CN1896738A - Fluorescent nano-particle with surface biological function, its production and use - Google Patents
Fluorescent nano-particle with surface biological function, its production and use Download PDFInfo
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- CN1896738A CN1896738A CN 200610025985 CN200610025985A CN1896738A CN 1896738 A CN1896738 A CN 1896738A CN 200610025985 CN200610025985 CN 200610025985 CN 200610025985 A CN200610025985 A CN 200610025985A CN 1896738 A CN1896738 A CN 1896738A
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Abstract
This invention relates to a preparation method and its application of nuclear shell fluorescence nanometer particle whose surface living things is functional. The particle has nuclear shell structure, fluorescence material is hit in the inner core; the outer shell is composed of fluorescence transparency material; and there is embellishing organic function group in the outer covering. The nanometer particle is formed by the reversal tiny emulsion method, and doing chemical modification in the surface to make it to be biology functional nanometer particle. The nanometer particle has important application prospect in the fields such as cell biology, ultramicrochemistry, within the AMD chemistry, living things big molecule detecting and medical in-vivo diagnosing.
Description
Background technology
In recent years, the Measurement for Biotechnique fast development, wherein the research of carrying out biomolecule in complex environment that develops into of hypersensitization detection technique of fluorescence provides condition.And the foundation of hypersensitization detection technique of fluorescence depends on nontoxic and the successful development biocompatibility luminescent material.
Organic fluorescent substance is classical fluorescent material, though organic fluorescent substance is because its intrinsic character has its shortcoming, as fluorescence efficiency problem or the like, but the fluorescent material as classics still has the field of its widespread use with respect to present inorganic fluorescent substance, as is applied to flow cytometry, is applied to antibody labeling or the like.
The biological function formed material is the popular domain in investigation of materials field always, in the biological function formed material, nano material since eighties of last century since the eighties because its special physicochemical character, more and more be subjected to the attention of scientists, thereby utilize the significant problem of nanotechnology research and solution biological field also to become one of important advanced research field.
Be applied to biological field as the functionalization material and but do not have more further investigation yet organic fluorescence materials and nano material combined, external existing research is modified at the fluorescent material of this type the surface of nano material by the method for chemistry.Yet fluorescent material is wrapped in does not but have relevant report within the nano material, more not with the surface active of nano particle, or claim " surface biological functionalization ", even the surface can connect the Research on ability of nucleic acid, protein, nucleotide, amino acid, antibody, polypeptide, animal and plant cells, subcellular structure, virus, bacterium or the like biomacromolecule or biosome itself.
Summary of the invention
Technical matters to be solved
The technical issues that need to address of the present invention provide hud typed fluorescent nano particles of a kind of surface biological functionalization and its production and application, only modify to overcome in the prior art fluorescent material, and can't make fluorescent nano material possess the defective of biomolecule combined function simultaneously in nano-material surface.
Technical scheme
One of content of the present invention provides a kind of hud typed fluorescent nano particles of surface biological functionalization, possesses the hud typed structure of kernel and shell: contain fluorescent material in its inner nuclear layer; Outer shell is made of the penetrating material of fluorescence; The outer shell surface is the decorative layer of organo-functional group.
A kind of preferred version of above-mentioned biological functional fluorescence nano particle is that said organo-functional group is amino, carboxyl or sulfydryl, perhaps its combination.
The another kind of preferred version of above-mentioned biological functional fluorescence nano particle is, said fluorescent material is fluorescein isothiocynate, RB 200, TRITC, phycoerythrin, fluorescein isothiocynate FITC is preferably selected in perhaps its combination.
The another kind of preferred version of above-mentioned biological functional fluorescence nano particle is that said outer shell composition is silicon dioxide, agarose, olefin polymer, polyacrylonitrile or epoxy compound, perhaps its combination.
Those of ordinary skill in the art need not special experiment and can understand, and preparing said outer shell composition can be inorganic integument, and for example amino silane, hydrosulphonyl silane can also be organic integument, for example glucosides, protein etc.The preferred amino silane of inorganic integument, the preferred glucosides of organic integument.Preferably, its composition is selected from silicon dioxide, agarose, olefin polymer, polyacrylonitrile, epoxy compound or its combination; Best, the outer shell component of described inner nuclear layer is a silicon dioxide.
Two of content of the present invention provides a kind of method for preparing the hud typed fluorescent nano particles of said surface biological functionalization, comprises the steps:
(1) provides the aqueous solution of isopropyl alcohol and fluorescent material;
(2) ammoniacal liquor and ethyl orthosilicate are taken up in order of priority add in the said aqueous solution of step (1), under the condition of room temperature, react and obtained fluorescent particles in 3～5 hours;
(3) in the alcoholic solution of the fluorescent particles of step (2), add amination, carboxylated or sulfhydrylization reagent,, promptly obtain the fluorescent nano particles of surface biological functionalization 25～60 ℃ of reactions 1～6 hour down.
The present invention provides the another kind of preparation method of the hud typed fluorescent nano particles of above-mentioned surface biological functionalization simultaneously, comprises the steps:
(1) provides the microemulsion of TritonX-100, n-hexyl alcohol, cyclohexane and fluorescent material;
(2) ammoniacal liquor and ethyl orthosilicate are taken up in order of priority add in the said aqueous solution of step (1), under the condition of room temperature, react and obtained fluorescent particles in 8～15 hours;
(3) in the alcoholic solution of the fluorescent particles of step (2), add amination, carboxylated or sulfhydrylization reagent,, promptly obtain the fluorescent nano particles of surface biological functionalization 25～60 ℃ of reactions 1～6 hour down.
The preparation method's of the hud typed fluorescent nano particles of two kinds of above-mentioned surface biological functionalization preferred version is, said amination, carboxylated or sulfhydrylization reagent are respectively N-(2-amino-ethyl)-3-TSL 8330,3-sulfydryl propyl trimethoxy silicane, 3-sulfydryl propyl trimethoxy silicane, also can be mercaptoacetic acid or mercaptopropionic acid.
Those of ordinary skill in the art need not special experiment and can understand, and said dressing agent is the silanes dressing agent, but is not limited to above-mentioned several.For selected outer shell component, those skilled in the art can select suitable shell layer forming agent for use according to prior art.For example when outer shell component is silicon dioxide, can select ethyl orthosilicate or other suitable shell layer forming agent for use.
A kind of preferred version of above-mentioned biological functional fluorescence nano particle preparation method is, contain in the said microemulsion system TritonX-100, n-hexyl alcohol, cyclohexane by, its volume ratio is 1: 1～3: 4～6.
Two of content of the present invention provides the application of above-mentioned biological functional fluorescence nano particle, and the said functional group that organises combines with nucleic acid, protein, nucleotide, amino acid or its derivant by chemical bond.
The another kind of above-mentioned biological functional fluorescence nano particle is applied as, and said functional group and the animal and plant cells or subcellular structure or virion of organising combines.
Beneficial effect
1, fluorescent material is only modified in nano-material surface and is compared in biological functional fluorescence nano particle of the present invention and the prior art, nano material is not only possessed outside the performance that fluorescence labeling can indicate easily, also possesses organo-functional group, combine with nucleic acid, protein, nucleotide, amino acid or its derivant by chemical bond, so the biologic applications function that combines with animal and plant cells or subcellular structure or virion.
2, experiment of the present invention shows, fluorescent material is wrapped in nano particle after, its luminosity is stable, even particle distribution, smooth surface, is that a kind of novel ultra micro detects nano material.
3, its outer shell of biological functional fluorescence nano particle of the present invention adopts the material that silicon dioxide, agarose etc. are nontoxic, have biocompatibility, makes to be applied to biochemical field and to become possibility.
4, preparation method of the present invention adopts organic fluorescent substance with low cost, shell to form agent etc., makes practical large-scale production have feasibility.
5, adopt nano particle parcel fluorescent material and biological function group, can effectively bring into play the surface area advantage of nano material, improve biological respinse efficient, accelerate the reaction time, reduce the total amount of reaction system simultaneously, make carry out trace detection and micro-reaction simple and easy to do.
6, the nano particle of biological functional provides the foundation for the research of the physicochemical property of the biomaterial on the nanometer level, and the expansion possibility of its application further is provided simultaneously.
7, on nano particle of the present invention, connect nucleic acid, protein, nucleotide, amino acid, antibody, polypeptide, animal and plant cells, subcellular structure, virus, bacterium or the like, can be widely used in the detection of each quasi-molecule and the spike treatment of disease.
Description of drawings
Fig. 1 is the transmission electron microscope photo of silicon dioxide parcel fluorescent nano particles.As can be seen from the figure, the nano particle that has wrapped up fluorescent material has very regular form, has good monodispersity, shows that silicon dioxide well is wrapped in fluorescent material wherein.
Fig. 2 is the fluorescent microscope photo of the nano particle of silicon dioxide parcel fluorescent material.As can be seen, parcel fluorescent material nano particle has good photoluminescent property, proves further that also silicon dioxide successfully is wrapped in fluorescent material wherein simultaneously among the figure.
Fig. 3 is the fluorescence spectrum of the nano particle of silicon dioxide parcel fluorescent material.As can be seen, parcel fluorescent material nano particle has fluorescence intensity preferably, proves further that also silicon dioxide successfully is wrapped in fluorescent material wherein simultaneously from collection of illustrative plates.
Fig. 4 is a Raman spectrum of modifying the nano particle of sulfydryl.From collection of illustrative plates as can be seen, 2167cm
-1The place is the Raman spectrum of SH.1328cm
-1Ownership is CH
2Wagging vibration spectrum, 1388cm
-1And 1464cm
-1Be CH
2The stretching vibration peak position, and 1594cm
-1Can point out stretching vibration peak position, 2934cm into the C-C chain
-1Near bands of a spectrum then belong to CH
2Antisymmetric stretching vibration, 395cm
-1The peak at place is that the vibration of C-C deformation of chain produces.(CH
2) n and Si-O
-The symmetrical stretching vibration of local mode appear at 1075cm
-1Near.At 1003cm
-1And 502cm
-1The place has corresponding
-O-Si-O
-The symmetrical stretching vibration of local mode.1231cm
-1The peak position at place is the flexible vibrations of C-Si, 668cm
-1And 730cm
-1The Raman peak position at two places then is to produce because of the stretching vibration of C-S key.The appearance of the Raman peaks of carbon silicon key, silicon oxygen bond, carbon-carbon bond, hydrocarbon key and carbon-sulfur bond has shown that sulfhydryl compound successfully has been connected on the surface of nano particle, and has the effective sulfydryl of part to be exposed on the surface of nano particle.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
The experimental technique of unreceipted actual conditions in the following example, usually according to normal condition, as the chemical products handbook, or the condition of advising according to manufacturer.All inorganic chemical reagents and organic solvent are available from Shanghai chemical reagent factory, and fluorescein isothiocynate, N-(2-amino-ethyl)-3-TSL 8330, mercaptoacetic acid, 3-sulfydryl propyl trimethoxy silicane (MPTS) are available from Sigma company.
The preparation method one of hud typed fluorescent nano particles
Isopropyl alcohol and water are evenly mixed ultrasonic 5min according to 5: 1 ratio.Take by weighing the fluorescent material fluorescein isothiocynate FITC of 0.1～0.8mg, be configured to aqueous solution, sonicated 10min.Get the upper strata stillness of night and pour in the three-neck flask, constantly stir and make its maintenance disperse state.Get the strong aqua of 1mL, it is slowly joined in the solution system of continuous stirring.Then get the ethyl orthosilicate of 1～3mL, equally it is slowly joined in the solution system of continuous stirring.System was reacted under the condition of room temperature 3～5 hours.Reaction product is poured out, washed particle 3～5 times with redistilled water.The vacuum drying 5 hours under 20～50 ℃ temperature of particle after the cleaning, it is standby to collect particle.From Fig. 1 we as can be seen silicon dioxide well fluorescent material is wrapped in wherein.
Embodiment 2
The preparation method two of hud typed fluorescent nano particles
TritonX-100, n-hexyl alcohol, cyclohexane are evenly mixed in 1: 2: 5 ratio, form the microemulsion system of transparent and stable.Place ultrasound wave to handle 30～60 minutes above-mentioned microemulsion system,, take out upper strata liquid after 6 minutes with ultrasonic Treatment and pour in the three-neck flask, stir and made it even in 30 minutes to wherein adding fluorescent material fluorescein isothiocynate FITC 0.5mg.Get the 1mL strong aqua with the dilution of 2mL redistilled water, after 30 minutes it is slowly joined in the microemulsion of continuous stirring, continue stirring and ammoniacal liquor was dispersed in the microemulsion in 30 minutes.After 1 hour, in microemulsion, drip the ethyl orthosilicate of 1～3mL, constantly stirred 10 hours simultaneously, and the temperature of system is remained between 15～30 ℃.In system, add acetone and make particle precipitation, perhaps the system standing over night is made the particle natural sedimentation, use the ethanol wash particle.Drying particulate sample under the condition of vacuum.
Embodiment 3
Fluorescent nano particles surface amido modified
Get the fluorescent nano particles that makes in 20mg embodiment 1 or 2, add in the methyl alcohol and the mixed liquor of glycerine of 30～50mL, use ultrasonic Treatment 20～60 minutes in 5: 3 ratio compositions; Take by weighing 1～3mL AEAPS[N-(2-amino-ethyl)-3-TSL 8330], use ultrasonic Treatment 10～60 minutes; These two kinds of solution are mixed, and reaction is 5 hours under 60 ℃ condition, takes out particle then and uses washed with methanol 3 times, then 40～80 ℃ of vacuum drying 2 hours, collects particle and obtains the fluorescent nano particles that finishing has amino biological functional.
Embodiment 4
The carboxyl modified on fluorescent nano particles surface
Get the fluorescent nano particles that makes in embodiment 1 or 2 and join (pH=4.5) in the buffer solution that consists of acetate ethanol, ultrasonic mixing; 3-sulfydryl propyl trimethoxy silicane (MPTS) joins in the same buffer solution.Two kinds of buffer solution are mixed, reacted under the temperature conditions of routine 2～4 hours, the centrifuging particle after same buffer solution washing three times, 60 ℃ of following vacuum drying, is collected particle.
The particle of collecting is scattered in the same buffer solution, in solution system, add mercaptoacetic acid, solution is uniformly dispersed, after system is reacted 2～4 hours at normal temperatures, particle is collected in centrifuging, wash the final vacuum drying several times, obtain the fluorescent nano particles of the biological functional of finishing carboxyl.
Embodiment 5
The sulfydryl modification on fluorescent nano particles surface
Get the fluorescent nano particles that makes in embodiment 1 or 2 and join in the acetate ethanol damping fluid (pH=4.5), ultrasonic evenly mixed; Simultaneously, 3-sulfydryl propyl trimethoxy silicane (MPTS) is joined in another acetate ethanol damping fluid.Mix above-mentioned two kinds of solution, behind reaction 1h under 25 ℃ the situation, take out particle, after the damping fluid (pH=4.5) of usefulness acetate ethanol cleans three times, vacuum drying 2h in the time of 60 ℃, collection table particle obtains showing the biological functional fluorescence nano particle that is modified with sulfydryl.As can be seen, sulfydryl has been modified the surface of fluorescent nano particles from the Raman sign collection of illustrative plates of Fig. 4.
Embodiment 6
Amido modified fluorescent nano particles is applied to Protein Separation
Get the biological functional fluorescence nano particle of the finishing amino of 1～3mg such as embodiment 3 preparations, join pH and be in 7.0～8.0 the phosphate buffer, adding consumption is 50～200 μ L crosslinking chemicals such as glutaraldehyde or the like, forms mixed solution.Described mixed solution is used ultrasonic Treatment 10～30 minutes.Under suitable temperature conditions, reacted 4～6 hours.After supernatant is removed in centrifuging, use phosphate buffer supersound washing 2～3 times then after, again particle is scattered in phosphate buffer solution.
Take by weighing a certain amount of Chinese medicine (glossy ganoderma, Radix Angelicae Sinensis, Radix Astragali or the like), handle according to the method for boiling medicine of traditional Chinese medicine, the impurity in the solution is removed in centrifuging, and it is standby to collect the supernatant that contains protein ingredient.
Get a certain amount of supernatant solution, to wherein adding a certain amount of particle solution, the vibration mixing, at room temperature reacted 1～3 hour, supernatant is removed in centrifuging, and with phosphate buffer solution washing 1～2 time, the particle that is connected with albumen with gained is scattered in the phosphate buffer solution standby again at last.
With the above-mentioned particle solution that is connected with albumen, join in the cancer cell or normal cell of in vitro culture, observe in the various different Chinese medicines different protein ingredients for the effect of the apoptosis and the Normocellular multiplication capacity of cancer cell.
Embodiment 7
The fluorescent nano particles of carboxyl modified is applied to RNA and disturbs
Get in a certain amount of the foregoing description 4 the biological functional fluorescence nano particle of having modified carboxyl of preparation, join pH and be in 7.0～8.0 the phosphate buffer, form mixed solution.Described mixed solution is used ultrasonic Treatment 10～30 minutes.
Get the little RNA (siRNA) of the two strands interference that is modified with amino particular sequence of q.s, join in the mixed solution of the above-mentioned particle that contains about 2mL.At room temperature reacted 3 hours, and keep constantly vibration, thereby amino on the siRNA and the carboxyl on the outer shell are reacted under the effect of fixing agent, and be directly connected in outer shell.After reaction finished, ultra-filtration and separation went out described particle, with phosphate buffer washing 3 times.The fluorescent nano particles that is connected with the double-stranded little RNA that disturbs that obtains like this places phosphate buffer to preserve.
With the above-mentioned particle solution that is connected with siRNA, join in the phagocytotic cell of having of in vitro culture, observe different siRNA sequences for the effect of cell-specific gene inhibition, also can be used for the transfection spike of cell and monitoring in real time.
Embodiment 8
Modify amino fluorescent nano particles and be applied to the cell monitoring
Get the biological functional fluorescence nano particle of the finishing amino of 1～3mg such as embodiment 3 preparations, join pH and be in 7.0～8.0 the phosphate buffer, adding consumption is 50～200 μ L crosslinking chemicals, forms mixed solution.Described mixed solution is used ultrasonic Treatment 10～30 minutes.Under suitable temperature conditions, reacted 4～6 hours.After supernatant is removed in centrifuging, use phosphate buffer supersound washing 2～3 times then after, again particle is scattered in phosphate buffer solution.
Get the monoclonal antibody of about 3 micrograms, join in the mixed solution of the above-mentioned particle that contains about 2mL.Reaction is 3 hours under 2～10 ℃ temperature of reaction, thereby amino on the antibody and the amino on the outer shell are reacted under the effect of fixing agent, makes antibody pass through Schiff Bond (Schiff key) and is directly connected in outer shell.After reaction finished, centrifuging went out described particle, with phosphate buffer washing 3 times.The fluorescent nano particles that is modified with monoclonal antibody that obtains like this places phosphate buffer to preserve, and utilizes the fluorescent nano particle that contains antibody molecule, can detect the denier harmful bacteria quickly and accurately.This nano particle adds in the lysate that detects sample, will adhere to one with bacterium; Then by centrifugal method, different according to the size of asking of nano particle and bacterial cell can make bacterium and nano particle coprecipitation get off; Be attached with from nano particle on the bacterium that separates, just can determine according to the luminescence phenomenon of these particles whether the bacterium that will detect exists.This detection method uses the specific antibody of anti-target bacteria to make fluorescent particles, makes the specificity of detection very high; In addition, owing to simultaneously thousands of fluorescent particles particle-bound bacterias are arranged, so even individual cells also can detect.
Claims (10)
1. the hud typed fluorescent nano particles of a surface biological functionalization possesses the hud typed structure of kernel and shell: contain fluorescent material in its inner nuclear layer; Outer shell is made of the penetrating material of fluorescence; The outer shell surface is the decorative layer of organo-functional group.
2. the hud typed fluorescent nano particles of surface biological functionalization according to claim 1 is characterized in that, said organo-functional group is amino, carboxyl or sulfydryl, perhaps its combination.
3. the hud typed fluorescent nano particles of surface biological functionalization according to claim 1 is characterized in that, said fluorescent material is fluorescein isothiocynate, RB 200, TRITC, phycoerythrin, perhaps its combination.
4. the hud typed fluorescent nano particles of surface biological functionalization according to claim 1 is characterized in that, said outer shell composition is silicon dioxide, agarose, olefin polymer, polyacrylonitrile or epoxy compound, perhaps its combination.
5. the hud typed fluorescent nano particles of surface biological functionalization according to claim 4 is characterized in that, said outer shell composition is a silicon dioxide.
6. the preparation method of the hud typed fluorescent nano particles of the described surface biological functionalization of claim 1 comprises the steps:
(1) provides the aqueous solution of isopropyl alcohol and fluorescent material;
(2) ammoniacal liquor and ethyl orthosilicate are taken up in order of priority add in the said aqueous solution of step (1), under the condition of room temperature, react and obtained fluorescent particles in 3～5 hours;
(3) in the alcoholic solution of the fluorescent particles of step (2), add amination, carboxylated or sulfhydrylization reagent,, promptly obtain the fluorescent nano particles of surface biological functionalization 25～60 ℃ of reactions 1～6 hour down.
7. the preparation method of the hud typed fluorescent nano particles of the described surface biological functionalization of claim 1 comprises the steps:
(1) provides the microemulsion of TritonX-100, n-hexyl alcohol, cyclohexane and fluorescent material;
(2) ammoniacal liquor and ethyl orthosilicate are taken up in order of priority add in the said aqueous solution of step (1), under the condition of room temperature, react and obtained fluorescent particles in 8～15 hours;
(3) in the alcoholic solution of the fluorescent particles of step (2), add amination, carboxylated or sulfhydrylization reagent,, promptly obtain the fluorescent nano particles of surface biological functionalization 25～60 ℃ of reactions 1～6 hour down.
8. according to the preparation method of the hud typed fluorescent nano particles of claim 6 or 7 described surface biological functionalization, it is characterized in that, said amination, carboxylated or sulfhydrylization reagent are respectively N-(2-amino-ethyl)-3-TSL 8330,3-sulfydryl propyl trimethoxy silicane, 3-sulfydryl propyl trimethoxy silicane, also can be mercaptoacetic acid or mercaptopropionic acid.
9. the application of the hud typed fluorescent nano particles of the described surface biological functionalization of claim 1 is characterized in that, the functional group that organises of said particle surface combines with nucleic acid, protein, nucleotide, amino acid or its derivant by chemical bond.
10. the application of the hud typed fluorescent nano particles of the described surface biological functionalization of claim 1 is characterized in that, organise functional group and the animal and plant cells or subcellular structure or virion of said particle surface combine.
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| CN101440279B (en) * | 2008-12-17 | 2011-11-16 | 暨南大学 | Fluorescent nano-particle with composite silica shell structure and preparation thereof |
| CN101526534A (en) * | 2009-03-10 | 2009-09-09 | 沈鹤柏 | Fluorescence immune chromatography test paper and preparing method and application thereof |
| CN103105492A (en) * | 2013-01-17 | 2013-05-15 | 重庆市科学技术研究院 | Fluorescence immunochromatography flu virus detection test paper |
| CN106165129A (en) * | 2014-04-10 | 2016-11-23 | 欧司朗光电半导体有限公司 | Luminaire and the method being used for manufacturing luminaire |
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| CN104897889A (en) * | 2015-05-28 | 2015-09-09 | 山东省医学科学院基础医学研究所 | Preparation method of fluorescent SiO2 colloidal reagent, and test paper adopting fluorescent SiO2 colloidal reagent |
| CN104897889B (en) * | 2015-05-28 | 2017-03-01 | 山东省医学科学院基础医学研究所 | Fluorescence SiO2The preparation method of colloidal agent and use fluorescence SiO2The reagent paper of colloidal agent |
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| CN109444251A (en) * | 2018-11-23 | 2019-03-08 | 亿纳谱（浙江）生物科技有限公司 | Application of the nanomatrix in detection of nucleic acids |
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