irradiation; the photothermal conversion efficiency of the HBP/PTX micelle is 30.27%; after five cycles of temperature rise and temperature reduction, the HBP/PTX micelle can still keep relatively stable photo-thermal conversion capability; can be used for combined treatment of tumor photothermal-chemotherapy, and has obvious effect, and no tumor recurrence is observed within 60 days.
Drawings
FIG. 1 is a dynamic laser particle size distribution diagram of HBP/PTX nanoparticles described in example 1 in an aqueous solution;
FIG. 2 is a UV-VIS-NIR absorption spectrum of HBP/PTX nanoparticles as described in example 1;
FIG. 3 is the photothermal conversion efficiency of the HBP/PTX nanoparticles described in example 1;
FIG. 4 is confocal microscopy imaging of HBP/PTX nanoparticles into cells;
FIG. 5 is a test of the toxicity of HBP/PTX nanoparticles on cells;
FIG. 6 shows the relative growth of tumors treated with HBP/PTX nanoparticles by photothermal therapy after tail vein injection in mice;
FIG. 7 is the relative tumor growth of HBP/PTX nanomicelles following combination therapy following tail vein injection in mice.
Detailed Description
The invention provides a self-assembled nano micelle, which is obtained by wrapping HBP and paclitaxel molecules by using poloxamer;
the HBP has a structural formula shown in formula (I):
in the invention, the mass ratio of HBP to paclitaxel is preferably 1: 4.5-5.5, more preferably 1: 4.8-5.2, and most preferably 1:5.
In the invention, the mass ratio of the HBP to the poloxamer is preferably 1: 5.5-6.5, more preferably 1: 5.8-6.2, and most preferably 1: 6.
In the invention, the particle size of the self-assembled nano micelle is 15-30 nm.
The self-assembly nano micelle is a self-assembly nano micelle loaded with near-infrared II region fluorescent micromolecule HBP and chemotherapeutic drug taxol molecules. The self-assembled micelle can improve the photo-thermal conversion efficiency of HBP under laser irradiation; particularly, the fluorescent signal of the micelle is greatly weakened due to the pi stacking effect among molecules, so that the micelle has obviously enhanced photothermal conversion efficiency, and the invention can realize high-efficiency synergistic killing of tumors.
The invention provides a preparation method of the self-assembled nano micelle in the technical scheme, which comprises the following steps:
mixing HBP with a structure shown in a formula (I) and paclitaxel, and dissolving in an organic solvent to obtain a mixed solution;
and mixing the mixed solution with a poloxamer aqueous solution, and stirring to obtain the self-assembled nano micelle.
In the present invention, the organic solvent is selected from dichloromethane.
In the present invention, the poloxamer aqueous solution is prepared by the following method:
and dissolving 8-12% of poloxamer by mass in a 3mol/L sodium chloride aqueous solution to obtain the poloxamer aqueous solution.
More specifically, Pluronic F127, which contained 10% by mass of the poloxamer, was dissolved in a 3mol/L aqueous solution of sodium chloride to obtain an aqueous solution of the poloxamer.
The invention has no special requirements on the sources of all raw materials, and can adopt commercial products.
In order to better perform the reaction, the HBP and the paclitaxel are preferably dissolved in an organic solvent, then the solution is dropwise added into a 3mol/L sodium chloride aqueous solution containing 10% of poloxamer, and the mixture is stirred at room temperature until the organic solvent is completely volatilized, so that the self-assembled nano micelle is obtained. In order to remove free poloxamer in the stirred product, the stirred product is preferably centrifuged; the centrifugation time is preferably 4-5 hours, and more preferably 4.5 hours; the rotation speed of the centrifugation is preferably 4000-5000 rpm, and more preferably 4500 rpm; the centrifugation is preferably carried out using ultrafiltration tubes with a molecular weight cut-off of 50 kDa; the temperature of the centrifugation is preferably-4 ℃.
The invention provides an application of the self-assembled nano-micelle in the technical scheme in preparing a medicine for treating tumor by combining photothermal therapy and chemotherapy. The self-assembled nanomicelle is denoted as HBP/PTX.
In order to investigate the lethality of HBP/PTX micelles, breast cancer cells (4T1 cells) were used as study cells.
In order to further illustrate the present invention, the following examples are provided to describe a self-assembled nano-micelle, a preparation method thereof and applications thereof in detail, but they should not be construed as limiting the scope of the present invention.
Comparative example 1
HBP (0.5mg) was dissolved in 1mL of methylene chloride, and then 5mL of a 3mol/L aqueous solution of sodium chloride (NaCl) containing 10% poloxamer (Pluronic F127) was added dropwise thereto, followed by stirring overnight until the methylene chloride was completely volatilized, to terminate the reaction. In order to remove free Pluronic F127 molecules in the product, an ultrafiltration tube with the molecular weight cutoff of 50kDa is used for centrifuging for 4.5 hours at the temperature of minus 4 ℃ and the rotating speed of 4500rpm, and the self-assembled nano micelle loaded with HBP and paclitaxel can be obtained.
Example 1
Preparation of HBP and paclitaxel loaded self-assembled nano-micelle (HBP/PTX)
HBP (0.5mg) and paclitaxel (2.5mg) (PTX) were dissolved in 1mL of dichloromethane, then 5mL of 3M aqueous sodium chloride (NaCl) solution containing 10% poloxamer (Pluronic F127) was added dropwise, and the reaction was stirred overnight until all dichloromethane was evaporated, terminating the reaction. In order to remove free Pluronic F127 molecules in the product, an ultrafiltration tube with the molecular weight cutoff of 50kDa is used for centrifuging for 4.5 hours at the temperature of minus 4 ℃ and the rotating speed of 4500rpm, and the self-assembled nano micelle loaded with HBP and paclitaxel can be obtained.
Example 2
Characterization of HBP/PTX nanomicelles
The HBP/PTX micelle obtained in example 1 is characterized by the invention (including ultraviolet-visible absorption spectrum, dynamic light scattering, photo-thermal conversion efficiency and photo-thermal stability), and the results are shown in FIGS. 1-4;
FIG. 1 is a UV-VIS absorption spectrum of the HBP/PTX micelle described in example 1. As can be seen from the figure, the near infrared absorption peak is 1012nm, and the method can be used for photothermal treatment under 1064nm laser irradiation.
FIG. 2 is a graph showing the dynamic laser particle size distribution of the HBP/PTX micelle described in example 1. As can be seen from the figure, the diameter of the nano-micelle particle formed by HBP/PTX is about 20 nm.
FIG. 3 is a graph of photothermal conversion efficiency of HBP/PTX micelles as described in example 1. The photothermal conversion efficiency of the HBP/PTX micelle was calculated to be 30.27%.
FIG. 4 is a graph showing the effect of the photothermal stability test of the HBP/PTX micelle described in example 1. As can be seen from the figure, the HBP/PTX micelle can still keep relatively stable photothermal conversion capacity after five cycles of temperature rise and temperature drop.
Example 3
Cell-entry ability and cytotoxicity of HBP/PTX nanomicelles
In order to study the cell-entering ability of the HBP/PTX nanomicelles, the HBP/PTX nanomicelles were observed by confocal microscopy after being incubated with mouse breast cancer cells (4T1 cells) for 1 hour, 2 hours and 4 hours, and the results are shown in FIG. 5, and FIG. 5 is an imaging image of laser confocal microscopy after the HBP/PTX nanomicelles are incubated with mouse breast cancer cells (4T 1). As can be seen from FIG. 5, the enrichment of intracellular HBP/PTX micelles gradually increased with time, and the HBP/PTX micelles achieved co-localization with lysosomes of 4T1 cells labeled by lyso-tracker. To investigate the killing of cells by HBP/PTX micelles, the results of incubation of HBP/PTX micelles with mouse breast cancer cells (4T1 cells) for 72 hours are shown in FIG. 6, and FIG. 6 is a graph of cell viability of HBP/PTX nanomicelles incubated with mouse breast cancer cells (4T1 cells). As can be seen from fig. 6, as the micelle concentration increases, the toxicity to tumor cells also increases.
Example 4
Photothermal-chemotherapy combination treatment experiment of HBP/PTX nano micelle particles at mouse living body level
For combined photothermal-chemotherapy treatment at the living level, 4T1 tumor bearing mice were divided into four groups, which included: first group, control group (saline only injection); second group, injection of HBP nanoparticles of control 1 while illuminating; third group, HBP/PTX micelles of example 1 (not illuminated); fourth, the HBP/PTX micelles of example 1 were injected and irradiated simultaneously. After the corresponding treatment of the mice, the tumor growth was measured, and the results are shown in FIG. 7, and FIG. 7 is the relative tumor growth of HBP/PTX nanomicelles after the tail vein injection of the mice for the combined treatment. According to the relative growth of the tumor, no significant treatment effect was observed in the second and third groups of mice, compared with the control group, the tumor in the fourth group was suppressed, and no recurrence of the tumor was observed in the next 60 days. The HBP/PYX micelle can realize the combined treatment effect on tumor photothermal-chemotherapy with obvious effect.
From the above examples, the present invention provides a self-assembled nano-micelle, which is obtained by encapsulating HBP and paclitaxel molecules using poloxamer. The self-assembled nano micelle provided by the invention not only can efficiently wrap HBP and paclitaxel molecules, but also can red-shift an absorption peak of HBP to a near-infrared II region in a J-type aggregation mode, so that the nano micelle obtains good photo-thermal conversion capability and photo-acoustic contrast capability in the near-infrared II region, and has a good inhibition effect on tumor growth. Can be efficiently enriched at the tumor part after tail vein injection, and can realize efficient near-infrared II-region photothermal and chemotherapy combined treatment under the condition of lower optical power. Also has more stable photo-thermal conversion efficiency. The experimental results show that: the HBP/PTX micelle can be used for photothermal therapy under 1064nm laser irradiation; the photothermal conversion efficiency of the HBP/PTX micelle is 30.27%; after five cycles of temperature rise and temperature reduction, the HBP/PTX micelle can still keep relatively stable photo-thermal conversion capability; can be used for combined treatment of tumor photothermal-chemotherapy, and has obvious effect, and no tumor recurrence is observed within 60 days.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (8)
1. A self-assembled nano-micelle is prepared by coating HBP and paclitaxel molecule with poloxamer;
the HBP has a structural formula shown in formula (I):
2. the self-assembled nanomicelle according to claim 1, wherein the mass ratio of HBP to paclitaxel is 1:4.5 to 5.5.
3. The self-assembled nanomicelle according to claim 1, wherein the mass ratio of HBP to poloxamer is 1:5.5 to 6.5.
4. The self-assembled nanomicelle according to claim 1, wherein the self-assembled nanomicelle has a particle size of 15 to 30 nm.
5. A method for preparing the self-assembled nano-micelle of any one of claims 1 to 4, comprising the following steps:
mixing HBP with a structure shown in a formula (I) and paclitaxel, and dissolving in an organic solvent to obtain a mixed solution;
and mixing the mixed solution with a poloxamer aqueous solution, and stirring to obtain the self-assembled nano micelle.
6. The method of claim 5, wherein the organic solvent is selected from dichloromethane.
7. The method according to claim 5, wherein the aqueous poloxamer solution is prepared by:
and dissolving 8-12% of poloxamer by mass in a 3mol/L sodium chloride aqueous solution to obtain the poloxamer aqueous solution.
8. Use of the self-assembled nano-micelle of any one of claims 1 to 4 or the self-assembled nano-micelle prepared by the preparation method of any one of claims 5 to 7 in preparation of a drug for treating tumor by photothermal-chemotherapy combination.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113350293A (en) * | 2021-06-01 | 2021-09-07 | 复旦大学 | Hybrid single micelle nanoparticle for encapsulating functional molecules and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103446040A (en) * | 2012-06-04 | 2013-12-18 | 复旦大学 | Docetaxel-coated polymeric micelle and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103446040A (en) * | 2012-06-04 | 2013-12-18 | 复旦大学 | Docetaxel-coated polymeric micelle and preparation method thereof |
Non-Patent Citations (2)
| Title |
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| WANLE SHENG，等: "Synthesis, Crystal Structure, and the Deep Near-Infrared Absorption/Emission of Bright AzaBODIPY-Based Organic Fluorophores", 《ORG. LETT.》 * |
| YICHENG ZHANG，等: "Surfactant-Stripped Micelles of Near Infrared Dye and Paclitaxel for Photoacoustic Imaging Guided Photothermal-Chemotherapy", 《SMALL》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113350293A (en) * | 2021-06-01 | 2021-09-07 | 复旦大学 | Hybrid single micelle nanoparticle for encapsulating functional molecules and preparation method thereof |
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