CN109913201A - Two area's fluorescent nano probe of near-infrared and its preparation and application based on black phosphorus - Google Patents
Two area's fluorescent nano probe of near-infrared and its preparation and application based on black phosphorus Download PDFInfo
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Abstract
The present invention relates to a kind of two area's fluorescent nano probe of near-infrared and its preparation method and application based on black phosphorus, preparation method includes the following steps: ball milling 1-200h after red phosphorus or black phosphorus and ball milling body are mixed, then hydrophobic ligand is added thereto, continue ball milling 1-200h, obtains the black phosphorus nano particle of surface modification hydrophobic ligand；It is in mass ratio that 1:100-200 is dissolved in volatile organic solvent by the black phosphorus nano particle of the surface modification hydrophobic ligand and amphipathic molecule, then volatilization removes organic solvent, it is vigorously stirred after obtained substance is mixed with water, obtains water-soluble two area's fluorescent nano probe of near-infrared based on black phosphorus.Two area's fluorescent nano probe of near-infrared that the preparation method obtains has relatively strong and wider fluorescence signal, and multi-wavelength excitation and multi-wavelength emission may be implemented, have broad application prospects in terms of bio-imaging.
Description
Technical field
The present invention relates to field of biomedicine more particularly to a kind of two area's fluorescent nano probe of near-infrared based on black phosphorus and
It is prepared and application.
Background technique
Black phosphorus has unique light as a kind of emerging two-dimensional semiconductor material, single layer or several layers of nanostructure
Electrical property (high carrier mobility, tunable band gap, high switch rate) and photo-thermal effect, in photoelectricity, energy reserves and biology doctor
Prescription face has attracted extensive concern.In biomedical aspect, a kind of basic element due to phosphorus as living organism and function,
Black phosphorus and its catabolite are considered to have excellent biocompatibility.But black phosphorus nanostructure is easy to and water and oxygen
It acts on and degrades, to influence its electrical and optical properties and application performance.Therefore how to pass through surface modification, improve its optics
Have become the hot spot of research with electrical properties and its application performance.The method of surface modification has physics cladding (as used at present
PLGA (polylactic-co-glycolic acid) coats black phosphorus quantum dot), covalent bonding is (such as by fluorescent dye covalent coupling in black phosphorus nanometer
Piece surface), coordination bonding (as being coordinated by the phosphorus atoms on organic metal titanium and black phosphorus surface).These methods are to a certain extent
Improve the stability of black phosphorus.Application No. is 201510968976.2 Chinese patent disclose it is a kind of with biocompatibility
Black phosphorus nano particle and its preparation method and application is modified black phosphorus nano particle using water-soluble biocompatiblity molecules, is obtained
To the nano particle for being used directly for biomedical applications (such as photoacoustic imaging, photo-thermal therapy, optical dynamic therapy).However,
Due to modifying nano particle using water-soluble biocompatiblity molecules, hydrone and oxygen easily with black phosphorus nano grain surface
Phosphorus atoms react, influence its physicochemical properties and service performance.
The tunable band gap of black phosphorus nanostructure determines it with adjustable luminosity.Since its luminosity is by surrounding
Environment (such as hydrone, oxygen) influences, and the photoluminescent property research in relation to black phosphorus nanoparticles solution is relatively fewer, especially there is no it
Report of the two area's photoluminescent property of near-infrared in field of biomedicine.Compared to one area's fluorescence of visible light and near-infrared, near-infrared two
The features such as area's fluorescence tissue penetration depths with higher, higher signal-to-noise ratio, lower tissue scatter, so that 2nd area of near-infrared
The sensitivity of imaging and contrast are all higher, have huge application potential on diagnostic imaging.
Summary of the invention
In order to solve the above technical problems, the object of the present invention is to provide a kind of two area's fluorescence nano of near-infrared based on black phosphorus
Probe and its preparation and application.Probe preparation method of the invention has easy to operate, easy to spread, the high feature of yield, should
Two area's fluorescent nano probe of near-infrared that method is prepared has relatively strong and wider fluorescence signal, and multi-wavelength may be implemented and swash
Hair and multi-wavelength emission, have broad application prospects in terms of bio-imaging.
The preparation side of the first purpose of the invention is to provide a kind of two area's fluorescent nano probe of near-infrared based on black phosphorus
Method, comprising the following steps:
(1) ball milling 1-200h (preferably 10-20h) after mixing red phosphorus or black phosphorus and ball milling body, is then added thereto
Hydrophobic ligand continues ball milling 1-200h (preferably 10-60h), obtains the black phosphorus nano particle of surface modification hydrophobic ligand；Institute
The mass ratio for stating red phosphorus or black phosphorus and ball milling body is 1:1-500 (preferably 1:100-300)；Red phosphorus or black phosphorus and the hydrophobicity
The mass ratio of ligand is 1:1-20；
(2) the black phosphorus nano particle of the surface modification hydrophobic ligand is dissolved in amphipathic molecule volatile organic molten
Agent, then volatilization removes organic solvent, obtained substance and will be vigorously stirred, and obtain water-soluble based on black phosphorus after water mixing
Two area's fluorescent nano probe of near-infrared.
Further, in step (1), the hydrophobic ligand is chain alkyl amine, long-chain alkyl alcohol, cyclic aromatic
One or more of the amine of class, the alcohol of the cyclic aromatic same clan, cholesterol, stigmasterol and derivative of the above substance.
Preferably, hydrophobic ligand is oleyl amine or cholesterol.
In step (1), hydrophobic ligand is made by the phosphate radical or phosphorus atoms chemistry on its functional group and black phosphorus surface
With.The present invention regulates and controls its two area's photoluminescent property of near-infrared by changing the surface modification ligand of black phosphorus nano particle, makes its tool
There is stronger two area's fluorescence of near-infrared.
Further, the ball milling body is ball milling pearl, and the partial size of the ball milling pearl is 0.3-50mm, rotational speed of ball-mill 500-
2000r/min。
Further, further comprising the steps of after hydrophobic ligand ball milling 1-200h is added in step (1):
By obtained product ultrasonic disperse in a dispersion medium, precipitating is added in Xiang Suoshu supernatant in centrifuging and taking supernatant
Then sediment is collected in agent, obtain the black phosphorus nano particle of the surface modification hydrophobic ligand.
Further, centrifugal rotational speed is 500~5000r/min.
Further, the decentralized medium is one of tetrahydrofuran, chloroform, hexamethylene, normal heptane and toluene or several
Kind.
Further, the precipitating reagent is methanol, ethyl alcohol, propyl alcohol, isopropanol, butanol, isobutanol, ether, acetone.
Further, in step (2), the amphipathic molecule is liposome, the phosphatide of Pegylation, poly- second two
One or more of alcohol-polylactic acid and polyethylene glycol-polycaprolactone copolymer.
Further, the mass ratio of the red phosphorus in step (1) or black phosphorus and the amphipathic molecule in step (2) is 1:100-
200。
It further, further include being centrifuged off insoluble matter after obtained substance and water are mixed, then in step (2)
The step of dialysis removal amphipathic molecule and freeze-drying.Obtained after freeze-drying can two area's fluorescence of near-infrared of long term storage receive
Rice probe powder.
Further, centrifugal rotational speed 500-5000r/min, the molecular cut off of bag filter are 8000-100,000Da.
A second object of the present invention is to provide it is a kind of using prepared by above-mentioned preparation method based on the near-infrared of black phosphorus
Two area's fluorescent nano probes, including black phosphorus nano particle, the black phosphorus nano grain surface is modified with hydrophobic ligand, described to dredge
Aqueous ligand surface is enclosed with amphipathic molecule, and the partial size of two area's fluorescent nano probe of near-infrared based on black phosphorus is 50-
200nm, excitation wavelength 800-1000nm, launch wavelength 900-1700nm.
Third object of the present invention is that claimed two area's fluorescent nano probe of near-infrared based on black phosphorus is close in preparation
Application in infrared 2nd areas fluorescence imaging preparation.
Multi-wavelength excitation may be implemented in two area's fluorescent nano probe of near-infrared of the invention, and wide wavelength transmitting is realized close red
Outer 2nd area fluorescence imaging.
Two area's fluorescent nano probe of near-infrared of the invention can realize the living body fluorescent imaging in 2nd area of near-infrared, can pass through
Oral or intravenous mode is transported in animal body, then under laser irradiation, the clear each internal organs and group for showing animal
It knits, anatomical structure feature, while the physiology mistake such as circulation, distribution, the metabolism of observation probe in vivo under laser irradiation can be used in
Journey.
According to the above aspect of the present invention, the present invention has at least the following advantages:
Near-infrared two area's fluorescent nano probe provided by the invention based on black phosphorus and between surface ligand have it is very strong
Interaction makes it have good lipophilicity, recycles amphipathic molecule to be coated on their surfaces, obtains a kind of chemical stabilization
Property and the higher nano-probe based on black phosphorus of biocompatibility.Two area's fluorescence nano of near-infrared based on black phosphorus of the invention is visited
Needle can be used for preparing two area's fluorescence imaging preparation of near-infrared, realize that bio-imaging can clearly show animal under laser irradiation
Each organs and tissues, the physiology courses such as circulation, distribution, the metabolism of anatomical structure feature and probe in vivo.
Probe preparation method of the invention has easy to operate, easy to spread, the high feature of yield.This method is prepared
Two area's fluorescent nano probe of near-infrared there is relatively strong and wider fluorescence signal, multi-wavelength excitation and multi-wavelength hair may be implemented
It penetrates, has broad application prospects in terms of bio-imaging.
The above description is only an overview of the technical scheme of the present invention, in order to better understand the technical means of the present invention,
And can be implemented in accordance with the contents of the specification, the following is a detailed description of the preferred embodiments of the present invention and the accompanying drawings.
Detailed description of the invention
Fig. 1 is the X-ray diffracting spectrum of raw material red phosphorus and product black phosphorus in the embodiment of the present invention 1；
Fig. 2 is that surface modification has the black phosphorus nano particle of oleyl amine (OM) in tetrahydrofuran solution in the embodiment of the present invention 2
Grain size distribution；
Fig. 3 is the transmission electron microscope picture for the black phosphorus nano particle that surface modification has oleyl amine (OM) in the embodiment of the present invention 2；
Fig. 4 is that surface modification has chloroform/tetrahydrofuran of the black phosphorus nano particle of oleyl amine (OM) molten in the embodiment of the present invention 2
The fluorescence spectra in liquid 2nd area of near-infrared under 808nm laser irradiation；
Fig. 5 is the hydration grain size distribution of the BP-OM@lipid-PEG nano particle prepared in the embodiment of the present invention 3；
Fig. 6 is the transmission electron microscope picture of the BP-OM@lipid-PEG nano particle prepared in the embodiment of the present invention 3；
Fig. 7 is close under 808nm laser irradiation for the BP-OM@lipid-PEG nano particle prepared in the embodiment of the present invention 3
The fluorescence spectra in infrared 2nd area；
Fig. 8 is that surface modification has the black phosphorus nano particle of cholesterol (Chol) molten in tetrahydrofuran in the embodiment of the present invention 4
Grain size distribution in liquid；
Fig. 9 is the transmission electron microscope picture for the black phosphorus nano particle that surface modification has cholesterol (Chol) in the embodiment of the present invention 4；
Figure 10 is the chloroform/tetrahydro for the black phosphorus nano particle that surface modification has cholesterol (Chol) in the embodiment of the present invention 4
The fluorescence spectra in tetrahydrofuran solution 2nd area of near-infrared under 808nm laser irradiation；
Figure 11 is the hydration grain size distribution of the BP-Chol@lipid-PEG nano particle prepared in the embodiment of the present invention 5；
Figure 12 is the transmission electron microscope picture of the BP-Chol@lipid-PEG nano particle prepared in the embodiment of the present invention 5；
Figure 13 be in the embodiment of the present invention 5 the BP-Chol@lipid-PEG nano particle for preparing under 808nm laser irradiation
The fluorescence spectra in 2nd area of near-infrared；
Figure 14 is to use 808nm the and 980nm laser of equal-wattage density to BP-Chol@in the embodiment of the present invention 5
Lipid-PEG nano particle is irradiated the collected two area's fluorescence spectrum of near-infrared of institute；
Figure 15 is using the BP-Chol@lipid-PEG nano particle prepared in embodiment 5 as two region probe of near-infrared,
It is injected into nude mouse by tail vein, carries out two area's imaging results of near-infrared of back blood vessel；
Figure 16 is in the embodiment of the present invention 7 after Mouse oral BP-Chol lipid-PEG nano particle, and different time points are adopted
Two area's image of gastrointestinal tract near-infrared of collection.
Specific embodiment
With reference to the accompanying drawings and examples, specific embodiments of the present invention will be described in further detail.Implement below
Example is not intended to limit the scope of the invention for illustrating the present invention.
Embodiment 1
It weighs 1.00g red phosphorus to be put into 100mL stainless steel jar mill, the stainless shot (quality of red phosphorus and ball milling pearl is added
Than being sealed for 1:150), ball grinder is fixed in ball mill, then with the revolving speed ball milling 96h of 500r/min, black phosphorus is obtained and receives
Rice grain powder.The X-ray diffracting spectrum (XRD) of raw material red phosphorus (RP) and product black phosphorus (BP) are shown in Fig. 1.
Embodiment 2
4g oleyl amine (molecular weight=267Da) is added in the black phosphorus powder of nanometric particles prepared to embodiment 1, continues ball milling
72h.Products therefrom is scattered in tetrahydrofuran, is centrifuged with the revolving speed of 1000r/min, removes precipitating.Ethanol in proper amount is added as heavy
Shallow lake agent makes black phosphorus-oleyl amine (BP-OM) nanoparticle aggregate form insoluble matter, is then centrifuged 5min with the revolving speed of 5000r/min, receives
Collect precipitating to redissolve in tetrahydrofuran.Acquired solution is centrifuged again with the revolving speed of 1000r/min, takes supernatant, i.e., BP-OM after purification
Nano particle.Fig. 2 is grain size distribution of the BP-OM nano particle in tetrahydrofuran, average grain diameter 21nm.Fig. 3 is BP-
The transmission electron microscope picture of OM, statistical average partial size are 14nm.
By BP-OM nanoparticles solution chloroform made above or tetrahydrofuran, taking concentration is 50 μ g/mLBP-OM
600 μ L of chloroform or tetrahydrofuran solution, is respectively placed in quartzy four-way micro-example pond, using 808nm laser irradiation, uses
900nm optical filter records their emission spectrum respectively in Fluorescence Spectrometer.Fig. 4 is BP-OM nano particle in chloroform
(CHCl3) and tetrahydrofuran (THF) solution in emission spectrum.
Embodiment 3
Embodiment is dispersed by 50mg phosphatide-polyethylene glycol (lipid-PEG) molecule (PEG chain segment molecular weight is 2000Da)
The tetrahydrofuran solution of the BP-OM nano particle of 2 preparations is added ultrapure water and carries out at room temperature after tetrahydrofuran volatilizees completely
It is vigorously stirred, mixing time 1min.Then 10min is centrifuged with the revolving speed of 3000r/min, insoluble matter is removed, by gained supernatant
Liquid dialysis removes extra lipid-PEG, and the molecular cut off of bag filter is 8000-100,000Da.Obtaining after freeze-drying can
The black phosphorus powder of nanometric particles of the bis- modifications of the OM and lipid-PEG of long term storage, is named as lipid-PEG nanometers of BP-OM@
Particle.Fig. 5 is the hydration grain size distribution of BP-OM lipid-PEG nano particle aqueous solution, and averagely hydration partial size is
120nm.Fig. 6 is the transmission electron microscope picture of BP-OM@lipid-PEG nano particle, and the average grain diameter of statistics is 70nm.
The 600 μ L of aqueous solution of 50 μ g/mLBP-OM@lipid-PEG nano particles is taken to be placed in quartzy four-way micro-example pond
In, using 808nm laser irradiation, its emission spectrum is measured in Fluorescence Spectrometer using 900nm optical filter.Fig. 7 is BP-OM@
The emission spectrum of the aqueous solution of lipid-PEG nano particle.
Embodiment 4
4g cholesterol (molecular weight=387Da) is added in the black phosphorus powder of nanometric particles prepared to embodiment 1, continues ball milling
72h.Products therefrom is scattered in tetrahydrofuran, is centrifuged with the revolving speed of 1000r/min, removes precipitating.Ethanol in proper amount is added as heavy
Shallow lake agent makes black phosphorus-cholesterol (BP-Chol) nanoparticle aggregate form insoluble matter, is then centrifuged with the revolving speed of 5000r/min
5min collects precipitating and redissolves in tetrahydrofuran.Acquired solution is centrifuged again with the revolving speed of 1000r/min, and supernatant liquor is purified
After obtain BP-Chol nano particle.Fig. 8 is grain size distribution of the BP-Chol nano particle in tetrahydrofuran, average grain diameter
For 14nm.Fig. 9 is the transmission electron microscope picture of BP-Chol nano particle, and statistical average partial size is 20nm.
By BP-Chol nanoparticles solution chloroform made above or tetrahydrofuran, taking concentration is 50 μ g/mLBP-
The chloroform or tetrahydrofuran solution of Chol nano particle are respectively placed in quartzy four-way micro-example pond, using 808nm laser
Irradiation, measures its emission spectrum using 900nm optical filter in Fluorescence Spectrometer.Figure 10 is the chloroformic solution of BP-Chol
(CHCl3) and tetrahydrofuran (THF) solution emission spectrum.
Embodiment 5
Embodiment is dispersed by 50mg phosphatide-polyethylene glycol (lipid-PEG) molecule (PEG chain segment molecular weight is 2000Da)
4 preparation BP-Chol nano particles tetrahydrofuran solution, at room temperature after tetrahydrofuran volatilize completely, addition ultrapure water into
Row is vigorously stirred, mixing time 1min.Then 10min is centrifuged with the revolving speed of 3000r/min, removes insoluble matter, it will be on gained
Clear liquid dialysis is through removing extra lipid-PEG.Obtained after freeze-drying can long term storage the bis- modifications of Chol and lipid-PEG
Black phosphorus powder of nanometric particles, be named as BP-Chol@lipid-PEG nano particle.Figure 11 is BP-Chol@lipid-
The hydration grain size distribution of PEG nano particle, average grain diameter 106nm.Figure 12 is BP-Chol@lipid-PEG nano particle
Transmission electron microscope picture, statistical average partial size be 97nm.
The 600 μ L of aqueous solution of 50 μ g/mLBP-Chol@lipid-PEG nano particles is taken to be placed in quartzy four-way micro-example
Chi Zhong records its emission spectrum using 900nm optical filter using 808nm laser irradiation in Fluorescence Spectrometer.Figure 13 is BP-
The emission spectrum of Chol@lipid-PEG nano particle aqueous solution.
In addition, it is micro to take the 600 μ L of aqueous solution of 1mg/mLBP-Chol@lipid-PEG nano particle to be placed in quartzy four-way
In sample cell, the 808nm laser and 980nm laser that equal-wattage density is respectively adopted are irradiated it.900nm is used respectively
Optical filter and 930nm optical filter record its emission spectrum in Fluorescence Spectrometer.Figure 14 is BP-Chol@lipid-PEG nanometers
The emission spectrum of grain aqueous solution.
Embodiment 6
The BP-Chol@lipid-PEG nano particle aqueous solution (1.3mg/mL) that embodiment 5 is obtained is through tail vein injection
Mode be transported in nude mouse, adopted using two area's imager of toy near-infrared (808nm laser irradiation, 1400nm optical filter)
Collect two area's fluorescence imaging signal of near-infrared of its back blood vessel.From Figure 15 (ScaleBar=5mm) as can be seen that black phosphorus nanometer
Grain has good two area's fluorescence imaging effect of near-infrared, may be used as two area's fluorescence imaging probe of near-infrared.
Embodiment 7
The BP-Chol@lipid-PEG nano particle aqueous solution (2mg/mL) that embodiment 5 is obtained is by the way of oral
It injects in nude mouse, and under two area's imager of toy near-infrared (808nm laser irradiation, 1250nm optical filter), observes naked
The abdomen imaging signal of mouse, observation time 30min.Figure 16 a, b, c are respectively 30 seconds, 5min, 30min time interval acquire
Two area's image of near-infrared of gastrointestinal tract, the image clearly show the structure letter of the Stomach duodenum of nude mice, small intestine and large intestine
Breath.
The above is only a preferred embodiment of the present invention, it is not intended to restrict the invention, it is noted that for this skill
For the those of ordinary skill in art field, without departing from the technical principles of the invention, can also make it is several improvement and
Modification, these improvements and modifications also should be regarded as protection scope of the present invention.
Claims (10)
1. a kind of preparation method of two area's fluorescent nano probe of near-infrared based on black phosphorus, which comprises the following steps:
(1) ball milling 1-200h after mixing red phosphorus or black phosphorus and ball milling body, is then added hydrophobic ligand thereto, continues ball milling
1-200h obtains the black phosphorus nano particle of surface modification hydrophobic ligand；The mass ratio of the red phosphorus or black phosphorus and ball milling body is 1:
1-500；The mass ratio of red phosphorus or black phosphorus and the hydrophobic ligand is 1:1-20；
(2) the black phosphorus nano particle of the surface modification hydrophobic ligand and amphipathic molecule are dissolved in organic solvent, then removed
Organic solvent mixes obtained substance and water, obtains two area's fluorescent nano probe of near-infrared based on black phosphorus.
2. preparation method according to claim 1, it is characterised in that: in step (1), the hydrophobic ligand is long-chain
Alkylamine, long-chain alkyl alcohol, the amine of the cyclic aromatic same clan, the alcohol of the cyclic aromatic same clan, cholesterol, stigmasterol and the above substance
One or more of derivative.
3. preparation method according to claim 1, it is characterised in that: the ball milling body is ball milling pearl, the ball milling pearl
Partial size is 0.3-50mm, rotational speed of ball-mill 500-200r/min.
4. preparation method according to claim 1, which is characterized in that in step (1), hydrophobic ligand ball milling 1- is added
It is further comprising the steps of after 200h:
Obtained product and decentralized medium are mixed, centrifuging and taking supernatant, precipitating reagent is added in Xiang Suoshu supernatant, then collects
Sediment obtains the black phosphorus nano particle of the surface modification hydrophobic ligand.
5. the preparation method according to claim 4, it is characterised in that: the decentralized medium is tetrahydrofuran, chloroform, hexamethylene
One or more of alkane, normal heptane and toluene.
6. preparation method according to claim 1, it is characterised in that: in step (2), the amphipathic molecule is lipid
One or more of body, the phosphatide of Pegylation, polyethylene glycol-polylactic acid and polyethylene glycol-polycaprolactone copolymer.
7. preparation method according to claim 1, it is characterised in that: in the red phosphorus or black phosphorus and step (2) in step (1)
Amphipathic molecule mass ratio be 1:100-200.
8. preparation method according to claim 1, it is characterised in that: in step (2), obtained substance and water are mixed
After further include being centrifuged off insoluble matter, then dialysis removal amphipathic molecule and freeze-drying the step of.
9. two area's fluorescence of near-infrared prepared by a kind of preparation method of any of claims 1-8 based on black phosphorus is received
Rice probe, it is characterised in that: including black phosphorus nano particle, the black phosphorus nano grain surface is modified with hydrophobic ligand, described
Hydrophobic ligand is coated with amphipathic molecule, and the partial size of two area's fluorescent nano probe of near-infrared based on black phosphorus is
50-200nm, excitation wavelength 800-1000nm, launch wavelength 900-1700nm.
10. near-infrared two area's fluorescent nano probe as claimed in claim 9 based on black phosphorus prepare two area's fluorescence of near-infrared at
As the application in preparation.
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