CN109913201B - Near-infrared two-region fluorescent nano probe based on black phosphorus and preparation and application thereof - Google Patents
Near-infrared two-region fluorescent nano probe based on black phosphorus and preparation and application thereof Download PDFInfo
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Abstract
The invention relates to a near-infrared two-zone fluorescent nano probe based on black phosphorus, a preparation method and application thereof, wherein the preparation method comprises the following steps: uniformly mixing red phosphorus or black phosphorus and a ball milling body, then carrying out ball milling for 1-200h, then adding a hydrophobic ligand into the mixture, and continuing ball milling for 1-200h to obtain black phosphorus nanoparticles with the hydrophobic ligand modified on the surface; dissolving the black phosphorus nanoparticles with the surface modified with the hydrophobic ligand and the amphiphilic molecules in a volatile organic solvent according to the mass ratio of 1:100-200, then volatilizing to remove the organic solvent, mixing the obtained substance with water uniformly, and then stirring vigorously to obtain the water-soluble near-infrared two-zone fluorescent nanoprobe based on the black phosphorus. The near-infrared two-region fluorescent nano probe obtained by the preparation method has stronger and wider fluorescent signals, can realize multi-wavelength excitation and multi-wavelength emission, and has wide application prospect in the aspect of biological imaging.
Description
Technical Field
The invention relates to the field of biomedicine, in particular to a near-infrared two-region fluorescent nano probe based on black phosphorus and preparation and application thereof.
Background
As an emerging two-dimensional semiconductor material, the single-layer or multi-layer nanostructure of the black phosphorus has unique photoelectric properties (high carrier mobility, tunable band gap and high switching rate) and photothermal effect, and attracts wide attention in the aspects of photoelectricity, energy storage and biomedicine. In the biomedical field, since phosphorus is an essential element of living organisms and functions, black phosphorus and its degradation products are considered to have excellent biocompatibility. However, the black phosphorus nanostructure is easily degraded by water and oxygen, thereby affecting its optical and electrical properties and application performance. Therefore, how to improve the optical and electrical properties and the application performance thereof by surface modification has become a hot point of research. The current methods for surface modification include physical coating (such as PLGA (polylactic-co-glycolic acid) coating black phosphorus quantum dots), covalent bonding (such as covalent coupling of fluorescent dye on the surface of black phosphorus nanosheet), and coordination bonding (such as coordination of organic metal titanium and phosphorus atoms on the surface of black phosphorus). These methods improve the stability of black phosphorus to a uniform degree. The chinese patent with application number 201510968976.2 discloses a black phosphorus nanoparticle with biocompatibility and a preparation method and application thereof, wherein the black phosphorus nanoparticle is modified by water-soluble biocompatible molecules to obtain nanoparticles which can be directly used in biomedical applications (such as photoacoustic imaging, photothermal therapy, photodynamic therapy, etc.). However, because the water-soluble biocompatible molecules are used to modify the nanoparticles, water molecules and oxygen are very likely to react with phosphorus atoms on the surface of the black phosphorus nanoparticles, which affects the physicochemical properties and the service performance of the black phosphorus nanoparticles.
The tunable band gap of the black phosphorus nanostructure determines that the black phosphorus nanostructure has adjustable luminescent properties. Because the luminescent property of the black phosphorus nanoparticle solution is influenced by the surrounding environment (such as water molecules and oxygen), the research on the fluorescence property of the black phosphorus nanoparticle solution is relatively less, and particularly, the near-infrared two-region fluorescence property of the black phosphorus nanoparticle solution is not reported in the biomedical field. Compared with visible light and near-infrared first-zone fluorescence, the near-infrared second-zone fluorescence has the characteristics of higher tissue penetration depth, higher signal-to-noise ratio, lower tissue scattering and the like, so that the sensitivity and contrast of near-infrared second-zone imaging are higher, and the near-infrared second-zone fluorescence has huge application potential in image diagnosis.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a black phosphorus-based near-infrared two-region fluorescent nano probe and preparation and application thereof. The probe preparation method has the characteristics of simple operation, easy popularization and high yield, and the near-infrared two-region fluorescent nano probe prepared by the method has stronger and wider fluorescent signals, can realize multi-wavelength excitation and multi-wavelength emission, and has wide application prospect in the aspect of biological imaging.
The invention aims to provide a method for preparing a black phosphorus-based near-infrared two-region fluorescent nano probe, which comprises the following steps of:
(1) uniformly mixing red phosphorus or black phosphorus with a ball mill body, performing ball milling for 1-200h (preferably 10-20h), adding a hydrophobic ligand, and performing ball milling for 1-200h (preferably 10-60h) to obtain black phosphorus nanoparticles with the surface modified with the hydrophobic ligand; the mass ratio of the red phosphorus or the black phosphorus to the ball milling body is 1:1-500 (preferably 1: 100-300); the mass ratio of the red phosphorus or black phosphorus to the hydrophobic ligand is 1: 1-20;
(2) and dissolving the black phosphorus nano-particles with the surface modified with the hydrophobic ligand and the amphiphilic molecules in a volatile organic solvent, then volatilizing to remove the organic solvent, mixing the obtained substance with water uniformly, and then violently stirring to obtain the water-soluble near-infrared two-zone fluorescent nano-probe based on the black phosphorus.
Further, in the step (1), the hydrophobic ligand is one or more of long-chain alkylamine, long-chain alkyl alcohol, cyclic aromatic amine, cyclic aromatic alcohol, cholesterol, stigmasterol and derivatives thereof.
Preferably, the hydrophobic ligand is oleylamine or cholesterol.
In the step (1), the hydrophobic ligand chemically reacts with phosphate radical or phosphorus atom on the black phosphorus surface through the functional group of the hydrophobic ligand. The invention regulates and controls the near-infrared two-region fluorescence property by changing the surface modification ligand of the black phosphorus nanoparticle, so that the black phosphorus nanoparticle has stronger near-infrared two-region fluorescence.
Furthermore, the ball milling body is ball milling beads, the particle size of the ball milling beads is 0.3-50mm, and the ball milling rotating speed is 500-2000 r/min.
Further, in the step (1), after adding the hydrophobic ligand and ball-milling for 1-200h, the method also comprises the following steps:
and ultrasonically dispersing the obtained product in a dispersion medium, centrifuging to obtain a supernatant, adding a precipitator into the supernatant, and collecting precipitates to obtain the black phosphorus nanoparticles with the surface modified hydrophobic ligand.
Further, the centrifugal rotating speed is 500-5000 r/min.
Further, the dispersion medium is one or more of tetrahydrofuran, chloroform, cyclohexane, n-heptane and toluene.
Further, the precipitant is methanol, ethanol, propanol, isopropanol, butanol, isobutanol, diethyl ether or acetone.
Further, in the step (2), the amphiphilic molecule is one or more of liposome, pegylated phospholipid, polyethylene glycol-polylactic acid and polyethylene glycol-polycaprolactone copolymer.
Further, the mass ratio of the red phosphorus or black phosphorus in the step (1) to the amphiphilic molecules in the step (2) is 1: 100-200.
Further, in the step (2), the obtained substance is mixed with water, and then the steps of removing insoluble substances by centrifugation, removing amphiphilic molecules by dialysis and freeze drying are included. And freeze-drying to obtain the near-infrared two-region fluorescent nano probe powder capable of being stored for a long time.
Further, the centrifugal rotation speed is 500-.
The second purpose of the invention is to provide a black phosphorus-based near-infrared two-zone fluorescent nano probe prepared by the preparation method, which comprises black phosphorus nano particles, wherein the surfaces of the black phosphorus nano particles are modified with hydrophobic ligands, the surfaces of the hydrophobic ligands are wrapped with amphipathic molecules, the particle size of the black phosphorus-based near-infrared two-zone fluorescent nano probe is 50-200nm, the excitation wavelength is 800-.
The third purpose of the invention is to protect the application of the near-infrared two-region fluorescent nano probe based on black phosphorus in the preparation of a near-infrared two-region fluorescent imaging preparation.
The near-infrared two-region fluorescent nano probe can realize multi-wavelength excitation and wide-wavelength emission and realize near-infrared two-region fluorescent imaging.
The near-infrared two-region fluorescent nano probe can realize living body fluorescence imaging of the near-infrared two-region, can be delivered into an animal body in an oral or intravenous injection mode, then clearly displays the characteristics of organs, tissues and anatomical structures of the animal under the irradiation of laser, and can be used for observing the physiological processes of the probe in vivo such as circulation, distribution, metabolism and the like under the irradiation of the laser.
By the scheme, the invention at least has the following advantages:
the near-infrared two-region fluorescent nano probe based on black phosphorus provided by the invention has strong interaction with surface ligands, so that the near-infrared two-region fluorescent nano probe has good lipophilicity, and amphiphilic molecules are coated on the surfaces of the near-infrared two-region fluorescent nano probe to obtain the black phosphorus-based nano probe with high chemical stability and biocompatibility. The near-infrared two-region fluorescent nano probe based on black phosphorus can be used for preparing a near-infrared two-region fluorescent imaging preparation, biological imaging is realized, and the characteristics of various organ tissues and anatomical structures of animals and physiological processes of the probe in vivo, such as circulation, distribution, metabolism and the like, can be clearly displayed under laser irradiation.
The preparation method of the probe has the characteristics of simple operation, easy popularization and high yield. The near-infrared two-region fluorescent nano probe prepared by the method has stronger and wider fluorescent signals, can realize multi-wavelength excitation and multi-wavelength emission, and has wide application prospect in the aspect of biological imaging.
The foregoing description is only an overview of the technical solutions of the present invention, and in order to make the technical solutions of the present invention more clearly understood and to implement them in accordance with the contents of the description, the following detailed description is given with reference to the preferred embodiments of the present invention and the accompanying drawings.
Drawings
FIG. 1 is an X-ray diffraction pattern of raw red phosphorus and product black phosphorus in example 1 of the present invention;
FIG. 2 is a graph showing the distribution of the particle size of black phosphorus nanoparticles surface-modified with Oleylamine (OM) in tetrahydrofuran solution in example 2 of the present invention;
FIG. 3 is a transmission electron microscope image of black phosphorus nanoparticles surface-modified with Oleylamine (OM) in example 2 of the present invention;
FIG. 4 is a fluorescence spectrum of a chloroform/tetrahydrofuran solution of black phosphorus nanoparticles surface-modified with Oleylamine (OM) in the near-infrared region under 808nm laser irradiation in example 2 of the present invention;
FIG. 5 is a graph of the hydrated particle size distribution of BP-OM @ lipid-PEG nanoparticles prepared in example 3 of the present invention;
FIG. 6 is a transmission electron micrograph of BP-OM @ lipid-PEG nanoparticles prepared in example 3 of the present invention;
FIG. 7 is a fluorescence spectrum of BP-OM @ lipid-PEG nanoparticles prepared in example 3 of the present invention in the near infrared region under 808nm laser irradiation;
FIG. 8 is a graph showing the distribution of the particle size of the cholesterol (Chol) -surface-modified Hexaphos nanoparticles in tetrahydrofuran solution in example 4 of the present invention;
FIG. 9 is a transmission electron micrograph of the nanoparticle of black phosphorus surface-modified with cholesterol (Chol) according to example 4 of the present invention;
FIG. 10 is a fluorescence spectrum of a chloroform/tetrahydrofuran solution of cholesterol (Chol) -surface-modified black phosphorus nanoparticles in the near-infrared region under 808nm laser irradiation in example 4 of the present invention;
FIG. 11 is a graph showing the distribution of the hydrated particle size of BP-Chol @ lipid-PEG nanoparticles prepared in example 5 of the present invention;
FIG. 12 is a transmission electron micrograph of BP-Chol @ lipid-PEG nanoparticles prepared in example 5 of the present invention;
FIG. 13 is a fluorescence spectrum of BP-Chol @ lipid-PEG nanoparticles prepared in example 5 of the present invention in the near infrared region under 808nm laser irradiation;
FIG. 14 is a near infrared two-region fluorescence spectrum collected by irradiating BP-Chol @ lipid-PEG nanoparticles with 808nm and 980nm lasers having the same power density in example 5 of the present invention;
FIG. 15 shows the result of near-infrared two-zone imaging of the blood vessels on the back of a nude mouse injected through the caudal vein using BP-Chol @ lipid-PEG nanoparticles prepared in example 5 as a near-infrared two-zone probe;
FIG. 16 is a graph of two near-infrared images of the gastrointestinal tract collected at different time points after the mouse of example 7 of the present invention orally takes BP-Chol @ lipid-PEG nanoparticles.
Detailed Description
The following detailed description of embodiments of the present invention is provided in connection with the accompanying drawings and examples. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1
Weighing 1.00g of red phosphorus, putting the red phosphorus into a 100mL stainless steel ball mill tank, adding stainless steel balls (the mass ratio of the red phosphorus to the ball milling balls is 1:150), sealing, fixing the ball mill tank in a ball mill, and then carrying out ball milling for 96 hours at the rotating speed of 500r/min to obtain black phosphorus nanoparticle powder. The X-ray diffraction patterns (XRD) of the raw material Red Phosphorus (RP) and the product Black Phosphorus (BP) are shown in figure 1.
Example 2
To the black phosphorus nanoparticle powder prepared in example 1, 4g oleylamine (molecular weight 267Da) was added and ball milling was continued for 72 h. The resulting product was dispersed in tetrahydrofuran and centrifuged at 1000r/min to remove the precipitate. Adding appropriate amount of ethanol as precipitant to aggregate black phosphorus-oleylamine (BP-OM) nanoparticles to form insoluble substance, centrifuging at 5000r/min for 5min, collecting precipitate, and dissolving in tetrahydrofuran. And centrifuging the obtained solution at the rotating speed of 1000r/min again, and taking the supernatant, namely the purified BP-OM nano particles. FIG. 2 is a graph showing the distribution of BP-OM nanoparticles in tetrahydrofuran, with an average particle size of 21 nm. FIG. 3 is a transmission electron micrograph of BP-OM, with a statistical average particle size of 14 nm.
And (3) respectively placing 600 mu L of the prepared BP-OM nanoparticle solution chloroform or tetrahydrofuran solution with the concentration of 50 mu g/mLBP-OM in a quartz four-way micro sample cell, irradiating by adopting 808nm laser, and respectively recording the emission spectra in a fluorescence spectrometer by using a 900nm optical filter. FIG. 4 shows BP-OM nanoparticles in chloroform (CHCl)3) And emission spectra in Tetrahydrofuran (THF) solution.
Example 3
50mg of phospholipid-polyethylene glycol (PEG) molecules (the molecular weight of a PEG chain segment is 2000Da) are dispersed in the tetrahydrofuran solution of the BP-OM nano particles prepared in the example 2, after the tetrahydrofuran is completely volatilized at room temperature, ultrapure water is added for vigorous stirring, and the stirring time is 1 min. Then centrifuging at 3000r/min for 10min to remove insoluble substances, dialyzing the obtained supernatant to remove excessive lipid-PEG, and obtaining a dialysis bag with the molecular weight cut-off of 8000-100,000 Da. And obtaining OM and lipid-PEG double-modified black phosphorus nanoparticle powder capable of being stored for a long time after freeze drying, and naming the powder as BP-OM @ lipid-PEG nanoparticle. FIG. 5 is a graph showing the distribution of hydrated particle size of BP-OM @ lipid-PEG nanoparticle aqueous solution, wherein the average hydrated particle size is 120 nm. FIG. 6 is a transmission electron micrograph of BP-OM @ lipid-PEG nanoparticles, with a statistical average particle size of 70 nm.
Placing 600 mu L of 50 mu g/mLBP-OM @ lipid-PEG nanoparticle aqueous solution in a quartz four-way micro sample cell, irradiating by adopting 808nm laser, and measuring the emission spectrum of the quartz four-way micro sample cell in a fluorescence spectrometer by using a 900nm optical filter. FIG. 7 is an emission spectrum of an aqueous solution of BP-OM @ lipid-PEG nanoparticles.
Example 4
To the black phosphorus nanoparticle powder prepared in example 1, 4g of cholesterol (molecular weight 387Da) was added and ball milling was continued for 72 h. The resulting product was dispersed in tetrahydrofuran and centrifuged at 1000r/min to remove the precipitate. Adding appropriate amount of ethanol as precipitant to aggregate black phosphorus-cholesterol (BP-Chol) nanoparticles to form insoluble substance, centrifuging at 5000r/min for 5min, collecting precipitate, and redissolving in tetrahydrofuran. And centrifuging the obtained solution at the rotating speed of 1000r/min again, and purifying the supernatant to obtain the BP-Chol nano particles. FIG. 8 is a distribution graph of BP-Chol nanoparticles in tetrahydrofuran, with an average particle size of 14 nm. FIG. 9 is a transmission electron micrograph of BP-Chol nanoparticles with a statistical average particle size of 20 nm.
And (3) respectively placing the prepared BP-Chol nanoparticle solution, chloroform or tetrahydrofuran solution with the concentration of 50 mu g/mLBP-Chol nanoparticles in a quartz four-way micro sample cell, irradiating by adopting 808nm laser, and measuring the emission spectrum of the BP-Chol nanoparticle solution in a fluorescence spectrometer by using a 900nm optical filter. FIG. 10 shows a chloroform solution of BP-Chol (CHCl)3) And emission spectrum of Tetrahydrofuran (THF) solution.
Example 5
50mg of phospholipid-polyethylene glycol (PEG) molecules (the molecular weight of a PEG chain segment is 2000Da) are dispersed in the tetrahydrofuran solution of the BP-Chol nanoparticles prepared in example 4, after the tetrahydrofuran is completely volatilized at room temperature, ultrapure water is added for vigorous stirring, and the stirring time is 1 min. Then, centrifugation was carried out at 3000r/min for 10min to remove insoluble matter, and the resulting supernatant was dialyzed to remove excess lipid-PEG. Obtaining the Chol and lipid-PEG double-modified black phosphorus nanoparticle powder which can be stored for a long time after freeze drying, and naming the powder as BP-Chol @ lipid-PEG nanoparticle. FIG. 11 is a graph showing the distribution of hydrated particle sizes of BP-Chol @ lipid-PEG nanoparticles, the average particle size of which is 106 nm. FIG. 12 is a transmission electron micrograph of BP-Chol @ lipid-PEG nanoparticles with a statistical average particle size of 97 nm.
Placing 600 mu L of 50 mu g/mLBP-Chol @ lipid-PEG nanoparticle aqueous solution in a quartz four-way micro sample cell, irradiating by adopting 808nm laser, and recording the emission spectrum of the quartz four-way micro sample cell in a fluorescence spectrometer by using a 900nm filter. FIG. 13 is an emission spectrum of an aqueous solution of BP-Chol @ lipid-PEG nanoparticles.
In addition, 600 mu L of 1mg/mLBP-Chol @ lipid-PEG nanoparticle aqueous solution is placed in a quartz four-way micro sample cell and is irradiated by 808nm laser and 980nm laser with the same power density respectively. The emission spectra were recorded in a fluorescence spectrometer using a 900nm filter and a 930nm filter, respectively. FIG. 14 is an emission spectrum of BP-Chol @ lipid-PEG nanoparticle aqueous solution.
Example 6
The BP-Chol @ lipid-PEG nanoparticle aqueous solution (1.3mg/mL) obtained in example 5 is delivered into a nude mouse body in a tail vein injection mode, and a near-infrared two-region fluorescence imaging signal of a blood vessel on the back of the nude mouse is collected by a small animal near-infrared two-region imager (808nm laser irradiation and 1400nm optical filter). As can be seen from fig. 15(ScaleBar ═ 5mm), the black phosphorus nanoparticles have good near-infrared two-zone fluorescence imaging effect, and can be used as near-infrared two-zone fluorescence imaging probes.
Example 7
The BP-Chol @ lipid-PEG nanoparticle aqueous solution (2mg/mL) obtained in example 5 is injected into a nude mouse body in an oral administration mode, and an abdominal imaging signal of the nude mouse is observed under a small animal near-infrared two-zone imager (808nm laser irradiation and 1250nm optical filter), wherein the observation time is 30 min. Fig. 16 a, b, c are respectively the near infrared two-region images of the gastrointestinal tract acquired at 30 second, 5min, 30min time intervals, which clearly show the structural information of the stomach, duodenum, small intestine and large intestine of the nude mouse.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, it should be noted that, for those skilled in the art, many modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A method for preparing a near-infrared two-region fluorescent nano probe based on black phosphorus is characterized by comprising the following steps:
(1) uniformly mixing red phosphorus or black phosphorus and a ball milling body, then carrying out ball milling for 1-200h, then adding a hydrophobic ligand into the mixture, and continuing ball milling for 1-200h to obtain black phosphorus nanoparticles with the hydrophobic ligand modified on the surface; the mass ratio of the red phosphorus or the black phosphorus to the ball grinding body is 1: 1-500; the mass ratio of the red phosphorus or black phosphorus to the hydrophobic ligand is 1: 1-20;
(2) and dissolving the black phosphorus nanoparticles with the surface modified with the hydrophobic ligand and the amphiphilic molecules in an organic solvent, removing the organic solvent, and uniformly mixing the obtained substance with water to obtain the black phosphorus-based near-infrared two-zone fluorescent nanoprobe.
2. The method of claim 1, wherein: in the step (1), the hydrophobic ligand is one or more of long-chain alkylamine, long-chain alkyl alcohol, cholesterol and stigmasterol.
3. The method of claim 1, wherein: the ball milling bodies are ball milling beads, the particle size of the ball milling beads is 0.3-50mm, and the ball milling rotating speed is 500-200 r/min.
4. The preparation method according to claim 1, wherein in the step (1), after adding the hydrophobic ligand and ball-milling for 1-200h, the method further comprises the following steps:
and uniformly mixing the obtained product with a dispersion medium, centrifuging to obtain a supernatant, adding a precipitator into the supernatant, and collecting precipitates to obtain the black phosphorus nanoparticles with the surface modified with the hydrophobic ligand.
5. The method of claim 4, wherein: the dispersion medium is one or more of tetrahydrofuran, chloroform, cyclohexane, n-heptane and toluene.
6. The method of claim 1, wherein: in the step (2), the amphiphilic molecules are one or more of liposome, pegylated phospholipid, polyethylene glycol-polylactic acid and polyethylene glycol-polycaprolactone copolymer.
7. The method of claim 1, wherein: the mass ratio of the red phosphorus or black phosphorus in the step (1) to the amphiphilic molecules in the step (2) is 1: 100-200.
8. The method of claim 1, wherein: in the step (2), the obtained substance is mixed with water uniformly, and then the steps of removing insoluble substances by centrifugation, removing amphiphilic molecules by dialysis and freeze drying are included.
9. A black phosphorus-based near-infrared two-zone fluorescent nanoprobe prepared by the preparation method of any one of claims 1 to 8, wherein: the fluorescent nanoprobe comprises black phosphorus nanoparticles, wherein a hydrophobic ligand is modified on the surface of each black phosphorus nanoparticle, amphiphilic molecules are wrapped on the surface of the hydrophobic ligand, the particle size of the black phosphorus-based near-infrared two-region fluorescent nanoprobe is 50-200nm, the excitation wavelength is 800-1000nm, and the emission wavelength is 900-1700 nm.
10. Use of the black phosphorus-based near-infrared two-zone fluorescent nanoprobe of claim 9 in the preparation of a near-infrared two-zone fluorescent imaging formulation.
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