CN113304265A - Hyaluronic acid baicalein iron nanoparticles and preparation method thereof - Google Patents
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Abstract
The invention discloses hyaluronic acid baicalein iron nanoparticles and a preparation method thereof. The hyaluronic acid baicalein iron nanoparticles provided by the invention are prepared by taking baicalein as a basic raw material and adopting a one-pot method, so that novel active targeting photo-thermal nanoparticles with high drug loading and uniform size are synthesized. In-vitro photothermal tests prove that the hyaluronic acid baicalein iron nanoparticles have excellent photothermal performance. Cell experiments prove that the hyaluronic acid baicalein iron nanoparticles have obvious tumor inhibition effect and are expected to be used for tumor treatment in combination with photothermal treatment and chemotherapy. The hyaluronic acid baicalein iron nanoparticle has simple process and high repeatability, does not use toxic organic reagents and surfactants, and has strong operability and wide application prospect.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to hyaluronic acid baicalein iron nanoparticles and a preparation method thereof.
Background
Tumors have become a significant health problem facing humans. The current therapeutic approaches for malignant tumors are mainly surgery, chemotherapy and radiotherapy. The three methods have large side effects and cannot effectively inhibit tumor metastasis and recurrence by only depending on chemotherapy drug treatment or surgical resection, so that the medical application is limited.
With the rise of the cross-discipline of medical and medical science, phototherapy has become a new type of therapy which is of great interest for the research of tumor therapy. Phototherapy includes photodynamic therapy and photothermal therapy. The photothermal therapy can effectively control the time and space for the photothermal therapy to be carried out in vivo by controlling the near-infrared laser switch, thereby realizing the photothermal toxicity generated at the tumor part, effectively reducing the whole toxic and side effects generated by chemical drugs in the clinical tumor treatment process and realizing the accurate treatment of the tumor. Photothermal therapy is a non-invasive and local tumor treatment modality, and has certain advantages over traditional tumor treatment modalities, including minimal invasion, reduction of side effects, and the like. However, most of the current photo-thermal agents are easily introduced with toxic ligands or use toxic reagents during the preparation process thereof, resulting in reduced biocompatibility and thus limited application. Therefore, it is necessary to develop a photo-thermal agent with good biocompatibility.
The baicalein is an active ingredient of herbal plant scutellaria baicalensis, has wide physiological activity and pharmacological effects of anti-inflammation, antivirus, anti-allergic reaction, antibiosis and the like, and can realize the anti-tumor effect by inducing tumor cell apoptosis, inhibiting tumor invasion and metastasis, inhibiting tumor angiogenesis and the like. However, the poor water solubility of baicalein causes the low bioavailability of baicalein, and the clinical application is limited. Hyaluronic acid is glycosaminoglycan widely existing in human bodies, is a main component of extracellular matrix, can be combined with CD-44 receptors highly expressed by various tumor cells, is applied to nanoparticles, is expected to realize active tumor targeting of the nanoparticles and enhance the tumor treatment effect.
In order to solve the problems, the hyaluronic acid baicalein iron nanoparticles are prepared, the preparation process is simple to operate, no toxic reagent is used, and the solubility of baicalein is improved. The mode of combining photo-thermal and chemotherapy is adopted to provide a new strategy for treating tumors.
Disclosure of Invention
According to the invention, baicalein is taken as a base material, and hyaluronic acid is embedded into a nano structure through coordination with metal ions, so that the hyaluronic acid baicalein iron photo-thermal nano particle is constructed, the solubility of baicalein is improved, and the hyaluronic acid baicalein iron photo-thermal nano particle has excellent photo-thermal conversion capability and tumor targeting performance and can remarkably enhance the tumor treatment effect.
In order to achieve the purpose, the invention adopts the following technical scheme:
adding an iron-containing compound, sodium hyaluronate and polyvinylpyrrolidone into pure water, stirring for dissolving, slowly dropwise adding a baicalein alcohol solution, stirring at room temperature, centrifuging, and washing with pure water to obtain hyaluronic acid baicalein iron nanoparticles;
as a further improvement of the invention, the steps are specifically as follows:
step (1): adding 1-900 mg of iron-containing compound, 0.33-300 mg of sodium hyaluronate and 6-5400 mg of polyvinylpyrrolidone into 1-6000 mL of pure water, and stirring and dissolving at room temperature;
step (2): dissolving 0.33-300 mg of baicalein in 0.5-3000 mL of an alcohol solution;
and (3): and (3) fully mixing the solution obtained in the step (2) with the solution obtained in the step (1) to ensure that the volume ratio of the two is 1: 1-1: 20, stirring for 2-48 h at room temperature, then carrying out ultrasonic treatment, washing with pure water, and centrifuging to obtain the hyaluronic acid baicalein iron nanoparticles.
The invention has the innovation that the hyaluronic acid baicalein iron nano photothermal system is prepared by unique components and a simple preparation process, the preparation process of the nano system is simple, toxic organic reagents are not used, the selected materials are economic and have good biological safety, good physical stability and high repeatability, and the solubility of the baicalein can be obviously improved; meanwhile, the nanoparticles have the characteristic of actively targeting to tumor parts, can obviously improve the anti-tumor curative effect by combining with photothermal chemotherapy, and have wide biomedical application prospect.
Drawings
FIG. 1 is an appearance diagram of hyaluronic acid baicalein iron nanoparticles;
FIG. 2 is a transmission electron microscope image of hyaluronic acid baicalein iron nanoparticles;
FIG. 3 is a particle size distribution diagram of hyaluronic acid baicalein iron nanoparticles;
FIG. 4 is an external light heat map of hyaluronan baicalein iron nanoparticles;
fig. 5 is a graph of the tumor cell inhibitory effect of hyaluronic acid baicalein iron nanoparticles.
Detailed Description
The present invention is further described in detail by the following examples, but the present invention is not limited to the following examples, and all equivalent modifications made according to the spirit of the present invention should be covered in the protection scope of the present invention.
Example 1
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): 30mg of ferrous ammonium sulfate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone are dissolved in 6mL of pure water, and stirred for 10min at room temperature;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 2
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): 30mg of ferrous ammonium sulfate, 20mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone are dissolved in 6mL of pure water, and stirred for 10min at room temperature;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 3
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): 30mg of ferrous ammonium sulfate, 30mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone are dissolved in 6mL of pure water and stirred for 10min at room temperature;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 4
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): dissolving 40mg of ferrous ammonium sulfate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone in 6mL of pure water, and stirring at room temperature for 10 min;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 5
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): dissolving 50mg of ferrous ammonium sulfate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone in 6mL of pure water, and stirring at room temperature for 10 min;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 6
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): 60mg of ferrous ammonium sulfate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone are dissolved in 6mL of pure water and stirred for 10min at room temperature;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 7
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): dissolving 40mg of ferric chloride, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone in 6mL of pure water, and stirring at room temperature for 10 min;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 8
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): dissolving 40mg of ferric nitrate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone in 6mL of pure water, and stirring at room temperature for 10 min;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 9
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): dissolving 40mg of ferrous ammonium sulfate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone in 6mL of pure water, and stirring at room temperature for 10 min;
step (2): dissolving 10mg of baicalein in 3mL of methanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 10
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): dissolving 40mg of ferrous ammonium sulfate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone in 6mL of pure water, and stirring at room temperature for 10 min;
step (2): dissolving 10mg of baicalein in 6mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 11
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): dissolving 40mg of ferrous ammonium sulfate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone in 6mL of pure water, and stirring at room temperature for 10 min;
step (2): dissolving 10mg of baicalein in 12mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 24 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 12
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): dissolving 40mg of ferrous ammonium sulfate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone in 6mL of pure water, and stirring at room temperature for 10 min;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring for 2 hours at room temperature, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 13
The embodiment is a preparation method of hyaluronic acid baicalein iron nanoparticles, which comprises the following steps:
step (1): dissolving 40mg of ferrous ammonium sulfate, 10mg of sodium hyaluronate and 64mg of polyvinylpyrrolidone in 6mL of pure water, and stirring at room temperature for 10 min;
step (2): dissolving 10mg of baicalein in 3mL of ethanol solution;
and (3): and (3) slowly dropwise adding the solution obtained in the step (2) into the solution obtained in the step (1), stirring at room temperature for 48 hours, centrifuging, adding pure water, performing ultrasonic dispersion, centrifuging, and repeatedly washing to obtain the hyaluronic acid baicalein iron nanoparticles.
Example 14
The appearance diagram of the hyaluronic acid baicalein iron nanoparticles is shown in figure 1; the transmission electron microscope results are shown in FIG. 2; the results of particle size measurements are shown in FIG. 3. As can be seen from the figure, the hyaluronic acid baicalein iron nanoparticles have small particle size and uniform distribution, and the average particle size is about 129 nm.
The power density is 1.0W/cm2Irradiating the hyaluronic acid baicalein iron nanoparticle suspension by using laser at 808nm, and recording the temperature change within 10 minutes of irradiation. The result is shown in fig. 4, the temperature of the hyaluronic acid baicalein iron nanoparticle suspension gradually rises along with the increase of the laser irradiation time, and the nanoparticles have good photothermal conversion performance.
Example 15
The cytotoxicity of the hyaluronic acid baicalein iron nanoparticles on breast cancer cells 4T1 is detected by adopting an MTT method. 4T1 cells in logarithmic growth phase were collected, adjusted to 7000 cells/well in 1640 medium containing 10% fetal bovine serum, inoculated into 96-well plates, and cultured overnight in a 5% CO2 incubator at 37 ℃. Blank group isThe culture medium without medicine, the control group is 4T1 cell sap cultured normally without medicine, the experimental group is baicalein with different concentrations and equivalent hyaluronic acid baicalein iron nanoparticles, each group has 6 multiple holes, and the experimental group is administered with 1.0W/cm after continuously culturing for 12h2Laser irradiation was performed for 5 minutes. After 24h the supernatant was discarded and washed 3 times with sterile PBS buffer, 100 μ L of serum free medium containing MTT was added again and incubated for 4h protected from light. The culture was terminated, the supernatant was discarded, 150. mu.L of DMSO solution was added to each well, shaken for 10 minutes, and the absorbance at a wavelength of 490nm was measured with a microplate reader, and the cell viability was calculated. As shown in fig. 5, the results show that the hyaluronic acid baicalein iron nanoparticles after laser irradiation have a significant inhibitory effect on 4T1 tumor cells.
Claims (7)
1. The hyaluronic acid baicalein iron nanoparticles are characterized by being prepared from metal iron ions, sodium hyaluronate, baicalein and polyvinylpyrrolidone.
2. The hyaluronic acid baicalein iron nanoparticle according to claim 1, wherein the preparation method comprises the following steps:
adding the iron-containing compound, sodium hyaluronate and polyvinylpyrrolidone into pure water, stirring for dissolving, slowly dropwise adding the baicalein alcoholic solution, stirring at room temperature, centrifuging, and washing to obtain the hyaluronic acid baicalein iron nanoparticles.
3. The hyaluronic acid baicalein iron nanoparticles as claimed in claims 1 and 2, which are prepared by the following steps:
step (1): adding 1-900 mg of iron-containing compound, 0.33-300 mg of sodium hyaluronate and 6-5400 mg of polyvinylpyrrolidone into 1-6000 mL of pure water, and stirring and dissolving at room temperature;
step (2): dissolving 0.33-300 mg of baicalein in 0.5-3000 mL of an alcohol solution;
and (3): and (3) fully mixing the solution obtained in the step (2) with the solution obtained in the step (1) to ensure that the volume ratio of the two is 1: 1-1: 20, stirring for 2-48 h at room temperature, then carrying out ultrasonic treatment, washing with pure water, and centrifuging to obtain the hyaluronic acid baicalein iron nanoparticles.
4. The hyaluronic acid baicalein iron nanoparticles according to claims 1 and 2, wherein the selected iron-containing compound is one or a mixture of more than two of ferrous ammonium sulfate, ferrous sulfate, ferric chloride, ferrous chloride, ferric sulfate, ferrous nitrate, ferric carbonate and hydrates thereof, and preferably is ferrous ammonium sulfate.
5. The hyaluronic acid baicalein iron nanoparticles according to claims 1 and 2, wherein the selected alcohol is one or a mixture of two of methanol and ethanol, preferably ethanol.
6. The hyaluronic acid baicalein iron nanoparticles according to claims 1 and 2, wherein the hyaluronic acid baicalein iron nanoparticles have an average particle size of 40-300 nm.
7. Hyaluronic acid baicalein iron nanoparticles according to claims 1 and 2, which can be used as tumor photothermal therapy in combination with chemotherapy.
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| CN107670036A (en) * | 2017-09-30 | 2018-02-09 | 中国科学院长春应用化学研究所 | A kind of dissociating method of iron coordination polymer nano particle and its application |
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| CN107670036A (en) * | 2017-09-30 | 2018-02-09 | 中国科学院长春应用化学研究所 | A kind of dissociating method of iron coordination polymer nano particle and its application |
Non-Patent Citations (1)
| Title |
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| ZHENDONG LIU等: ""Facile synthesis of Fe–baicalein nanoparticles for photothermal/chemodynamic therapy with accelerated FeIII/FeII conversion"", 《J. MATER. CHEM. B》 * |
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Application publication date: 20210827 |