CN101092487A - Method for dyeing fluorescent microballons - Google Patents
Method for dyeing fluorescent microballons Download PDFInfo
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- CN101092487A CN101092487A CN 200710058397 CN200710058397A CN101092487A CN 101092487 A CN101092487 A CN 101092487A CN 200710058397 CN200710058397 CN 200710058397 CN 200710058397 A CN200710058397 A CN 200710058397A CN 101092487 A CN101092487 A CN 101092487A
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Abstract
This invention relates to a method for dyeing polymer microspheres to obtain fluorescent polymer microspheres. The method comprises: uniformly mixing fluorescein 0.01-80%, polymer microspheres 0.1-80%, emulsifier 0-10%, tackifier 0-10%, and solvent (one or more of good solvents and poor solvents) 18.9-99.89%, dyeing under 1-101 kPa in dark for 1-720 h, taking out the dyed polymer microspheres, and washing repeatedly. The obtained fluorescent polymer microspheres have such advantages as simple process, high fluorescent brightness, wide fluorescent spectrum range, uniform particle size distribution and low relative standard deviation, and can be used as absolute counting microspheres of flow cytometry, fluoroimmunoassay microspheres, biosensor, microfluidic chip, and calibrator of fluorescence microscope.
Description
Technical field
The present invention relates to analytical separation material technology field, particularly a kind of dyeing process of fluorescent microsphere.
Background technology
Flow cytometry can be applicable to high throughput analysis, the metabolic process analysis, and many fields such as drug invention, this method has high sensitivity, selectivity and convenience, can detect a plurality of parameters of a sample simultaneously, provides cell many-sided information.But in flow cytometry, be the accurate measurement number of cells, need a kind of absolute counting fluorescent microsphere as the interior reference substance that detects, require counting microballoon epigranular, fluorescence intensity is even, fluorescence emission spectrum a wider range.The domestic market does not have the product of homemade fluorescent microsphere at present, product is external import, the fluorescent microsphere majority that flow cytometry is used always is from InterfacialDynamics Corporation (IDC), companies such as Bangs Laboratories, other offshore companies such as BD, coulter etc. also act on behalf of fluorescent microsphere absolute counting product, the product of Bangs Laboratories company is mainly acted on behalf of by domestic crystalline substance U.S. company, domestic hospital at different levels and each province and city Center for Disease Control agents useful for same are offshore company's product, the price of these external reagent is very high, mainly be because preparation particle diameter and the uniform fluorescent microsphere technology of light intensity are more loaded down with trivial details, complexity, so cost is high.
Domestic patent CN1782020 has invented the silica fluorescent microballoon of bag year cadmium telluride fluorescence quantum, and patent CN1690163 adopts the induction phase political reform to obtain the polymkeric substance bag and carries the quantum dot fluorescent microsphere, but because particle diameter is less, is difficult to use in flow cytometry analysis; Patent CN1693411 adopts spray drying process to prepare magnetic fluorescent microspheres, but spray-drying process easily makes the fluorescein inactivation in the actually operating, patent CN1475805 mixes fluorescein simultaneously in the synthetic process, made magnetic fluorescent microspheres, but the brightness of fluorescent microsphere is difficult to improve, United States Patent (USP) is after the eighties, there are many pieces of patents to relate to the synthetic and matched reagent and the instrument research of fluorescent microsphere, as USP5073498, USP4157323, USP4336173, USP4714682, USP4774189 has related to the synthetic method of fluorescent microsphere and the use principle of fluorescein, but, because flow cytometry requires very high to the degree of uniformity of fluorescent microsphere, and for detecting emmission spectrum a wider range of a plurality of cell mass requirement fluorescent microspheres simultaneously, therefore how to prepare cheap, high brightness, particle diameter and light intensity are even, the fluorescent microsphere of wide fluorescence emission spectral limit all is the research emphasis in flow cytometry field all the time.
The calibration object of fluoroimmunoassay, biosensor, micro-control streaming chip, fluorescent microscope to the requirement of fluorescent microsphere and flow cytometer require close, fluoroimmunoassay, biosensor, micro-control streaming chip require fluorescent microsphere specificity to catch cell, nucleic acid, antibody or antigen to be detected, this just requires the fluorescent microsphere surface to have certain functional group, can catch material to be detected; And be used for the fluorescent microsphere calibration object of fluorescent microscope to the homogeneity of scope, fluorescent brightness and the particle diameter of fluorescence emission spectrum, be inspired the colour temperature of fluorescence, very high requirement is all arranged, how to make cheap, high performance fluorescent microsphere, always be the research emphasis in analytical separation field.
Summary of the invention
The present invention aims to provide that a kind of technology is simple, fluorescent brightness is high, fluorescence emission spectrum wide ranges, particle diameter and the uniform fluorescent microsphere of light distribution, and it can be applicable to absolute counting microballoon, fluoroimmunoassay microballoon, biosensor, the micro-control streaming chip of flow cytometer, the calibration object of fluorescent microscope etc. and analyzes separation field.
The dyeing process of fluorescent microsphere provided by the invention:
The dyeing process of a kind of fluorescent microsphere of the present invention, get the fluorescein of 0.01-80%, the polymer microballoon of 0.1-80%, add the emulsifying agent of 0-10%, the tackifier of 0-10%, the solvent that adds 18.9-99.89% again, solvent can be one or more the mixture in good solvent and the poor solvent, behind the system homodisperse under 1-101kPa lucifuge dyeing 1-720h, polymer microballoon after the dyeing is taken out, and washing for several times then.
Described micro polymer ball material is polyacrylate(s) and multipolymer, polystyrene type and multipolymer thereof or silica gel light transmission better polymerization thing material; Described fluorescein is alkaline safranine, pyrocatecholsulfon-phthalein, bromopyrogallol red, acridine, phenanthridines class such as the pyridine of bromination second, propidium iodide, rhodamine class nucleic acid fluorescein(e) dye, tetraiodofluorescein, coumarins, fluorescein isothiocyanate class, Xylene Brilliant Cyanine G albumen fluorescein(e) dye, algae is red/azurin, perdinin phyllochlorin, allophycocyanin cell dye, and one or more in Cadmium Sulfide class, cadmium selenide class or the zinc sulphide mineral-type fluorescein(e) dye.
Described polymer microballoon comprises the polymer microballoon that contains fluorescein or do not contain fluorescein, and the particle diameter of polymer microballoon is the 0.1-20 micron.Containing the fluorescein microballoon need keep in Dark Place, and storage temperature is-20～4 ℃.
Described good solvent comprises in halogenated alkane, alkane, ester class, ketone and the furans polymkeric substance good solvent one or more; Described poor solvent comprises in ethers, alcohols, sulfone, amides and the aqueous polymer poor solvent one or more.
Described solvent is trichloromethane, methylene dichloride, tetracol phenixin, two bromo ethane, as toluene, ethylbenzene, dimethylbenzene, normal hexane, normal heptane, hexanaphthene, benzene, as ethyl acetate, butylacetate, acetone, tetrahydrofuran (THF), ether, methyl ether, methyl alcohol, ethanol, propyl alcohol, butanols, dimethyl sulfoxide (DMSO), N, dinethylformamide and water.
Described emulsifying agent comprises one or more in sodium palmitate, sodium stearate, sodium lauryl sulphate, Sodium dodecylbenzene sulfonate, cetyl trimethylammonium bromide, N-domiphen, F-68, paraoctyl phenol Soxylat A 25-7, Span, emulsifying agent Tween, polyoxyethylene octylphenol ether, Soxylat A 25-7, polyethenoxy ether or the bovine serum albumin.
Described tackifier comprise one or more in gelatin, sodium lignosulfonate, oxygen cm-chitosan, the basic Mierocrystalline cellulose of hydroxyl first (second), polyvinylpyrrolidone, polyacrylic acid, glycerine, sodium alginate or the polyoxyethylene glycol.
The polymer fluorescent microspheres of preparation, particle diameter and fluorescence intensity are even, relative standard deviation is little, the fluorescent microsphere of various different brightness all can obtain, when on flow cytometer, analyzing, forward angle light scatter light numerical value, lateral angle scattered light numerical value and brightness number distribute very narrow, not with the cell distribution region overlapping; The fluorescence emission spectrum wide ranges, under same excitation light source, green fluorescence (FL-1), yellow fluorescence (FL-2) and red fluorescence (FL-3) all can obtain, and cover the fluorescence spectrum scope of most cells staining agent, have satisfied the requirement of flow cytometer to the fluorescent microsphere emmission spectrum.
Polymer microballoon can adopt normally used method, as processing molding method, is first with the polymer materials dissolution with solvents, can simultaneously fluorescein be dissolved in the solvent to add; Under dispersed with stirring such as mechanical stirring, magnetic agitation condition, oil phase is joined aqueous phase gradually then, perhaps by film such as SPG film, microfiltration membrane, oil phase is dispersed in aqueous phase, the lucifuge 1-24h that volatilizees in air takes out washing then for several times with polymer microballoon; Described water comprises one or more in common emulsifying agent, tackifier, pH value conditioning agent, low mass molecule alcohol class, inorganic salt, the sucrose.
In a word, compare with existing material, the fluorescent microsphere that the present invention relates to has that preparation technology is simple, fluorescent brightness is high, fluorescence emission spectrum wide ranges, size distribution are even, relative standard deviation is little, can be applicable to absolute counting microballoon, fluoroimmunoassay microballoon, biosensor, the micro-control streaming chip of flow cytometer, the calibration object of fluorescent microscope etc. and analyzes separation field.
Description of drawings
Fig. 1: the photo of fluorescent microsphere when no exciting light;
Fig. 2: fluorescent microsphere is at λ
EPhoto when=450～480nm, spectral filter＞515nm, the jaundice green fluorescence;
Fig. 3: fluorescent microsphere is at λ
EPhoto when=515～545nm, spectral filter＞590nm, rubescent look fluorescence;
Fig. 4: fluorescent microsphere is at λ
EPhoto when=350～380nm, spectral filter＞420nm, jaundice look fluorescence.
The kind of color and fluorescein is relevant, uses different exciting lights and spectral filter, thus be not that fluorescein can both excite, and the application range of products of this patent is very wide.λ
EThe expression excitation wavelength.
Specific implementation method
Provide embodiments of the invention below, be to further specify, rather than limit the scope of the invention of the present invention.
Embodiment 1:
Get the 0.001g fluorescein isothiocyanate, 0.01g particle diameter is 5 microns, relative standard deviation, and (market is on sale less than 2% crosslinked polystyrene microsphere, doubly think happy chromatographic technique development centre as Tianjin), after in fluorescein and microballoon, adding 0.1g dimethyl sulfoxide (DMSO) infiltration fluorescein and polystyrene microsphere, add the 9.889g trichloromethane again, mix back lucifuge dyeing 12h under 1kPa, the polystyrene microsphere after the dyeing is taken out, washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is 4%, is analyzing brightness on the flow cytometer between 2000-2200, and the fluorescence emission spectral limit is between 500-530nm.
Embodiment 2:
Get the 8g acridine orange, 0.01g particle diameter is 5 microns, relative standard deviation less than 10% silica gel microball, after in fluorescein and microballoon, adding 0.1g N, dinethylformamide infiltration fluorescein and silica gel microball, add 1.89g water again, mix back lucifuge dyeing 1h under 50kPa, silica gel microball after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is 15%, is analyzing brightness on the flow cytometer between 5000-10000, and the fluorescence emission spectral limit is between 500-600nm.
Embodiment 3:
Get the 0.1g trypaflavine, the 8g particle diameter is 5 microns, relative standard deviation less than 4% cross linked polyacrylate microballoon, adds 1.9g ethanol in fluorescein and microballoon, mixes back lucifuge dyeing 24h under 101kPa, polyacrylic acid microballoon after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is 5%, is analyzing brightness on the flow cytometer between 50-100, and the fluorescence emission spectral limit is between 500-650nm.
Embodiment 4:
Get 0.04g trypaflavine, 0.02g alkalescence safranine, 0.01g rhodamine, 0.04g particle diameter is 9 microns, relative standard deviation less than 2% crosslinked polystyrene microsphere, after in fluorescein and microballoon, being sequentially added into 0.1g N, dinethylformamide, 0.2g Span, 0.2g glycerine infiltration fluorescein and polystyrene, add 9.39g water again, mix back airtight lucifuge dyeing 720h under normal pressure, polystyrene microsphere after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is being analyzed brightness between 8000-8500 less than 4% on the flow cytometer, the fluorescence emission spectral limit is between 500-700nm.By the fluorescent microsphere of present embodiment preparation by different excitation, the photo when obtaining the fluorescent microscope photo (* 400) of different fluorescence emission spectral limits: Fig. 1 for no exciting light; Fig. 2 is that fluorescent microsphere is at λ
EPhoto when=450～480nm, spectral filter＞515nm, the jaundice green fluorescence; Fig. 3 is that fluorescent microsphere is at λ
EPhoto when=515～545nm, spectral filter＞590nm, rubescent look fluorescence; Fig. 4 is that fluorescent microsphere is at λ
EPhoto when=350～380nm, spectral filter＞420nm, jaundice look fluorescence.λ
EIt is Olympus CX51 that expression excites light wavelength, used fluorescent microscope.
Embodiment 5:
Getting the 0.04g cadmium selenide is the quantum dot fluorescence element of shell for nuclear, Cadmium Sulfide, get the 0.04g particle diameter and be 9 microns, relative standard deviation less than crosslinked polystyrene-maleic anhydride microballoon of 2%, after in fluorescein and microballoon, being sequentially added into 0.5g sodium lauryl sulphate, 0.5g paraoctyl phenol Soxylat A 25-7 infiltration fluorescein and microballoon, add 1.92g two bromo ethane, the 1g hexanaphthene that mixes again, add 6g water again behind the dyeing 1h, lucifuge dyeing 48h under 50kPa then, microballoon after the dyeing is taken out, and washing for several times.The fluorescence light intensity relative standard deviation of thus obtained microsphere is being analyzed brightness between 500-800 less than 4% on the flow cytometer, the fluorescence emission spectral limit is between 530-560nm.
Embodiment 6:
Get 0.04g zinc sulphide quantum dot fluorescence element, 0.01g perdinin phyllochlorin, get the 0.05g particle diameter and be 9 microns, relative standard deviation less than crosslinked polystyrene-methylene-succinic acid microballoon of 2%, after in fluorescein and microballoon, being sequentially added into 0.5g polyvinylpyrrolidone, 0.5g polyoxyethylene glycol infiltration fluorescein and microballoon, add 4.92g methylene dichloride, 4g normal heptane again, mix back lucifuge dyeing 72h under 40kPa, microballoon after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is being analyzed brightness between 500-800 less than 4% on the flow cytometer, the fluorescence emission spectral limit is between 530-650nm.
Embodiment 7:
Get 0.04g acridine orange, 0.04g rhodamine, 0.04g tonka bean camphor, get the 0.04g particle diameter and be 9 microns, relative standard deviation less than crosslinked polystyrene-vinylformic acid microballoon of 2%, in fluorescein and microballoon, be sequentially added into 0.1g sodium palmitate, 0.1g F-68,0.1g sodium lignosulfonate, 0.1g polyacrylic acid, 4g ethylbenzene, 5.44g normal hexane, mix back lucifuge dyeing 12h under 1kPa, microballoon after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is being analyzed brightness between 8000-8500 less than 4% on the flow cytometer, the fluorescence emission spectral limit is between 500-700nm.
Embodiment 8:
Get 0.04g pyrocatecholsulfon-phthalein, 0.04g bromopyrogallol red, 0.04g tetraiodofluorescein, get the 0.5g particle diameter and be 9 microns, relative standard deviation less than crosslinked polystyrene-methacrylic acid microballoon of 2%, after in fluorescein and microballoon, being sequentially added into 0.1g sodium stearate, 0.1g tween 80,0.1g gelatin, 0.1g sodium alginate infiltration fluorescein and microballoon, be sequentially added into 4g toluene, 4.98g tetracol phenixin again, mix back lucifuge dyeing 48h under 1kPa, microballoon after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is being analyzed brightness between 1000-1500 less than 4% on the flow cytometer, the fluorescence emission spectral limit is between 500-700nm.
Embodiment 9:
Get 0.04g propidium iodide, 0.04g algae red/azurin, 0.04g cadmiumsulfide quantum dot, get the 0.1g particle diameter and be 6 microns, relative standard deviation and be 20% polystyrene microsphere (can adopt the machine-shaping method preparation), in fluorescein and microballoon, be sequentially added into 0.1g cetyl trimethylammonium bromide, 0.1g Soxylat A 25-7,0.1g oxygen cm-chitosan, 8.98g methyl alcohol, 0.4g benzene, 0.1g tetrahydrofuran (THF), mix back lucifuge dyeing 72h under 1kPa, microballoon after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is being analyzed brightness between 400-1 000 less than 30% on the flow cytometer, the fluorescence emission spectral limit is between 500-700nm.
Embodiment 10:
Get the pyridine of 0.04g bromination second, 0.06g CdSe quantum dots, get the 0.1g particle diameter and be 7 microns, relative standard deviation and be 10% polystyrene microsphere (can adopt the machine-shaping method preparation), in fluorescein and microballoon, be sequentially added into 0.1g cetyl trimethylammonium bromide, 0.1g polyoxyethylene octylphenol ether, 0.1g Walocel MT 20.000PV, 9g methyl ether, 0.5g butylacetate, mix back lucifuge dyeing 72h under 1kPa, microballoon after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is being analyzed brightness between 400-800 less than 15% on the flow cytometer, the fluorescence emission spectral limit is between 500-650nm.
Embodiment 11:
Get 0.004g Xylene Brilliant Cyanine G, 0.006g allophycocyanin, get the 0.02g particle diameter and be 7 microns, relative standard deviation and be 11% polystyrene-maleic anhydride copolymer microsphere (can adopt the machine-shaping method preparation), in fluorescein and microballoon, be sequentially added into 0.01g Sodium dodecylbenzene sulfonate, 0.01g polyethenoxy ether, 0.01g Natvosol, 0.92g propyl alcohol, 0.01g ethyl acetate, 0.01g dimethylbenzene, mix back lucifuge dyeing 72h under 1kPa, microballoon after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is being analyzed brightness between 800-1500 less than 15% on the flow cytometer, the fluorescence emission spectral limit is between 530-750nm.
Embodiment 12:
Getting the 0.04g fluorescein isothiocyanate, getting the 0.05g particle diameter is that 20 microns, relative standard deviation are 10%, painted polystyrene-Sipacril 2739OF microballoon (can adopt the machine-shaping method preparation), in fluorescein and microballoon, be sequentially added into 0.1g Sodium dodecylbenzene sulfonate, 0.1g bovine serum albumin, 4.51g butanols, 0.1g ether, 0.1g acetone, mix back airtight lucifuge dyeing 240h under normal pressure, microballoon after the dyeing is taken out, and washing for several times then.The fluorescence light intensity relative standard deviation of thus obtained microsphere is being analyzed brightness between 2000-2500 less than 14% on the flow cytometer, the fluorescence emission spectral limit is between 450-550nm.
The present invention discloses and discloses the dyeing process of fluorescent microsphere, can be by using for reference this paper disclosure.Although high brightness polychrome list of the present invention disperses fluorescent microsphere and preparation method thereof to be described by preferred embodiment, but those skilled in the art obviously can change method as herein described in not breaking away from content of the present invention, spirit and scope, more particularly, the replacement that all are similar and change apparent to those skilled in the artly, they are regarded as being included in spirit of the present invention, scope and the content.
Claims (8)
1. the dyeing process of a fluorescent microsphere, it is characterized in that: the fluorescein of getting 0.01-80%, the polymer microballoon of 0.1-80%, add the emulsifying agent of 0-10%, the tackifier of 0-10%, the solvent that adds 18.9-99.89% again, solvent are one or more the mixture in good solvent and the poor solvent, behind the system homodisperse under 1-101kPa lucifuge dyeing 1-720h, polymer microballoon after the dyeing is taken out, and washing for several times then.
2. the dyeing process of fluorescent microsphere as claimed in claim 1 is characterized in that described micro polymer ball material is polyacrylate(s) and multipolymer, polystyrene type and multipolymer thereof or silica gel light transmission better polymerization thing material; Described fluorescein is alkaline safranine, pyrocatecholsulfon-phthalein, bromopyrogallol red, acridine, phenanthridines class such as the pyridine of bromination second, propidium iodide, rhodamine class nucleic acid fluorescein(e) dye, tetraiodofluorescein, coumarins, fluorescein isothiocyanate class, Xylene Brilliant Cyanine G albumen fluorescein(e) dye, algae is red/azurin, perdinin phyllochlorin, allophycocyanin cell dye, and one or more in Cadmium Sulfide class, cadmium selenide class or the zinc sulphide mineral-type fluorescein(e) dye.
3. the dyeing process of fluorescent microsphere as claimed in claim 1 or 2 is characterized in that described polymer microballoon comprises the polymer microballoon that contains fluorescein or do not contain fluorescein, and the particle diameter of polymer microballoon is the 0.1-20 micron.
4. the dyeing process of fluorescent microsphere as claimed in claim 3 is characterized in that the described microballoon that contains fluorescein need keep in Dark Place, and storage temperature is-20～4 ℃.
5. the dyeing process of fluorescent microsphere as claimed in claim 1 is characterized in that described good solvent comprises in halogenated alkane, alkane, ester class, ketone and the furans polymkeric substance good solvent one or more; Described poor solvent comprises in ethers, alcohols, sulfone, amides and the aqueous polymer poor solvent one or more.
6. the dyeing process of fluorescent microsphere as claimed in claim 5, it is characterized in that described solvent is trichloromethane, methylene dichloride, tetracol phenixin, two bromo ethane, as toluene, ethylbenzene, dimethylbenzene, normal hexane, normal heptane, hexanaphthene, benzene, as ethyl acetate, butylacetate, acetone, tetrahydrofuran (THF), ether, methyl ether, methyl alcohol, ethanol, propyl alcohol, butanols, dimethyl sulfoxide (DMSO), N, dinethylformamide and water.
7. the dyeing process of fluorescent microsphere as claimed in claim 1 is characterized in that described emulsifying agent comprises one or more in sodium palmitate, sodium stearate, sodium lauryl sulphate, Sodium dodecylbenzene sulfonate, cetyl trimethylammonium bromide, N-domiphen, F-68, paraoctyl phenol Soxylat A 25-7, Span, emulsifying agent Tween, polyoxyethylene octylphenol ether, Soxylat A 25-7, polyethenoxy ether or the bovine serum albumin.
8. the dyeing process of fluorescent microsphere as claimed in claim 1 is characterized in that described tackifier comprise one or more in gelatin, sodium lignosulfonate, oxygen cm-chitosan, the basic Mierocrystalline cellulose of hydroxyl first (second), polyvinylpyrrolidone, polyacrylic acid, glycerine, sodium alginate or the polyoxyethylene glycol.
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