CN102604637B - The preparation method of the rear-earth-doped inorganic fluorescent nano-particle of biotin modification - Google Patents
The preparation method of the rear-earth-doped inorganic fluorescent nano-particle of biotin modification Download PDFInfo
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Abstract
The preparation method of the rear-earth-doped inorganic fluorescent nano-particle of a kind of biotin modification of disclosure.Utilize BTA-N, N, N ', N '-tetramethylurea hexafluorophosphoric acid ester (HBTU) and DIPEA (DIEA) are activator, at anhydrous N, in the solvent of dinethylformamide, the carboxyl of biotin being activated, then reacting formation amido link with the amino of nano-particle, thus realizing the biotin modification of rear-earth-doped inorganic fluorescent nano grain surface.Adopt biotin modification rear-earth-doped inorganic fluorescent nano-particle prepared by this method can carry out rapid and stable connection with Avidin, simultaneously because this connection can be carried out sensitive response by the specific luminescence of rare earth ion of doping in nano-particle, it was shown that the Application of micron obtained by this preparation method is in the potentiality of biomarker and immunoassay field.
Description
Technical field
The preparation method that the present invention relates to a kind of biotin modification inorganic nano material, the preparation method especially relating to the rear-earth-doped inorganic fluorescent nano-particle of a kind of biotin modification.
Background technology
Inorganic fluorescent nano-particle rear-earth-doped in recent years is subject to people's attention with features such as its higher physical and chemical stability, excellent luminescent properties, the field such as the information of being widely used in shows, green illumination, biomarker, solaode.Particularly in when being applied to biomarker, compared to fluorescent dye conventional at present and semiconductor-quantum-point, due to inorganic rare earth nano luminescent material have that luminous efficiency height, toxicity is low, line width, fluorescence lifetime length and launch the comprehensive advantages such as tunable wave length, be the fluorescent biolabels material of new generation being generally expected at present.And in biomarker and immunoassay field, high-affinity (the binding constant K of biotin (biotin) and Avidin (avidin) or Streptavidin (streptavidin)a=1015M-1) make both can quickly combine under relatively low concentration and keep stablizing of complex, this cohesive process is almost irreversible.Based on the unique combination characteristic that biotin and Avidin have, getting final product the bioactive substances such as coupled antigen antibody in conjunction with the two and detect, this kind of characteristic makes biotin-avidin system become the rapid bio-analysis system of development in recent years.Therefore, being combined with biotin-avidin system by rear-earth-doped inorganic fluorescent nano-particle and be conducive to carrying out biological markers detection even bio-imaging sensitive, efficient, this field also increasingly receives the concern of Chinese scholars.And the basis carrying out this area research is how to be connected to biotin or Avidin nano grain surface, current existing achievement in research is typically with 1-ethyl-3-(3-dimethyl aminopropyl)-carbodiimides (EDC) and N-hydroxy-succinamide (NHS) is cross-linking agent, " aqueous phase " environment of buffer solution carries out biotin and the connection of inorganic nanoparticles that the functional group such as amino or carboxyl is contained on surface, in this connection procedure, biotin, Avidin and the nano-particle dissolubility in buffer solution is the key factor affecting reaction yield；EDC there is also the problem of intermediate product hydrolysis simultaneously, and these all limit the productivity of this coupled reaction.(list of references: GregT.Hermanson, BioconjugateTechniques, 2ndedition, AcademicPress, Inc., (2008)；Chun-HuaYanetal, J.Phys.Chem.C, Vol.112, No.17,6589-6593, (2008)).The present invention takes " solid-phase synthesis " that in organic reaction, amide synthesis is conventional, use BTA-N, N, N ', N '-tetramethylurea hexafluorophosphoric acid ester (HBTU) is condensing agent and N, N-diisopropylethylamine (DIEA) is activator, at anhydrous N, in " oil phase " solvent of dinethylformamide, the carboxyl of biotin is activated, then formation amido link is reacted with the amino of nano-particle, it is possible to successfully realize the biotin modification to multiple inorganic nanoparticles, embodied the broad applicability of this method.The rear-earth-doped inorganic fluorescent of biotin modification prepared by the method is nanocrystalline, rapid and stable connection can be carried out with Avidin, utilize the specific luminescence of the rare earth ion of doping in nano-particle that this connection is responded simultaneously, namely can be applicable to out-phase or homogeneous fluorescent immunoassay.
Summary of the invention
It is an object of the invention to propose a kind of preparation method making rear-earth-doped inorganic nano-crystal finishing biotin.
The present invention adopts the following technical scheme that
1. the preparation method of a rear-earth-doped inorganic nano-crystal finishing biotin.It is characterized in that: weigh BTA-N, N, N ', N '-tetramethylurea hexafluorophosphoric acid ester (HBTU) and N, N-diisopropylethylamine (DIEA) and biotin, at anhydrous N, in " oil phase " solvent of dinethylformamide, the carboxyl of biotin is activated, then amido link is formed with after the amino stoichiometric number hour of nano-particle, then with the nano-particle of DMF and deionized water wash reaction generation repeatedly, vacuum drying oven dries, namely obtains the rear-earth-doped inorganic fluorescent nano-particle of finishing biotin.
2. the preparation method of the rear-earth-doped inorganic fluorescent nano-particle of the biotin modification as described in item 1, it is characterised in that the addition mole ratio of reactant:
Nano-particle: 1 part；
BTA-N, N, N ', N '-tetramethylurea hexafluorophosphoric acid ester: 1～5 part；
DIPEA: 1～10 part；
Biotin: 0.5～5 part.
3. taking the preparation method as described in item 1 and 2, the rear-earth-doped inorganic fluorescent nano-particle adopted, the rare earth element adulterated is Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, and nano grain surface is amino.
4. the rear-earth-doped inorganic fluorescent nano grain surface in order to confirm as described in item 1 and 2 carries out the feasibility of the preparation method of biotin modification, and the present invention chooses rear-earth-doped yttrium fluoride natrium (NaYF4) nano-particle and gadolinium fluoride (GdF3) nano-particle is examples of implementation, the present invention has broad applicability, is not limited only to both examples above.
5. rear-earth-doped inorganic nanoparticles modified biological element detection and checking.Shown by Fourier transform infrared spectroscopy detection, after the effect through HBTU/DIEA, nano grain surface modified biological element, create two new infrared vibration absworption peak: 1217cm-1And 1153cm-1, this corresponds to the C-N vibration absorption peak of biotin；Nano-particle is corresponding to the vibration absorption peak 1635cm of the N-H of amino simultaneously-1Disappear, create a new absworption peak 1685cm-1, this is the vibration absorption peak of C=O in amido link, illustrates that the amino of particle surface has reacted with the carboxyl of biotin and generates amido link, and namely biotin is successfully connected to nano grain surface.
It addition, by the GdF before modification3The GdF of nano-particle and the finishing biotin prepared according to the method as described in item 1 and 23Nano-particle is dissolved separately in phosphate buffer, it is added thereto to the same amount of Avidin (Avidin-RhBITC) being connected to rhodamine isothiocyanate, centrifugation after cultivation a period of time, clean for several times with phosphate buffer, again the nano-particle after cleaning is dissolved separately in phosphate buffer, fluorescence plate reading machine is tested.The GdF of unmodified biotin3Nano-particle can only at a small amount of fluorescent dye RhBITC of surface adsorption due to it, and the emission peak intensity that solution is corresponding is also more weak；And it is modified with the GdF of biotin3Nano-particle can pass through RhBITC on Biotin-Avidin reaction forming, and its solution can detect the stronger emission peak corresponding to RhBITC.
6. the purposes of the rear-earth-doped inorganic fluorescent nano-particle adopting the obtained biotin modification of preparation method as described in item 1 and 2, it is characterised in that: for biomarker and immunoassay.Avidin is dissolved in carbonate buffer solution, and it is diluted in 96 microwell plates that variable concentrations joins high-affinity, cultivation a period of time makes Avidin be tagged on microwell plate by physical absorption, then clean for several times to remove free Avidin with carbonate buffer solution, then the biotin labeled nano-particle prepared is dissolved in phosphate buffered solution, take in the micropore that the nanoparticles solution of same volume same concentrations joins labelling variable concentrations Avidin, clean for several times with phosphate buffer after cultivating a period of time, fluorescence plate reading machine carries out spectral detection.
Biotin has been gone up owing to nano grain surface is modified, fluorescence plate reading machine detects, result shows the increase of the Avidin concentration along with microwell plate labelling, the finishing being connected to has the nano-particle of biotin more many, detect that the rare earth ion fluorescence intensity of correspondence is also more big, good linear relationship is there is between Avidin concentration and fluorescence intensity, Avidin is close or the protein concentration of plain coupling to illustrate to utilize the fluorescence of nano-particle to detect, this detection can reach higher sensitivity, its limit can reach nM, indicate this biotin labeled fluorescent nano particle and be applied to the prospect in biomarker field.
By the rear-earth-doped inorganic fluorescent nano-particle of biotin labeling prepared by the present invention, preparation process is simple, reproducible.The present invention with adopt at present both at home and abroad generally carry out the method that biotin modification is nanocrystalline in aqueous compared with, owing to reaction carries out in " oil phase " solvent, the water solublity of granule and biotin is required relatively low, avoids the hydrolysis of intermediate product simultaneously, thus reaction yield is higher.The rear-earth-doped inorganic fluorescent nano-particle of this biotin modification that we obtain, rapid and stable connection can be carried out with Avidin, simultaneously in nano-particle, this connection also can be carried out sensitive response by the rare earth ion characteristic luminescence of doping, it was shown that the materials application prepared by this method is in the potentiality in biomarker field.
Accompanying drawing explanation
Accompanying drawing 1:(a) reaction mechanism that combines under HBTU/DIEA effect of biotin and amidized nano-particle.
Accompanying drawing 2:(a) not modified with (b) biotin modification after NaYF4: 5%Ce, 5%Tb nano-particle fluorescence spectrum in aqueous and luminous photo.
Accompanying drawing 3:(a) not modified with (b) biotin modification after NaYF4: the Fourier transform infrared spectroscopy of 20%Yb, 2%Er nano-particle.
Accompanying drawing 4:(a) not modified with (b) biotin modification after GdF3Nano-particle and the reacted fluorescence spectrum of Avidin-RhBITC.
Accompanying drawing 5: Avidin is carried out the step of fluoroscopic examination by the nano-particle after biotin modification.
Accompanying drawing 6: the NaYF after biotin modification4: 20%Yb, 2%Er nano-particle be connected with the variable concentrations Avidin being marked on microwell plate after fluorometric investigation analyze result.
Detailed description of the invention
The preparation method of the rear-earth-doped inorganic fluorescent nano-particle of biotin labeling provided by the present invention, its substantive features and remarkable advantage can pass through following example and be confirmed further, but the present invention is not limited only to examples of implementation.
Example 1:NaYF4: 5%Ce, 5%Tb nano grain surface connects the preparation of biotin.Weigh 30mg BTA-N, N, N ', N '-tetramethylurea hexafluorophosphoric acid ester (HBTU) and 30mg biotin are dissolved in the N of 0.9mL, dinethylformamide (DMF), the carboxyl of biotin is carried out activation 12 hours by the DIPEA (DIEA) adding 0.1mL, is subsequently adding the 30mg surface NaYF with amino4: 5%Ce, 5%Tb nano-particle, after concussion is reacted 12 hours, with the nano-particle of DMF and deionized water wash reaction generation repeatedly, dry in vacuum drying oven, the NaYF of finishing biotin can be obtained4: 5%Ce, 5%Tb inorganic nanoparticles.
Example 2:NaYF4: 20%Yb, 2%Er nano grain surface connects the preparation of biotin.HBTU and the 50mg biotin weighing 75mg is dissolved in the DMF of 1.8mL, and the carboxyl of biotin is carried out activation 8 hours by the DIEA adding 0.2mL, is subsequently adding the 50mg surface NaYF with amino4: 20%Yb, 2%Er nano-particle, after concussion is reacted 8 hours, with the nano-particle of DMF and deionized water wash reaction generation repeatedly, dry in vacuum drying oven, the NaYF of finishing biotin can be obtained4: 20%Yb, 2%Er inorganic nanoparticles.
Example 3:NaYF4: 1%Dy nano grain surface connects the preparation of biotin.HBTU and the 20mg biotin weighing 10mg is dissolved in the DMF of 0.9mL, and the carboxyl of biotin is carried out activation 24 hours by the DIEA adding 0.1mL, is subsequently adding the 15mg surface NaYF with amino4: 1%Dy nano-particle, after concussion is reacted 24 hours, with the nano-particle of DMF and deionized water wash reaction generation repeatedly, dry in vacuum drying oven, the NaYF of finishing biotin can be obtained4: 1%Dy inorganic nanoparticles.
Example 4:GdF3: 5%Tb nano grain surface connects the preparation of biotin.HBTU and the 50mg biotin weighing 50mg is dissolved in the DMF of 0.8mL, and the carboxyl of biotin is carried out activation 10 hours by the DIEA adding 0.2mL, is subsequently adding the 50mg surface GdF with amino3: 5%Tb nano-particle, after concussion is reacted 10 hours, with the nano-particle of DMF and deionized water wash reaction generation repeatedly, dry in vacuum drying oven, the GdF of finishing biotin can be obtained3: 5%Tb inorganic nanoparticles.
Example 5:GdF3: 50%Eu nano grain surface connects the preparation of biotin.HBTU and the 100mg biotin weighing 100mg is dissolved in the DMF of 3mL, and the carboxyl of biotin is carried out activation 8 hours by the DIEA adding 0.3mL, is subsequently adding the 20mg surface GdF with amino3: 50%Eu nano-particle, after concussion is reacted 12 hours, with the nano-particle of DMF and deionized water wash reaction generation repeatedly, dry in vacuum drying oven, the GdF of finishing biotin can be obtained3: 50%Eu inorganic nanoparticles.
Example 6: 1mg Avidin is dissolved in carbonate buffer solution, and it is diluted in 96 microwell plates that variable concentrations joins high definition conjunction property, cultivation a period of time makes Avidin be tagged on microwell plate by physical absorption, clean for several times to remove free Avidin followed by carbonate buffer solution, then by the biotin labeled NaYF of preparation in example 24: 20%Yb, 2%Er nano-particle is dissolved in phosphate buffered solution, take in the micropore that the nanoparticles solution of same volume same concentrations joins variable concentrations Avidin labelling, clean for several times with phosphate buffer after cultivating a period of time, under 980nm excites, fluorescence plate reading machine carries out fluorescence spectrum detection.
Claims (5)
1. the preparation method of the rear-earth-doped inorganic fluorescent nano-particle of biotin modification, it is characterized in that: utilize BTA-N, N, N', N'-tetramethylurea hexafluorophosphoric acid ester and N, N-diisopropylethylamine is activator, in the solvent of anhydrous DMF, the carboxyl of biotin is activated, then react with the amino of nano-particle, thus realizing rear-earth-doped inorganic fluorescent nano grain surface to connect biotin.
2. the preparation method of the rear-earth-doped inorganic fluorescent nano-particle of biotin modification as claimed in claim 1, it is characterised in that the addition mole ratio of reactant: nano-particle: 1 part；BTA-N, N, N', N'-tetramethylurea hexafluorophosphoric acid ester: 1～5 part；N, N-diisopropylethylamine: 1～10 part；Biotin: 0.5～5 part.
3. the preparation method of the rear-earth-doped inorganic fluorescent nano-particle of biotin modification such as claim 1 or 2, the rear-earth-doped inorganic fluorescent nano-particle adopted, the rare earth element adulterated is Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, and nano grain surface is amino.
4. the preparation method of the rear-earth-doped inorganic fluorescent nano-particle of biotin modification such as claim 1 or 2, it is characterized in that: utilize BTA-N, N, N', N'-tetramethylurea hexafluorophosphoric acid ester and N, N-diisopropylethylamine makes rear-earth-doped sodium yttrium fluoride nanoparticle surface carry out biotin modification in anhydrous DMF, and nanoparticle component is: xLn3+-(1-x)NaYF4, wherein Ln3+=Yb3+、Er3+、Tm3+、Ho3+、Eu3+、Gd3+、Tb3+、Dy3+、Sm3+、Nd3+、Pr3+, 0 < x 50atom%.
5. the preparation method of the rear-earth-doped inorganic fluorescent nano-particle of biotin modification such as claim 1 or 2, it is characterized in that: utilize BTA-N, N, N', N'-tetramethylurea hexafluorophosphoric acid ester and N, N-diisopropylethylamine makes rear-earth-doped gadolinium fluoride nano grain surface carry out biotin modification in anhydrous DMF, and nanoparticle component is: yLn3+-(1-y)GdF3, wherein Ln3+=Yb3+、Er3+、Tm3+、Ho3+、Eu3+、Tb3+、Dy3+、Sm3+、Nd3+、Pr3+, 0 < y 50atom%.
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| CN116426282B (en) * | 2023-03-09 | 2024-04-12 | 深圳市光与生物科技有限公司 | Biotin modified rare earth doped inorganic material and preparation method thereof |
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