CN113845904B - Preparation of boron-nitrogen doped graphene quantum dots and application of boron-nitrogen doped graphene quantum dots in boron neutron capture therapeutic drugs - Google Patents

Preparation of boron-nitrogen doped graphene quantum dots and application of boron-nitrogen doped graphene quantum dots in boron neutron capture therapeutic drugs Download PDF

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CN113845904B
CN113845904B CN202111231001.3A CN202111231001A CN113845904B CN 113845904 B CN113845904 B CN 113845904B CN 202111231001 A CN202111231001 A CN 202111231001A CN 113845904 B CN113845904 B CN 113845904B
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CN113845904A (en
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邢更妹
李嘉程
李娟�
崔荣丽
陈奎
常亚男
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Institute of High Energy Physics of CAS
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/65—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon
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    • 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
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    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
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Abstract

The invention discloses preparation of boron-nitrogen doped graphene quantum dots and application of the boron-nitrogen doped graphene quantum dots in boron neutron capture treatment drugs, and relates to the field of chemical and biomedical tumor diagnosis and treatment. Which is prepared from graphene quantum dots and 10 b boric acid aqueous solution is used as a raw material to synthesize the boron-nitrogen doped graphene quantum dot, the boron-nitrogen doped graphene quantum dot has high boron content, excellent optical properties, good biocompatibility and low toxicity, realizes in-vivo fluorescence imaging, can also target breast cancer tumors and enrich the breast cancer tumor parts, but can be rapidly metabolized and discharged in healthy tissues, and the properties enable the boron-nitrogen doped graphene quantum dot to be used as a novel boron transport agent suitable for BNCT treatment, so that diagnosis and BNCT treatment of the breast cancer tumors are realized.

Description

Preparation of boron-nitrogen doped graphene quantum dots and application of boron-nitrogen doped graphene quantum dots in boron neutron capture treatment drugs
Technical Field
The invention relates to the field of chemical and biomedical tumor diagnosis and treatment, in particular to preparation of boron-nitrogen doped graphene quantum dots and application of the boron-nitrogen doped graphene quantum dots in boron neutron capture treatment medicines.
Background
Boron Neutron Capture Therapy (BNCT) as a novel precise tumor therapy by intracellular localization in tumor cells 10 B captures thermal neutrons to generate alpha particles by nuclear fission reaction 7 Li recoils the nucleus, selectively killing the tumor cells. BNCT is based on nuclear capture and nuclear fission reactions, due to non-radioactivity 10 B atoms (the content of the B atoms in natural boron element is 20 percent) can generate neutron capture and further generate nuclear fission, 10 b is activated after being irradiated by neutrons of a certain energy 11 B and subsequently split into high-energy alpha particles and 7 li recoil nucleus, the nuclear reaction formula is:
B 10 +n th →[B 11 ] * →α+Li 7 +2.31MeV
high energy alpha particles and 7 li recoil nuclei can be dissociated at the moment of reaction in a fine pitch (about 5 to 9 μm) of the target (cell) diameter. Since the lethal intensity of the capture reaction is limited by the boron-containing cells, BNCT can be considered as a biological and physical targeted radiation therapy, wherein the success or failure of BNCT depends on whether the tumor takes up sufficient amounts of the tumor 10 B, i.e. ensuring that a sufficient amount of 10 B is selectively delivered to the interior of tumor cells and reduces the absorption of normal tissues of human body near the tumor as much as possible 10 And B, avoiding the damage of the normal tissues of the human body caused by nuclear capture and nuclear fission reaction.
The artificial boron delivery has more varieties, but currently, the clinical treatment can be used for only two types: one is a polyhedral boron hydride anion, also known as sodium boron clathrate or BSH (Na) 2 B 12 H 11 SH), used mainly in japan; the other is a dihydroxyborophenylalanine derivative, also known as borocagophenylalanine or BPA, used in clinical trials mainly in the United states, europe, japan, argentina, and tortuosity, among others. BPA and BSH were both administered intravenously and the tumor foci were neutron irradiated, with a neutron source provided by a specially adapted nuclear reactor. By the time of 1994, the date of the year,low energy is mainly used in Japan: (<0.5 eV), because of the limited penetration depth of low-energy thermal neutron beam to human tissue, the subsequent us, europe and japan adopted the hyperthermia neutron beam (the energy of the hyperthermia neutron is 0.5eV to 10 keV) with stronger penetration ability and stronger energy in clinical trial.
Ideally, BNCT is highly selective, targeting tumor cells without causing radiation damage to normal cells and tissues surrounding the tumor, and can deliver doses of up to 60-70 Gy into tumor cells over 1-2 dosing sessions, as compared to conventional external beam photon radiation therapy requiring 6-7 weeks. However, the effectiveness of BNCT depends on 10 The relative uniformity of B distribution in tumors, which is still an unsolved problem in BNCT, has limited the development of BNCT.
Meanwhile, BNCT boron transporters still remain a difficult problem to be solved urgently at present. The most important requirements for boron delivery agents are: 1. the toxicity of the whole body of the human body is low, the intake of the normal tissues of the human body is low, and the intake of the tumor cells is higher along with the increase of the malignancy of the tumor cells, namely the higher the malignancy of the tumor cells is. 2. The concentration of boron delivery agent in the tumor was 2010B/g.3. The boron delivery agent is rapidly cleared from the patient's blood and normal tissues during BNCT, but persists within the tumor. However, there are currently no boron transporters that simultaneously meet the above requirements. Therefore, there is an urgent need to find a boron-containing complex as an effective boron delivery agent, which can significantly increase the water solubility of highly lipid-soluble drugs, slow down the half-life of the drugs, and improve the bioavailability.
Disclosure of Invention
The invention aims to solve the problems and provides a preparation method of boron-nitrogen doped graphene quantum dots and an application of the boron-nitrogen doped graphene quantum dots in boron neutron capture treatment drugs.
In order to realize the purpose, the invention adopts the following technical scheme:
boron-nitrogen doped graphene quantum dot, graphene quantum dot and preparation method thereof 10 B boric acid water solution is used as a raw material, wherein the graphene quantum dots and the graphene quantum dots 10 The mass ratio of the boric acid aqueous solution B is 1.
Preferably, the particle size of the boron-nitrogen doped graphene quantum dot is 40-70 nm.
According to the preparation method of the boron-nitrogen doped graphene quantum dot, the boron-nitrogen doped graphene quantum dot is synthesized by adopting a vapor deposition method.
Preferably, the method specifically comprises the following steps:
a. dissolving soluble starch in water, mixing and stirring to obtain a solution, adding the solution into a reaction kettle to perform hydrothermal reaction to obtain a reaction solution, centrifuging and filtering the reaction solution, and freeze-drying the upper layer solution to obtain graphene quantum dot powder;
b. mixing graphene quantum dot powder with 10 B, after uniformly mixing the boric acid aqueous solution, freeze-drying to obtain a powdery product, putting the powdery product into a tube furnace, and introducing NH into the tube furnace 3 Carrying out reaction to obtain boron-nitrogen doped graphene quantum dots;
c. and washing the boron-nitrogen doped graphene quantum dots in hot water, and freeze-drying to obtain boron-nitrogen doped graphene quantum dot powder.
Preferably, in the step a, the set temperature of the reaction kettle is 150-200 ℃, and the hydrothermal reaction time is 60-120 min.
Preferably, the 10 The concentration of the boric acid aqueous solution B is 0.1-1 mg/mL, 10 b in an aqueous solution of boric acid 10 The abundance of B was 95%.
Preferably, in the step b, the set temperature of the tube furnace is 700-900 ℃.
The boron-nitrogen doped graphene quantum dot is applied to tumor BNCT treatment medicines.
Preferably, the use comprises targeting breast cancer tumor tissue and enriching at the breast cancer tumor site.
Preferably, the application comprises as a boron delivery agent 10 B is sent toWithin tumor cells.
The invention has the beneficial effects that:
the invention constructs a graphene quantum dot and 10 the method for synthesizing the boron-nitrogen doped graphene quantum dots (BNGO) by using the boric acid aqueous solution as the raw material has excellent optical properties, good biocompatibility and low toxicity, and has important application prospects in the fields of biological imaging, chemical sensing, photocatalysis, drug delivery and the like. Experiments prove that the graphene quantum dots and the graphene quantum dots are used in the invention 10 The BNGO synthesized by using the boric acid B aqueous solution as the raw material can target breast cancer tumors and is enriched at the breast cancer tumor parts, and the BNGO in healthy tissues can be rapidly metabolized and excreted, thereby providing conditions for realizing BNCT treatment. Therefore, BNGO can be used as a novel boron delivery agent suitable for BNCT treatment to realize the diagnosis of breast cancer tumors and BNCT treatment.
Drawings
FIG. 1 is a schematic drawing of a BNGO nanoparticle atomic particle microscope AFM of the present invention.
FIG. 2 is a fluorescence emission spectrum of BNGOs of the present invention.
FIG. 3 is a graph showing the effect of BNGO on the survival rate of breast cancer cells 4T 1.
Fig. 4 is a schematic representation of the cell morphology of breast cancer cells without BNGO after neutron irradiation.
Fig. 5 is a schematic diagram of cell morphology of breast cancer cells containing BNGO after neutron irradiation.
FIG. 6 shows the results of control experiments observed by the optical microscope C1-203; panel (a) shows breast cancer cells containing BNGO and panel (b) shows breast cancer cells without BNGO.
FIG. 7 is a graph showing the effect of BNGO on the number of monoclonal cells.
FIG. 8 is an ex vivo graph of mouse major organs and breast cancer tumor model after BNGO injection.
Detailed Description
The invention provides a preparation method of boron-nitrogen doped graphene quantum dots and application of the boron-nitrogen doped graphene quantum dots in boron neutron capture treatment drugs, and in order to make advantages and technical schemes of the invention clearer and clearer, the invention is described in detail with specific embodiments.
The raw materials required by the invention can be purchased from commercial sources.
The invention relates to graphene quantum dots and 10 b boric acid aqueous solution is used as raw material to synthesize boron-nitrogen doped graphene quantum dots (BNGO), graphene quantum dots and the like 10 The mass ratio of the boric acid aqueous solution B is 1, wherein the graphene quantum dots are prepared from soluble starch and water as raw materials, the soluble starch has no reducing substances, the chemical property is stable, the adsorption force is strong, and the flowability of the medicine can be obviously improved. Meanwhile, a large amount of nutrients are needed for the rapid propagation of tumor cells, and the boron-nitrogen doped graphene quantum dots enter the tumor cells through the endocytosis of the tumor cells.
The boron-nitrogen doped graphene quantum dots (BNGO) provided by the invention have excellent optical properties, good biocompatibility and low toxicity, the particle size of the boron-nitrogen doped graphene quantum dots is 40-70 nm, the BNGO can be enriched in tumor tissues based on EPR effect due to abundant blood vessels, wide vascular wall gaps, complete structure and lymphatic backflow loss in solid tumor tissues, and conversely, the BNGO is less prone to penetrate through the vascular wall due to compact capillary endothelial gaps and complete structure in human healthy tissues, so that the distribution of the BNGO in human normal tissues is reduced, therefore, the BNGO provided by the invention can target tumor tissues, especially breast cancer tumor tissues, is enriched in tumor parts without influencing the human healthy tissues, has passive targeting on the tumor tissues, is suitable for a novel boron delivery agent for BNCT treatment, and realizes diagnosis and BNCT treatment of tumors.
The preparation method of the boron-nitrogen doped graphene quantum dot of the invention is explained in detail below.
Example 1:
the boron-nitrogen doped graphene quantum dot provided by the invention is synthesized by adopting a vapor deposition method, and the preparation method specifically comprises the following steps:
a. dissolving 0.25g of soluble starch in 25ml of water, mixing and stirring to obtain a dissolved solution, adding the dissolved solution into a reaction kettle at the temperature of 190 ℃ to perform hydrothermal reaction for 120min to obtain a reaction solution, centrifuging and filtering the reaction solution, removing lower-layer solids in the reaction solution, and taking an upper-layer solution to perform freeze drying to obtain graphene quantum dot powder;
b. 0.1g of graphene quantum dot powder and 100ml 10 B aqueous boric acid solution (concentration 1 mg/mL), 10 The abundance of B is 95 percent), freeze-drying to obtain a powdery product, putting the powdery product into a tube furnace, setting the temperature of the tube furnace to 900 ℃, and introducing NH into the furnace 3 Reacting to obtain boron-nitrogen doped graphene quantum dots;
c. and washing the boron-nitrogen doped graphene quantum dots in hot water for multiple times, and freeze-drying to obtain boron-nitrogen doped graphene quantum dot powder.
The boron-nitrogen doped graphene quantum dot framework prepared by the method has the advantages that the content of boron is about 20%, the content of nitrogen is about 20%, the content of boron is high, and the particle size of the boron-nitrogen doped graphene quantum dot is 40-70 nm, as shown in figure 1.
The breast cancer cells and BNGOs are selected for culture, and the result shows that BNGO can enter the breast cancer cells in a targeted manner, the fluorescence imaging effect of the breast cancer cells based on BNGO is observed under a fluorescence microscope, and the fluorescence emission spectrum of BNGOs is shown in FIG. 2.
BNGO has good fluorescence characteristic, when excited by exciting light of 350-380 nm, can emit green fluorescence between 420-530 nm, and because BNGO can excite stronger fluorescence under different excitation wavelengths, BNGO is suitable for quantitative analysis of cell optical imaging.
Example 2
In order to verify the application effect of the boron-nitrogen doped graphene quantum dot prepared in the embodiment 1 in the BNCT treatment process, human breast cancer cells 4T1 and BNGOs are selected for culture, and the result shows that the BNGOs can enter the breast cancer cells in a targeted manner and perform fluorescence imaging.
Effect of BNGO on survival of breast cancer cells 4T1 as shown in figure 3, IC50=176.45ug/mL of breast cancer cells 4T1 after BNCT treatment.
In the experimental process, the cell morphology of the breast cancer cell containing the boron-nitrogen doped graphene quantum dots and the cell morphology of the breast cancer cell not containing the boron-nitrogen doped graphene quantum dots after 24 hours of single BNCT treatment are observed, and fig. 4 shows the cell morphology of the breast cancer cell not containing the boron-nitrogen doped graphene quantum dots after neutron irradiation, so that the breast cancer cell not incubated by BNGO medicines is still full and has good extensibility, the proliferation condition is good, and the cell nucleus and cytoplasm are normal. Fig. 5 shows the cell morphology of the breast cancer cell containing boron-nitrogen doped graphene quantum dots after neutron irradiation, and it can be seen that the breast cancer cell incubated by the BNGO drug has rounded cells after neutron irradiation, cannot grow normally adherent, has abnormal cell morphology and is difficult to observe the cell nucleus, so that the BNGO can be used for significantly inhibiting the breast cancer cell in BNCT treatment.
Example 3
In order to study the influence of the boron-nitrogen doped graphene quantum dots prepared in example 1 on the breast cancer cell 4T1 monoclonal. Set up the control experiment, to cultivate breast cancer cell 4T1 and BNGOs good with culturing in the experimental group of control experiment, after hatching 24h resuspend in the culture medium, after neutron stream irradiation 1h through the accelerator, transplant again to culture medium in, utilize the cell count board to record the quantity of breast cancer cell 4T1 this moment, to cultivate the breast cancer cell 4T1 after the irradiation in the culture medium for 7 days, adopt the crystal violet dyeing method to dye the breast cancer cell 4T1 in the culture medium, count the quantity of breast cancer cell 4T1 in the culture medium this moment, because crystal violet can dye the cytoplasm of cell, so through the dyeing area of observing the culture medium, can determine the quantity of cell. In order to better verify the influence of BNGO on the breast cancer cells 4T1, the experiment is also provided with a control group, the control group is not cultured with BNGOs except the breast cancer cells 4T1, and other experimental conditions and operations are the same as those of the experiment group. The control experiment results are shown in fig. 6 and 7, the experiment results verify that the boron-nitrogen doped graphene quantum dots can influence the number of monoclonal cells of breast cancer cells 4T1, and after the boron-nitrogen doped graphene quantum dots are added into a culture dish according to 200ug/mL and incubated for 24 hours, the boron-nitrogen doped graphene quantum dots are added into the culture dish every 10 hours 5 Boron element capable of being phagocytized by 4T1 of breast cancer cellsAbout 20-40 ug.
Example 4
In order to verify that the boron-nitrogen doped graphene quantum dot prepared in the embodiment 1 has a good targeting effect on breast cancer tumors. The axillary mammary gland fat pad planted with common cells is used as a breast cancer tumor model of a mouse, and the dosage of boron-nitrogen doped graphene quantum dots is 200 mg/kg according to the weight of the mouse. The boron-nitrogen doped graphene quantum dots are injected into a mouse body through rat tail vein injection, after 4 hours of injection, the distribution of the boron-nitrogen doped graphene quantum dots in each organ of the mouse is observed in an anatomical mode, as shown in figure 8, the boron-nitrogen doped graphene quantum dots obtained through observation have a tumor targeted enrichment function, can be enriched and subjected to luminescence imaging at a breast cancer tumor, quantitative imaging monitoring of a drug at the breast cancer tumor part is achieved, and the BNCT treatment effect is favorably improved.
Example 5
The boron-nitrogen doped graphene quantum dot provided by the invention is synthesized by adopting a vapor deposition method, and the preparation method specifically comprises the following steps:
a. dissolving 0.25g of soluble starch in 25ml of water, mixing and stirring to obtain a dissolved solution, adding the dissolved solution into a reaction kettle at the temperature of 200 ℃ to perform hydrothermal reaction for 60min to obtain a reaction solution, centrifuging and filtering the reaction solution, removing lower-layer solids in the reaction solution, and taking an upper-layer solution to perform freeze drying to obtain graphene quantum dot powder;
b. 0.1g of graphene quantum dot powder and 100ml 10 B an aqueous solution of boric acid (concentration 0.1 mg/mL), 10 The abundance of B is 95 percent), freeze-drying to obtain a powdery product, putting the powdery product into a tube furnace, setting the temperature of the tube furnace to 700 ℃, and introducing NH into the furnace 3 Reacting to obtain boron-nitrogen doped graphene quantum dots;
c. and washing the boron-nitrogen doped graphene quantum dots in hot water for multiple times, and freeze-drying to obtain boron-nitrogen doped graphene quantum dot powder.
Example 6
The boron-nitrogen doped graphene quantum dot provided by the invention is synthesized by adopting a vapor deposition method, and the preparation method specifically comprises the following steps:
a. dissolving 0.25g of soluble starch in 25ml of water, mixing and stirring to obtain a dissolved solution, adding the dissolved solution into a reaction kettle at the temperature of 150 ℃ to perform hydrothermal reaction for 100min to obtain a reaction solution, centrifuging and filtering the reaction solution, removing lower-layer solids in the reaction solution, and then taking an upper-layer solution to perform freeze drying to obtain graphene quantum dot powder;
b. 0.1g of graphene quantum dot powder and 100ml 10 B aqueous boric acid solution (concentration 0.5 mg/mL), 10 The abundance of B is 95 percent), the mixture is frozen and dried to obtain a powdery product, the powdery product is placed in a tube furnace, the temperature of the tube furnace is set to be 800 ℃, and NH is introduced into the furnace 3 Reacting to obtain boron-nitrogen doped graphene quantum dots;
c. and washing the boron-nitrogen doped graphene quantum dots in hot water for multiple times, and freeze-drying to obtain boron-nitrogen doped graphene quantum dot powder.
The parts which are not described in the invention can be realized by taking the prior art as reference.
It should be noted that: any equivalents or obvious modifications thereof which may occur to persons skilled in the art and which are given the benefit of this description are deemed to be within the scope of the invention.

Claims (5)

1. The preparation method of the boron-nitrogen doped graphene quantum dot is characterized in that the boron-nitrogen doped graphene quantum dot is formed by combining graphene quantum dots and graphene quantum dots 10 B boric acid water solution is used as a raw material, wherein the graphene quantum dots and the graphene quantum dots 10 The mass ratio of the boric acid aqueous solution B is 1, the particle size of the boron-nitrogen doped graphene quantum dots is 40-70nm, and the boron-nitrogen doped graphene quantum dots are synthesized by a vapor deposition method, and the method specifically comprises the following steps:
a. dissolving soluble starch in water, mixing and stirring to obtain a solution, adding the solution into a reaction kettle to perform hydrothermal reaction to obtain a reaction solution, centrifuging and filtering the reaction solution, and freeze-drying the upper layer solution to obtain graphene quantum dot powder;
b. preparing graphene quantum dot powderAnd 10 b, uniformly mixing the boric acid aqueous solution, freeze-drying to obtain a powdery product, placing the powdery product in a tube furnace, and introducing NH into the tube furnace 3 Carrying out reaction to obtain boron-nitrogen doped graphene quantum dots;
c. and washing the boron-nitrogen doped graphene quantum dots in hot water, and freeze-drying to obtain boron-nitrogen doped graphene quantum dot powder.
2. The preparation method of the boron-nitrogen doped graphene quantum dot according to claim 1, wherein in the step a, the set temperature of a reaction kettle is 150 to 200 ℃, and the hydrothermal reaction time is 60 to 120min.
3. The method for preparing boron-nitrogen doped graphene quantum dots according to claim 1, wherein the method is characterized in that 10 The concentration of the boric acid aqueous solution B is 0.1 to 1mg/mL, 10 b in an aqueous solution of boric acid 10 The abundance of B was 95%.
4. The method for preparing the boron-nitrogen doped graphene quantum dot according to claim 1, wherein in the step b, the set temperature of a tube furnace is 700-900 ℃.
5. The boron-nitrogen doped graphene quantum dot prepared by the preparation method of the boron-nitrogen doped graphene quantum dot according to claim 1, and application of the boron-nitrogen doped graphene quantum dot in tumor boron neutron capture treatment drugs.
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