CN101864291A - Fluorescent nanoparticles Ru(bpy)3/SiO2, preparation method and application thereof - Google Patents
Fluorescent nanoparticles Ru(bpy)3/SiO2, preparation method and application thereof Download PDFInfo
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- CN101864291A CN101864291A CN201010185659A CN201010185659A CN101864291A CN 101864291 A CN101864291 A CN 101864291A CN 201010185659 A CN201010185659 A CN 201010185659A CN 201010185659 A CN201010185659 A CN 201010185659A CN 101864291 A CN101864291 A CN 101864291A
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Abstract
The invention relates to fluorescent nanoparticles Ru(bpy)3/SiO2, a preparation method and application thereof. The fluorescent nanoparticles have nuclear shell structures; the nuclear shell structure is formed by taking tris(2,2'-bipyridyl)ruthenium as a core, covering silicon dioxide with netlike structure on the surface of the tris(2,2'-bipyridyl)ruthenium and carrying active amino groups on the surface of the silicon dioxide, wherein the mass ratio of the tris(2,2'-bipyridyl)ruthenium to the silicon dioxide is 1:5 to 1:8; and every milligram of nanoparticles comprises 385nmol of amino group. The silicon fluorescent nanoparticles Ru(bpy)3/SiO2 have the advantages of uniform size, high monodispersity, mean diameter of 70+/-6nm, high light stability and difficult dye leakage in aqueous solution. The fluorescent probe is applied to a protein microarray chip to detect HIV p24 antigen after marking streptavidin; the analysis method is a sandwich fluorescence immunoassay method; and the result shows that the fluorescence intensity is in good positive relationship with p24 concentration and the analytical sensitivity is 3.1ng/mL. The result shows that the nanoparticles, serving as a novel fluorescent probe, can be applied to the systems of the protein microarray chip and fluorescence immunoassay and the like for high flexibility detection.
Description
Technical field
The present invention relates to a kind of fluorescent nano particles Ru (bpy)
3/ SiO
2, its preparation method and application.
Background technology
Acquired immune deficiency syndrome (AIDS) is by the caused a kind of serious communicable disease of HIV (human immunodeficiency virus) infection.Still do not having at present under the situation that vaccine is used to prevent AIDS, it is treatment and the important means that reduces aids transmission that in time correct diagnosis HIV infects.At present, generally the acquired immune deficiency syndrome (AIDS) routine diagnostic method of Cai Yonging is the ELISA method, but the ELISA method is generally carried out on 96 orifice plates, have reagent consumption big, detect the cost height, detection time is long, detection sensitivity is not high enough and can not realize the quantized shortcoming of high pass, be difficult to realize the high-throughput to a large amount of colonies, highly sensitive, rapid detection, as HIV generaI investigation, the monitoring to the more serious regional crowd of epidemic situation, the blood source examination etc. of donating blood.
The protein microarray chip technology is to adopt microarray method, sample protein is carried out the analytical technology of high-throughput, highly sensitive, high specific.Report such as Li QS adopts the early diagnosis .Wu of protein microarray chip implementation to HIV-1, and report such as JQ adopts the CD4+ of protein microarray chip detection acquired immune deficiency syndrome (AIDS) and the surface antigen of CD8+T cell.Reports such as Burgess are made fluorescent marker with Cy3 and are adopted protein microarray synchronous detection HIV, three kinds of viruses of HBV, HCV.But be applied to protein microarray chip detection HIV and do not see reported in literature as yet with the nanoparticle thing of marking.The detection probes of protein microarray chip comprises that mainly chemoluminescence, enzyme, fluorescence etc. are several.Wherein but the advantage of making probe with fluorescent substance is duplicate detection, can uses that multiple fluorescent substance carries out that multiple labeling detects simultaneously to multiple analytes etc.The fluorescent probe that uses mainly comprises common organic fluorescent dye, rare earth compounding and fluorescent nano particles etc. at present.With respect to the above two, the advantage of fluorescent nano particles is good light stability, fluorescence intensity height, detection sensitivity height, good biocompatibility etc.Thereby, in recent years nanoparticle is applied to bioanalysis fields such as protein microarray chip as fluorescent probe and is developed rapidly and widespread use.At present, the nanoparticle that can be used as probe mainly contains noble metal nano particles, semiconductor-quantum-point, and the nano silicon particles of doping fluorescent molecule etc.Petra Pavlickova utilizes nanometer gold to prepare the protein chip that can detect serum immune globulin antibody.People such as Jesse V.Jokerst utilize the CdSe/ZnS quantum dot successfully to detect three kinds of main cancer index PROTEIN C EA as the fluorescent marker on the protein chip, CA125 and Her-2/Neu.Utilization rare earth compounding doped silica nano particles such as Zhang Heng carry out time resolved fluoro-immunoassay to HBsAg.People such as Santra are with fluorescence dye Ru (bpy)
3With silicon-dioxide compound fluorescent nano particle mark goat anti-human igg, be used to discern human peripheral SmlgG
+Bone-marrow-derived lymphocyte all obtains high detection sensitivity.Owing to can wrap up a large amount of fluorescence molecules in the nano particle of the nano silicon particles of doping fluorescent molecule, thereby have strong fluorescence intensity and a detection sensitivity, and the type nanoparticle also has good water-solubility, Bc, is easy to characteristics such as preparation and surperficial easily modification, thereby becomes the focus of present research.
Summary of the invention
One of purpose of the present invention is to provide a kind of fluorescent nano particles Ru (bpy)
3/ SiO
2
Two of purpose of the present invention is to provide the preparation method of this fluorescent particles.
Three of purpose of the present invention is to utilize this fluorescent particles detecting the antigenic application of HIV p24
A kind of fluorescent nano particles Ru (bpy)
3/ SiO
2It is characterized in that this fluorescent nano particles is a nucleocapsid structure, nucleocapsid structure is kernel with the tris (bipyridine) ruthenium, at the cancellated silicon-dioxide of the surface coverage of tris (bipyridine) ruthenium, have the active amino group on surface, titanium dioxide osmanthus, wherein the mass ratio of tris (bipyridine) ruthenium and silicon-dioxide is: 1: 180～1: 190, and every milligram of nanoparticle contains 70～80nmol amino.
Above-mentioned fluorescent nano particles is a regular spherical, and median size is 64～76nm.
A kind ofly prepare above-mentioned fluorescent nano particles Ru (bpy)
3/ SiO
2Method, it is characterized in that the concrete steps of this method are: after hexanaphthene, n-hexyl alcohol and Triton X-100 are mixed by 20: 1: 10～25: 1: 14 volume ratio, add entry, reentering Ru (bpy) to the solution clear
3The aqueous solution, control Triton X-100 and Ru (bpy)
3Mol ratio be 6340: 1～6360: 1; Mol ratio by 10: 1: 5～10: 1: 7 after stirring adds tetraethoxy, 3-aminopropyl trimethoxysilane and ammoniacal liquor successively, and the mol ratio ratio of tetraethoxy and Triton X-100 is 1: 9～1: 10; Stirring reaction is 22～26 hours under the lucifuge; Add the acetone breakdown of emulsion, ultra-sonic dispersion, centrifugation is washed to remove tensio-active agent and unreacted raw material impurity with dehydrated alcohol and ultrapure water respectively then, after the vacuum-drying, obtains the surface and has amino Ru (bpy)
3/ SiO
2Fluorescent nano particles.
A kind of above-mentioned Ru (bpy)
3/ SiO
2Fluorescent nano particles is as the application of fluorescent probe in detecting HIV p24 antigen.
Prepared hud typed dye adulterated luminescence from silicon nanoparticle Ru (bpy)
3/ SiO
2The size homogeneous, monodispersity is good, and median size is 70 ± 6nm; And have good light stability, only decayed 8% with 100W xenon lamp its fluorescence intensity after maximum emission wavelength shines 90 minutes; Be difficult for that in the aqueous solution dyestuff takes place and reveal, the dyestuff that continuous ultrasound was revealed after 1 hour is less than 0.05%.The present invention will be applied to protein microarray chip detection HIV p24 antigen first behind this fluorescent probe mark streptavidin, the analytical procedure that adopts is the sandwich fluoroimmunoassay, the result shows that fluorescence intensity and p24 concentration are good positive correlation, and sensitivity for analysis is 3.1ng/mL.The result shows, this nanoparticle can be applicable to systems such as the protein microarray chip of highly sensitive detection and fluoroimmunoassay as a kind of novel fluorescent probe.
Description of drawings
Fig. 1 is Ru of the present invention (bpy)
3/ SiO
2The TEM figure of nano-fluorescent grain.
Fig. 2 is 1mg/mLRu (bpy)
3With 0.5mg/mL nano fluorescent particle Ru (bpy)
3/ SiO
2Uv-visible absorption spectra.
Fig. 3 is 1mg/mLRu (bpy)
3With 0.5mg/mL nano fluorescent particle Ru (bpy)
3/ SiO
2452nm excited fluorescent spectrum.
Fig. 4 is Ru of the present invention (bpy)
3/ SiO
2The photobleaching experiment of nano fluorescent particle in water.
Fig. 5 is Ru of the present invention (bpy)
3/ SiO
2The dyestuff of nano fluorescent particle in water revealed experiment.
Fig. 6 is Ru of the present invention (bpy)
3/ SiO
2Fluorescence spectrum behind the nano fluorescent particle mark SA under 452nm excites, wherein Ru (bpy)
3/ SiO
2, Ru (bpy)
3/ SiO
2-BSA and Ru (bpy)
3/ SiO
2The concentration of-BSA-SA is respectively 0.5,0.25,0.25mg/mL).
Fig. 7 is Ru of the present invention (bpy)
3/ SiO
2The principle schematic of nano fluorescent particle mark SA
Fig. 8 is that (the 1st～6 dot matrix, the p24 antigen concentration is respectively 330,33 to chip scanning figure, 3.3,0.33,0.033,0 μ g/mL.The insolubilized antibody concentration of each dot matrix is respectively from top to bottom, 0.1,1,10,50,100,200,500 μ g/mL).
Fig. 9 for the p24 analytic curve of microarray protein chip (insolubilized antibody, vitamin H-goat-anti HIV p24 polyclonal antibody and nanoparticle-streptavidin marker concentrations are respectively 100 μ g/mL, 0.2mg/mL, 0.3mg/mL).
Embodiment
One, instrument and reagent: Hitachi F-7000 spectrophotofluorometer (HIT); Hitachi U-3010 ultraviolet-visible spectrophotometer (HIT); Hitachi CR22G/II supercentrifuge (HIT); JEOL 200CX transmission electron microscope (Jeol Ltd.).Genepix 4000B chip scanner (U.S. Axon Instruments company); OminiGrid 300 chip point sample instruments (U.S. Genomics Solution company).
Tris (bipyridine) ruthenium (Rubpy)
3, 3-aminopropyl trimethoxysilane (APTMS), tetraethoxy (TEOS), TritonX-100 etc. be analytical pure, available from SIGMA company; N-hexyl alcohol, acetone, ammoniacal liquor etc. are analytical pure, available from person of outstanding talent Shen, Shanghai chemical reagent company limited; Bovine serum albumin (BSA), streptavidin (SA) etc. are all available from Beijing Xin Jingke Bioisystech Co., Ltd.HIV p24 antigen, vitamin H-goat-anti HIV p24 polyclonal antibody is purchased the Fitzgerald company in the U.S., and goat-anti HIV p24 monoclonal antibody is purchased the Bioisystech Co., Ltd in Beijing Bo Feikang.Aldehyde slide is purchased in Baiao Science and Technology Co. Ltd., Shanghai.Various damping fluids are: analysis buffer (dilution buffer liquid): 0.1mol/l PBS, 0.1%BSA, 0.1%Tween-20, pH7.4.Washings: 0.05mol/l PBS, 0.05%Tween-20, pH7.4.Confining liquid: 0.1mol/L PBS, pH7.4,2%BSA, 0.01% sodium azide.Point sample buffer:60%0.01mol/l PBS+40% glycerine, pH7.4.
Two, experimental technique
1.Ru (bpy)
3/ SiO
2The preparation of fluorescent nano particles: with the 7.5.mL hexanaphthene, the 1.7mL n-hexyl alcohol, 1.8mLTriton X-100 joins in the round-bottomed flask successively, stir and it was mixed in 20 minutes, add 400 μ L water again, continue to be stirred to the solution clear, add 100 μ L 5mg/mL Ru (bpy)
3The aqueous solution stirs and adds 100uL TEOS and 10 μ L APTMS after 5 minutes more successively, adds 60 μ L ammoniacal liquor after 10 minutes, and lucifuge stirs reaction down 24 hours.After finishing, reaction adds the proper amount of acetone breakdown of emulsion, ultra-sonic dispersion, 12000 rev/mins of following centrifugations, it is inferior to remove impurity such as tensio-active agent and unreacted raw material to give a baby a bath on the third day after its birth with dehydrated alcohol and ultrapure water respectively then, after the vacuum-drying, obtain the surface and have amino Ru (bpy)
3/ SiO
2Nano particle.Fig. 1 is synthetic nucleocapsid fluorescent nano particle Ru (bpy)
3/ SiO
2Transmission electron microscope figure, it is spherical that nanoparticle is rule as seen from Figure 1, size is homogeneous relatively, particle diameter is 70 ± 6nm, does not have inter-adhesively between the nanoparticle, monodispersity is fine.
Referring to Fig. 2, Ru (bpy)
3/ SiO
2Nanoparticle and Ru (bpy)
3Abosrption spectrogram similar, their maximum absorption wavelength is 452nm, wherein Ru (bpy)
3/ SiO
2It is owing to Ru (bpy) in nanoparticle that the maximum absorption band of nanoparticle slows down
3The reduction of relative content causes.Referring to Fig. 3, Ru (bpy)
3/ SiO
2The nanoparticle maximum emission wavelength is 590nm, with Ru (bpy)
3Emission maximum ripple (600nm) compare, its maximum emission wavelength blue shift about 10nm.This is because Ru (bpy)
3Maximum emission wavelength and its surrounding environment bigger relation is arranged, in the time of in the aqueous solution, the SiO behind the parcel
2Shell has hindered Ru (bpy)
3And the interaction between the polar water molecules, thereby make maximum emission wavelength generation blue shift.Experiment records the pure Ru of 1mg/mL (bpy)
3Fluorescence intensity lower than 0.5mg/mL nano particle on the contrary be because the Ru (bpy) of high density
3Take place due to the autofluorescence cancellation.
2. photobleaching experiment and dyestuff are revealed test
With concentration is the pure Ru (bpy) of 1mg/mL
3Dyestuff and Ru (bpy)
3/ SiO
2The nanoparticle aqueous solution shines as excitation light source with the 100W xenon lamp respectively, sample is 5cm apart from the distance of xenon lamp, measured the fluorescence intensity at a maximum emission wavelength place every 15 minutes, test 90min altogether, observe of the variation of two kinds of fluorescence intensity of solution with irradiation time.
The nano particle for preparing is got 1mg to be distributed in the 4mL water, survey its fluorescence intensity, surveyed the back ultrasonic 15 minutes, centrifugation, abandoning supernatant is dispersed in the nano particle that precipitates in the 4mL water again and surveys its fluorescence intensity, and then ultrasonic 15min, centrifugation also will precipitate to be dissolved in again and survey its fluorescence intensity in the 4mL water again, repeat above-mentioned steps for several times, by the measure of the change Ru (bpy) of fluorescence intensity
3/ SiO
2Nanoparticle dye molecule Ru (bpy) behind the ultrasonic different time in the aqueous solution
3Leakiness.
Referring to Fig. 4, pure Ru (bpy)
3Dyestuff has decayed about 56% through the xenon lamp irradiation back fluorescence intensity of 90min, and Ru (bpy)
3/ SiO
2It is about 8% that nanoparticle has only been decayed, and shows that it has the ability of good anti-photobleaching.Referring to Fig. 5, the fluorescence intensity that nano particle is revealed after testing through dyestuff has only reduced less than 0.05%, and Ru (bpy) is described
3/ SiO
2Nanoparticle has satisfactory stability in the aqueous solution, dyestuff does not almost take place reveal.
3. the amino quantitative experiment of nano grain surface
Utilizing aminocompound and ninhydrin reaction to generate the bluish voilet material has the principle of obvious absorption peaks to measure amino at the 563nm place.In 2 5.0ml centrifuge tubes, add 5 μ L APTMS, 1.0mg Ru (bpy) respectively
3/ SiO
2Nano particle, the ninidrine solution and the 1.5mL water that add 0.5mL 0.056mol/L then to every centrifuge tube, the last NaOH solution that in centrifuge tube, adds 0.1mL 0.1mol/L respectively, 80 ℃ of heating in water bath 5 minutes, its absorption at the 563nm place is measured with the U-3010 ultraviolet-visible spectrophotometer in the cooling back.
Measuring Ru (bpy)
3/ SiO
2During the surface amino groups quantity of nanoparticle, do standard working curve with the absorbancy that APTMS measures the 563nm place as standard substance, relation conefficient is 0.996, and the associated straight lines equation is y=-0.00155x-0.00362.Then with Ru (bpy)
3/ SiO
2Nanoparticle uses the same method and measures the absorbancy (amino of supposing inside nanoparticles does not react) at 563nm place, and the above-mentioned straight-line equation of substitution can be calculated the quantity of nanometer ball surface amino groups.The result is that nanometer ball about 70nm contains the 385nmol amino of having an appointment for every milligram for prepared diameter under the condition that adds 10 μ lAPTMS.
4 nanoparticle label SA
Get 1mg Ru (bpy)
3/ SiO
2Nano particle, ultra-sonic dispersion is (pH7.2) in the 0.1mol/L phosphate buffer soln, the glutaraldehyde water solution that adds 4.0mgBSA and 0.3mL 1%, stirring at room reaction 24 hours, then that nano particle is centrifugal, phosphate buffer soln thorough washing is to remove unreacted BSA molecule etc., and redispersion adds the SA of 100 μ g and the glutaraldehyde water solution of 100 μ L 0.1% in the 1mL phosphate buffer soln, continue stirring reaction 24 hours under the room temperature, add the NaBH of 0.5mg
4, room temperature reaction 2 hours.The nanoparticle that the surface indicates the SA molecule is after centrifugal, washing, with the 0.05mol/LNH of pH8.0
4HCO
3The aqueous solution is elutriant, (1.0 * 30cm) posts carry out further separation and purification with Sephadex G-50, there is the component of maximum absorption to be collected in together with the fluorescence intensity height and at the 280nm place, the final SA solution that gets the 2mL nanometer particle to mark, packing stored frozen behind the adding 1%BSA.
Ru (bpy)
3/ SiO
2The principle schematic of nanometer particle to mark SA, referring to Fig. 7, with the nanoparticle of surface amination at first with the BSA bonding, and then SA is connected on the nanoparticle of BSA parcel by glutaraldehyde.Like this owing between SA and nanoparticle, there is snappiness BSA bridge preferably, make the nanoparticle of mark SA easier with other biomolecular reaction, and keep the activity of SA.With spectrophotofluorometer difference measure R u (bpy)
3/ SiO
2The fluorescence spectrum of nanoparticle, nanoparticle-BSA combination and nanoparticle-BSA-SA combination, the result can find that referring to shown in Figure 6 their emmission spectrum figure is similar, its maximum emission wavelength all is 590nm.
5 microarray protein chips detect HIV p24 antigen
Goat-anti HIV p24 monoclonal anti body and function analysis buffer is diluted to concentration series: 0,0.1,1,10,50,100,200,500 μ g/mL, point sample, 8 * 8array, dot spacing 300 μ m, 6 microarray dot matrix of concurrent are on a slice aldehyde slide sheet base, and 4 ℃ are spent the night.Every dot matrix adds 40 μ L confining liquids and spends the night for 4 ℃, washing.Add 25 μ L different concns p24 antigens successively toward 1～6 dot matrix, p24 antigen concentration series is 0,0.033,0.33,3.3,33,330 μ g/mL, 37 ℃ of reaction 1h, washing, each dot matrix adds 25 μ l 0.2mg/mL vitamin Hs-goat-anti HIV p24 polyclonal antibody respectively, 37 ℃ of reaction 1.5h, washing.Add 25 μ L 0.3mg/mL nanoparticle-streptavidin markers (NPs-SA) respectively toward each dot matrix, room temperature reaction 1h, the washing back is measured on chip scanner.
In the chip testing experiment, result according to condition experiment, other condition is constant when fixing, change the concentration of vitamin H-goat-anti HIV p24 polyclonal antibody, carry out the fluoroimmunoassay test respectively, found that the fluorescence intensity level that records increases with the increase of the concentration of vitamin H-goat-anti HIV p24 polyclonal antibody, but when its concentration reached certain value (0.2mg/mL), fluorescent signal no longer increased with the increase of its concentration.It is constant to fix other condition, changes the concentration of NPs-SA, and the fluorescence intensity level that records increases with the increase of NPs-SA concentration, but when NPs-SA concentration reaches 0.3mg/mL, platform occurs.Therefore, we select the concentration of vitamin H-goat-anti HIV p24 polyclonal antibody and NPs-SA to be respectively 0.2 and 0.3mg/mL.Chip scanning result such as Fig. 8 and shown in Figure 9.By Fig. 8,9 as can be seen, same microarray dot matrix is along with the increase of insolubilized antibody concentration, fluorescence intensity increases, and different microarray dot matrix are under the insolubilized antibody concentration same case, fluorescence intensity increases with the p24 antigen concentration, and fluorescence intensity and p24 concentration are good positive correlation.When insolubilized antibody point sample concentration is 100 μ g/mL, be limited to 3.1ng/mL with 3 times of background signal (n=10) the standard deviation antigenic lowest detection of detection HIV p24 of calculating this method as lowest detectable limit.
Claims (4)
1. a fluorescent nano particles Ru (bpy)
3/ SiO
2It is characterized in that this fluorescent nano particles is a nucleocapsid structure, this nucleocapsid structure is kernel with the tris (bipyridine) ruthenium, at the cancellated silicon-dioxide of the surface coverage of tris (bipyridine) ruthenium, have the active amino group on surface, titanium dioxide osmanthus, wherein the mass ratio of tris (bipyridine) ruthenium and silicon-dioxide is: 1: 180～1: 190, and every milligram of nanoparticle contains 70～80nmol amino.
2. fluorescent nano particles Ru according to claim 1 (bpy)
3/ SiO
2, it is characterized in that this fluorescent nano particles is a regular spherical, median size is 64～76nm.
3. one kind prepares fluorescent nano particles Ru according to claim 1 (bpy)
3/ SiO
2Method, it is characterized in that the concrete steps of this method are: after hexanaphthene, n-hexyl alcohol and Triton X-100 are mixed by 20: 1: 10～25: 1: 14 volume ratio, add entry, reentering Ru (bpy) to the solution clear
3The aqueous solution, control Triton X-100 and Ru (bpy)
3Mol ratio be 6340: 1～6360: 1; Mol ratio by 10: 1: 5～10: 1: 7 after stirring adds tetraethoxy, 3-aminopropyl trimethoxysilane and ammoniacal liquor successively, and the mol ratio ratio of tetraethoxy and Triton X-100 is 1: 9～1: 10; Stirring reaction is 22～26 hours under the lucifuge; Add the acetone breakdown of emulsion, ultra-sonic dispersion, centrifugation is washed to remove tensio-active agent and unreacted raw material impurity with dehydrated alcohol and ultrapure water respectively then, after the vacuum-drying, obtains the surface and has amino Ru (bpy)
3/ SiO
2Fluorescent nano particles.
4. a Ru according to claim 1 (bpy)
3/ SiO
2Fluorescent nano particles is as the application of fluorescent probe in detecting HIV p24 antigen.
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| CN102174635A (en) * | 2010-12-31 | 2011-09-07 | 中国科学院海洋研究所 | Application of streptavidin combined functional fluorescent magnetic nano granules |
| CN102527355A (en) * | 2010-12-18 | 2012-07-04 | 中国科学院兰州化学物理研究所 | Method for preparing bipyridine bonding silica gel filler |
| CN104031634A (en) * | 2014-05-22 | 2014-09-10 | 中山大学 | Ratio fluorescence nano probe, and preparation method and application thereof |
| CN105295907A (en) * | 2015-10-26 | 2016-02-03 | 南昌大学 | Preparation method of functional rare earth long-afterglow nanocomposite and latent fingerprint imaging application of functional rare earth long-afterglow nanocomposite |
| CN109232663A (en) * | 2018-11-08 | 2019-01-18 | 云南大学 | A kind of preparation method and its HIV reverse transcriptase inhibition application of ruthenium complex |
| CN109294556A (en) * | 2018-09-29 | 2019-02-01 | 南开大学 | A kind of preparation method of the silicon nano compound of the transmitting red fluorescence of bipyridyl ruthenium functionalization |
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2010
- 2010-05-26 CN CN201010185659A patent/CN101864291A/en active Pending
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| 谢春娟: "复合荧光二氧化硅纳米颗粒的制备及其在生物分析和光催化降解中的应用", 《上海大学博士学位论文》 * |
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| CN102527355A (en) * | 2010-12-18 | 2012-07-04 | 中国科学院兰州化学物理研究所 | Method for preparing bipyridine bonding silica gel filler |
| CN102174635A (en) * | 2010-12-31 | 2011-09-07 | 中国科学院海洋研究所 | Application of streptavidin combined functional fluorescent magnetic nano granules |
| CN102174635B (en) * | 2010-12-31 | 2013-07-31 | 中国科学院海洋研究所 | Application of streptavidin combined functional fluorescent magnetic nano granules |
| CN104031634A (en) * | 2014-05-22 | 2014-09-10 | 中山大学 | Ratio fluorescence nano probe, and preparation method and application thereof |
| CN104031634B (en) * | 2014-05-22 | 2015-11-11 | 中山大学 | A kind of ratio fluorescent nano probe and its preparation method and application |
| CN105295907A (en) * | 2015-10-26 | 2016-02-03 | 南昌大学 | Preparation method of functional rare earth long-afterglow nanocomposite and latent fingerprint imaging application of functional rare earth long-afterglow nanocomposite |
| CN105295907B (en) * | 2015-10-26 | 2017-06-30 | 南昌大学 | The preparation method of functional rare earth long-persistence nano composite and its latent fingerprint imaging application |
| CN109294556A (en) * | 2018-09-29 | 2019-02-01 | 南开大学 | A kind of preparation method of the silicon nano compound of the transmitting red fluorescence of bipyridyl ruthenium functionalization |
| CN109232663A (en) * | 2018-11-08 | 2019-01-18 | 云南大学 | A kind of preparation method and its HIV reverse transcriptase inhibition application of ruthenium complex |
| CN109232663B (en) * | 2018-11-08 | 2020-09-25 | 云南大学 | Preparation method of ruthenium complex and application of ruthenium complex in HIV reverse transcriptase inhibition |
| CN110426524A (en) * | 2019-08-21 | 2019-11-08 | 安邦（厦门）生物科技有限公司 | A kind of double interpretation reverse type detection systems of abo blood group and detection method |
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Application publication date: 20101020 |