CN105001865A - Novel method for converting oil-soluble up-conversion nano particles into water-soluble up-conversion nano particles - Google Patents
Novel method for converting oil-soluble up-conversion nano particles into water-soluble up-conversion nano particles Download PDFInfo
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Abstract
The invention discloses a novel method for converting oil-soluble up-conversion nano particles into water-soluble up-conversion nano particles. The novel method for converting the oil-soluble up-conversion nano particles into the water-soluble up-conversion nano particles comprises the specific following steps that firstly, the oil-soluble up-conversion nano particles subjected to centrifugal purification are dispersed in a certain volume of chloroform, so that an oil-soluble up-conversion nano particle solution with the concentration being 10-30 mg/ml is obtained; secondly, molecules containing hydrophile groups are dissolved in a certain volume of deionized water, and the concentration of the deionized water is made to be 1-100 mM; thirdly, the solution prepared in the first step and the solution prepared in the second step are mixed, a magnetic stirring reaction is conducted on the mixed solution for 3-24 hours at the indoor temperature; finally, the up-conversion nano particles are transferred into water, so that the water-soluble up-conversion nano particles are obtained. The novel method has the advantages that implement is convenient and fast, operation is easy, further special treatment is not needed, and the reaction condition is mild; in addition, the efficiency of converting the oil-soluble up-conversion nano particles into the water-soluble up-conversion nano particles is high through the method, and particle colloid is quite stable; meanwhile, the particles are modified with functional groups which can act with other biomolecules easily, and thus the application range of the particles on the aspects of fluorescence analysis, biological detection, biological making, cell imaging and the like is widened.
Description
Technical field
The invention belongs to technical field of nano material, be specifically related to a kind of novel method oil-soluble upper conversion nano particle being transferred to water-soluble upper conversion nano particle.
Background technology
Upper conversion nano particle is a kind of nano material that the light of near infrared long wavelength can be transformed into short-wavelength light, the process of its luminescence is anti-Stokes displacement process, under the exciting of continuous near infrared light, launch the light of short wavelength, wherein that most study is lanthanon (Er
3+, Ho
3+and Tm
3+) NaYF that mixes
4nanocrystal, its luminous efficiency is higher, and emmission spectrum is narrow, and fluorescence lifetime is long, and background interference during for detecting and scattered light disturb more weak, in cell imaging research, biological detection, biomarker, targeted drug conveying etc., have larger application potential.
It is high that recent research can prepare fluorescence efficiency, and granule-morphology is homogeneous, the lanthanon (Er of good dispersity
3+, Ho
3+and Tm
3+) NaYF that adulterates
4nanocrystal, but the preparation of most upper conversion particles is synthesized in high temperature organic solvent, the particle surface obtained wraps up one deck organic ligand, show as extremely strong hydrophobicity, so just greatly limit the application of conversion particles in cell imaging, biomarker, biological detection etc.Therefore convert hydrophobic upper conversion nano particle to water miscible upper conversion nano particle, modify simultaneously and can just become with the active reactive group of other molecularity the problem needing solution badly.
The existing method realizing hydrophobic upper conversion nano particle to turn by changing surface group aqueous phase has: 1, by upper conversion particles pan coating one deck silicon shell, realize aqueous phase transfer by silica-based upper connection hydrophilic radical; 2, utilize strong oxidizer that the double bond in hydrophobic group is oxidized to carboxyl, in realization, conversion particles turns aqueous phase; 3, to utilize and the stronger hydrophilic ligand in return agent of upper conversion particles binding ability, replace the hydrophobic group on conversion particles surface, in realization, conversion particles turns aqueous phase; 4, utilize the hydrophobic side alkyl chain of amphiphilic polymer molecule and the Van der Waals force of particle surface hydrophobic nature alkyl chain, make the hydrophobic side alkyl chain of amphipathic nature polyalcohol molecule be embedded into the clearance space of hydrophobic nature alkyl chain, in realization, conversion particles turns aqueous phase.Wherein ligand exchange conventional turns aqueous phase method, bag can be reduced the stability of particle colloid greatly by one deck silicon shell, part oxidizing reaction is time-consuming, and productive rate is lower, utilize amphipathic nature polyalcohol molecule hydrophobic side embedding inlay technique can cause the instability of particle colloid, easy coagulation.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, provide a kind of convenient and swift, simple to operate, reaction conditions is gentle, efficiency is high and the method by ligand exchange, conversion nano particle on oil soluble being transferred to water-soluble upper conversion nano particle that particle colloid is more stable.
For achieving the above object, the present invention is based on the exchange principle of conversion nano particle surface part and hydrophilic molecule group, utilize hydrophilic radical and lanthanon (Er
3+, Ho
3+and Tm
3+) NaYF that adulterates
4ion positive and negative charge effect in nanocrystal, in realization, conversion nano particle transfers to the object of aqueous phase from oil phase.Concrete technical scheme of the present invention transfers conversion nano particle on oil soluble to water miscible novel method for a kind of, and its process comprises the following steps:
Step one, by conversion nano Granular composite on the oil soluble of centrifugal purification in the chloroform of certain volume, obtain conversion nano particle solution on oil soluble that concentration is 10 ~ 30mg/ml;
Step 2, by the molecular melting containing hydrophilic radical in the deionized water of certain volume, make its concentration be 1 ~ 100mM;
Step 3, solution mixing above-mentioned steps one, step 2 obtained, room temperature lower magnetic force stirring reaction 3 ~ 24h, obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase.
According to the method described above oil-soluble upper conversion nano particle is transferred to water-soluble, turns aqueous phase method and relate to following several feature:
One, the hydrophobic grouping of oil-soluble upper conversion nano particle comprises oleic acid base, oleyl amine base etc.;
Two, for water soluble molecules that the hydrophilic molecule of ligand exchange is containing phosphate, 1 ~ 3 phosphate is contained in its one end, the other end contains hydrophilic radical, mainly comprise: Alendronic Acid, 1-hydroxyethyl-1,1-bisphosphate, 3-phosphoric acid propionic acid, aminomethyl phosphonic acid, ciliatine, Medronate, 1-amino-ethyl phosphoric acid etc.;
Turn aqueous phase technology relative to existing upper conversion particles, the present invention produce beneficial effect and be: 1, the invention provides and a kind ofly conveniently go up the method that conversion nano particle turns aqueous phase, simple to operate, without the need to further special processing, reaction conditions is gentle; 2, to turn aqueous phase efficiency higher for method provided by the invention, particle colloid is more stable, modify simultaneously and gone up the functional group be easy to other biological molecularity, and the upper conversion nano particle turning aqueous phase has good biocompatibility, therefore, its application in fluorometric analysis, biological detection, biomarker, cell imaging etc. is extended.
For investigation the inventive method turns the stability of aqueous phase particle, devise a series of investigation to granule stability and test.With Alendronic Acid, 1-hydroxyethyl-1,1-bisphosphate, 3-phosphoric acid propionic acid three kinds of water soluble molecules for example, specific experiment scheme is as follows: secure ph is the phosphate buffer soln 3mL of 3,4,5,6,7,8,9,10,11,12.1. respectively get the buffered soln 170 μ L of different pH value, the Alendronic Acid adding 30 μ L is respectively the upper conversion particles of part, and with the laser of 980nm for excitation light source, record its fluorescence intensity at various ph values, fluorescence intensity figure is shown in accompanying drawing 1.Accompanying drawing 1 shows that the water-soluble nanoparticles after changing has good stability.2. respectively get the buffered soln 170 μ L of different pH value, 1-hydroxyethyl-1, the 1-bisphosphate adding 30 μ L is respectively the upper conversion particles of part, and with the laser of 980nm for excitation light source, record its fluorescence intensity at various ph values, fluorescence intensity figure is shown in accompanying drawing 2.Accompanying drawing 2 shows that the water-soluble nanoparticles after changing has good stability.3. respectively get the buffered soln 170 μ L of different pH value, the 3-phosphoric acid propionic acid adding 30 μ L is respectively the upper conversion particles of part, and with the laser of 980nm for excitation light source, record its fluorescence intensity at various ph values, fluorescence intensity figure is shown in accompanying drawing 3.Accompanying drawing 3 shows that the water-soluble nanoparticles after changing has good stability.To sum up, accompanying drawing 1,2 and 3 shows, this stability turning the water-soluble upper conversion nano particle that aqueous phase method obtains is better.
For investigating the inventive method phase transition effect over time, designing and having carried out time investigation.Specifically be implemented as follows:
1. the chloroformic solution 1ml of conversion nano particle on the oil soluble getting 30mg/ml, add the Alendronic Acid aqueous solution 2ml of 20mM, normal temperature lower magnetic force stirring reaction, the reaction times be 0,1,5,10,20,60,120,180,240,300min time get supernatant liquor 20 μ L, be diluted to 200 μ L with deionized water, record fluorescent value respectively.Experimental result shows, after 3 hours, fluorescence intensity reaches stable.
2. the chloroformic solution 1ml of conversion nano particle on the oil soluble getting 30mg/ml, add the 1-hydroxyethyl-1 of 20mM, 1-bisphosphate aqueous solution 2ml, normal temperature lower magnetic force stirring reaction, the reaction times be 0,1,5,10,20,60,120,180,240,300min time get supernatant liquor 20 μ L, be diluted to 200 μ L with deionized water, record fluorescent value respectively.Experimental result shows, after 3 hours, fluorescence intensity reaches stable.
3. the chloroformic solution 1ml of conversion nano particle on the oil soluble getting 30mg/ml, add the 3-phosphoric acid propionic acid aqueous solution 2ml of 20mM, normal temperature lower magnetic force stirring reaction, the reaction times be 0,1,5,10,20,60,120,180,240,300min time get supernatant liquor 20 μ L, be diluted to 200 μ L with deionized water, record fluorescent value respectively.Experimental result shows, after 3 hours, fluorescence intensity reaches stable.
Above-mentioned experimental result shows, normal temperature lower magnetic force churning time can be controlled in more than 3 hours.
In order to verify that the inventive method obtains the reliability and stability of upper conversion particles, design and carried out the mtt assay cytotoxicity experiment of water-soluble upper conversion particles, as the foundation evaluating water-soluble upper conversion particles biological safety and the application potential in biological direction.Specifically be implemented as follows: water-soluble nanoparticles 50 μ g/ml, the 100 μ g/ml of equivalent different concns, 150 μ g/ml, 200 μ g/ml, 300 μ g/ml, 400 μ g/ml and HeLa cell are cultivated 24h, then detect cell survival rate, result cell survival rate is more than 80%.Result shows that the inventive method obtains conversion nano particle and has lower vitro cytotoxicity and good biocompatibility.
In addition, in order to verify the application of upper conversion nano particle in cell imaging that the inventive method obtains, designing and having carried out cell imaging experiment.Result shows that water-soluble upper conversion nano particle prepared by the inventive method is at cell imaging, and there is good application prospect in biomarker direction.
Accompanying drawing explanation
Fig. 1 is the laser of 980nm when being excitation light source, and clinic effect of alendronate is the upper conversion nano particle fluorescence intensity figure at various ph values of part.
Fig. 2 is the laser of 980nm when being excitation light source, and 1-hydroxyethyl-1,1-di 2 ethylhexyl phosphonic acid is the upper conversion nano particle fluorescence intensity figure at various ph values of part.
Fig. 3 is the laser of 980nm when being excitation light source, and 3-phosphonic acids propionic acid is the upper conversion nano particle fluorescence intensity figure at various ph values of part.
Fig. 4 be preparation oil soluble on conversion nano particle TEM figure.
Fig. 5 is the TEM figure of the water-soluble upper conversion nano particle of preparation.
Fig. 6 is fluorescence spectrum figure and the fluorescence imaging of conversion nano particle on oil soluble.
Fig. 7 is fluorescence spectrum figure and the fluorescence imaging of water-soluble upper conversion nano particle.
Embodiment
Below in conjunction with embodiment, the present invention is described in further details, but protection scope of the present invention is not limited thereto.
Embodiment 1
Step one, by after conversion nano particle centrifugation on oil soluble, be dissolved in the chloroform of 5ml, preparation concentration be 10mg/ml oil soluble on transform nanoparticles solution, its TEM figure is shown in Fig. 4, and its fluorescence spectrum figure and fluorescence imaging are shown in Fig. 6;
Step 2, be dissolved in the deionized water of 5ml by hydrophilic molecule Alendronic Acid, preparation concentration is the aqueous solution of 25mM;
Step 3, the solution mixing that step one, step 2 are obtained, under 25 DEG C of conditions, magnetic agitation reaction 3h, namely obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase, its TEM figure is shown in Fig. 5, and its fluorescence spectrum figure and fluorescence imaging are shown in Fig. 7.
To sum up, the test comparison of Fig. 4 and Fig. 5 and the test comparison of Fig. 6 and Fig. 7, show that the upper conversion nano particle of the inventive method turns aqueous phase effect fine.
Embodiment 2
Step one, by after conversion nano particle centrifugation on oil soluble, be dissolved in the chloroform of 5ml, preparation concentration is the upper conversion nanoparticles solution of 20mg/ml, step 2, is dissolved in the deionized water of 5ml by water soluble molecules Alendronic Acid, and preparation concentration is the aqueous solution of 50mM;
Step 3, solution mixing step one, step 2 obtained, under 25 DEG C of conditions, magnetic agitation reaction 3h, final upper conversion nano transfer of granules, in aqueous phase, obtains water-soluble upper conversion nano particle.
In addition, its transmissioning electric mirror test result and fluorometric investigation result similar to Example 1, show that the upper conversion nano particle of the inventive method turns aqueous phase effect fine.
Embodiment 3
Step one, by after conversion nano particle centrifugation on oil soluble, be dissolved in the chloroform of 5ml, preparation concentration is the upper conversion nanoparticles solution of 30mg/ml;
Step 2, be dissolved in the deionized water of 5ml by water soluble molecules Alendronic Acid, preparation concentration is the aqueous solution of 100mM;
Step 3, solution mixing step one, step 2 obtained, under 25 DEG C of conditions, magnetic agitation reaction 3h, namely obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase.
In addition, its transmissioning electric mirror test result and fluorometric investigation result similar to Example 1, show that the upper conversion nano particle of the inventive method turns aqueous phase effect fine.
Embodiment 4
Step one, by after conversion nano particle centrifugation on oil soluble, be dissolved in the chloroform of 5ml, preparation concentration is the upper conversion nanoparticles solution of 10mg/ml;
Step 2, be dissolved in the deionized water of 5ml by water soluble molecules 1-hydroxyethyl-1,1-bisphosphate, preparation concentration is the aqueous solution of 25mM;
Step 3, solution mixing step one, step 2 obtained, under 25 DEG C of conditions, magnetic agitation reaction 3h, namely obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase.
In addition, its transmissioning electric mirror test result and fluorometric investigation result similar to Example 1, show that the upper conversion nano particle of the inventive method turns aqueous phase effect fine.
Embodiment 5
Step one, by after conversion nano particle centrifugation on oil soluble, be dissolved in the chloroform of 5ml, preparation concentration is the upper conversion nanoparticles solution of 20mg/ml;
Step 2, be dissolved in the deionized water of 5ml by water soluble molecules 1-hydroxyethyl-1,1-bisphosphate, preparation concentration is the aqueous solution of 50mM;
Step 3, solution mixing step one, step 2 obtained, under 25 DEG C of conditions, magnetic agitation reaction 3h, namely obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase.
In addition, its transmissioning electric mirror test result and fluorometric investigation result similar to Example 1, show that the upper conversion nano particle of the inventive method turns aqueous phase effect fine.
Embodiment 6
Step one, by after conversion nano particle centrifugation on oil soluble, be dissolved in the chloroform of 5ml, preparation concentration is the upper conversion nanoparticles solution of 30mg/ml;
Step 2, be dissolved in the deionized water of 5ml by water soluble molecules 1-hydroxyethyl-1,1-bisphosphate, preparation concentration is the aqueous solution of 100mM;
Step 3, solution mixing step one, step 2 obtained, under 25 DEG C of conditions, magnetic agitation reaction 3h, namely obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase.
In addition, its transmissioning electric mirror test result and fluorometric investigation result similar to Example 1, show that the upper conversion nano particle of the inventive method turns aqueous phase effect fine.
Embodiment 7
Step one, by after conversion nano particle centrifugation on oil soluble, be dissolved in the chloroform of 5ml, preparation concentration is the upper conversion nanoparticles solution of 10mg/ml;
Step 2, be dissolved in the deionized water of 5ml by water soluble molecules 3-phosphoric acid propionic acid, preparation concentration is the aqueous solution of 25mM;
Step 3, solution mixing step one, step 2 obtained, under 25 DEG C of conditions, magnetic agitation reaction 3h, namely obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase.
In addition, its transmissioning electric mirror test result and fluorometric investigation result similar to Example 1, show that the upper conversion nano particle of the inventive method turns aqueous phase effect fine.
Embodiment 8
Step one, by after conversion nano particle centrifugation on oil soluble, be dissolved in the chloroform of 5ml, preparation concentration is the upper conversion nanoparticles solution of 20mg/ml;
Step 2, be dissolved in the deionized water of 5ml by water soluble molecules 3-phosphoric acid propionic acid, preparation concentration is the aqueous solution of 50mM;
Step 3, solution mixing step one, step 2 obtained, under 25 DEG C of conditions, magnetic agitation reaction 3h, namely obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase.
In addition, its transmissioning electric mirror test result and fluorometric investigation result similar to Example 1, show that the upper conversion nano particle of the inventive method turns aqueous phase effect fine.
Embodiment 9
Step one, by after conversion nano particle centrifugation on oil soluble, be dissolved in the chloroform of 5ml, preparation concentration is the upper conversion nanoparticles solution of 30mg/ml;
Step 2, be dissolved in the deionized water of 5ml by water soluble molecules 3-phosphoric acid propionic acid, preparation concentration is the aqueous solution of 100mM;
Step 3, the solution mixing that step one, step 2 are obtained, under 25 DEG C of conditions, magnetic agitation reaction 3h, namely obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase.
In addition, its transmissioning electric mirror test result and fluorometric investigation result similar to Example 1, show that the upper conversion nano particle of the inventive method turns aqueous phase effect fine.
To sum up embodiment shows, the inventive method does not transform concentrations of nanoparticles, the restriction of water soluble ligand kind, concentration and impact by oil soluble, turns aqueous phase respond well according to the upper conversion nano particle of the inventive method.
Claims (4)
1. conversion nano particle on oil soluble is transferred to a novel method for water-soluble upper conversion nano particle, it comprises the following steps:
Step one, by conversion nano Granular composite on the oil soluble of centrifugal purification in the chloroform of certain volume, obtain conversion nano particle solution on oil soluble that concentration is 10 ~ 30mg/ml;
Step 2, by the molecular melting containing hydrophilic radical in the deionized water of certain volume, make its concentration be 1 ~ 100mM;
Step 3, solution mixing above-mentioned steps one, step 2 obtained, room temperature lower magnetic force stirring reaction 3 ~ 24h, obtains water-soluble upper conversion nano particle in final upper conversion nano transfer of granules to aqueous phase.
2. a kind of novel method conversion nano particle on oil soluble being transferred to water-soluble upper conversion nano particle as claimed in claim 1, is characterized in that: on oil soluble, conversion nano particle surface is coated with oil-containing acidic group, the hydrophobic molecule that oil is amino etc.
3. a kind of novel method conversion nano particle on oil soluble being transferred to water-soluble upper conversion nano particle as claimed in claim 1, is characterized in that: the described molecule containing hydrophilic radical is that phosphate is contained in one end, and the other end contains the molecule of hydrophilic radical R.
4. a kind of novel method conversion nano particle on oil soluble being transferred to water-soluble upper conversion nano particle as claimed in claim 3, it is characterized in that: described is 1 ~ 3 containing the quantity of the phosphate of one end in the molecule of hydrophilic radical, and its other end hydrophilic radical R can be-OH ,-CHO ,-COOH or-NH
2deng, the quantity of hydrophilic radical R is 1 ~ 3, and the carbon chain length connecting phosphate and R is 2 ~ 5 carbonatomss.
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