CN114262609A - Self-flashing fluorescent dye for long-time super-resolution fluorescence imaging of lysosome and synthetic method and application thereof - Google Patents
Self-flashing fluorescent dye for long-time super-resolution fluorescence imaging of lysosome and synthetic method and application thereof Download PDFInfo
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Abstract
The invention relates to self-flashing fluorescent dyes for long-time super-resolution fluorescence imaging of lysosomes, and a synthesis method and application thereof. The fluorescent dye related to the invention is in a dark state with a closed-loop structure in an aqueous solution with the pH value of more than 5.5, so that the dye exists in a small amount of fluorescent state only in an acidic lysosome, and the accurate positioning of the lysosome is achieved. In addition, the dye has reciprocating change of a fluorescence state and a dark state in a lysosome so as to achieve the self-flashing effect, realize dynamic and long-time super-resolution fluorescence imaging of the lysosome, and monitor the pH, distribution, size and the like of the lysosome.
Description
Technical Field
The invention belongs to the field of super-resolution fluorescent dyes, and particularly relates to a self-flashing fluorescent dye for lysosome long-time super-resolution fluorescence imaging and application thereof in the field of fluorescence imaging.
Background
Lysosomes are single-membrane organelles containing large amounts of hydrolytic enzymes capable of accepting and degrading macromolecules from endocytosis, secretion, autophagy, and phagocytosis processes. These processes often occur with highly dynamic processes such as lysosomal fusion, division, interaction with other organelles, and the like. In situ, real-time analysis of lysosomes within living cells is critical for lysosome-related studies. Fluorescence microscopy, with its unique advantages, has thus become an important analytical tool for real-time monitoring of lysosomes. In particular, the rapidly developed super-resolution imaging technology in recent years has promoted the study of lysosomes in living cells to nano-scale spatial resolution.
However, effective control of the switch is difficult to achieve with conventional lysosomal fluorescent dyes at lysosomal pH and the photostability is poor, which makes such dyes unusable for single molecule localization microscopy and the like. In addition, the switching molecules currently used in single molecule localization microscopy generally require strong fluorescence or require activating light, plus new species, which can cause damage to living cells. The above factors greatly limit the study of lysosome function. The self-flashing fluorescent dye can overcome the problems to a great extent, and can realize the conversion of the fluorescent state on and the dark state off of the molecule under the condition of not activating light or adding species, thereby being used for super-resolution imaging of a single-molecule positioning microscope under the condition of low excitation power. However, lysosome-targeted self-flashing super-resolution fluorescent dyes remain rare, mainly because the dye under acidic conditions of lysosome pH exists mostly in the fluorescent state, and the transition to the dark state is difficult to achieve. Therefore, how to regulate the transition of the fluorescence state to the dark state is critical for the development of lysosome self-flashing super-resolution fluorescent dye pairs. The development of the dye can promote the real-time monitoring of lysosomes of living cells at the nanoscale, and promote the related research of the lysosomes.
Disclosure of Invention
The invention relates to a self-flashing fluorescent dye for long-time super-resolution fluorescence imaging of lysosomes. The dye is structurally characterized in that a 2-aminopyridine derivative is used for carrying out locking ring, so that the ratio of the fluorescence state to the dark state of the dye rhodamine 6G is regulated and controlled. The fluorescent dye related to the invention is in a dark state with a closed-loop structure in an aqueous solution with the pH value of more than 5.5, so that the dye exists in a small amount of fluorescent state only in an acidic lysosome, and the accurate positioning of the lysosome is achieved. In addition, the dye has reciprocating change of a fluorescence state and a dark state in a lysosome so as to achieve the self-flashing effect, realize dynamic and long-time super-resolution fluorescence imaging of the lysosome, and monitor the pH, distribution, size and the like of the lysosome.
The self-flashing fluorescent dye for long-time super-resolution fluorescence imaging of lysosome is characterized in that a rhodamine 6G matrix is used as a base, a locking ring is formed through 2-aminopyridine derivatives, the structural formula is shown as follows,
wherein R is1，R2，R3，R4If one is not H, the remaining substituents are H; specifically, H, (CH)2CH2)nCH3、COONH-R5Any one of the groups; r5Is (CH)2CH2)nCH3N, N-dimethylaminoethyl, benzylpurine and 2-morpholinylethyl.
n is an integer between 0 and 4.
The synthesis steps are as follows:
the specific synthesis steps are as follows:
putting the rhodamine derivative into 1, 2-dichloroethane, then adding phosphorus oxychloride into the reaction solution, and reacting for 4-8h at 80 ℃. And then removed under reduced pressure to give a violet crude product. The crude product was dissolved in acetonitrile and 0.5mL of triethylamine and 2-aminopyridine derivatives were added and reacted at 80 ℃ for 10-24 h. The solvent was removed under reduced pressure and basic alumina column chromatography gave a white solid.
In the synthesis step, the mass ratio of the rhodamine derivative to the 2 aminopyridine derivative is 1: 3-5; the volume ratio of the mass of the rhodamine derivative to the phosphorus oxychloride is 1:0.005-0.01 mg/mL; the volume ratio of the mass of the rhodamine derivative to the 1, 2-dichloroethane is 1:0.1-0.2 mg/mL; the volume ratio of the mass of the rhodamine derivative to the acetonitrile is 1:0.1-0.2 mg/mL.
The dye can be used for long-time dynamic super-resolution fluorescence imaging of lysosomes in living cells, and monitoring the dynamic change of the lysosomes under the nanoscale.
The invention has the following features:
the dye has the advantages of simple synthesis method, low price, easy functionalization and the like.
The dye reduces the pKa of molecules by introducing the 2-aminopyridine derivatives into a rhodamine 6G system, so that only a small amount of ring-opened fluorescent state molecules exist in lysosomes.
The dye can accurately position lysosomes and realize super-resolution fluorescence imaging of the lysosomes.
The dye exists in a closed-loop dark state in most parts in lysosomes and can keep higher stability in the lysosomes. The conversion of the fluorescence state and the dark state enables the dye to realize self-flashing, and carries out long-time super-resolution fluorescence imaging on lysosomes, thereby carrying out real-time monitoring on the distribution, pH change, lysosome size and interaction of the lysosomes.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained according to the drawings without inventive efforts.
FIG. 1 is a nuclear magnetic hydrogen spectrum of the dye Lyso-532 in example 1;
FIG. 2 is a nuclear magnetic carbon spectrum of the dye Lyso-532 in example 1;
FIG. 3 is a high resolution mass spectrum of the dye Lyso-532 in example 1;
FIG. 4 is a fluorescence spectrum of the dye Lyso-532 in example 1 at different pH;
FIG. 5 is a graph of the normalized fluorescence intensity at 561nm of the dye Lyso-532 in example 1 at various pHs;
FIG. 6 is a super resolution image of Lyso-532 dye on lysosomes in living cells in example 1;
FIG. 7 is a super-resolution imaging and intensity analysis plot of the dye Lyso-532 on a single lysosome in example 1;
FIG. 8 is a long-term super-resolution imaging of the dye Lyso-532 in example 1 on dynamic lysosomes in living cells;
FIG. 9 is a long-term super-resolution imaging of the dye LysoH-532 in example 3 on dynamic lysosomes in living cells;
FIG. 10 is a long-term super-resolution imaging of the dye LysoNN-532 of example 5 on dynamic lysosomes in living cells.
Detailed Description
The preparation method of the present invention will be described in detail with reference to the accompanying drawings, which are provided for illustration only and are not intended to limit the scope of the present invention.
Example 1
Synthesis of dye Lyso-532
Rho19(100mg,0.22mmol) was placed in 20mL of 1, 2-dichloroethane, then 1.0mL of phosphorus oxychloride was added to the reaction solution, and reacted at 80 ℃ for 4 h. The reaction solution was cooled and removed under reduced pressure to give a purple crude product. The crude product was dissolved in 20mL acetonitrile and 0.5mL triethylamine was added followed by 2-amino-6-methylpyridine (400mg,2.16 mmol). The reaction is carried out for 10h at 80 ℃. The solvent was removed under reduced pressure and basic alumina column chromatography (developing solvent dichloromethane: methanol 400: 1; vol.) afforded 50mg of a white solid in 45% yield.
The high resolution mass spectrum data is as follows:
HRMS(ESI)m/z[M+H]+: calculated value: 505.2604, Experimental value: 505.2652.
the nuclear magnetic hydrogen spectrum is shown in the following figure 1, and the specific data is as follows:
1H NMR(400MHz,CDCl3)δ8.23(d,J＝8.3Hz,1H),8.05–7.98(m,1H), 7.51–7.46(m,2H),7.36(t,J＝7.9Hz,1H),7.13–7.07(m,1H),6.59(d,J＝7.3Hz, 1H),6.35(s,2H),6.19(s,2H),3.35(s,2H),3.19(dd,J＝13.7,6.7Hz,4H),2.19(s, 3H),1.80(s,6H),1.28(t,J＝7.1Hz,6H).
the nuclear magnetic carbon spectrum is shown in the following figure 2, and the specific data are as follows:
13C NMR(101MHz,CDCl3)δ168.17,155.87,153.64,152.37,149.62,146.80, 136.92,133.47,130.94,128.08,127.90,124.50,123.06,118.10,116.47,111.77, 109.43,96.34,66.35,38.46,29.72,23.23,16.69,14.81.
after detection, the structure is shown as the formula.
The compound Lyso-532 obtained in this example was dissolved in a dimethylsulfoxide solution to prepare a 2mM dye mother solution, and test solutions of different concentrations were prepared as needed and detected by fluorescence spectroscopy at pH.
Testing of the response of Lyso-532 to pH. 20 mu L of mother liquor is put into 4mL of buffer solutions with different pH values to prepare 10 mu M of fluorescent probe test solution, and then the fluorescent probe test solution is put into a quartz cuvette for testing fluorescence spectra under different pH conditions.
Example 2
Synthesis of dye LysoNH-532
Rho19(300mg,0.67mmol) was placed in 30mL of 1, 2-dichloroethane, and then 2.0mL of phosphorus oxychloride was added to the reaction solution and reacted at 80 ℃ for 8 h. The reaction solution was cooled and removed under reduced pressure to give a purple crude product. The crude product was dissolved in 30mL acetonitrile and 0.5mL triethylamine was added followed by 2-amino-5-methylaminocarbonylpyridine (900mg,5.95 mmol). The reaction is carried out for 24h at 80 ℃. The solvent was removed under reduced pressure and basic alumina column chromatography (developing solvent dichloromethane: methanol 300: 1; vol.) afforded 93 mg of a white solid in 25% yield.
The high resolution mass spectrum data is as follows:
HRMS(ESI)m/z[M+H]+: calculated values: 548.2662, Experimental value: 548.2671.
the nuclear magnetic hydrogen spectrum comprises the following specific data:
1H NMR(400MHz,CDCl3)δ8.22(d,J＝8.4Hz,1H),8.02–7.93(m,1H), 7.50–7.44(m,2H),7.37(t,J＝8.1Hz,1H),7.14–7.06(m,1H),6.55(d,J＝7.2Hz, 1H),6.32(s,2H),6.18(s,2H),3.34(s,2H),3.12(dd,J＝13.5,6.5Hz,4H),2.27(s, 3H),1.82(s,6H),1.27(t,J＝7.2Hz,6H).
after detection, the structure is shown as the formula.
Example 3
Synthesis of dye LysoH-532
Rho19(100mg,0.22mmol) was placed in 15mL of 1, 2-dichloroethane, and then 0.5mL of phosphorus oxychloride was added to the reaction solution and reacted at 80 ℃ for 4 h. The reaction solution was cooled and removed under reduced pressure to give a purple crude product. The crude product was dissolved in 15mL acetonitrile and 0.5mL triethylamine was added followed by 2-aminopyridine (500mg,5.32 mmol). The reaction is carried out for 12h at 80 ℃. The solvent was removed under reduced pressure and basic alumina column chromatography (developing solvent dichloromethane: methanol 400: 1; vol.) afforded 74mg of a white solid in 67% yield.
The high resolution mass spectrum data is as follows:
HRMS(ESI)m/z[M+H]+: calculated values: 491.2447, Experimental value: 491.2442.
the nuclear magnetic hydrogen spectrum comprises the following specific data:
1H NMR(400MHz,CDCl3)δ8.23(d,J＝8.1Hz,1H),8.04–8.00(m,1H), 7.52–7.47(m,2H),7.35(t,J＝7.8Hz,1H),7.28(t,J＝7.9Hz,1H),7.10–7.07(m, 1H),6.62(d,J＝7.3Hz,1H),6.34(s,2H),6.17(s,2H),3.37(s,2H),3.19(dd,J＝ 13.5,6.6Hz,4H),1.81(s,6H),1.25(t,J＝7.35Hz,6H).
after detection, the structure is shown as the formula.
Example 4
Synthesis of dye LysopM-532
Rho19(300mg,0.67mmol) was placed in 40mL of 1, 2-dichloroethane, and then 2.0mL of phosphorus oxychloride was added to the reaction solution and reacted at 80 ℃ for 8 h. The reaction solution was cooled and removed under reduced pressure to give a purple crude product. The crude product was dissolved in 40mL acetonitrile and 0.5mL triethylamine was added followed by 2-amino-4-methylpyridine (900mg,8.32 mmol). The reaction is carried out for 24h at 80 ℃. The solvent was removed under reduced pressure and basic alumina column chromatography (developing solvent dichloromethane: methanol 300: 1; vol.) afforded 243mg of white solid in 72% yield.
The high resolution mass spectrum data is as follows:
HRMS(ESI)m/z[M+H]+: calculated values: 505.2604, Experimental value: 505.2617.
the nuclear magnetic hydrogen spectrum comprises the following specific data:
1H NMR(400MHz,CDCl3)δ8.21(d,J＝8.2Hz,1H),8.02–7.93(m,1H), 7.50–7.44(m,2H),7.37(d,J＝8.2Hz,1H),7.21(d,J＝8.3Hz,1H),6.54(d,J＝ 7.2Hz,1H),6.33(s,2H),6.18(s,2H),3.41(s,2H),3.11(dd,J＝13.6,6.6Hz,4H), 2.15(s,3H),1.83(s,6H),1.28(t,J＝7.4Hz,6H).
after detection, the structure is shown as the formula.
Example 5
Synthesis of dye LysoNN-532
Rho19(300mg,0.67mmol) was placed in 50mL of 1, 2-dichloroethane, and then 2.0mL of phosphorus oxychloride was added to the reaction solution and reacted at 80 ℃ for 6 h. The reaction solution was cooled and removed under reduced pressure to give a purple crude product. The crude product was dissolved in 50mL acetonitrile and 0.5mL triethylamine was added followed by 2-amino-4- (dimethylaminoethylamino) carbonyl-pyridine (900mg,4.32 mmol). The reaction is carried out for 16h at 80 ℃. The solvent was removed under reduced pressure and basic alumina column chromatography (developing solvent dichloromethane: methanol 50: 1; volume ratio) gave 122mg of a white solid in 30% yield.
The high resolution mass spectrum data is as follows:
HRMS(ESI)m/z[M+H]+: calculated values: 605.3240, Experimental value: 605.3231.
the nuclear magnetic hydrogen spectrum comprises the following specific data:
1H NMR(400MHz,CDCl3)δ8.25(d,J＝8.2Hz,1H),8.00–7.91(m,1H), 7.50–7.44(m,3H),7.25(d,J＝8.3Hz,1H),6.57(d,J＝7.2Hz,1H),6.34(s,2H), 6.20(s,2H),3.42(s,2H),3.11(dd,J＝13.4,6.5Hz,4H),2.27(t,J＝7.7Hz,2H), 2.14(t,J＝7.8Hz,2H),2.11(s,6H),1.83(s,6H),1.28(t,J＝7.4Hz,6H).
after detection, the structure is shown as the formula.
Example 6
Fluorescence spectrum test of the dye Lyso-532 prepared in example 1 at different pH. 20 mu L of Lyso-532 mother liquor is added into 4mL of buffer solutions with different pH values to prepare a fluorescence probe test solution with the final concentration of 10 mu M, and the fluorescence spectrum test is carried out.
As shown in fig. 4, the dye Lyso-532 is substantially in a closed-loop state above pH 5.5, substantially free of fluorescence; the pH value is reduced below 5.5, and the molecules gradually change from a non-fluorescent closed-loop structure to a fluorescent open-loop structure. As shown in FIG. 4, the maximum emission peak of the ring-opened form of Lyso-532 was around 561 nm.
As shown in FIG. 5, the maximum of the dye Lyso-532 at 561nm is plotted as a function of pH. The fluorescence of Lyso-532 is gradually increased with the decrease of pH, and the highest fluorescence intensity of Lyso-532 is obtained at pH 2.5, which indicates that the proportion of the open-loop structure is maximized.
Example 7
Super resolution imaging of Lyso-532 dye prepared in example 1 on lysosomes in living cells. mu.L of the mother liquor was added to a cell culture dish containing 1mL of culture medium at 37 deg.C，5％CO2Incubation for 0.5h, followed by fluorescence imaging of lysosomes under a super-resolution microscope.
As shown in fig. 6, the dye Lyso-532 achieves accurate localization of lysosomes and tracks lysosomal movement over a long period of time.
As shown in fig. 7, (a) is super-resolution imaging of the dye Lyso-532 to individual lysosomes; (b) for the intensity analysis of single lysosome, the resolution of the visible dye Lyso-532 to the single lysosome can reach 104 nm.
As shown in fig. 8, the dye Lyso-532 tracked lysosomes of individual lysosomes in real time. The lysosome moved 4.48 μm from the starting point to the end point within 0-100 s and then was in an inert state, with essentially no movement within 100-300 s. This demonstrates that the dye Lyso-532 is capable of super-resolution fluorescence imaging of lysosomes and long-term monitoring.
Example 8
Super resolution imaging of LysoH-532 dye prepared in example 3 on lysosomes within living cells. mu.L of the mother liquor was added to a cell culture dish containing 1mL of the culture solution at 37 ℃ with 5% CO2Incubation for 0.5h, followed by fluorescence imaging of lysosomes under a super-resolution microscope.
As shown in FIG. 9 below, the dye LysoH-532 precisely localizes lysosomes, which were tracked over a long period of time within 0-300 s. The lysosome had a total motion of 3.23 μm from start to end within 300s, while there was essentially no motion in other lysosomes. This suggests that the dye Lyso-532 can also achieve long-term super-resolution fluorescence imaging of lysosomes.
Example 9
Super resolution imaging of LysoNN-532 dye prepared in example 5 on lysosomes in living cells. mu.L of the mother liquor was added to a cell culture dish containing 1mL of the culture solution at 37 ℃ with 5% CO2Incubation for 0.5h, followed by fluorescence imaging of lysosomes under a super-resolution microscope.
As shown in fig. 10 below, the dye LysoNN-532 precisely localizes lysosomes, enabling long-term super-resolution fluorescence imaging of lysosomes.
Claims (9)
1. A self-flashing fluorescent dye for lysosome long-time super-resolution fluorescence imaging is characterized in that the structural formula of the dye is shown as follows,
wherein R is1，R2，R3，R4If one is not H, the remaining substituents are H; specifically, H, (CH)2CH2)nCH3、COONH-R5Any one of the groups; r5Is (CH)2CH2)nCH3N, N-dimethylaminoethyl, benzylpurine or 2-morpholinoethyl, N is an integer between 0 and 4.
2. The self-flashing fluorescent dye for long-time super-resolution fluorescence imaging of lysosomes according to claim 1, wherein the dye is prepared by using rhodamine 6G as a parent substance and carrying out ring locking through a 2-aminopyridine derivative.
3. A method of synthesis of self-flashing fluorochrome for long time super-resolved fluorescence imaging of lysosomes according to any of claims 1-2, wherein the dye is prepared by ring locking of 2-aminopyridine derivatives using rhodamine 6G as a precursor.
4. The method for synthesizing a class of self-flashing fluorescent dyes for long-time super-resolution fluorescence imaging of lysosomes according to claim 3, wherein: the specific method for synthesizing is as follows:
putting the rhodamine derivative into 1, 2-dichloroethane, adding phosphorus oxychloride into the reaction solution, and reacting for 4-8h at 80 ℃; then, removing the purple crude product under reduced pressure; dissolving the crude product in acetonitrile, adding 0.5mL of triethylamine and 2-aminopyridine derivatives, and reacting at 80 ℃ for 10-24 h; the solvent was removed under reduced pressure and basic alumina column chromatography gave a white solid.
5. The method for synthesizing a class of self-flashing fluorescent dyes for long-time super-resolution fluorescence imaging of lysosomes according to claim 3, wherein: the mass ratio of the rhodamine derivative to the 2 aminopyridine derivative in the synthesis step is 1: 3-5.
6. The method for synthesizing a class of self-flashing fluorescent dyes for long-time super-resolution fluorescence imaging of lysosomes according to claim 3, wherein: the volume ratio of the mass of the rhodamine derivative to the phosphorus oxychloride is 1:0.005-0.01 mg/mL.
7. The method for synthesizing a class of self-flashing fluorescent dyes for long-time super-resolution fluorescence imaging of lysosomes according to claim 3, wherein: the volume ratio of the mass of the rhodamine derivative to the 1, 2-dichloroethane is 1:0.1-0.2 mg/mL.
8. The method for synthesizing a class of self-flashing fluorescent dyes for long-time super-resolution fluorescence imaging of lysosomes according to claim 3, wherein: the volume ratio of the mass of the rhodamine derivative to the acetonitrile is 1:0.1-0.2 mg/mL.
9. Use of the self-blinking fluorescent dye for long-time super-resolution fluorescence imaging of lysosomes according to claim 1 in the fields of fluorescence imaging and switching materials.
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| CN105567216A (en) * | 2015-10-27 | 2016-05-11 | 西北大学 | Lysosome targeted fluorescent probe and preparation method and application thereof |
| CN110272431A (en) * | 2018-03-16 | 2019-09-24 | 中国科学院大连化学物理研究所 | The light-operated role in fluorescent molecule switch and its synthetic method of a kind of targeting of lysosome and application |
| CN110272432A (en) * | 2018-03-16 | 2019-09-24 | 中国科学院大连化学物理研究所 | A kind of light-operated role in fluorescent molecule switch of acid resistance and its synthetic method and application |
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| CN105567216A (en) * | 2015-10-27 | 2016-05-11 | 西北大学 | Lysosome targeted fluorescent probe and preparation method and application thereof |
| CN110272431A (en) * | 2018-03-16 | 2019-09-24 | 中国科学院大连化学物理研究所 | The light-operated role in fluorescent molecule switch and its synthetic method of a kind of targeting of lysosome and application |
| CN110272432A (en) * | 2018-03-16 | 2019-09-24 | 中国科学院大连化学物理研究所 | A kind of light-operated role in fluorescent molecule switch of acid resistance and its synthetic method and application |
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