Self-flickering fluorescent dye for super-resolution fluorescence imaging and synthesis and application thereof

A technology of super-resolution fluorescence and fluorescent dyes, which is applied in the field of self-scintillation fluorescent dyes and their synthesis and application, which can solve the problems of lack of self-scintillation molecules and lack of systematic research on imaging requirements, and achieve high photostability and high quantum yield.

Active Publication Date: 2020-06-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such self-scintillation molecules are currently scarce, and there is no systematic research on whether the self-scintillation performance meets the imaging requirements. It is urgent to establish a set of molecular design models to meet the needs of super-resolution multicolor fluorescence imaging.

Method used

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  • Self-flickering fluorescent dye for super-resolution fluorescence imaging and synthesis and application thereof
  • Self-flickering fluorescent dye for super-resolution fluorescence imaging and synthesis and application thereof
  • Self-flickering fluorescent dye for super-resolution fluorescence imaging and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Synthesis of Intermediate 1

[0089]

[0090] 3-Methyl-4-bromobenzoic acid (5.03g, 23mmol), NBS (4.5g, 25mmol), AIBN (76.8mg, 0.47mmol) were dissolved in 50mL carbon tetrachloride (CCl 4 ), heated to reflux for 72h. After the reaction, the solvent was distilled off under reduced pressure, separated and purified through a silica gel column (200-300 mesh) using petroleum ether and ethyl acetate (20:1) as developing solvents to obtain 6 g of the white target compound, with a yield of 86%.

[0091] Synthesis of Intermediate 2

[0092]

[0093] 1 (6g, 20mmol) was dissolved in 50mL of 10% sodium carbonate solution and stirred at 70°C for 2h. After the reaction was completed, dilute hydrochloric acid was added, and after the precipitate was precipitated, it was filtered and dried. After separation and purification on a silica gel column (200-300 mesh) with dichloromethane and methanol (20:1) as the developing solvent, 3 g of the white target product was obtained, with...

Embodiment 2

[0131] Synthesis of Intermediate 1

[0132]

[0133] 3-Methyl-4-bromobenzoic acid (5g, 24mmol), NBS (2.25g, 12.5mmol), AIBN (38mg, 0.24mmol) were dissolved in 30mL carbon tetrachloride (CCl 4 ), heated to reflux for 40h. After the reaction, the solvent was distilled off under reduced pressure, separated and purified through a silica gel column (200-300 mesh) using petroleum ether and ethyl acetate (20:1) as developing solvents to obtain 3 g of the white target compound, with a yield of 85%.

[0134] Synthesis of Intermediate 2

[0135]

[0136] 1 (6g, 20mmol) was dissolved in 50mL of 10% sodium carbonate solution and stirred at 70°C for 2h. After the reaction was completed, dilute hydrochloric acid was added, and after the precipitate was precipitated, it was filtered and dried. After separation and purification on a silica gel column (200-300 mesh) with dichloromethane and methanol (20:1) as the developing solvent, 1.5 g of the white target product was obtained, with...

Embodiment 3

[0163] Synthesis of Intermediate 1

[0164]

[0165] 3-Methyl-4-bromobenzoic acid (2.5g, 12mmol), NBS (4.5g, 25mmol), AIBN (76.8mg, 0.47mmol) were dissolved in 50mL carbon tetrachloride (CCl 4 ), heated to reflux for 80h. After the reaction, the solvent was distilled off under reduced pressure, separated and purified through a silica gel column (200-300 mesh) using petroleum ether and ethyl acetate (20:1) as the developing solvent to obtain 5 g of the white target compound, with a yield of 80%.

[0166] Synthesis of Intermediate 2

[0167]

[0168] 1 (3g, 10mmol) was dissolved in 50mL of 10% sodium carbonate solution and stirred at 70°C for 2h. After the reaction was completed, dilute hydrochloric acid was added, and after the precipitate was precipitated, it was filtered and dried. After separation and purification on a silica gel column (200-300 mesh) with dichloromethane and methanol (20:1) as the developing solvent, 2 g of the white target product was obtained, wi...

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Abstract

The invention provides a self-flickering fluorescent dye for super-resolution fluorescence imaging as well as synthesis and application thereof. According to the dye, azetidine is introduced into the4,5-sites of silicon rhodamine to inhibit intramolecular rotation, so that the characteristics of high quantum yield and high stability are achieved; meanwhile, under normal physiological conditions,fluorescence and non-fluorescence forms of the probe can be mutually converted through intramolecular interaction, so that the probe can be applied to living cell super-resolution imaging, the structural formula of the probe is shown as (1), and the dye can be combined with an antibody to perform specific labeling imaging on tubulin in cells. The dye can be widely applied to the fields of proteinlabeling, super-resolution fluorescence imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescent dyes, and in particular relates to a self-scintillation fluorescent dye for super-resolution fluorescence imaging and its synthesis and application. Background technique [0002] Optical microscopy has long been an important tool in biomedical research due to its non-contact and non-invasive advantages. However, the resolution of traditional optical microscopes is greater than 200nm, which cannot be used to clearly observe biological structures within 200nm. Super-resolution optical imaging is the most significant breakthrough in the field of optical microscopic imaging in this century. It gets rid of the limitation of optical diffraction limit and provides an unprecedented tool for life science research. Current super-resolution techniques mainly include structured light illumination microscopy (SIM), stimulated emission depletion microscopy (STED), and stochastic optical positioning and rec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06G01N21/64
CPCC09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1096G01N21/6428
Inventor 徐兆超乔庆龙刘晓刚郑加柱
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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