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Application of fluorescent dye with intramolecular switch in super-resolution imaging

A technology of super-resolution imaging and fluorescent dyes, applied in organic dyes, analytical materials, luminescent materials, etc., can solve the problems of photobleaching and can not meet the long-term imaging.

Pending Publication Date: 2021-06-11
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

The main problem limiting its application is that the methine chains of this type of dye are completely exposed, and the excited state is easily attacked by singlet oxygen to cause photobleaching, which cannot meet the needs of long-term imaging.

Method used

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  • Application of fluorescent dye with intramolecular switch in super-resolution imaging
  • Application of fluorescent dye with intramolecular switch in super-resolution imaging
  • Application of fluorescent dye with intramolecular switch in super-resolution imaging

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Synthesis of Dye CyS-4C

[0052] The synthetic route and product structure of the intermediate hemicyanine are as follows:

[0053]

[0054] Weigh N-methyl-2,3,3-trihydroindole (300mg, 1mmol) and malondialdehyde derivatives (284mg, 1mmol) into a single-necked bottle, add solvent acetic anhydride 3mL, heat up to 90°C and stir 2 hours. The solvent was removed under reduced pressure, and silica gel column chromatography (dichloromethane / methanol=50 / 1, V / V) gave 181 mg of a reddish-brown solid with a yield of 60%.

[0055] Its high-resolution mass spectrometry data are as follows:

[0056] HRMS (ESI): m / z: [M] + : Calculated: 345.1961, Experimented: 345.1964.

[0057] After testing, its structure is shown in the above formula.

[0058] Synthesis of Intermediate N-thioacetylbutyl-2,3,3-trimethylindoline

[0059]

[0060] Weigh the compound N-(4-bromobutyl)-2,3,3-trimethyltrihydroindole (150mg, 0,4mmol), potassium thioacetate (46mg, 0.4mmol) into a round bottom fl...

Embodiment 2

[0088] Synthesis of Dye CyS-3C

[0089] The synthetic route and product structure of the intermediate hemicyanine are as follows:

[0090]

[0091] Weigh N-methyl-2,3,3-trihydroindole (300mg, 1mmol) and malondialdehyde derivatives (312mg, 1mmol) into a single-necked bottle, add solvent acetic anhydride 3mL, heat up to 110°C and stir 1 hour. The solvent was removed under reduced pressure, and silica gel column chromatography (dichloromethane / methanol=50 / 1, V / V) gave 181 mg of a reddish-brown solid with a yield of 60%.

[0092] Its high-resolution mass spectrometry data are as follows:

[0093] HRMS (ESI): m / z: [M] + : Calculated: 345.1961, Experimented: 345.1964.

[0094] After testing, its structure is shown in the above formula.

[0095] Synthesis of Intermediate N-thioacetylpropyl-2,3,3-trimethyltrihydroindole

[0096]

[0097] Weigh the compound N-(3-bromopropyl)-2,3,3-trimethyltrihydroindole (300mg, 0.8mmol), and potassium thioacetate (1.14mg, 10mmol) into a ro...

Embodiment 3

[0119] Synthesis of Dye CyS-2C

[0120] The synthetic route and product structure of the intermediate hemicyanine are as follows:

[0121]

[0122] Weigh N-methyl-2,3,3-trihydroindole (300mg, 1mmol) and malondialdehyde derivatives (284mg, 1mmol) into a single-necked bottle, add solvent acetic anhydride 3mL, heat up to 110°C and stir 2 hours. The solvent was removed under reduced pressure, and silica gel column chromatography (dichloromethane / methanol=50 / 1, V / V) gave 181 mg of a reddish-brown solid with a yield of 60%.

[0123] Its high-resolution mass spectrometry data are as follows:

[0124] HRMS (ESI): m / z: [M] + : Calculated: 345.1961, Experimented: 345.1964.

[0125] After testing, its structure is shown in the above formula.

[0126] Synthesis of intermediate 2-thioacetyl-bromoethane

[0127]

[0128] The compound 1,2-dibromoethane (500 μL, 5.8 mmol) was dissolved in N,N-dimethylacetamide to form a solution (S1), and the compound potassium thioacetate (726 mg...

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Abstract

The invention relates to an application of a fluorescent dye with an intramolecular switch in super-resolution imaging. The dye is pentamethine cyanine with the intramolecular switch. The switch is in a closed-loop state in most organic solvents, in a solid state and in a wide pH range from acidity to alkalinity of an aqueous solution, and molecules are protected from photobleaching. Under an imaging condition, a small amount of molecules can be subjected to ring opening under the action of protons, salt ions, laser, proteins and other substances in cells, and closed-loop molecules still account for most of the molecules. The molecules are low in ring-opening proportion, high in ring-opening molecule brightness, high in light stability and suitable for super-resolution imaging.

Description

technical field [0001] The invention belongs to the technical field of fluorescence imaging, and in particular relates to the application of a fluorescent dye with an intramolecular switch in super-resolution imaging. Background technique [0002] Fluorescence imaging technology is one of the most powerful tools in the field of modern life sciences. The emergence of super-resolution imaging technology has improved the resolution of fluorescence imaging to the single-molecule scale. The long-term real-time and dynamic tracking and observation of life activities at the nanometer scale relying on super-resolution technology is a powerful driving force for the development of life sciences. [0003] In order to achieve higher positioning accuracy, super-resolution microscopy imaging requires more photons per unit time, which puts higher requirements on the brightness of dyes. In addition, compared with the traditional confocal fluorescence microscope, the intensity of the laser ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N21/64C09K11/06C09B23/08C09B23/10
CPCG01N21/6428C09K11/06C09B23/083C09B23/107C09K2211/1029C09K2211/1037
Inventor 徐兆超刘文娟
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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