CN105606557B - A kind of gold nanorods/poly- (3,4 dioxoethyl) thiophene nanometer diagnosis and treatment probe and its preparation method and application - Google Patents
A kind of gold nanorods/poly- (3,4 dioxoethyl) thiophene nanometer diagnosis and treatment probe and its preparation method and application Download PDFInfo
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- CN105606557B CN105606557B CN201610082882.XA CN201610082882A CN105606557B CN 105606557 B CN105606557 B CN 105606557B CN 201610082882 A CN201610082882 A CN 201610082882A CN 105606557 B CN105606557 B CN 105606557B
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 title claims abstract description 132
- 239000000523 sample Substances 0.000 title claims abstract description 83
- 238000003745 diagnosis Methods 0.000 title claims abstract description 79
- 238000011282 treatment Methods 0.000 title claims abstract description 79
- NBLHGCDPIWAGAS-UHFFFAOYSA-N 2-ethylthiolane-3,4-dione Chemical compound O=C1C(SCC1=O)CC NBLHGCDPIWAGAS-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 33
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 96
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 229930192474 thiophene Natural products 0.000 claims abstract description 48
- 239000003814 drug Substances 0.000 claims abstract description 41
- 238000003384 imaging method Methods 0.000 claims abstract description 14
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004847 absorption spectroscopy Methods 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000012360 testing method Methods 0.000 claims description 23
- 239000010931 gold Substances 0.000 claims description 20
- 229910052737 gold Inorganic materials 0.000 claims description 20
- 229940079593 drug Drugs 0.000 claims description 17
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 12
- 238000011068 loading method Methods 0.000 claims description 12
- 229910004042 HAuCl4 Inorganic materials 0.000 claims description 11
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 10
- 238000002835 absorbance Methods 0.000 claims description 9
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- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 238000000862 absorption spectrum Methods 0.000 claims description 4
- 239000002105 nanoparticle Substances 0.000 claims description 4
- 235000007164 Oryza sativa Nutrition 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 3
- 230000009514 concussion Effects 0.000 claims description 3
- 235000009566 rice Nutrition 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
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- 238000001514 detection method Methods 0.000 abstract description 12
- 230000000694 effects Effects 0.000 abstract description 10
- 239000000178 monomer Substances 0.000 abstract description 4
- 238000011065 in-situ storage Methods 0.000 abstract description 3
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- 239000003945 anionic surfactant Substances 0.000 abstract description 2
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
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- 229920001817 Agar Polymers 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- -1 Dioxoethyl Chemical group 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- 239000002086 nanomaterial Substances 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical class [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
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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
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/01—Arrangements or apparatus for facilitating the optical investigation
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Abstract
The present invention discloses a kind of gold nanorods/poly- (3,4 dioxoethyls) thiophene nanometer diagnosis and treatment probe and its preparation method and application, in preparation process, by means of the effect of anion surfactant and moderate strength oxidant hydrogen peroxide, make monomer EDOT in gold nanorods in situ Polymerization, obtain gold nanorods/poly- (3,4 dioxoethyl) thiophene nucleocapsid compound that gold nanorods are coated very well by poly- (3,4 dioxoethyl) thiophene.The absworption peak red shift of the compound ultraviolet-visible absorption spectroscopy is to 790nm or so, it is used for diffusing reflection imaging system using the compound as multifunctional nano diagnosis and treatment probe, image with enhancing, simultaneously, this nucleocapsid compound can realize the load and release of medicine, make detection, diagnosis, treatment while carry out, turn into a kind of new multifunctional nano diagnosis and treatment probe, in the great application prospect of biomedical sector.
Description
Technical field
The present invention relates to bio-imaging field.More particularly, to a kind of gold nanorods/poly- (3,4- dioxoethyl) thiophene
Nanometer diagnosis and treatment probe and its preparation method and application.
Background technology
Diffusing reflection (Diffusion Reflection, DR) is a kind of optical diagnostic method, is studied by Israel Fixler
Report first room.It is simple, safe, cheap, by low emittance, has low penetration depth, it is thin can to disclose tissue
Topographical information in born of the same parents.In DR, light source is moved with certain step-length, and it puts with the change of distance (ρ) between detector
The histiocytic intensity of reflected light (Γ) being placed on detector can be detected with the change of this distance.(journal
Of biophotonics, 2012,263-273.) and (International journal of nanomedicine, 2012,
49.) 7,4 have play-by-play.In DR detections, gold nano grain (GNPs) is due to nontoxic, biocompatibility and including big suction
The special optical property such as section and the adjustable scattering nature of visible region is received, makes it as multifunctional nano diagnosis and treatment probe, it is right
Tumour cell and atherosclerosis have high sensitivity (Journal of biomedical optics, 2013,18,
061226-061226 and Nano letters, 2014,14,2681-2687), gold of the gold nanorods (GNRs) as special construction
Nano material, due to its surface enhanced effect (SPR), there is stronger absorption and scattering property in visible and near infrared region,
It is more preferable as optics multifunctional nano diagnosis and treatment probe selectivity, sensitivity in DR imaging methods, more particularly paid close attention to.
But either gold nano grain (GNPs), or gold nanorods (GNRs) are easy to reunite, influence imaging effect due to high surface energy
Fruit is, it is necessary to carry out suitable surface modification, to prevent its reunion, due to cyano group (- CN), sulfydryl (- SH), amido (- NH2) and gold
There is aggregation strong, therefore that there is the protectiveness polymer of these functional groups to be commonly used to suppress gold nano grain
(Technol.-Mat.Sci.Edit., 2014,29,180-184.), but these modifications do not enable the SPR performances of gold increase
By force.Therefore, the compound of the gold nanorods (GNRs) and organic or inorganic material of appropriate surfaces modification is prepared, is on the one hand suppressed
(GNRs) aggregation, on the one hand it is enhanced its SPR performance, it is excellent in terms of selectivity and sensitivity in being detected applied to DR
In GNRs, still with extremely challenging.
Poly- (3,4- dioxoethyl) thiophene (PEDOT) tool one kind has promising conducting polymer very much, and it has high
Electrical conductivity, narrow band gap width, excellent environmental stability, good biocompatibility, wide visible, near-infrared (NIR) absorb
And scattering property, be reported and be applied in many fields such as electrochromism, antistatic, microwave absorption, however, biology into
As field, document and patent report there is no.
The content of the invention
First purpose of the present invention is to provide a kind of gold nanorods/poly- (3,4- dioxoethyls) thiophene multifunctional nano
Diagnosis and treatment probe, this nanometer of diagnosis and treatment probe is gold nanorods/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound, and the compound is with gold
Nanometer rods are core, and poly- (3,4- dioxoethyl) thiophene is shell, have excellent surface enhanced effect, and gold nano in the compound
It rod good dispersion, will not assemble, be coated well by poly- (3,4- dioxoethyl) thiophene；And this nanometer of diagnosis and treatment probe helps to make
The characteristics of detection, diagnosis, treatment are carried out simultaneously.
Second object of the present invention is that providing a kind of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment visits
The preparation method of pin, the preparation method is simply controllable, not only inhibits the aggregation of gold nanorods but also enhances its surface enhanced
Performance.
Third object of the present invention is that providing a kind of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment visits
Application of the pin in diffusing reflection imaging, this nanometer of diagnosis and treatment probe is used in the diffusing reflection detection of diffusing reflection imaging system, had
Excellent surface enhanced effect and the image of enhancing, imaging effect are good.
Fourth object of the present invention is that providing a kind of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment visits
Application of the pin in drug loading and release.
To reach above-mentioned first purpose, the present invention uses following technical proposals：
A kind of gold nanorods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, the nanometer diagnosis and treatment probe are Jenner
Rice rod/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound；The draw ratio of gold nanorods is 3 in the nucleocapsid compound:1-5:
1, gold nanorods length 30nm~50nm；A diameter of 80~300nm of the nucleocapsid compound.
Preferably, the ultraviolet-visible absorption spectroscopy of the gold nanorods/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound
To have a wide absworption peak in 500nm~540nm, maximum absorption band between 760~800nm be present.
Further, the core of the gold nanorods/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound is gold nanorods, shell
For poly- (3,4- dioxoethyls) thiophene.
To reach above-mentioned second purpose, the present invention uses following technical proposals：
The preparation method of a kind of gold nanorods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, comprises the following steps：
1) preparation of gold nanorods：A. by HAuCl4NaBH is added after being mixed and stirred for CTAB4, form mixed solution；
After mixed solution is stirred into 10min, then more than 1h is placed, as seed-solution；
B. by HAuCl4Mixed with CTAB, add AgNO3, add ascorbic acid so that and solution turned clear, then to gained
Above-mentioned seed-solution is added in limpid solution, after mixed solution places 24h, centrifuges, obtains gold nanorods；
2) preparation of gold nanorods/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound：To EDOT and SDS mixed solution
Gold nanorods obtained by middle addition step 1), after stirring 5min, add H2O2, 8~16h of stirring reaction, is centrifuged at 60 DEG C
Separation, with volume ratio 1:1 water/ethanol is washed 3 times, obtains precipitum；24h is dried in vacuo at 50 DEG C of precipitum, obtains gold nano
The gold nanorods that rod is coated very well by poly- (3,4- dioxoethyl) thiophene/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound, its
In, EDOT, SDS, H2O2, the mol ratio between gold nanorods be 1:0.5:2.5:0.002~1:1.5:7.5:0.008.
Preferably, in step 1) a, in the mixed solution, HAuCl4Concentration be 2.2 × 10-4~2.4 × 10-4M,
CTAB concentration is 9.0 × 10-2~10-1M, NaBH4Concentration be 5.0 × 10-4~6.0 × 10-4M。
Preferably, in step 1) b, in the limpid solution of gained, HAuCl4Concentration be 2 × 10-4~5 × 10-4M、CTAB
Concentration be 8.0 × 10-2~1.0 × 10-1M、AgNO3Concentration be 1.0 × 10-4~2.0 × 10-4M, the concentration of ascorbic acid
For 5.0 × 10-5~7.0 × 10-5M；The volume ratio of the limpid solution of gained and seed-solution is 800:1~1000:1.
Further, the preparation method of seed-solution is bibliography Chemistry of Materials in step 1),
The improvement that seed mediated growth method is carried out in 2003,15,1957-1962., the seed mediated growth method after improvement overcome bibliography method
It is difficult to the deficiency for controlling golden rod Size Distribution very well, gained gold rod size distribution is evenly and golden rod draw ratio is bigger.
Further, in the preparation of compound of the present invention, aoxidized by means of anion surfactant and moderate strength
The effect of agent hydrogen peroxide, monomer EDOT is set to obtain gold nanorods by poly- (3,4- dioxy second in gold nanorods in situ Polymerization
Base) gold nanorods/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound for coating very well of thiophene.
To reach above-mentioned 3rd purpose, the present invention uses following technical proposals：
A kind of application of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe in diffusing reflection imaging.
Preferably, the application refers to be used to overflow by gold nanorods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe
Reflection detection.
It is highly preferred that described examine gold nanorods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe for diffusing reflection
The method of survey is：Solid bodies mould is made, incident light, detection solid bodies mould are used as using the laser that wavelength is respectively 650nm and 780nm
Surface diffusing reflection light intensity Γ (ρ) is with light source and the change of body mould distance (ρ).Its slope size shows a nanometer diagnosis and treatment probe imaging effect
Fruit, slope is bigger, is more advantageous to be imaged.
Further, the making of the solid bodies mould (solid phantoms) includes the making of basic mode and tests original mold
Make；The making of the basic mode refers to：By 10% intralipid, 3% india ink, remaining 87% volume distilled water
Mix, then 1.2g/100mL agarose powder is added into mixed liquor, after being mixed evenly, cooled down in vacuum and solid
Change；The making of the test original mold refers to：By 10% intralipid, 3% india ink, remaining 87% volume, which contains, to be received
The solution of rice diagnosis and treatment probe nano particle is mixed, then 1.2g/100mL agarose powder is added into mixed liquor, is mixed
After uniformly, cool down and solidify in vacuum.
Further, the intralipid is commercially available that specifications and models are：Lipfundin MCT/LCT
20%, B.Braun Melsungen AG, Germany；The india ink is commercially available, mass concentration 0.1%；The agar
Icing Sugar end is commercially available, purchased from SeaKem LE Agarose, Lonza, USA.
Preferably, the detection solid bodies mould surface light intensity refers to document with light source and the change of body mould distance, method
" journal of biophotonics, 2012,263-273. " and " International journal of
nanomedicine,2012,7,449.”
In the present invention, intralipid is to be used for scattering process, and india ink has absorption.
To reach above-mentioned 4th purpose, the present invention uses following technical proposals：
A kind of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe answering in drug loading and release
With.
Preferably, the application process in drug loading and release is：Compound concentration is different dense 3-20 μ g/mL's
The ethanol solution of the tested medicine of degree, tests its ultra-violet absorption spectrum, using the absorbance at absworption peak as ordinate, is tested medicine
Concentration value be abscissa, establish standard curve；Gold nanorods/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound is dispersed in
In the ethanol solution of tested medicine, shaking table concussion 24h, after centrifugation, then through being tested drug solution washing 4 times, make unsupported
Tested medicine on to gold nanorods/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound all elutes, and tests eluent
Absorbance, contrasted with standard curve, obtain the medicament contg of unsupported residual in the solution, and then draw the load medicine of sample
Amount.
Preferably, by the way of Spontaneous release, gold nanorods/poly- (3,4- dioxoethyl) thiophene core of medicine will be loaded with
Shell compound is put into the bag filter that molecular cut off is 10000Da, is sunk in dissolution medium ethanol and is stirred, different time interval
Dissolution medium is taken, tests its absorbance, so as to draw release amount of medicine.
The present invention arrives the absorbability of infrared (IR) by poly- (3,4- dioxoethyls) thiophene wide visible, near-infrared (NIR)
Energy and biocompatibility, with reference to the surface enhanced characteristic of gold nanorods, in gold nanorods in situ Polymerization, obtain gold nano
The gold nanorods that rod is coated very well by poly- (3,4- dioxoethyl) thiophene/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound, should
Compound enhances the surface enhanced performance of gold nanorods, and the compound is solid bodies mould as nanometer diagnosis and treatment probe manufacturing
(solid phantoms) is used for DR imaging systems, and obtain than single gold nanorods more strengthens as nanometer diagnosis and treatment probe
Image.The microcellular structure that the macromolecular chain of poly- (3,4- dioxoethyl) thiophene is cross-linked to form simultaneously, it is possible to achieve medicine is born
Carry and discharge, be expected to make detection, diagnosis, treatment while carry out, gold nanorods/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound
Combined with diffusing reflection detecting system, in the great application prospect of biomedical sector.
Beneficial effects of the present invention are as follows：
The preparation method of gold nanorods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe of the present invention is simply controllable,
Not only inhibit the aggregation of gold nanorods but also enhance its surface enhanced performance, the compound multifunctional nano that will be prepared
Diagnosis and treatment probe manufacturing is solid bodies mould, for diffusing reflection imaging system, is obtained than single gold nanorods as nanometer diagnosis and treatment
The image that probe more strengthens.There is drug loading and release function simultaneously, be expected to realize detection, diagnosis, treatment while carry out.
Brief description of the drawings
The embodiment of the present invention is described in further detail below in conjunction with the accompanying drawings.
Shown in Fig. 1 the gold nanorods of the embodiment of the present invention 1/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound (Figure 1A),
Poly- (3,4- in the gold nanorods (Figure 1B) of embodiment 1, comparative example 1 in gold nanosphere (Fig. 1 C) and comparative example 2
Dioxoethyl) thiophene ball (Fig. 1 D) transmission electron microscope picture.
Fig. 2 shows the gold nanorods of the embodiment of the present invention 1/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound, embodiment 1
Gold nanosphere and poly- (3,4- dioxoethyls) the thiophene ball in comparative example 2 is ultraviolet in gold nanorods, comparative example 1
Visible absorption spectra.
Each curve shows (curve a), the gold nanorods of the embodiment of the present invention 1/poly- (3,4- dioxoethyls) on the basis of water in Fig. 3
Thiophene nucleocapsid compound (curve b), gold nanorods (gold nanosphere (the curve d) in curve c) and comparative example 1 of embodiment 1
Diffusing reflection testing result.
Fig. 4 shows that the medicine of gold nanorods/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound of the embodiment of the present invention 1 is released
Put curve.
Embodiment
In order to illustrate more clearly of the present invention, the present invention is done further with reference to preferred embodiments and drawings
It is bright.Similar part is indicated with identical reference in accompanying drawing.It will be appreciated by those skilled in the art that institute is specific below
The content of description is illustrative and be not restrictive, and should not be limited the scope of the invention with this.
Embodiment 1
The preparation of gold nanorods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, step are as follows：
1) preparation of gold nanorods：A. the HAuCl by 250 μ L concentration for 0.01M4It is 0.1M's with 9.75mL concentration
CTAB, after being mixed and stirred for, add the NaBH that 600 μ L concentration are 0.01M4, after mixed solution is placed and stirs 10min, go
Fall stirring, at least 1h is placed, as seed-solution；
B. in flask, the HAuCl for being 0.01M by CTAB and 5mL concentration that 95mL concentration is 0.1M4After mixing, add
1.2mL concentration is 0.01M AgNO3, then add the ascorbic acid that 550 μ L concentration are 0.01M, solution turned clear, before addition
The μ L of seed-solution 120 that face makes, mixed solution place 24h, centrifuge, obtain gold nanorods；
Length 30nm~50nm of gained gold nanorods, draw ratio 4:1, on ultraviolet-visible absorption spectroscopy, exist respectively
There is absworption peak at 510nm and 690nm；
2) preparation of gold nanorods/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound：Prepared first by above-mentioned
Gold nanorods 1mg is added in 3mL 0.1mmol EDOT and 0.15mmolSDS mixed solution and stirs 5min, then adds again
Enter oxidant 0.75mmol H2O2, at 60 DEG C, stirring reaction 8h, it is centrifuged, 3 is washed with water/ethanol (1/1, v/v)
It is secondary, precipitum is obtained, precipitum is dried in vacuo 24h at 50 DEG C, and it is fine by poly- (3,4- dioxoethyl) thiophene to obtain gold nanorods
The gold nanorods of cladding/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound is gold nanorods/poly- (3,4- dioxoethyls) thiophene
Fen nanometer diagnosis and treatment probe, its transmission electron microscope picture as shown in Figure 1A, wherein, gold nanorods are core, poly- (3,4- dioxoethyl) thiophene
Fen is shell；
80~90nm of diameter of gained nucleocapsid compound nanometer diagnosis and treatment probe, on ultraviolet-visible absorption spectroscopy, absworption peak point
Other red shift is to 530nm and 790nm, as shown in Figure 2.
The diffusing reflection test of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe：
The making of solid bodies mould：The making of basic mode：By 10% intralipid for scattering process, for inhaling
3% india ink received, remaining 87% volume is distilled water, then the 1.2g/100mL for solidifying solution is added into mixed solution
Agarose powder, after being mixed evenly, mixed liquor is poured into the container of certain volume, it is 5 small that the container is positioned over into vacuum
When, cool down and solidify；
Test specimens molding is made：The preparation method for repeating above-mentioned basic mode, difference be, distilled water is changed into containing gold nanorods/
The solution of poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe nano particle.
Diffusing reflection is tested：Diffusing reflection is tested in the special equipment built based on lossless optical image technology
Carried out on (NEGOH-OP TECHNOLOGIES, Israel), method according to document " journal of biophotonics,
2012,263-273. " and " International journal of nanomedicine, the method in 2012,7,449. ",
The laser diode that wavelength is respectively 650nm and 780nm is used to radiate as light source, the optical fiber of 125 μ m diameters, one
Photodiode is as detector, and during detection, the surface of body mould is in close contact therewith to scatter light with detection.Light source is with 250 μm of steps
Long movement, makes the light intensity of arrival photodiode can be tested with (ρ) change of the distance of light source and detector.Initial distance
Close to 1mm, final distance about 5 or 6mm.Reflective light intensity Γ (ρ) at photodiode, digital instrument can be applied
(Agilent Technologies, Mso7034a, Santa Clara, CA, USA) is tested and is for data processing, its slope size
Showing a nanometer diagnosis and treatment probe imaging effect, slope is bigger, is more advantageous to be imaged, as can be seen from Figure 3, what the present invention was prepared
The imaging effect of nanometer diagnosis and treatment probe is good.
Gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe is in drug loading and the simulation test of release：
Drug loading is tested：Using DEX A.A as aids drug, the test that loaded, discharges：Compound concentration
For 3 μ g/mL, 5 μ g/mL, 10 μ g/mL, 13 μ g/mL, 15 μ g/mL, 20 μ g/mL DEX A.A ethanol solution, test it
Ultra-violet absorption spectrum, it is ordinate to take the absorbance at its absworption peak 235nm, and the concentration of DEX A.A is abscissa, is built
Day-mark directrix curve；
10mg gold nanorods/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound is dispersed in 1mL and contains 10mg acetic acid
In the ethanol solution of dexamethasone, at 37 DEG C, shaking table concussion 24h, centrifuge, obtain supernatant 1.；Reuse 1mL's respectively
DEX A.A solution washs gold nanorods/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound four times, so that unsupported arrive
DEX A.A on gold nanorods/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound all elutes, and obtains supernatant
2. 3. 4. liquid；1. it 2. 3. will 4. mix, dilute 1000 times, test its absorbance, be contrasted with standard curve, be obtained unsupported residual
Medicament contg in the solution is stayed, and then draws the drugloading rate of sample；
Insoluble drug release is tested：Insoluble drug release uses Spontaneous release method：Gold nanorods/poly- (3,4- bis- of medicine will be loaded with
Oxygen ethyl) thiophene nucleocapsid compound be put into molecular cut off be 10000Da bag filter in, be submerged into dissolution medium ethanol
In, stirred at a temperature of 37 DEG C, different time interval takes dissolution medium, tests its absorbance, so as to draw release amount of medicine.
After tested, during drug loading 48h, gained probe is 11% to the load capacity of medicine, and 120h releasable 83%, knot
Fruit is as shown in Figure 4.
Embodiment 2
The preparation of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe：
Preparation method differs only in embodiment 1, in step 2), the amount of monomer EDOT material is changed to
0.2mmol, the time of stirring reaction are changed to 12h, and a nanometer diagnosis and treatment probe gold nanorods/poly- (3,4- dioxoethyl) thiophene is prepared
Fen nucleocapsid compound；
150~160nm of diameter of gained nucleocapsid compound, on ultraviolet-visible absorption spectroscopy, absworption peak red shift to 535nm and
694nm。
The diffusing reflection test of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe：
Method of testing is close with embodiment 1 with embodiment 1, diffusing reflection test performance.
Gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe is in drug loading and the simulation test of release：
Method of testing is with embodiment 1, and after measured, as drug loading 48h, gained probe is to the load capacity of medicine
16%, and 130h releasable 83%.
Embodiment 3
The preparation of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe：
Preparation method differs only in embodiment 1, in step 2), the amount of monomer EDOT material is changed to
0.3mmol, the time of stirring reaction are changed to 16h, and nanometer diagnosis and treatment probe gold nanorods of the present invention/poly- (3,4- dioxies are prepared
Ethyl) thiophene nucleocapsid compound；
Diameter 280nm~300nm of gained nucleocapsid compound, on ultraviolet-visible absorption spectroscopy, absworption peak red shift to 538nm
And 700nm.
The diffusing reflection test of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe：
Method of testing is close with embodiment 1 with embodiment 1, diffusing reflection test performance.
Gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe is in drug loading and the simulation test of release：
Method of testing is with embodiment 1, and after measured, as drug loading 48h, gained probe is to the load capacity of medicine
20%, and 142h releasable 85%.
Embodiment 4
Embodiment 1 is repeated, difference is, by step 1) a, CTAB concentration is changed to 0.11M, and remaining condition is constant, system
It is standby to obtain gold nanorods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, the performance of gained nanometer diagnosis and treatment probe
It is close with embodiment 1.
Embodiment 5
Embodiment 1 is repeated, difference is, by step 1) b, CTAB concentration is changed to 0.085M, and remaining condition is constant, system
It is standby to obtain nanometer rods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, the performance of gained nanometer diagnosis and treatment probe with
It is close in embodiment 1.
Embodiment 6
Embodiment 1 is repeated, difference is, by step 1) b, AgNO3Concentration be changed to 0.008M, remaining condition is constant,
Nanometer rods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, the performance of gained nanometer diagnosis and treatment probe is prepared
It is close with embodiment 1.
Embodiment 7
Embodiment 1 is repeated, difference is, by step 1) b, AgNO3Concentration be changed to 0.016M, remaining condition is constant,
Nanometer rods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, the performance of gained nanometer diagnosis and treatment probe is prepared
It is close with embodiment 1.
Embodiment 8
Embodiment 1 is repeated, difference is, by step 1) b, the concentration of ascorbic acid is changed to 0.013M, and remaining condition is not
Become, nanometer rods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, gained nanometer diagnosis and treatment probe is prepared
Performance is close with embodiment 1.
Embodiment 9
Embodiment 1 is repeated, difference is, by step 1) b, the addition of seed-solution is changed to 127 μ L, and remaining condition is not
Become, nanometer rods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, gained nanometer diagnosis and treatment probe is prepared
Performance is close with embodiment 1.
Embodiment 10
Embodiment 1 is repeated, difference is, by step 1) b, the addition of seed-solution is changed to 102 μ L, and remaining condition is not
Become, nanometer rods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, gained nanometer diagnosis and treatment probe is prepared
Performance is close with embodiment 1.
Embodiment 11
Embodiment 1 is repeated, difference is, by step 1) b, HAuCl4Concentration be changed to 0.004M, remaining condition is constant,
Nanometer rods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, the performance of gained nanometer diagnosis and treatment probe is prepared
It is close with embodiment 1.
Embodiment 12
Embodiment 1 is repeated, difference is, by step 1) a, HAuCl4Concentration be changed to 0.009M, remaining condition is constant,
Gold nanorods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, the property of gained nanometer diagnosis and treatment probe is prepared
Can be close with embodiment 1.
Embodiment 13
Embodiment 1 is repeated, difference is, by step 1) a, NaBH4Concentration be changed to 0.0088M, remaining condition is constant,
Gold nanorods/poly- (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, after tested, the property of gained nanometer diagnosis and treatment probe is prepared
Can be close with embodiment 1.
Comparative example 1
A kind of preparation of nano-probe, step are as follows：
The preparation of gold nanosphere (GNSs)：By 414 μ L 50%HAuCl4Mix, boil with 200mL distilled water, boiling
Under state, the sodium citrates of 4.04mL 10%, solution heating stirring 5min are added；Mixed liquor is placed at room temperature again, until cooling
Get off, then by centrifuging three times, washing separation, obtain gold nanosphere nanometer diagnosis and treatment probe；
The diameter about 20nm of gained gold nanosphere (GNSs), on ultraviolet-visible absorption spectroscopy, absworption peak 530nm.
Comparative example 2
The preparation of poly- (3,4- dioxoethyls) thiophene (PEDOT) ball：Preparation of the method with nanometer diagnosis and treatment probe in embodiment 1
Step 2), differ only in, be added without gold nanorods, poly- (3,4- dioxoethyl) thiophene (PEDOT) ball nanometer is prepared and examines
Treat probe；
Poly- (3,4- dioxoethyl) the thiophene bulb diameter about 150nm of gained, on ultraviolet-visible absorption spectroscopy, have from 400-
900nm wide absorption.
Comparative example 3
Repeat " the diffusing reflection survey of gold nanorods/poly- (3,4- dioxoethyls) thiophene nanometer diagnosis and treatment probe in embodiment 1
Examination " part, is differed only in, will be " compound containing gold nanorods/poly- (3,4- dioxoethyl) thiophene nucleocapsid during test specimens molding is made
Thing nanoparticles solution " changes " solution containing gold nanosphere in comparative example 1 " into or " contains poly- (3,4- bis- in comparative example 2
Oxygen ethyl) thiophene ball solution " or " solution containing gold nanorods in embodiment 1 ".
Fig. 3 shows that gold nanorods in the embodiment of the present invention 1/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound nanometer is examined
Treat probe diffusing reflection detection slope be more than in comparative example 3 only using gold nanorods as probe and gold nanosphere as spy
Slope during pin.
Obviously, the above embodiment of the present invention is only intended to clearly illustrate example of the present invention, and is not pair
The restriction of embodiments of the present invention, for those of ordinary skill in the field, may be used also on the basis of the above description
To make other changes in different forms, all embodiments can not be exhaustive here, it is every to belong to this hair
Row of the obvious changes or variations that bright technical scheme is extended out still in protection scope of the present invention.
Claims (9)
- The preparation method of a kind of gold nanorods/poly- 1. (3,4- dioxoethyl) thiophene nanometer diagnosis and treatment probe, it is characterised in that described Nanometer diagnosis and treatment probe is gold nanorods/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound；Gold nano in the nucleocapsid compound The draw ratio of rod is 3:1~5:1, gold nanorods length 30nm~50nm；A diameter of 80~300nm of the nucleocapsid compound；The preparation method comprises the following steps：1) preparation of gold nanorods：A. by HAuCl4NaBH is added after being mixed and stirred for CTAB4, form mixed solution；Will be mixed After closing solution stirring 10min, then more than 1h is placed, as seed-solution；B. by HAuCl4Mixed with CTAB, add AgNO3, add ascorbic acid so that and solution turned clear, then it is limpid to gained Solution in add above-mentioned seed-solution, after mixed solution places 24h, centrifuge, obtain gold nanorods；2) preparation of gold nanorods/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound：Add into EDOT and SDS mixed solution Enter gold nanorods obtained by step 1), after stirring 5min, add H2O2, 8~16h of stirring reaction at 60 DEG C, carry out centrifugation point From with volume ratio 1:1 water/ethanol is washed 3 times, obtains precipitum；24h is dried in vacuo at 50 DEG C of precipitum, obtains gold nanorods The gold nanorods coated very well by poly- (3,4- dioxoethyl) thiophene/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound, wherein, EDOT、SDS、H2O2, the mol ratio between gold nanorods be 1:0.5:2.5:0.002~1:1.5:7.5:0.008.
- 2. preparation method according to claim 1, it is characterised in that the gold nanorods/poly- (3,4- dioxoethyl) thiophene The ultraviolet-visible absorption spectroscopy of fen nucleocapsid compound is to have an absworption peak in 500nm~540nm, is existed between 760~800nm Maximum absorption band.
- 3. preparation method according to claim 1, it is characterised in that in step 1) a, in the mixed solution, HAuCl4's Concentration is 2.2 × 10-4~2.4 × 10-4M, CTAB concentration are 9.0 × 10-2~10-1M, NaBH4Concentration be 5.0 × 10-4~ 6.0×10-4M；In step 1) b, in the limpid solution of gained, HAuCl4Concentration be 2 × 10-4~5 × 10-4M, CTAB's is dense Spend for 8.0 × 10-2~1.0 × 10-1M、AgNO3Concentration be 1.0 × 10-4~2.0 × 10-4M, the concentration of ascorbic acid is 5.0 ×10-5~7.0 × 10-5M；The volume ratio of the limpid solution of gained and seed-solution is 800:1~1000:1.
- 4. gold nanorods/poly- (3,4- dioxoethyls) thiophene that a kind of preparation method as claimed in claim 1 is prepared is received Application of the rice diagnosis and treatment probe in diffusing reflection imaging.
- 5. gold nanorods/poly- (3,4- dioxoethyls) thiophene that a kind of preparation method as claimed in claim 1 is prepared is received Application of the rice diagnosis and treatment probe in drug loading and release.
- 6. application according to claim 4, it is characterised in that the application refers to gold nanorods/poly- (3,4- dioxy second Base) thiophene nanometer diagnosis and treatment probe for diffusing reflection detect.
- 7. application according to claim 6, it is characterised in that described by gold nanorods/poly- (3,4- dioxoethyl) thiophene Nanometer diagnosis and treatment probe is used for the method that diffusing reflection detects：Make solid bodies mould, respectively using 650nm and 780nm laser as Incident light, detect change of the solid bodies mould surface diffusing reflection light intensity with distance between light source and body mould.
- 8. application according to claim 7, it is characterised in that the making of the solid bodies mould includes the making and survey of basic mode The making of sample mold；The making of the basic mode refers to：By 10% intralipid, 3% india ink, remaining 87% body Product distilled water is mixed, then 1.2g/100mL agarose powder is added into mixed liquor, cold in vacuum after being mixed evenly But and solidify；The making of the test original mold refers to：By 10% intralipid, 3% india ink, remaining 87% body The solution of the product probe nano particle of diagnosis and treatment containing nanometer is mixed, then 1.2g/100mL agarose powder is added into mixed liquor, is mixed After conjunction stirs, it is placed in vacuum, cooling and solidification.
- 9. application according to claim 5, it is characterised in that the method for the application is：Compound concentration is in 3-20 μ g/mL Various concentrations tested medicine ethanol solution, test its ultra-violet absorption spectrum, using the absorbance at absworption peak as ordinate, The concentration value of tested medicine is abscissa, establishes standard curve；Gold nanorods/poly- (3,4- dioxoethyls) thiophene nucleocapsid is compound Thing is dispersed in the ethanol solution of tested medicine, shaking table concussion 24h, after centrifugation, then through being tested drug solution washing 4 times, The unsupported tested medicine on gold nanorods/poly- (3,4- dioxoethyl) thiophene nucleocapsid compound is all eluted, survey Eluent absorbance is tried, is contrasted with standard curve, obtains the medicament contg of unsupported residual in the solution, and then draw sample Drugloading rate；The gold nanorods for being loaded with medicine/poly- (3,4- dioxoethyls) thiophene nucleocapsid compound is put into molecular cut off and is In 10000Da bag filter, to sink in dissolution medium ethanol and stir, different time interval takes dissolution medium, tests its absorbance, So as to draw release amount of medicine.
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