CN102154437B - Application of rhodamine 6G ramifications - Google Patents
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- CN102154437B CN102154437B CN 201110090721 CN201110090721A CN102154437B CN 102154437 B CN102154437 B CN 102154437B CN 201110090721 CN201110090721 CN 201110090721 CN 201110090721 A CN201110090721 A CN 201110090721A CN 102154437 B CN102154437 B CN 102154437B
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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 rhodamine 6G derivative of volution in molecule as the purposes of Cytolysosome fluorescent dye.
Background technology
Lysosome (lysosome) is a kind of organoid in 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 viable cell lysosomal molecular probe for the lysosomal biological function of research, and the diagnosis of live body cancer cells 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 for studying 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 (lysotracker green DND-26 etc.) of developing as the most frequently used Invitrogen.The drawbacks common of such probe comprises that (1) background signal is higher, causes non-specific mark; (2) stability is low, easily by optical quenching, loses fluorescence property; (3) short in intracellular retention period, prolongation in time, the cell internal probe easily runs off.
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 volution in molecule (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, weak acid environment in lysosome 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 lysosome, namely have sensitivity to acid, and this analog derivative has advantages of low background, high stability and in cell retention period long.
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 ring rhodamine 6G derivatives in molecule, 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 in molecule.
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, and is as amino in one-level, and secondary is amino, tertiary amine base etc.; Two of the synthetic raw material that contains Rhodamine Derivatives is the compounds that contain primary amine; The constitutional features of this compounds is at least 2, interval methylene radical between the substituting group of primary amine substituting group and the molecule the other end.
Have after a class rhodamine 6G derivative of volution in molecule and dissimilar cell hatch, enter the lysosome of cell.Slightly acidic in lysosome 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 to carry out single-minded, stable mark to the lyase physical efficiency of different cells.
A class rhodamine 6G derivative with volution in molecule is isomerizated in lysosome as 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 in molecule can be used as dissimilar cell; (2) the rhodamine 6G derivative is long in intracellular retention time, and light stability is high; (3) such rhodamine 6G derivative can be used for lysosome in long-time mark, track cells.
Description of drawings
Fig. 1 is that the rhodamine 6G-quadrol of the embodiment of the present invention 1 is caused the fluorescence spectrum figure that produces by different acidity.
Fig. 2 is that the rhodamine 6G-quadrol of the embodiment of the present invention 1 produces the graph of a relation of fluorescence intensity under different acidity.
Fig. 3 is that the rhodamine 6G-quadrol of the embodiment of the present invention is used for the lysosomal collection of illustrative plates of fluorescence labeled cell.(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 be in the embodiment of the present invention 1 LysoTracker Green DND-26 at the retention time detection figure of L929 Cytolysosome.In Fig. 4, A: cellular form under visible light; B: cell detects fluorescence after by the LysoTracker mark at once; C: detect fluorescence after the cell cultures 24h of mark.
Fig. 5 be in the embodiment of the present invention 1 rhodamine 6G-quadrol at the retention time detection figure of L929 Cytolysosome.In Fig. 5, A: cellular form under visible light; B: cell detects fluorescence after by rhodamine 6G-quadrol mark at once; C: detect fluorescence after the cell cultures 24h of mark.
Fig. 6 be in the embodiment of the present 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 that the rhodamine 6G-quadrol of the embodiment of the present invention 1 and Lysotracker Green are in the fluorescent quenching intensity contrast of L929 Cytolysosome.
Fig. 8 is that the rhodamine 6G-quadrol of the embodiment of the present invention 1 is used for the lysosomal figure of real-time fluorescence labeled cell.In Fig. 8, A～H represents respectively the fluoroscopic examination figure after cell is by rhodamine 6G- quadrol mark 0,1,2,3,4,5,6,7h.
Fig. 9 is H
2O
2With the impact detection figure of HOCl on the fluorescence emitting characteristics of rhodamine 6G-quadrol.
Figure 10 be different metal ion pair rhodamine 6G-quadrol fluorescence emitting characteristics affect detection figure.
Embodiment
Embodiment 1
1) rhodamine 6G (2g) joins in the flask that contains the 20mL quadrol, and this system of induction stirring is being removed responseless solvent in reaction under 80 ℃ after 12h, by silicagel column separate, purifying obtains rhodamine 6G-quadrol, its chemical structural formula is:
R＝-NH
2，-N(CH
3)
2，-CH
2-N(CH
3)
2。
2) detect contain 5 Yuans rings in molecule 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, 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 in embodiment 1, the acid of rhodamine 6G-ethylene diamine derivative causes generation fluorescence chemical reaction scheme:
3) lysosome probe (the LysoTracker Green that rhodamine 6G-quadrol (10 μ g/mL) and Invitrogen company is produced, DND-26,1 μ M) simultaneously with dissimilar cell (MEEF, L929, Raw264.7, SF9) hatch 30min after, observe under laser confocal microscope 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, after being superposeed, two kinds of different fluorescence find, 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.Then (detecting wavelength is 535～580nm) to measure respectively the rhodamine 6G of cell under the 530nm exciting light-quadrol red fluorescence emissive porwer; And the fluorescent emission intensity of cell under the 488nm exciting light (detecting wavelength is 490～525nm).Under the 488nm exciting light, in cell 490～525nm fluorescent emission intensity in time increase and reduce, after 24h, can't detect fluorescent emission, illustrate that intracellular LysoTracker Green DND-26 loses.Under the 530nm exciting light, in cell, the increase in time of 535～580nm fluorescent emission intensity does not change, after 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, in cell, 490～525nm fluorescent emission intensity reduces with the increase of light application time, and after 5min, fluorescent emission intensity has descended 50%, illustrates that intracellular LysoTracker GreenDND-26 light stability is poor.Under the 530nm exciting light, in cell, 535～580nm fluorescent emission intensity does not change with the increase of light application time, after 5min, the emissive porwer basic identical (greater than 90%) of fluorescent emission intensity when there is no illumination detected, the light stability high (referring to Fig. 7) of the interior rhodamine 6G-quadrol of cell be described.
6) after rhodamine 6G-quadrol (10 μ g/mL) is hatched 30min with the L929 cell, nutrient solution is removed, add the fresh nutrient solution that contains TNF-a (TNF-α, 50ng/mL), make cell trigger cell under TNF-α effect dead.In the 8h process of hatching with TNF-α, by the lysosomal shape (the 530nm exciting light records 535～580nm fluorescent emission intensity in 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) add respectively hydrochloric acid (0.1mM) in the methanol solution of rhodamine 6G-quadrol (1 μ g/mL), 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, add hydrochloric acid after fluorescence intensity increased by 1000 times; Add the later fluorescence intensity of hydrogen peroxide there is no considerable change, add the later fluorescence intensity of hypochlorous acid to increase about 5 times, the impact of above-mentioned various different metal ion pair fluorescence intensities is all 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 many kinds of metal ions 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 after reaction 12h under 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 that obtains and the experimental result of rhodamine 6G-ethylene diamine derivative are similar, illustrate both as the performance of the lysosomal specific probe of cell basic identical.
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 being removed responseless solvent in reaction under 80 ℃ after 12h, by silicagel column separate, purifying obtains rhodamine 6G-propylene diamine.
2) utilize rhodamine 6G-propylene diamine to repeat the step 2 of embodiment 1), 3), 4), 5), 6), 7), the result that obtains and the experimental result of rhodamine 6G-quadrol are similar, illustrate both as the performance of the lysosomal specific probe of cell basic identical.
Claims (1)
1. a class rhodamine 6G derivative for the preparation of the application in highly selective, the lysosomal Cytolysosome fluorescent dye of labeled cell steady in a long-term, is characterized in that 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 ring rhodamine 6G derivatives in molecule, the raw material of synthetic described rhodamine 6G derivative is rhodamine 6G and contains aminocompound, and the constitutional features of described aminocompound is that an end of molecule contains an one-level amino; The other end that contains the compound of one-level amino contains other substituting group, and described substituting group is that one-level is amino, secondary amino or tertiary amine base; The structure that contains the compound of one-level amino is at least 2, interval methylene radical between the substituting group of primary amine substituting group and the molecule the other end.
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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 |
| CN102633789B (en) * | 2012-03-31 | 2014-06-25 | 天津师范大学 | Compound containing double-rhodamine B and preparation method and application of compound |
| CN102633787B (en) * | 2012-03-31 | 2014-09-24 | 王竞择 | Bio-fluorescent stain 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 |
| CN103242328A (en) * | 2013-04-11 | 2013-08-14 | 天津师范大学 | p-N-methyl acetamidophenyl rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof |
| CN103242331A (en) * | 2013-04-11 | 2013-08-14 | 天津师范大学 | Rhodamine 6GpH fluorescent molecular probe containing biphenyl group as well as preparation method and application thereof |
| CN103242327A (en) * | 2013-04-11 | 2013-08-14 | 天津师范大学 | P-N-methyl cyclopentaldehyde rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof |
| CN104096230B (en) * | 2014-04-29 | 2016-06-22 | 厦门生光生物科技有限公司 | A kind of light pyrogenicity cytoactive detection nano material and preparation method thereof |
| CN105542752B (en) * | 2015-12-14 | 2018-02-13 | 济南大学 | A kind of formaldehyde fluorescence probe and its preparation method and application |
| CN106908432B (en) * | 2017-04-17 | 2019-07-26 | 吉林大学 | A kind of albumen base lysosome fluorescence indicator |
| CN110016065B (en) * | 2018-01-08 | 2021-06-25 | 厦门大学 | Rhodamine-sialic acid conjugate, synthetic method thereof and lysosome imaging application |
| CN115287780A (en) * | 2022-09-13 | 2022-11-04 | 北华大学 | Lignocellulose-based intelligent color-changing composite fiber material and preparation method thereof |
Citations (1)
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| US20090017449A1 (en) * | 2007-06-20 | 2009-01-15 | President And Fellows Of Harvard College | Compounds and methods for assaying fusion of an individual, enveloped virus with target membrane |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090017449A1 (en) * | 2007-06-20 | 2009-01-15 | President And Fellows Of Harvard College | Compounds and methods for assaying fusion of an individual, enveloped virus with target membrane |
Non-Patent Citations (4)
| Title |
|---|
| Jia-Sheng Wu et al..Rhodamine-Based Hg2+-Selective Chemodosimeter in Aqueous Solution: Fluorescent OFF-ON.《Organic Lett》.2007,907-910. * |
| Medicinal Chemistry》.2009,6015–6019. * |
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