CN101602942A - A kind of organic molecular probe material and preparation method thereof with nucleocapsid structure - Google Patents
A kind of organic molecular probe material and preparation method thereof with nucleocapsid structure Download PDFInfo
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- CN101602942A CN101602942A CN 200910069818 CN200910069818A CN101602942A CN 101602942 A CN101602942 A CN 101602942A CN 200910069818 CN200910069818 CN 200910069818 CN 200910069818 A CN200910069818 A CN 200910069818A CN 101602942 A CN101602942 A CN 101602942A
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Abstract
A kind of organic molecular probe material with nucleocapsid structure, core are transition metal complex, and shell is parents' polymkeric substance, and metal ion is Ru
2+(ruthenium), Os
2+(osmium) or Re
+(rhenium), part are single or polysubstituted phenanthroline and single or polysubstituted 2,2 '-dipyridyl; Parents' polymkeric substance is the multipolymer that polyethylene glycol methacrylate-styrene polymer and Dimethylaminoethyl Methacrylate form.Advantage of the present invention is to have nucleocapsid structure, its with transition metal complex fluorescent material inclusion in parents' polymkeric substance, help strengthening ligand exchange in the fluorescent material opposing complex cell environment and cell quick oxidative metabolism to fluorescent material, thus the fluorescence radiation performance of stable complex; Owing to this class globe-type luminescence nanoparticle has been realized fast the double-tagging function of trace labelling and long-term follow mark in good time to the transfection function of implanting the fluorescence protein gene plasmid, therefore make its application more extensive.
Description
[technical field]
The present invention relates to the molecular probe material in the fluorescence imaging technology, especially a kind of organic molecular probe material and preparation method thereof with nucleocapsid structure.
[background technology]
The appearance of molecular imaging technology, it is all multifactor to give the credit to the development of molecular biology and cytobiology, the fluorescence molecule label probe of high specific and the development of cell imaging equipment etc.In recent years, because the fluorescence imaging technology has intuitively, the mark target spot is various, expense is cheap and simple operation and other advantages, has become a focus of current research cytobiology.Many traditional organic dye are widely used in the research of cell imaging as the fluorescent probe molecule of chemical marker method as fluorescein derivative, rhodamine, ultramarine element, glimmering (BODIPY) series derivates of fluorine boron and some rare earth compoundings and inorganic quantum dot.But these materials are in the defective that all exists some to be difficult to overcome aspect chemiluminescent labelling and the living imaging, such as: organic dye is easy to be bleached and oxidative metabolism in vivo, and its excitation spectrum often is in the high-energy district and causes a little less than the penetration power and the background luminescence serious interference; Also there is certain application limitation in inorganic cadmium class quantum dot owing to finally want metabolism to go out toxic ions such as cadmium and selenium.Therefore exploitation has stable luminescent property, cell-penetrating power is strong, biocompatibility reaches the clear and definite novel molecular probe material of target by force becomes the root problem that the fluorescence imaging technology must solve.
In recent years, based on transition metal complex have that stability of photoluminescence is strong, luminous zone is narrow, absorption and emission wavelength is in infrared and characteristics such as near infrared, carry out the research that chemical labeling is used for the fluorocyte imaging technique as fluorescent molecular probe.Transition metal complex is had the following advantage as the cell fluorescence image forming material: 1) its stability of photoluminescence is strong, is convenient to the target of research is carried out long original position and time-space resolution tracking, and constantly extracts relevant target information in this process; 2) the narrow background interference that helps getting rid of the luminous of mark image forming material and archebiosis light of its luminous zone; 3) it excites spectrum width, is convenient to adopt the exciting light in biological printing opacity ' window ' district that the mark image forming material is excited, thereby gets rid of the injury of tissue and the penetration power of enhancing exciting light, thereby helps the correlation circumstance of track cells inside.
[summary of the invention]
The objective of the invention is at above-mentioned existing problems, provide that a kind of stable luminescent property, cell-penetrating power are strong, that biocompatibility reaches target by force is clear and definite and the preparation method is simple has organic molecular probe material of nucleocapsid structure and preparation method thereof.
Technical scheme of the present invention:
A kind of organic molecular probe material with nucleocapsid structure, the core that forms nucleocapsid structure is a transition metal complex, shell is parents' polymkeric substance; The metal ion of described transition metal complex is Ru
2+(ruthenium), Os
2+(osmium) or Re
+(rhenium), part are single the replacement or polysubstituted coffee sound of vomiting quinoline and single replace or polysubstituted 2, and 2 '-dipyridyl, its substituting group are 4-{9,9 '-(two replace fluorenyl) }-phenyl or 4-{9,9 '-[N, N '-(two carbazyl alkyl)] fluorenyl }-phenyl; Parents' polymkeric substance is the multipolymer that polyethylene glycol methacrylate-styrene polymer (PEGMA) and Dimethylaminoethyl Methacrylate (DMAEMA) form, and its structural formula is DMAEMA
51-b-PEGMA
65-b-DMAEMA
51
A kind of as above-mentioned preparation method with organic molecular probe material of nucleocapsid structure, its step is as follows: 1) synthetic method prepares described transition metal complex and parents' polymkeric substance respectively routinely; 2) parents' polymkeric substance and the transition metal complex with above-mentioned preparation is dissolved in the methylene dichloride, steam solvent then, add pH again and be 7.1 PBS buffered soln, adopt the ultrasonic dispersing system, be the polycarbonate membrane filtration of 0.20um～0.75um with the aperture then, can make the nano spherical particle of organic molecular probe material with nucleocapsid structure.
The mol ratio of described parents' polymkeric substance and transition metal complex is 1: 1～10.
The weight ratio of described parents' polymkeric substance and transition metal complex and methylene dichloride is 1: 100～500.
The weight ratio of described parents' polymkeric substance and transition metal complex and PBS buffered soln is 1: 1000～5000.
A kind of as above-mentioned organic molecular probe material with nucleocapsid structure, be used for pair cell and carry out the Infrared fluorescence mark, method is the nanoparticle of the organic molecular probe material with nucleocapsid structure of preparation to be cultivated with 293T cell and common cancer cells be no more than 1 hour, under 360～800nm optical excitation, this nanoparticle 580～900nm wavelength region launch single infrared/near-infrared fluorescent, can carry out the Infrared fluorescence mark by pair cell, the diameter of described nanoparticle is less than 100nm.
A kind of as above-mentioned organic molecular probe material with nucleocapsid structure, be used for fluorescin transfection mark, method be will the preparation the organic molecular probe material with nucleocapsid structure nanoparticle with the implantation fluorescence protein gene plasmid combine after, with 293T cell and common cancer cells co-cultivation 24～72 hours, can realize fluorescin transfection mark, also keep the infrared/near-infrared luminous performance of this nanoparticle simultaneously.
The structure explanation of organic molecular probe material of the present invention:
Organic molecular probe material of the present invention has nucleocapsid structure, and its core is a transition metal complex, and shell is parents' polymkeric substance; The part of transition metal complex is single the replacement or polysubstituted coffee sound of vomiting quinoline and single replacement or polysubstituted 2,2 '-dipyridyl, its substituting group is 4-{9,9 '-(two replace fluorenyl) }-phenyl or 4-{9,9 '-[N, N '-(two carbazyl alkyl)] fluorenyl }-phenyl, be that the structure of the transition metal complex of part is wherein with coffee sound of vomiting quinoline
M＝Ru，n＝3，n′＝2，X
-＝anion
M＝Os，n＝3，n′＝2，X
-＝anion
M＝Re(CO
3Cl)，n＝1，n′＝0，X
-＝0，
With 2,2 '-dipyridyl is that the structure of the transition metal complex of part is
M＝Ru，n＝3，n′＝2，X
-＝anion
M＝Os，n＝3，n′＝2，X
-＝anion
M＝Re(CO
3Cl)，n＝1，n′＝0，X
-＝0，
Its substituting group 4-{9,9 '-(two replace fluorenyl) }-structure of phenyl is
m＝0-10，
4-{9,9 '-[N, N '-(two carbazyl alkyl)] fluorenyl }-structure of phenyl is
m＝0-10；
Parents' polymkeric substance is the multipolymer that polyethylene glycol methacrylate-styrene polymer (PEGMA) and Dimethylaminoethyl Methacrylate (DMAEMA) form, and structural formula is DMAEMA
51-b-PEGM
65-b-DMAEMA
51, its structure is
R＝CH
3；CH
2CH
3。
Advantage of the present invention is, this organic molecular probe material has nucleocapsid structure, its with transition metal complex fluorescent material inclusion in parents' polymkeric substance, help strengthening ligand exchange in the fluorescent material opposing complex cell environment and cell quick oxidative metabolism to fluorescent material, thus the fluorescence radiation performance of stable complex; This preparation methods is simple, cost is low; Simultaneously, owing to this class globe-type luminescence nanoparticle has been realized fast the double-tagging function of trace labelling and long-term follow mark in good time to the transfection function of implanting the fluorescence protein gene plasmid, therefore make its application more extensive.
[embodiment]
Embodiment 1:
1) transition metal complex Re (phen) (CO)
3Cl is 3-{2-[9,9-two [6-(N-carbazyl hexyl) fluorenyls]] }-phenyl-adjacent coffee sieve quinoline chlorination three carbonyls close the synthetic of rhenium:
With 3-{2-[9,9-two [6-(N-carbazyl hexyl) fluorenyl]]-phenyl-adjacent coffee sieve quinoline 422mg (0.5mmol) and Re (CO)
3Cl 181mg (0.5mmol) adds in the 50mL toluene, back flow reaction 12 hours, and steaming desolventizes, and then resistates is used the silica gel column chromatography chromatography, and methylene dichloride is the wash-out meter, can make transition metal complex Re (phen) (CO)
3390 milligrams of Cl, productive rate 68%.
1H NMR (400MHz, CDCl
3, TMS) δ=9.59 (d, J=1.6Hz, 1H), 9.40 (d, J=4.4Hz, 1H), 8.52 (t, J=3.4Hz, 2H), 8.03 (dd, J=3.6Hz, 7.6Hz, 4H), 7.95 (dd, J=8.8Hz, 15.2Hz, 2H), 7.86 (d, J=7.6Hz, 1H), 7.83 (t, J=8.0Hz, 1H), 7.76 (d, J=7.2Hz, 1H), 7.68 (d, J=8.0Hz, 1H), 7.64 (s, 1H), 7.38 (t, J=8.0Hz, 5H), 7.32 (t, J=7.2Hz, 1H), 7.28 (d, J=8.4Hz, 5H), 7.16 (t, J=7.4Hz, 4H), 4.15 (t, J=7.2Hz, 4H), 2.10-1.93 (m, 4H), 1.68 (t, J=6.4Hz, 4H), 1.20-1.12 (m, 8H), and 0.65-0.61 (m, 4H)
13C NMR (75MHz, CDCl
3, TMS) δ=196.9,189.6,153.0,152.2,150.9,147.1,145.3,143.0,140.3,140.2,139.9,137.9,134.7,133.7,130.7,130.5,128.2,127.8,127.7,125.5,122.9,122.8,122.7,121.9,121.0,120.4,120.2,118.6,118.5,108.6,55.4,42.9,40.2,29.6,28.7,26.7,23.6. ultimate analysis theoretical value C
64H
54ClN
4O
3Re:C, 66.91; H, 4.74; N, 4.88. actual value: C, 67.45; H, 4.88; N, 4.75.Above-mentioned analytical data shows that the structure of title complex is 3-{2-[9,9-two [6-(N-carbazyl hexyl) fluorenyls]] }-phenyl-adjacent coffee sieve quinoline chlorination three carbonyls close rhenium Re (phen) (CO)
3Cl.
2) parents' polymkeric substance DMAEMA
51-b-PEGMA
65-b-DMAEMA
51Synthetic:
Adopt Transfer Radical Polymerization (ATRP), with N, two (the 2-bromine isobutyryl) propylene diamine of N-are initiator, in 500 milliliters round bottom reaction flask, add monomer polyethylene glycol methacrylate-styrene polymer (PEGMA) 9.5mL (21.6mmol), CuBr 51.6mg (0.36mmol) and tetrahydrofuran (THF) 200mL, this reaction mixture is used nitrogen replacement 30 minutes; And then add hexamethyl tetramine 98 μ L (0.36mmol) and N, and two (2-bromine isobutyryl) the propylene diamine 73.6mg (0.18mmol) of N-, this reaction mixture was 40 ℃ of reactions 6 hours; Add second monomer Dimethylaminoethyl Methacrylate (DMAEMA) 6mL (35.6mmol) again, continue reaction 12 hours at 40 ℃; Reaction solution is the drip washing solvent with acetone, adopts the silica gel chromatography column chromatography for separation to go out Catalysts Cu Br, obtains product with petroleum ether precipitation after steaming solvent, with its vacuum-drying 24 hours, can make 12 gram parents polymkeric substance after the filtration.
1H NMR (400MHz, D
2O, TMS): δ=4.19 (COO-CH
2-CH
2-N (CH
3)
2,-COO-CH
2-CH
2-O-), 3.72 (O-CH
2-CH
2-O-), 3.36 (O-CH
3), 2.76 (O-CH
2-CH
2-N (CH
3)
2), 2.36 (N (CH
3)
2) .GPC:Mn=47,113, Mw/Mn=1.14. determines that according to the methyl number of DMAEMA and PEGMA the structure of parents' polymkeric substance is DMAEMA
51-b-PEGMA
65-b-DMAEMA
51
3) with the above-mentioned parents' polymkeric substance 30mg (0.64umol) that makes and transition metal complex Re (phen) (CO)
3Cl2.78mg (2.5umol) is dissolved in 1mL CH
2Cl
2In and thorough mixing dissolving become the solution of homogeneous, then with solvent C H
2Cl
2Under 45 ℃, steam, obtain a yellow transparent gel; Add the pH value then and be 7.1 PBS damping fluid 30mL, sonic oscillation 30 minutes, adopt the aperture to be the polycarbonate membrane filtration of 0.45um after, can make the nano spherical particle of organic molecular probe material with nucleocapsid structure.Uv-absorbing is at 368nm; Excite down at the 380nm wavelength, emission wavelength is 580nm; Adopting transmission electron microscope to record particle dia is 40nm～55nm.
Nonactive bovine serum of 17ul and the above-mentioned nano spherical particle that makes of 151uL are mixed, evenly be added drop-wise to then and preset mankind kidney cell HEK293T (well cell density 8 * 10
4) 24 hole enzyme joint inspection drafting boards in, co-cultivation is 1 hour in the standard cell lines incubator, with the PBS damping fluid cell is cleaned 3 times then, (Nikon, Japan) fluorescent microscope excites the globe-type luminescence nanoparticle enters cell as fluorescence labeling material the situation of observing down at the 380nm wavelength to adopt TE 2000-U.The result proves, co-cultivation in the time of 1 hour cell be marked as redness, the co-cultivation redness that cell is labeled in the time of 2 hours is darker.
Embodiment 2:
1) transition metal complex Ru (bpy)
3(PF
6)
2Promptly three 5-[2-[9,9-two [6-(N-carbazyl hexyl) fluorenyl]]]-phenyl-2,2 '-dipyridyl } close the synthetic of ruthenious hexafluorophosphate:
With 5-[2-[9,9-two [6-(N-carbazyl hexyl) fluorenyl]]]-phenyl-2,2 '-dipyridyl 169.5mg (0.3mmol) and [Ru (DMSO)
4] Cl
248.5mg (0.1mmol) add in the 20mL ethanolic soln, under the lucifuge condition, refluxed 24 hours; Add 80mg KPF then
6(80mg) continue to reflux 2 hours; Add 30 ml waters behind the cool to room temperature, filter out precipitated product, and with 5 ml water washed twice; Adopt silica gel column chromatography then, go out product, can obtain the pulverous transition metal complex Ru of 104mg red solid (bpy) after the vacuum-drying with the eluent methylene chloride that contains 3% acetone
3(PF
6)
2MS(MALDI-ToF)：m/z?1941.2.
1H?NMR(500MHz，CDCl3)：8.62(bs，3H，PyH)，8.55(bs，3H，PyH)，8.01(bs，3H，PyH)，7.97(bs，3H，PyH)，7.91(d，6H，J＝7.4Hz，PhH)，7.86(bs，3H，PyH)，7.83(d，6H，J＝7.4Hz，PhH)，7.81(bs，3H，PyH)，7.75(d，3H，J＝7.7Hz，fluo-H)，7.71(d，3H，J＝7.7Hz，fluo-H)，7.60(3，3H，fluo-H)，7.58(d，3H，J＝7.7Hz，fluo-H)，7.51(bs，3，PyH)，7.36-7.31(m，9H，fluoreneH)，2.01(t，12H，J＝8.0Hz，CH
2)，1.09-1.04(m，36Hz，CH
2)，0.73(t，18H，J＝7.0Hz，CH
3)，0.67(s，12H，CH
2).
13C?NMR(125MHz，CDCl3)：157.04，156.90，151.81，151.16，149.86，144.03，141.45，140.57，138.49，138.21，134.09，128.32，127.91，127.47，127.00，126.13，125.75，124.42，124.28，123.07，121.47，120.23，120.04，55.36，40.49，31.58，29.79，23.91，22.67，14.10。Above-mentioned analytical results shows the structural formula of title complex be three { 5-[2-[9,9-two [6-(N-carbazyl hexyl) fluorenyl]]]-phenyl }-2,2 '-dipyridyl } close ruthenious hexafluorophosphate [Ru (bpy)
3(PF
6)
2].
2) polymkeric substance DMAEM
51-b-PEGM
65-b-DMAEMA
51Synthetic: identical with embodiment 1;
3) with above-mentioned parents' polymkeric substance 30mg (0.64umol) that makes and transition metal complex Ru (bpy)
3(PF
6)
29.2mg (3.0umol) be dissolved in 5mL CH
2Cl
2In and thorough mixing dissolving become the solution of homogeneous, then with CH
2Cl
2Solvent steams under 35 ℃ and obtains a yellow transparent gel; Add the pH value then and be 7.1 PBS damping fluid 30mL, sonic oscillation 30 minutes, adopt the aperture to be the polycarbonate membrane filtration of 0.20um after, can make the nano spherical particle of organic molecular probe material with nucleocapsid structure.Uv-absorbing is at 465nm; Excite down at the 465nm wavelength, emission wavelength is at 650nm; Adopt transmission electron microscope to record particle dia between 65-85nm.
The PBS solution of the above-mentioned nano spherical particle that makes of 160uL and the plasmid (pEGFP-C2,2.0 μ g) of implanting green fluorescence protein gene are mixed, add the nonactive bovine serum of 15ul then and mix; Again this solution evenly is added drop-wise to and presets mankind kidney cell HEK293T (well cell density 8 * 10
4) 24 hole enzyme joint inspection drafting boards in, co-cultivation is 36 hours in the standard cell lines incubator, with the PBS damping fluid cell is cleaned 3 times then, adopt TE2000-U (Nikon, Japan) the fluorescent microscope situation that observation globe-type luminescence nanoparticle enters cell as fluorescence labeling material under the 465nm wavelength excites; And adopt the 490nm wavelength to excite the transfection situation of observing fluorescence protein gene.The result proves, co-cultivation is after 36 hours, excites down cell for red at the 465nm wavelength, illustrate the globe-type luminescence nanoparticle still stable existence in cell; When adopting the 490nm wavelength to excite, the part cell is green, and the transfection success of fluorescence protein gene is described.
Claims (7)
1. the organic molecular probe material with nucleocapsid structure is characterized in that; The core that forms nucleocapsid structure is a transition metal complex, and shell is parents' polymkeric substance; The metal ion of described transition metal complex is Ru
2+(ruthenium), Os
2+(osmium) or Re
+(rhenium), part are single the replacement or polysubstituted phenanthroline and single replace or polysubstituted 2, and 2 '-dipyridyl, its substituting group are 4-{9,9 '-(two replace fluorenyl) }-phenyl or 4-{9,9 '-[N, N '-(two carbazyl alkyl)] fluorenyl }-phenyl; Parents' polymkeric substance is the multipolymer that polyethylene glycol methacrylate-styrene polymer (PEGMA) and Dimethylaminoethyl Methacrylate (DMAEMA) form, and its structural formula is DMAEMA
51-b-PEGMA
65-b-DMAEMA
51
2. preparation method who has the organic molecular probe material of nucleocapsid structure according to claim 1, it is characterized in that step is as follows: 1) synthetic method prepares described transition metal complex and parents' polymkeric substance respectively routinely; 2) parents' polymkeric substance and the transition metal complex with above-mentioned preparation is dissolved in the methylene dichloride, steam solvent then, add pH again and be 7.1 PBS buffered soln, adopt the ultrasonic dispersing system, be the polycarbonate membrane filtration of 0.20um～0.75um with the aperture then, can make the nano spherical particle of organic molecular probe material with nucleocapsid structure.
3. according to the described preparation method with organic molecular probe material of nucleocapsid structure of claim 2, it is characterized in that: the mol ratio of described parents' polymkeric substance and transition metal complex is 1: 1～10.
4. according to the described preparation method with organic molecular probe material of nucleocapsid structure of claim 2, it is characterized in that: the weight ratio of described parents' polymkeric substance and transition metal complex and methylene dichloride is 1: 100～500.
5. according to the described preparation method with organic molecular probe material of nucleocapsid structure of claim 2, it is characterized in that: the weight ratio of described parents' polymkeric substance and transition metal complex and PBS buffered soln is 1: 1000～5000.
6. organic molecular probe material that has nucleocapsid structure according to claim 1, it is characterized in that: be used for pair cell and carry out the Infrared fluorescence mark, method is the nanoparticle of the organic molecular probe material with nucleocapsid structure of preparation to be cultivated with 293T cell and common cancer cells be no more than 1 hour, under 360～800nm optical excitation, this nanoparticle 580～900nm wavelength region launch single infrared/near-infrared fluorescent, can carry out the Infrared fluorescence mark by pair cell, the diameter of described nanoparticle is less than 100nm.
7. organic molecular probe material that has nucleocapsid structure according to claim 1, it is characterized in that: be used for fluorescin transfection mark, method be will the preparation the organic molecular probe material with nucleocapsid structure nanoparticle with the implantation fluorescence protein gene plasmid combine after, with 293T cell and common cancer cells co-cultivation 24～72 hours, can realize fluorescin transfection mark, also keep the infrared/near-infrared luminous performance of this nanoparticle simultaneously.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101792531A (en) * | 2010-03-24 | 2010-08-04 | 浙江大学 | Preparation method of fluorescent polymer with hydrophilic outer shell and hydrophobic inner core |
| CN102277386A (en) * | 2011-04-26 | 2011-12-14 | 苏州大学 | Bi-component gene carrier and application thereof |
| CN106632264A (en) * | 2016-12-19 | 2017-05-10 | 山东大学 | Probe for clearly distinguishing cell membrane-lipid raft microdomain from non-lipid-raft microdomain by using two fluorescence colors and simultaneously imaging microdomains and application of probe |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1304523C (en) * | 2005-11-30 | 2007-03-14 | 东南大学 | Rare-earth nano luninous particle based on fluorescent energy transfer principle and its preparing method |
| CN1966534A (en) * | 2006-10-25 | 2007-05-23 | 东华大学 | Inorganic-organic core-shell type rare earth high polymer material and its preparation method |
| KR100853086B1 (en) * | 2007-04-25 | 2008-08-19 | 삼성전자주식회사 | Nanocrystal-metal oxide composite, preparation method thereof |
| CN101067079B (en) * | 2007-05-25 | 2010-05-19 | 上海师范大学 | Nanometer hybridized phosphor in core-shell structure and its preparation process |
| CN101362944B (en) * | 2008-09-25 | 2011-01-19 | 湖南大学 | Method for preparing long-term durability luminous nano granule of core-shell rare-earth complexes |
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2009
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101792531A (en) * | 2010-03-24 | 2010-08-04 | 浙江大学 | Preparation method of fluorescent polymer with hydrophilic outer shell and hydrophobic inner core |
| CN101792531B (en) * | 2010-03-24 | 2011-12-07 | 浙江大学 | Preparation method of fluorescent polymer with hydrophilic outer shell and hydrophobic inner core |
| CN102277386A (en) * | 2011-04-26 | 2011-12-14 | 苏州大学 | Bi-component gene carrier and application thereof |
| CN102277386B (en) * | 2011-04-26 | 2013-06-05 | 苏州大学 | Bi-component gene carrier and application thereof |
| CN106632264A (en) * | 2016-12-19 | 2017-05-10 | 山东大学 | Probe for clearly distinguishing cell membrane-lipid raft microdomain from non-lipid-raft microdomain by using two fluorescence colors and simultaneously imaging microdomains and application of probe |
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|---|---|
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