Self-flickering rhodamine spiro thioester fluorescent dye, synthesis method thereof and application of self-flickering rhodamine spiro thioester fluorescent dye in field of super-resolution imaging

A technique of fluorescent dye and synthesis method, which is applied in the application field of self-blinking rhodamine spirothioester fluorescent dye in the field of super-resolution imaging, achieving the effects of good specificity, good self-blinking performance, and accurate positioning

Active Publication Date: 2021-06-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition to the above factors will have a certain impact on the physiological activity of the cells, the photostability and brightness of the dyes are also required to be higher, and most of the traditional fluorescent dyes cannot meet the above requirements

Method used

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  • Self-flickering rhodamine spiro thioester fluorescent dye, synthesis method thereof and application of self-flickering rhodamine spiro thioester fluorescent dye in field of super-resolution imaging
  • Self-flickering rhodamine spiro thioester fluorescent dye, synthesis method thereof and application of self-flickering rhodamine spiro thioester fluorescent dye in field of super-resolution imaging
  • Self-flickering rhodamine spiro thioester fluorescent dye, synthesis method thereof and application of self-flickering rhodamine spiro thioester fluorescent dye in field of super-resolution imaging

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] When R 1 =R 2 =CH 2 CH 3 , when n=1, a kind of synthetic route of self-scintillation rhodamine spirothioester fluorescent dye P1 is as follows:

[0054]

[0055] in,

[0056] Synthesis of Intermediate 1:

[0057]

[0058] 3-Hydroxy-N,N-diethylaniline (2.9037g, 17.6mmol) and phthalic anhydride (2.6319g, 17.8mmol) were placed in a 100mL two-necked flask, vacuumed and replaced with nitrogen three times. Under the protection of nitrogen, 20 mL of toluene was added to the flask with a syringe, and the solution was black. After heating to reflux for 16 h, the solution changed from black to purple. The reaction solution was poured into 100 mL of water, filtered with suction, and the filter cake was washed with a small amount of methanol to obtain a pale pink solid. The obtained solid was recrystallized with isopropanol, and the recrystallized solid was washed with a small amount of methanol to obtain a pale yellow solid (3.407 g, yield 61.8%).

[0059] Its high-re...

Embodiment 2

[0108] Dissolve P1 in DMSO to prepare a test stock solution with a concentration of 1 mM. Select toluene, tetrahydrofuran, 1,4-dioxane, ethyl acetate, chloroform, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, methanol and water as test solvents, dilute to The final concentration is 10 -5 M, test its UV-Vis absorption spectrum and fluorescence emission spectrum, respectively, to investigate the sensitivity of its ground state and excited state to the solvent environment. Such as Figure 7 with 8 As shown, the experimental results show that both the ground state and the excited state of the molecule are insensitive to the solvent environment, and it can be further applied to cells.

Embodiment 3

[0110] The 1mM mother liquor of P1 was prepared into different pH values ​​with dilute solutions of hydrochloric acid and sodium hydroxide and the final concentration was 10 -5 The aqueous solution of M, then test its UV-Vis absorption spectrum and fluorescence emission spectrum respectively, calculate pK cycl value, to investigate whether it can maintain most of the closed-loop non-luminous state under physiological acidity. Such as Figure 9 , 10 As shown in and 11, the experimental results show that under the physiological condition of pH 7.4, most of the molecules are in a closed-loop and non-luminous state, which is one of the necessary conditions for STORM super-resolution imaging.

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Abstract

The invention relates to a self-flickering rhodamine spiro thioester fluorescent dye, a synthesis method thereof and application of the self-flickering rhodamine spiro thioester fluorescent dye in the field of super-resolution imaging. One end of a rhodamine spiro thioester fluorescent matrix is linked with a substrate molecule chlorinated alkyl derivative of a Halo protein tag through piperazine, and the specific structure is shown as a formula (1). The rhodamine spirothioate fluorescent dye disclosed by the invention has the excellent performance of self-flickering without adding a stabilizer and strong activating light in cells, and is suitable for being applied to random optical reconstruction microimaging (STORM) in living cells.

Description

technical field [0001] The invention belongs to the field of fluorescent dyes, and in particular relates to the application of a class of self-blinking rhodamine spirothioester fluorescent dyes in the field of super-resolution imaging. Background technique [0002] The 2014 Nobel Prize in Chemistry was awarded to three physicists: Eric Betzig, Stefan W.Hell and W.E.Moerner, in recognition of their outstanding contributions to the development of super-resolution fluorescence imaging technology. Super-resolution optical microscopy raises the resolution limit from a few hundred nanometers to a few nanometers. Compared with electron microscopy and scanning electron microscopy, super-resolution optics is very suitable for live cell imaging with its unique non-invasive and highly specific multicolor labeling, thus enabling scientists to observe different molecules in cells at the nanoscale on the movement. [0003] Therefore, in recent years, super-resolution fluorescence imagin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/00C09B57/00G01N21/64
CPCC09K11/00C09B57/00G01N21/6428C09K2211/1044C09K2211/1088C09K2211/1092Y02P20/55
Inventor 徐兆超吴绍维李锦乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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