CN102154437A - Application of rhodamine 6G ramifications - Google Patents
Application of rhodamine 6G ramifications Download PDFInfo
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- CN102154437A CN102154437A CN 201110090721 CN201110090721A CN102154437A CN 102154437 A CN102154437 A CN 102154437A CN 201110090721 CN201110090721 CN 201110090721 CN 201110090721 A CN201110090721 A CN 201110090721A CN 102154437 A CN102154437 A CN 102154437A
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Abstract
The invention provides application of rhodamine 6G ramifications, and relates to the use of the molecule inner spiral ring-containing rhodamine 6G ramifications which are taken as cell lysosome fluorescent coloring agent. The rhodamine 6G ramifications are the molecule inner 5 member ring-containing rhodamine 6G ramifications which can be used as the cell lysosome fluorescent colouring agent to stably mark the cell lysosome at high selectivity and for a long term. The application of the rhodamine 6G ramifications has the beneficial effects that (1) the azyl and molecule inner 5 member ring-containing rhodamine 6G ramifications can be taken as a lysosome fluorescent labeled substance for the cells with different types; (2) the rhodamine 6G ramifications are long in retention time and high in photostability in the cell; and (3) the rhodamine 6G ramifications can be used for labeling and tracking the lysosome in the cell for a long time.
Description
Technical field
The present invention relates to a class and have the purposes of the rhodamine 6G derivative of intramolecularly volution as the Cytolysosome fluorescent dye.
Background technology
Lysosome (lysosome) is a kind of organoid in the eukaryotic cell, and its internal medium is slightly acidic (pH 4～6), contains multiple lytic enzyme.Lysosome not only has intracellular digestive function, also with the development of cell autophagy, apoptosis, immune defense, cancer have direct related (1, Luis Avila J.[Structure and function oflysosomes] .Acta Cient Venez.1974; 25:130-131; 2, Luzio JP, Pryor PR, Bright NA.Lysosomes:fusion and function.Nat Rev Mol Cell Biol.2007; 8:622-632; 3, Kroemer G, Jaattela M.Lysosomes and autophagy in cell death control.Nat Rev Cancer.2005; 5:886-897), therefore development and application can mark and is followed the trail of in the viable cell lysosomal molecular probe for the lysosomal biological function of research, and the diagnosis of live body cancer cells all have important meaning (4, Groth-Pedersen L, Ostenfeld MS, Hoyer-Hansen M, Nylandsted J, Jaattela M.Vincristine induces dramatic lysosomal changes and sensitizes cancer cells to lysosome-destabilizing siramesine.Cancer Res.2007; 67:2217-2225; 5, Urano Y, Asanuma D, HamaY, et al.Selective molecular imaging of viable cancer cells with pH-activatable fluorescence probes.Nat Med.2009; 15:104-109).
Now existing multiple can the lysosomal molecular probe of mark, be used to study lysosomal biological function.These probes contain weakly alkaline substituted radical mostly, can selective aggregation in the lysosome of low pH value, the oxytropism fluorescent probe of developing as the most frequently used Invitrogen (lysotracker green DND-26 etc.).The drawbacks common of such probe comprises that (1) background signal than higher, causes non-specific mark; (2) stability is low, easily by optical quenching, and the forfeiture fluorescence property; (3) short in intracellular retention period, prolongation in time, the cell internal probe runs off easily.
According to bibliographical information with rhodamine 6G with contain amino compound quadrol, propylene diamine and N, the N-dimethyl-ethylenediamine prepared the rhodamine 6G derivative that a class has the intramolecularly volution (6, Wu J, Hwang I, Kim KS, Kim JS.Rhodamine-based Hg2+-selective chemodosimeter in aqueous solution:fluorescent OFF-ON.Organic Lett, 2007,9 (5): 907-910).This analog derivative is after entering Cytolysosome, the intravital weak acid environment of lyase excites this analog derivative generation isomerization, making it to become can fluorescigenic molecule, and its fluorescence intensity changes with the change of pH value in the lysosome, promptly have sensitivity to acid, and this analog derivative has low background, high stability and in cell retention period long advantage.
Summary of the invention
The object of the present invention is to provide the application of a class rhodamine 6G derivative.
The chemical structural formula of a described class rhodamine 6G derivative is as follows:
R＝-NH
2，-N(CH
3)
2，-CH
2-N(CH
3)
2
A described class rhodamine 6G derivative is that a class has 5 Yuans rings of intramolecularly rhodamine 6G derivative, and a described class rhodamine 6G derivative can be used as the Cytolysosome fluorescent dye and is used for highly selective, labeled cell lysosome steady in a long-term.
The constitutional features of a described class rhodamine 6G derivative is that derivative has 5 Yuans rings of intramolecularly.
One of synthetic raw material that contains the rhodamine 6G derivative is rhodamine 6G, the raw material of the bright 6G derivative of synthesizing rhodamine two for containing aminocompound, the constitutional features of described aminocompound is that an end of molecule contains an one-level amino; The other end of two the compound that contains one-level amino of the raw material of the bright 6G derivative of synthesizing rhodamine can contain other substituting group, as one-level amino, and secondary amino, tertiary amine base etc.; Two of the synthetic raw material that contains the rhodamine derivative is the compounds that contain primary amine; The constitutional features of this compounds is between the substituting group of the primary amine substituting group and the molecule the other end at least 2 methylene radical at interval.
Have after class rhodamine 6G derivative of intramolecularly volution and dissimilar cell hatch, enter the lysosome of cell.The intravital slightly acidic of lyase excites the isomerization of this analog derivative, and making it to become can fluorescigenic molecule.Not only retention time is long in Cytolysosome for a described class rhodamine 6G derivative, and stability is high, is difficult for by optical quenching, not with intracellular active substance reaction.Utilize a described class rhodamine 6G derivative that the lyase physical efficiency of different cells is carried out single-minded, stable mark.
Class rhodamine 6G derivative with intramolecularly volution is isomerizated in lysosome to having the molecule of fluorescent characteristic.Specificity and stability to this mark in different cells are tested.
The invention has the beneficial effects as follows: (1) one class contains the lysosome fluorescent mark material that rhodamine 6G derivative amino, that have 5 Yuans rings of intramolecularly can be used as dissimilar cells; (2) the rhodamine 6G derivative is long in intracellular retention time, the light stability height; (3) such rhodamine 6G derivative can be used for lysosome in long-time mark, the track cells.
Description of drawings
Fig. 1 is that the rhodamine 6G-quadrol of the embodiment of the invention 1 is caused the fluorescence spectrum figure that produces by different acidity.
Fig. 2 is the rhodamine 6G-quadrol of the embodiment of the invention 1 produces fluorescence intensity under different acidity a graph of a relation.
Fig. 3 is used for the lysosomal collection of illustrative plates of fluorescence labeled cell for the rhodamine 6G-quadrol of the embodiment of the invention.(lysosome of rhodamine 6G-quadrol mark produces red fluorescence, and the lysosome of commercially available dyestuff LysoTracker Green DND-26 mark produces green fluorescence).
Fig. 4 is that LysoTracker Green DND-26 detects figure in the retention time of L929 Cytolysosome in the embodiment of the invention 1.In Fig. 4, A: cellular form under the visible light; B: cell detects fluorescence after by the LysoTracker mark at once; C: detect fluorescence behind the cell cultures 24h of mark.
Fig. 5 is that rhodamine 6G-quadrol detects figure in the retention time of L929 Cytolysosome in the embodiment of the invention 1.In Fig. 5, A: cellular form under the visible light; B: cell detects fluorescence after by rhodamine 6G-quadrol mark at once; C: detect fluorescence behind the cell cultures 24h of mark.
Fig. 6 be in the embodiment of the invention 1 rhodamine 6G-quadrol and commercially available dyestuff Lysotracker Green in the retention time contrast of L929 Cytolysosome.In Fig. 6, A: cell by dye marker after fluorescence intensity at once; B: the fluorescence intensity that cell detects after by dye marker 24h.
Fig. 7 is the rhodamine 6G-quadrol of the embodiment of the invention 1 and the Lysotracker Green fluorescent quenching intensity contrast at the L929 Cytolysosome.
Fig. 8 is used for the lysosomal figure of real-time fluorescence labeled cell for the rhodamine 6G-quadrol of the embodiment of the invention 1.In Fig. 8, A～H represents the fluoroscopic examination figure after cell is by rhodamine 6G- quadrol mark 0,1,2,3,4,5,6,7h respectively.
Fig. 9 is H
2O
2With the influence detection figure of HOCl to the fluorescence emitting characteristics of rhodamine 6G-quadrol.
Figure 10 is that the influence of the fluorescence emitting characteristics of different metal ion pair rhodamine 6G-quadrol detects figure.
Embodiment
Embodiment 1
1) rhodamine 6G (2g) joins in the flask that contains the 20mL quadrol, and this system of induction stirring is removed responseless solvent behind the reaction 12h down at 80 ℃, obtains rhodamine 6G-quadrol by silicagel column separation, purifying, and its chemical structural formula is:
R＝-NH
2，-N(CH
3)
2，-CH
2-N(CH
3)
2。
2) detect contain 5 Yuans rings of intramolecularly rhodamine 6G-quadrol (1 μ g/mL) fluorescent emission intensity of (7.0,6.5,6.0,5.5,5.0,4.5,4.0) in the buffered soln of different pH values.Discovery is under the condition of pH4.0 and 7.0, and the fluorescence intensity of rhodamine 6G-quadrol improves 1000 times (Ex:530/Em 560nm) (referring to Fig. 1 and 2), and it is as follows that the acid of rhodamine 6G-ethylene diamine derivative causes generation fluorescence chemical reaction scheme among the embodiment 1:
3) with lysosome probe (the LysoTracker Green of rhodamine 6G-quadrol (10 μ g/mL) with the production of Invitrogen company, DND-26,1 μ M) while and dissimilar cell (MEEF, L929, Raw264.7, SF9) hatch 30min after, under laser confocal microscope, observe two kinds of fluorescence dyes in different cells to lysosomal mark situation.Cytolysosome under the 530nm exciting light sends the red fluorescence of rhodamine 6G-quadrol, cell sends the green fluorescence of LysoTracker Green under the 488nm exciting light, find after two kinds of different fluorescence are superposeed, red fluorescence is regional identical with the green fluorescence distribution, rhodamine 6G is described--the zone of quadrol mark is regional consistent with LysoTracker GreenDND-26 mark, rhodamine 6G--quadrol can single-minded labeled cell in lysosome (referring to Fig. 3).
4) rhodamine 6G-quadrol (10 μ g/mL) and LysoTracker Green DND-26 (1 μ M) are hatched 30min with the L929 cell simultaneously after, nutrient solution is removed, add fresh nutrient solution, allow the cell continued growth.Under different growth times (0,24h), take out the part cell.(detecting wavelength is 535～580nm) to measure the rhodamine 6G-quadrol red fluorescence emissive porwer of cell under the 530nm exciting light then respectively; And the fluorescent emission intensity of cell under the 488nm exciting light (detecting wavelength is 490～525nm).Under the 488nm exciting light, in the cell 490～525nm fluorescent emission intensity in time increase and reduce, after the 24h, detect less than fluorescent emission, illustrate that intracellular LysoTracker Green DND-26 loses.Under the 530nm exciting light, the increase in time of 535～580nm fluorescent emission intensity does not change in the cell, after the 24h, fluorescent emission intensity fundamental sum identical when initial (greater than 95%) illustrates that rhodamine 6G-quadrol does not have significantly sacrificing (referring to Fig. 4～6) in cell.
5) after rhodamine 6G-quadrol (10 μ g/mL) is hatched 30min with the L929 cell simultaneously with LysoTracker Green DND-26 (1 μ M), nutrient solution is removed, added fresh nutrient solution, allow cell at mercury lamp strong illumination (100-W, C-SHG1, Nikon company).Respectively the different light time (0,1,2,4,5min) measure the fluorescent emission intensity of cell under 488nm or 530nm exciting light.Under the 488nm exciting light, 490～525nm fluorescent emission intensity reduces with the increase of light application time in the cell, and after the 5min, fluorescent emission intensity has descended 50%, illustrates that intracellular LysoTracker GreenDND-26 light stability is poor.Under the 530nm exciting light, 535～580nm fluorescent emission intensity does not change with the increase of light application time in the cell, after the 5min, detect the emissive porwer basic identical (greater than 90%) of fluorescent emission intensity when not having illumination, the light stability height (referring to Fig. 7) of the interior rhodamine 6G-quadrol of cell be described.
6) after rhodamine 6G-quadrol (10 μ g/mL) and L929 cell are hatched 30min, nutrient solution is removed, added and fresh contain tumour necrosis factor-a (TNF-α, nutrient solution 50ng/mL) allow cell trigger cell death under TNF-α effect.In the 8h process of hatching with TNF-α, by the lysosomal shape (530nm exciting light, 535～580nm fluorescent emission intensity in the record cell) of a L929 cell of the every 15min record of laser confocal microscope.The lysosomal volume of finding the L929 cell increased and increases along with the time, and in the 8h necrocytosis, lysosomal volume sharply increases, and (referring to Fig. 8) then breaks.This explanation rhodamine 6G-quadrol can be used for the real-time mark lysosome and observe the dynamic change of lysosome structure.
7) in the methanol solution of rhodamine 6G-quadrol (1 μ g/mL), add hydrochloric acid (0.1mM) respectively, hydrogen peroxide (5mM), the metal ion (K that clorox (5mM) or various 1mM are different
+, Na
+, Ca
2+, Mg
2+, Zn
2+, Cu
+, Co
2+) after, detect the fluorescent emission intensity of rhodamine 6G-quadrol under the 530nm exciting light.Compare with the methanol solution of rhodamine 6G-quadrol, fluorescence intensity has increased by 1000 times behind the adding hydrochloric acid; Fluorescence intensity does not have considerable change after adding hydrogen peroxide, and fluorescence intensity has increased about 5 times after the adding hypochlorous acid, and the influence of above-mentioned various different metal ion pair fluorescence intensities then all is lower than 5 times.Illustrate that rhodamine 6G-quadrol is sensitive to acid, and very low to the sensitivity of hydrogen peroxide, clorox and metal ion.This test explanation hydrogen peroxide, clorox and multiple metal ion etc. detect the interference very little (referring to Fig. 9 and 10) of acidity to rhodamine 6G-quadrol.
Embodiment 2: rhodamine 6G-N, the N-dimethyl-ethylenediamine is as the application of Cytolysosome fluorescence dye
1) rhodamine 6G (2g) is joined contain 20mLN, in the flask of N-dimethyl-ethylenediamine, this system of induction stirring is being removed responseless solvent behind the reaction 12h down at 80 ℃, by silicagel column separate, purifying obtains rhodamine 6G-N, the N-dimethyl-ethylenediamine.
2) utilize rhodamine 6G-N, the N-dimethyl-ethylenediamine repeats the step 2 of embodiment 1), 3), 4), 5), 6), 7), the result who obtains and the experimental result of rhodamine 6G-ethylene diamine derivative are similar, illustrate that the two is basic identical as the performance of the lysosomal specific probe of cell.
Embodiment 3: rhodamine 6G-propylene diamine is as the application of Cytolysosome fluorescence dye
1) rhodamine 6G (2g) is joined in the flask that contains the 20mL propylene diamine, induction stirring is removed responseless solvent behind the reaction 12h down at 80 ℃, obtains rhodamine 6G-propylene diamine by silicagel column separation, purifying.
2) utilize rhodamine 6G-propylene diamine to repeat the step 2 of embodiment 1), 3), 4) and, 5), 6) and, 7), the result who obtains and the experimental result of rhodamine 6G-quadrol are similar, illustrate that the two is basic identical as the performance of the lysosomal specific probe of cell.
Claims (3)
1. a class rhodamine 6G derivative is used for highly selective, labeled cell lysosome steady in a long-term as the Cytolysosome fluorescent dye; The chemical structural formula of a described class rhodamine 6G derivative is as follows:
R＝-NH
2，-N(CH
3)
2，-CH
2-N(CH
3)
2
2. a class rhodamine 6G derivative is that a class has 5 Yuans rings of intramolecularly rhodamine 6G derivative according to claim 1.
3. one of synthetic raw material that contains rhodamine 6G derivative according to claim 1 is rhodamine 6G, the raw material of the bright 6G derivative of synthesizing rhodamine two for containing aminocompound, the constitutional features of described aminocompound is that an end of molecule contains an one-level amino; The other end of two the compound that contains one-level amino of the raw material of the bright 6G derivative of synthesizing rhodamine can contain other substituting group, and described substituting group is an one-level amino, secondary amino or tertiary amine base; Two of the synthetic raw material that contains the rhodamine derivative is the compounds that contain primary amine; The structure of this compounds is between the substituting group of the primary amine substituting group and the molecule the other end at least 2 methylene radical at interval.
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102627635A (en) * | 2012-03-31 | 2012-08-08 | 天津师范大学 | Rhodamine 6 G oxadiazole compound and preparation method and application thereof |
| CN102633789A (en) * | 2012-03-31 | 2012-08-15 | 天津师范大学 | Compound containing double-rhodamine B and preparation method and application of compound |
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| CN102633787A (en) * | 2012-03-31 | 2012-08-15 | 王竞择 | Bio-fluorescent stain and preparation method and application thereof |
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2011
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| CN102633789A (en) * | 2012-03-31 | 2012-08-15 | 天津师范大学 | Compound containing double-rhodamine B and preparation method and application of compound |
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| CN102633787A (en) * | 2012-03-31 | 2012-08-15 | 王竞择 | Bio-fluorescent stain and preparation method and application thereof |
| CN102627635A (en) * | 2012-03-31 | 2012-08-08 | 天津师范大学 | Rhodamine 6 G oxadiazole compound and preparation method and application thereof |
| CN102633790B (en) * | 2012-03-31 | 2014-07-30 | 天津师范大学 | Pyridine rhodamine oxadiazole compound as well as preparation method and application thereof |
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| CN106908432A (en) * | 2017-04-17 | 2017-06-30 | 吉林大学 | A kind of albumen base lysosome fluorescence indicator and its application |
| CN106908432B (en) * | 2017-04-17 | 2019-07-26 | 吉林大学 | A kind of albumen base lysosome fluorescence indicator |
| CN110016065A (en) * | 2018-01-08 | 2019-07-16 | 厦门大学 | Rhodamine-sialic acid conjugate and its synthetic method and lysosome imaging applications |
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