CN110787295A - Boron neutron capture therapeutic reagent and preparation method and application thereof - Google Patents

Boron neutron capture therapeutic reagent and preparation method and application thereof Download PDF

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Publication number
CN110787295A
CN110787295A CN201911138309.6A CN201911138309A CN110787295A CN 110787295 A CN110787295 A CN 110787295A CN 201911138309 A CN201911138309 A CN 201911138309A CN 110787295 A CN110787295 A CN 110787295A
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boron
neutron capture
preparation
borohydride
capture therapeutic
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台国安
邵伟
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Nanjing University of Aeronautics and Astronautics
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Nanjing University of Aeronautics and Astronautics
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
    • A61K41/009—Neutron capture therapy, e.g. using uranium or non-boron material
    • A61K41/0095—Boron neutron capture therapy, i.e. BNCT, e.g. using boronated porphyrins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Abstract

The invention discloses a boron neutron capture therapeutic reagent and a preparation method and application thereof. The invention adopts a CVD tube furnace high-temperature inorganic reaction method, the boron source in the quartz tube is heated at high temperature in a reducing gas environment to exceed the melting point and volatilize, and the boron source is directly combined with the surface of the magnetic nano particle to obtain the nano particle with the core-shell structure. The invention is different from the preparation of BNCT reagent by an organic solution method, and provides a simple, high-efficiency, controllable and macro-preparation method of BNCT inorganic nano-material. The boron-coated superparamagnetic core-shell structured nanoparticle prepared by the invention can be used as a targeted drug in BNCT cancer treatment.

Description

Boron neutron capture therapeutic reagent and preparation method and application thereof
Technical Field
The invention belongs to the field of research and development of neutron therapeutic drugs, and particularly relates to a boron neutron capture therapeutic reagent, a preparation method thereof and application thereof in the field of BNCT.
Background
With the development of nano-materials, nano-materials compounded by inorganic substances/organic substances are receiving attention. In order to improve the functions or properties of single nanoparticles, researchers modify the surfaces of the single nanoparticles by using other inorganic substances/organic substances, and coat a layer of other materials on the surface of a core material to form a special core-shell structure, so that the chemical properties, physical properties, thermodynamic properties, optical and electrical properties, catalytic properties, magnetic properties and the like of the nanoparticles can be changed, and some special functions can be realized. Boron Neutron Capture Therapy (BNCT) is a new type of cancer therapy that uses neutron source irradiation to initiate the boron-10 nuclear fission reaction to release energy, thereby killing cancer cells.
At present, the synthesis method of the core-shell structure nano particle mainly adopts organic solution synthesis, such as a sol-gel method, a surface chemical reaction method, an ultrasonic chemical method and the like. The methods have the disadvantages of more reactants, complex process, low yield, low controllability and no wide application potential. In addition, the mainstream drugs for BNCT cancer treatment are organic synthetic drugs. Two drugs (BSH and BPA) against mainstream tumors (brain glioma and melanoma) have been put into clinical use, but since these two drugs are bound to cancer cells by biological properties and can only treat specific cancer cells, targeting accuracy is low, and in addition, the organic synthesis process is complicated, which leads to a high price, and wide applicability is limited. Therefore, a BNCT medicament with simple and efficient process, strong practicability and low cost is urgently needed.
Disclosure of Invention
One of the objects of the present invention is to provide a boron neutron capture therapeutic agent.
The other purpose is to provide a preparation method of the boron neutron capture therapeutic agent.
The third purpose is to provide the application of the boron neutron capture therapeutic agent in the aspect of cancer treatment.
In order to achieve the purpose, the invention adopts the following technical scheme: a boron neutron capture therapeutic agent, the boron neutron capture therapeutic agent Fe3O4The @ B MNPs are boron-coated superparamagnetic core-shell structured nanoparticles, and the nanoparticles are Fe3O4NPs。
A preparation method of boron neutron capture therapeutic agent comprises mechanically mixing superparamagnetic nanoparticles with boron source, and pouring into quartz boat; placing the quartz boat in a CVD quartz tube, and removing oxygen in the quartz tube by vacuumizing; and introducing reducing gas, heating at high temperature in a reducing gas environment to exceed the melting point of the boron source, volatilizing, keeping for 1-120 min to enable the boron source to be fully combined with the magnetic nanoparticles, and obtaining the boron-coated superparamagnetic core-shell structure nanoparticles after the reaction is finished.
Further, the superparamagnetic nano-particle is Fe3O4The MNPs have a particle size of 6-500 nm.
Further, the boron source is solid boron source powder.
Further, the mass ratio of the boron source to the superparamagnetic nano particles is 1:5-5: 1.
Further, the boron source is sodium borohydride, sodium boron deuteride, potassium borohydride, lithium tri-sec-butylborohydride, potassium tri-isobutyl borohydride, lithium tri-amyl borohydride or lithium triethylborohydride.
Further, the reducing gas is hydrogen, a hydrogen-argon mixed gas, a hydrogen-nitrogen mixed gas, or a hydride gas.
Further, the heating temperature is 500-1000 ℃.
Use of a boron neutron capture therapeutic agent in the treatment of cancer.
The invention provides a preparation method of a Boron Neutron Capture Therapy (BNCT) reagent, which can prepare large-area boron-coated superparamagnetic core-shell structured nanoparticles (Fe) by utilizing the in-situ reaction of reactants in a CVD (chemical vapor deposition) tube furnace3O4@ BMNPs), the method has simple process, relatively high yield and higher controllability, and simultaneously has excellent properties of a boron shell material and a magnetic core, and is expected to be applied in the BNCT drug research field.
Compared with the prior art, the invention has the following technical advantages:
(1) the core-shell structure nano particles prepared by the method have no hysteresis phenomenon, have good superparamagnetism and high magnetic response rate;
(2) the core-shell structure nano particles prepared by the method have uniform particle size distribution and better dispersity;
(3) the invention controls the particle size of the core-structure nano particles by controlling the reaction temperature rise rate, and can be prepared in a large area;
(4) the boron-coated magnetic core-shell structured nanoparticles prepared by the method meet the basic requirements of BNCT medicines, and the core material is magnetic particles, so that the magnetic field can be regulated and precisely guided into the position of cancer cells in a targeted manner, and the treatment efficiency is improved;
(5) the method has the advantages of low equipment requirement, simple process flow, good controllability, specific functions of BNCT medicines, and capability of meeting large-scale production more easily than a solution synthesis method, and is a potential and valuable technology.
Drawings
FIG. 1 is a schematic structural view of a reaction apparatus used in the embodiment of the present invention.
FIG. 2 is a graph of small-sized superparamagnetic Fe according to example 1 of the present invention3O4Scanning electron micrographs of MNPs.
FIG. 3 is a view showing small-sized superparamagnetic Fe according to example 1 of the present invention3O4Transmission electron micrographs of MNPs.
FIG. 4 is small-sized superparamagnetic Fe of example 1 of the present invention3O4Magnetization curves of MNPs.
FIG. 5 shows boron neutron-capture therapeutic agents Fe prepared in examples 2 and 3 of the present invention3O4Scanning electron micrographs of @ B MNPs (Panel A is the sample from example 2; Panel B is the sample from example 3).
FIG. 6 shows boron neutron-capture therapeutic agents Fe prepared in examples 2 and 3 of the present invention3O4X-ray photoelectron spectroscopy of @ B MNPs (example 2 samples in the upper panel; example 3 samples in the lower panel).
FIG. 7 shows a boron neutron-capture therapeutic agent Fe prepared according to an embodiment of the present invention3O4Transmission electron micrographs of @ B MNPs (Panel A is the sample from example 2; Panel B is the sample from example 3).
Fig. 8 is a schematic structural view of a channel device manufactured in embodiment 4 of the present invention.
FIG. 9 shows Fe in example 4 of the present invention3O4Photographs of the movements of the @ B MNPs in the channel.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It should be noted that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. Further, it is to be understood that when terms or/and are used in this specification, they specify the presence of features, steps, operations, reagents, and/or combinations thereof.
In order that those skilled in the art can more clearly understand the technical solution of the present invention, the following detailed description of the specific preferred embodiments of the present invention will be given with reference to the accompanying drawings.
As shown in FIG. 1, the apparatus used was a CVD system composed of a hydrogen flow meter, a quartz tube, a tube furnace, a heating temperature zone and a substrate; the quartz tube is arranged in the tube furnace, one side of the quartz tube is connected with a hydrogen high-pressure gas cylinder through a hydrogen flowmeter, and the other side of the quartz tube is connected with a vacuum mechanical pump.
Example 1
This example is used to provide small particle size superparamagnetic Fe as used in the present invention3O4Preparation of MNPs.
The technical scheme comprises the following steps:
(1) FeCl was measured in an amount of 0.945g3·6H2And placing the O into a 100mL beaker, adding 70mL of glycol, and carrying out ultrasonic treatment for 40 min-1 h until the solution is clear.
(2) And (3) measuring 4.20g of anhydrous sodium acetate (NaAc), adding into the clarified solution obtained in the step (1), and magnetically stirring for 1h until the solution is clarified again to obtain a reaction precursor solution.
(3) And transferring the precursor solution into a hydrothermal synthesis reaction kettle, and placing the reaction kettle in a forced air drying oven at 200 ℃ for reaction for 10 hours.
(4) After the reaction is finished, taking out the polytetrafluoroethylene lining in the reaction kettle, pouring the supernatant, and pouring the black product at the bottom into a 100mL beaker. The washing is carried out for more than three times by using absolute ethyl alcohol and deionized water respectively, and a mode of magnetically separating a product from a washing liquid by using a magnet replaces centrifugal washing in the process of washing the product.
(5) Drying the cleaned product in a 60 ℃ blast drying oven for 6h to obtain Fe3O4MNPs。
FIG. 2 is small particle size superparamagnetic Fe3O4Scanning electron micrographs of MNPs. FIG. 3 is a transmission electron micrograph. Fig. 4 is a magnetization curve.
Example 2
The technical scheme comprises the following steps:
(1) 40mg of NaHB was measured in a glove box4The powder was placed in a 2mL centrifuge tube and filled with NaHB4Taking out the centrifugal tube of the powder from the glove box;
(2) 10mg of Fe was measured3O4MNPs are poured into the container with NaHB4The centrifuge tube of (1) is shaken by hand until the mixed powder is fully and uniformly (black and no white crystal);
(3) pouring the mixed powder in the step (2) into a quartz boat, and quickly placing the quartz boat in a quartz tube;
(4) vacuumizing to remove oxygen in the quartz tube, and introducing hydrogen to ensure that the flow rate is 10 sccm;
(5) and (3) turning on a temperature control switch of the CVD furnace, and setting a program as follows: the temperature was raised to 550 ℃ at a heating rate of 10 ℃/min and maintained at 550 ℃ for 10 min.
(6) After the reaction is finished, waiting for the furnace temperature to be cooled to room temperature, taking out the quartz boat, and collecting the reacted powder to a new 2mL centrifuge tube;
(7) taking the reacted powder, performing ultrasonic treatment and centrifugal cleaning by using deionized water and absolute ethyl alcohol (three times respectively), and placing the powder in a 60 ℃ forced air drying oven for drying or performing ultrasonic dispersion in the ethyl alcohol for storage.
Example 3
The technical scheme comprises the following steps:
(1) 20mg of NaHB was measured in a glove box4The powder was placed in a 2mL centrifuge tube and filled with NaHB4Taking out the centrifugal tube of the powder from the glove box;
(2) 10mg of Fe was measured3O4MNPs are poured into the container with NaHB4The centrifuge tube of (1) is fully hand-cranked until the mixed powder is uniform (black and no white crystal);
(3) pouring the mixed powder in the step (2) into a quartz boat, and quickly placing the quartz boat in a quartz tube;
(4) vacuumizing to remove oxygen in the quartz tube, and introducing hydrogen to ensure that the flow rate is 10 sccm;
(5) and (3) turning on a temperature control switch of the CVD furnace, and setting a program as follows: the temperature was raised to 550 ℃ at a rate of 20 ℃/min and maintained at 550 ℃ for 10 min.
(6) After the reaction is finished, waiting for the furnace temperature to be cooled to room temperature, taking out the quartz boat, and collecting the reacted powder to a new 2mL centrifuge tube;
(7) taking the reacted powder, performing ultrasonic treatment and centrifugal cleaning by using deionized water and absolute ethyl alcohol (three times respectively), and placing the powder in a 60 ℃ forced air drying oven for drying or performing ultrasonic dispersion in the ethyl alcohol for storage.
Because a lot of samples and test results are obtained in the experiment, as shown in fig. 7, a transmission electron microscope scanning image of one sample under different scales is preferably selected from embodiments 2-3. FIG. 7A is Fe observed at 100nm scale3O4The MNPs are local images under the scale of 5nm after being amplified by combining with the graph 7B, a core-shell structure is formed by wrapping a deep area around a shallow area, the interface of the two areas is combined in the graph 7B, the shallow area is made of a shell material of boron, and the deep area is made of ferroferric oxide nano particles which are core materials.
Example 4
This example is intended to further illustrate the Fe prepared in the present invention3O4Application prospect and potential of @ B MNPs in the aspect of boron neutron cancer treatment.
The technical scheme comprises the following steps:
(1) 5mg of Fe prepared in example 1 were taken3O4@ B MNPs and dispersed in 2mL of polyethylene glycol-200 by sonication
(PEG-200)。
(2) At the same time, three slides were used to make a simple channel device, as shown in FIG. 8.
(3) Taking a small amount of the dispersed liquid drops in the step (1) by using a dropper, putting the dispersed liquid drops into a channel of the device manufactured in the step (2), putting the channel on an Electron Microscope (EM) objective table, simultaneously using a magnet to manufacture an external magnetic field, observing the movement of the particles in the external magnetic field, and photographing and recording, wherein the movement is shown in figure 9.
In this example, Fe dispersed in PEG-200 organic solvent3O4The @ B MNPs move in the channel under the regulation of an external magnetic field. Compared with the existing BNCT treatment of cancer, the organically synthesized boron-containing medicament mainly realizes target targeting based on the biological pairing property of the medicament and specific cancer cells, while Fe in the invention3O4@B MThe NPs benefit from the assembly synthesis of a shell material of boron and a magnetic core material, have the advantages of stable implementation and accurate targeted introduction of external magnetic field regulation and control, have no selectivity on target cancer cells, and have simple preparation process and easy realization of large-area preparation. The boron-coated superparamagnetic core-shell structure nanoparticle provided by the invention has huge development and application potential in the BNCT field.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that those skilled in the art can make various improvements and modifications without departing from the principle of the present invention, and these improvements and modifications should also be construed as the protection scope of the present invention.

Claims (8)

1. A boron neutron capture therapeutic agent, characterized by: the boron neutron capture therapeutic agent Fe3O4The @ B MNPs are boron-coated superparamagnetic core-shell structured nanoparticles, and the nanoparticles are Fe3O4NPs。
2. A method for preparing the boron neutron capture therapeutic agent of claim 1, wherein: fully and mechanically mixing the superparamagnetic nano particles with a boron source and pouring the mixture into a quartz boat; placing the quartz boat in a CVD quartz tube, and removing oxygen in the quartz tube by vacuumizing; and introducing reducing gas, heating at high temperature in a reducing gas environment to exceed the melting point of the boron source, volatilizing, keeping for 1-120 min to enable the boron source to be fully combined with the magnetic nanoparticles, and obtaining the boron-coated superparamagnetic core-shell structure nanoparticles after the reaction is finished.
3. The method of claim 2, wherein: the superparamagnetic nano particle is Fe3O4NPs with the particle size of 3-500 nm.
4. The method of claim 2, wherein: the boron source is solid boron source powder.
5. The method of claim 2, wherein: the boron source is sodium borohydride, sodium boron deuteride, potassium borohydride, lithium tri-sec-butylborohydride, potassium tri-isobutyl borohydride, lithium tri-amyl borohydride or lithium tri-ethyl borohydride.
6. The method of claim 2, wherein: the reducing gas is hydrogen, hydrogen-argon mixed gas, hydrogen-nitrogen mixed gas or hydride gas.
7. The method of claim 2, wherein: the heating temperature is 500-1000 ℃.
8. Use of the boron neutron capture therapeutic agent of claim 1 for cancer therapy.
CN201911138309.6A 2019-11-20 2019-11-20 Boron neutron capture therapeutic reagent and preparation method and application thereof Pending CN110787295A (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1970087A (en) * 2006-09-26 2007-05-30 东南大学 Organic metal carborane target formulation and its preparation method
EP2277544A1 (en) * 2009-07-08 2011-01-26 Nelica Ciobanu Biocompatible magnetic nano-clusters containing iron oxide respectively iron oxide - boron with primary use in magnetic drug targeting and boron neutron capture therapy
JP2014192454A (en) * 2013-03-28 2014-10-06 Hitachi Metals Ltd Manufacturing method of composite coated soft magnetic metal powder, composite coated soft magnetic metal powder, and powder magnetic core using the same
CN105132884A (en) * 2015-09-25 2015-12-09 南京航空航天大学 Method for preparing atom-stage boron film through chemical vapor deposition
CN108500285A (en) * 2017-02-28 2018-09-07 中国科学院大连化学物理研究所 It is a kind of to support or the preparation method of non-supported transition metal@h-BN core-shell structure copolymer nanostructures
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Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1970087A (en) * 2006-09-26 2007-05-30 东南大学 Organic metal carborane target formulation and its preparation method
EP2277544A1 (en) * 2009-07-08 2011-01-26 Nelica Ciobanu Biocompatible magnetic nano-clusters containing iron oxide respectively iron oxide - boron with primary use in magnetic drug targeting and boron neutron capture therapy
JP2014192454A (en) * 2013-03-28 2014-10-06 Hitachi Metals Ltd Manufacturing method of composite coated soft magnetic metal powder, composite coated soft magnetic metal powder, and powder magnetic core using the same
CN105132884A (en) * 2015-09-25 2015-12-09 南京航空航天大学 Method for preparing atom-stage boron film through chemical vapor deposition
CN108500285A (en) * 2017-02-28 2018-09-07 中国科学院大连化学物理研究所 It is a kind of to support or the preparation method of non-supported transition metal@h-BN core-shell structure copolymer nanostructures
WO2019204645A1 (en) * 2018-04-18 2019-10-24 Cedars-Sinai Medical Center Nanoparticles for boron neutron capture therapy and for diagnosing, detecting, and treating cancer

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Title
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KANAT DUKENBAYEV等: "Fe3O4 Nanoparticles for Complex Targeted Delivery and Boron Neutron Capture Therapy", 《NANOMATERIALS》 *
YINGHUAI ZHU等: "Boron Drug Delivery via Encapsulated Magnetic Nanocomposites: A New Approach for BNCT in Cancer Treatment", 《JOURNAL OF NANOMATERIALS》 *

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