CN114671897A - Preparation method of size-separated double-layer-like gold nano-vesicles - Google Patents
Preparation method of size-separated double-layer-like gold nano-vesicles Download PDFInfo
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- CN114671897A CN114671897A CN202210396548.7A CN202210396548A CN114671897A CN 114671897 A CN114671897 A CN 114671897A CN 202210396548 A CN202210396548 A CN 202210396548A CN 114671897 A CN114671897 A CN 114671897A
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 title claims abstract description 90
- 239000010931 gold Substances 0.000 title claims abstract description 89
- 229910052737 gold Inorganic materials 0.000 title claims abstract description 89
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000002105 nanoparticle Substances 0.000 claims abstract description 58
- 238000004416 surface enhanced Raman spectroscopy Methods 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 19
- 239000003446 ligand Substances 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 19
- -1 perfluorobiphenyl diphenol Chemical compound 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 239000006228 supernatant Substances 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000005119 centrifugation Methods 0.000 claims description 3
- 238000012377 drug delivery Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000003384 small molecules Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 abstract description 9
- 238000010168 coupling process Methods 0.000 abstract description 9
- 238000005859 coupling reaction Methods 0.000 abstract description 9
- 238000000926 separation method Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003745 diagnosis Methods 0.000 abstract description 4
- 239000002356 single layer Substances 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 238000001338 self-assembly Methods 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- ODAJDDMWMREWGL-UHFFFAOYSA-N 2,3,4,5,6,7,8-heptafluoronaphthalen-1-ol Chemical compound FC1=C(F)C(F)=C2C(O)=C(F)C(F)=C(F)C2=C1F ODAJDDMWMREWGL-UHFFFAOYSA-N 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- 229920000469 amphiphilic block copolymer Polymers 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000001000 micrograph Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002343 gold Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
- A61K9/1273—Polymersomes; Liposomes with polymerisable or polymerised bilayer-forming substances
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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Abstract
The invention belongs to the field of material synthesis, and relates to a preparation method of size-separated double-layer-like gold nano vesicles. Compared with single-layer gold nano vesicles formed by single gold nanoparticles, the gold nano vesicles have stronger plasma coupling characteristic, ultraviolet absorption shows larger red shift, and the size separation and double-layer-like gold nano vesicles have potential application prospects in the aspects of SERS sensing platforms and biological diagnosis and treatment.
Description
Technical Field
The invention belongs to the field of material synthesis, and particularly relates to a simple method for preparing size-separated bilayer-like vesicles by modifying gold nanoparticles with two different sizes by using an oligoethylene glycol perfluorobiphenyl diphenol organic micromolecule ligand.
Background
The information in this background section is only for enhancement of understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art that is already known to a person of ordinary skill in the art.
The gold nanoparticle self-assembly has special plasma coupling characteristic and has wide application value in the aspects of biosensing, medical diagnosis and the like. Compared with the self-assembly of gold nanoparticles with single size, the binary mixed system has unique advantages in preparing the self-assembly body with ordered and complex structure. The two-dimensional or three-dimensional structure formed by modifying gold nanoparticles by using micromolecules or amphiphilic block copolymers through drying is widely reported, and the reports of binary component self-assembly in solution are less.
The binary components in the solution can be controllably self-assembled to simplify the potential application of the solution, and the method has important research value. At present, after different gold nanoparticles are respectively modified by one or two different block copolymers, a self-assembly body with separated size is prepared instead of a bilayer-like gold nano vesicle by performing self-assembly through repeated centrifugal purification and dialysis in water. Theoretically, the size-separated self-assembly formed by the gold nanoparticles modified by the block copolymer has certain application limitation: (1) the template self-assembly is usually adopted, and the plasma coupling characteristic of gold nanoparticles embedded in the template self-assembly is weakened; (2) the chain length of the block copolymer is small, the molecules are long, the internal space of the vesicle is small, and the effective load space in the vesicle is reduced; (3) at present, gold nanoparticles modified by amphiphilic block copolymers are difficult to form a quasi-double-layer gold nanoparticle vesicle structure with separated size.
It is also worth noting that although reports have been made on the preparation of gold nanoparticle vesicles from single-size gold nanoparticles modified by small organic molecules, no studies have been reported on the formation of size-separated bilayer-like gold nanoparticle vesicles from two different-size gold nanoparticles.
Disclosure of Invention
In order to overcome the problems, the invention designs a simple method for self-assembling gold nano vesicles with separated sizes and double-layer-like sizes by utilizing an oligoethylene glycol perfluorobiphenyl diphenol organic micromolecule ligand and two gold nano particles with different sizes. The small gold nano-particles form vesicles in the inner part, and the large gold nano-particles are attached to the surface of the small nano-vesicles to form the vesicles. The size separation and double-layer-like gold nano vesicles have stronger plasma coupling and have important significance in the aspects of precision biosensing, biological micro reactors and the like.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
in a first aspect of the invention, a preparation method of size-separated double-layer-like gold nano vesicles is provided, and comprises the following steps:
taking the gold nanoparticles modified by citric acid for centrifugal treatment, and removing supernatant to obtain a gold nanoparticle concentrated solution;
mixing two gold nanoparticle concentrated solutions with different diameters to obtain a mixed solution;
adding the mixed solution into an organic solvent containing an organic micromolecular ligand of oligo-polyethylene glycol perfluorobiphenyl diphenol, oscillating and standing to obtain the compound;
wherein the structural formula of the organic micromolecule ligand containing the oligo-polyethylene glycol perfluorobiphenyl diphenol is as follows:
wherein n is a natural number greater than zero.
The research finds that: the double-layer-like gold nano vesicle prepared by the invention has coupling between gold nano particles with single size and cross coupling between two gold nano particles with different sizes, so that a multiple plasma coupling mode exists, and the unique optical performance is shown. The size separation and double-layer-like gold nano-vesicle has important significance for expanding self-assembly research, preparing an SERS sensing platform and the like.
In a second aspect of the invention, size-separated, bilayer-like gold nanovesicles prepared by the above-described method are provided.
The invention has the beneficial effects that:
(1) the invention can prepare the size-separated double-layer-like gold nano-vesicles, wherein the large gold nano-particles form self-assemblies on the outer sides, and the small gold nano-particles form self-assemblies on the inner sides. Compared with the gold nano vesicles formed by single gold nanoparticles, the double-layer-like gold nano vesicles with the separated sizes have stronger plasma coupling effect and obvious red shift of ultraviolet absorption.
(2) The size-separated double-layer-like gold nano-vesicle prepared by the method fully utilizes local plasma resonance and good biocompatibility of the gold nano-particles, and meanwhile, the drug loading of the hollow vesicle inside can realize the cooperative treatment of tumors.
(3) The preparation method is simple, has strong practicability, and has potential application value in the aspects of drug delivery, medical diagnosis and treatment, catalytic carriers, biosensing, biological microreactors and the like.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a schematic diagram of preparation of size-separated bilayer-like gold nanovesicles;
FIG. 2 is a scanning transmission electron microscope image of a size-separated bilayer-like gold nano-vesicle prepared in example 1 of the present invention;
fig. 3 is an ultraviolet absorption spectrum of size separation type bilayer gold nanovesicles and monolayer gold nanovesicles prepared in example 1 of the present invention.
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.
As introduced by the technical background, the existing gold nanoparticle self-assembly plasma coupling performance is poor, and reports of the gold nanoparticle self-assembly of the novel organic micromolecule modified gold nanoparticles with different sizes into the double-layer-like gold nanoparticle vesicles with separated sizes are not reported. Therefore, the invention provides a preparation method for self-assembling oligo-polyethylene glycol perfluorobiphenyl diphenol organic small molecular ligand and two gold nanoparticles with different sizes into a size-separation bilayer-like gold nano vesicle.
In a first aspect of the invention, a preparation method of size-separated double-layer-like gold nano vesicles is provided, which comprises the following steps:
(1) taking gold nanoparticles (500 mu L) modified by citric acid, and centrifuging in a centrifuge tube;
(2) the supernatant was removed and the two gold nanoparticle concentrates of different sizes were mixed (25. mu.L);
(3) taking an organic solvent (475 mu L) containing the oligo-polyethylene glycol perfluorobiphenyl diphenol organic micromolecule ligand in a glass bottle;
(4) adding the gold nanoparticle concentrated solution in the step (2) into a glass bottle;
(5) quickly oscillating and standing.
In a typical embodiment, the gold nanoparticle concentrates of two different sizes are prepared by the following steps: the centrifugation rotation speed of the gold nanoparticles with the diameter of 5-20nm is 10000-14800rpm, and the centrifugation time is 20-50 min.
In a typical embodiment, the synthesis of the ligand when the ligand n is 1,2,3 can be referred to patent CN 113651739 a.
In a typical embodiment, the solvent is 1, 4-dioxane, tetrahydrofuran, preferably tetrahydrofuran.
In a typical embodiment, the concentration of the oligoethylene glycol perfluorobiphenyl diphenol organic small molecular ligand tetrahydrofuran solution is 0.05mM or 2mM, and double-layer-like gold nano vesicles which are uniform in size and stably dispersed in the solution can be prepared by the oligoethylene glycol perfluorobiphenyl diphenol organic small molecular ligand tetrahydrofuran solution and two kinds of gold nano particles different in size.
In a typical embodiment, the standing time is 30-90min, so that the gold nanoparticles can be better dispersed, and the size-separated double-layer-like gold nanoparticle vesicles with strong plasma resonance coupling performance can be obtained.
The invention provides the application of the size-separated double-layer-like gold nano-vesicle in aspects of drug delivery, biological diagnosis and treatment, catalytic carriers, biological microreactors and the like
The present invention is described in further detail below with reference to specific examples, which should be construed as illustrative rather than restrictive.
Example 1(n ═ 3):
5nm and 15nm citric acid modified gold nanoparticles (colloidal gold, commercially available, manufacturer: BBI solutions) (500. mu.L. times.2) were centrifuged at 14800rpm for 50min and 11500rpm for 30min, respectively. The supernatant was removed, and the concentrated gold nanoparticles were mixed (25. mu.L) and added to a solution of perfluoronaphthol ligand tetrahydrofuran terminated with triethylene glycol (0.05mM, 475. mu.L), rapidly shaken for 1-2s, and allowed to stand for 90 min. The scanning transmission electron microscope image and the ultraviolet absorption contrast image of the monolayer gold nano vesicle formed by the single gold nano particle are respectively shown in fig. 2 and fig. 3;
example 2(n ═ 3):
5nm and 20nm citric acid modified gold nanoparticles (500 μ L × 2) were centrifuged at 14800rpm for 50min and 10000rpm for 20min, respectively. Removing supernatant, mixing concentrated gold nanoparticles (25 μ L), adding perfluoronaphthol ligand tetrahydrofuran solution (0.05mM, 475 μ L) with triethylene glycol at the end, rapidly shaking for 1-2s, and standing for 90 min;
example 3(n ═ 3):
10 nm and 20nm citric acid modified gold nanoparticles (500. mu.L. times.2) were centrifuged at 12000rpm for 30min and 10000rpm for 20min, respectively. Removing supernatant, mixing concentrated gold nanoparticles (25 μ L), adding perfluoronaphthol ligand tetrahydrofuran solution (0.05mM, 475 μ L) with triethylene glycol at the end, rapidly shaking for 1-2s, and standing for 90 min;
example 4(n ═ 2):
5 and 15nm citric acid modified gold nanoparticles (500. mu.L. times.2) were centrifuged at 14800rpm for 50min or 11500rpm for 30min, respectively. Removing supernatant, mixing concentrated gold nanoparticles (25 μ L), adding perfluoronaphthol ligand tetrahydrofuran solution (0.05mM, 475 μ L) with diethylene glycol at the tail end, rapidly shaking for 1-2s, and standing for 90 min;
example 5(n ═ 1):
5nm and 15nm citric acid modified gold nanoparticles (500. mu.L. times.2) were centrifuged at 14800rpm for 50min and 11500rpm for 30min, respectively. Removing supernatant, mixing concentrated gold nanoparticles (25 μ L), adding tetrahydrofuran solution (0.05mM, 475 μ L) of perfluoronaphthol ligand with diethylene glycol at the tail end, rapidly shaking for 1-2s, and standing for 90 min;
as can be seen from FIG. 2, the small gold nanoparticles form vesicles on the inner side, the large nanoparticles are attached to the surface to form a phase-separated self-assembly body, and the size separation occurs, and the hollow vesicle cavity is formed inside, so that the size separation and the bilayer-like vesicle structure are fully proved. As can be seen from FIG. 3, the bilayer-like vesicle generates obvious red shift compared with a monolayer gold nano vesicle formed by single gold nano particles, has stronger plasma coupling, and can be applied to various biochemical detection technical fields, so the invention has great utilization value. Meanwhile, due to the unique cavity structure, the catalyst has important research value in the fields of drug transportation, biological microreactors, catalytic carriers and the like.
It should be noted that the above-mentioned embodiments are only preferred embodiments of the present invention, and the present invention is not limited thereto, and although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications and equivalents can be made in the technical solutions described in the foregoing embodiments, or equivalents thereof. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A preparation method of size-separated double-layer-like gold nano vesicles is characterized by comprising the following steps:
taking the gold nanoparticles modified by citric acid for centrifugal treatment, and removing supernatant to obtain a gold nanoparticle concentrated solution;
mixing two gold nanoparticle concentrated solutions with different diameters to obtain a mixed solution;
adding the mixed solution into an organic solvent containing an organic micromolecular ligand of oligo-polyethylene glycol perfluorobiphenyl diphenol, oscillating and standing to obtain the compound;
wherein the structural formula of the organic micromolecule ligand containing the oligo-polyethylene glycol perfluorobiphenyl diphenol is as follows:
wherein n is a natural number greater than zero.
2. The method for preparing size-separated, bilayer-like gold nanovesicles according to claim 1, wherein the specific conditions of centrifugation are as follows: the rotation speed is 10000-14800rpm, and the time is 20-50 min.
3. The method of preparing size separated, bilayer-like gold nanovesicles of claim 1, wherein the gold nanoparticles have a diameter of 5-20 nm.
4. The method of preparing size-separating, bilayer-like gold nanovesicles of claim 1, wherein the diameters of two different sizes of gold nanoparticles are 5 and 15nm, 5 and 20nm, or 10 and 20nm, respectively.
5. The method for preparing size-separated double-layer-like gold nano vesicles as claimed in claim 1, wherein the oligomeric ethylene glycol-containing perfluorobiphenyl diphenol organic small molecule ligand is DiOFBL, TrOFBL or TeOFBL.
6. The method for preparing size-separated, bilayer-like gold nanovesicles according to claim 1, wherein the concentration of the ligand solution is 0.05 to 2 mM.
7. The method for preparing size-separated, bilayer-like gold nanovesicles according to claim 1, wherein the organic solvent is 1, 4-dioxane or tetrahydrofuran.
8. The method for preparing size-separated, bilayer-like gold nanovesicles according to claim 1, wherein the time of shaking is 1-2 s;
or standing for 30-90 min.
9. A size-separated, bilayer-like gold nanovesicle prepared by the method of any one of claims 1-8.
10. The size separated, bilayer-like gold nanovesicles of claim 9, wherein the bilayer-like gold nanovesicles are used in SERS sensing platforms, drug delivery, biological micro-reactors, or catalytic carriers.
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- 2022-04-15 CN CN202210396548.7A patent/CN114671897A/en active Pending
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| KR20120094872A (en) * | 2011-02-17 | 2012-08-27 | 이화여자대학교 산학협력단 | Producing method of au nanoparticle pattern having localized surface plasmon resonance coupling property, and au nanoparticle pattern by the same |
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| Title |
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| PENG HUANG等: "Biodegradable Gold Nanovesicles with an Ultrastrong Plasmonic Coupling Effect for Photoacoustic Imaging and Photothermal Therapy", 《ANGEW. CHEM. INT. ED. 》, vol. 52, pages 13958 - 13964, XP055349235, DOI: 10.1002/anie.201308986 * |
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