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2,7-bis(4-vinylpyridine)-9-fluorenone salt-based two-photon fluorescent cell nucleus localization probe material and its preparation method and application

A technology of vinylpyridine and two-photon fluorescence, which is applied in luminescent materials, biochemical equipment and methods, chemical instruments and methods, etc., can solve the problems of large Rayleigh scattering of excitation light, difficult performance and real-time continuous observation for a long time, and achieve fluorescence Stable and clear nuclear localization, long-lasting fluorescence effect

Active Publication Date: 2017-09-12
SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] The purpose of the present invention is to solve the problems existing in the performance of the existing commercial fluorescent cell nucleus localization probe materials that it is difficult to perform long-term real-time continuous observation, the excitation light is located in the non-biological optical window of the visible light band, and the Rayleigh scattering of the excitation light is large.

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  • 2,7-bis(4-vinylpyridine)-9-fluorenone salt-based two-photon fluorescent cell nucleus localization probe material and its preparation method and application
  • 2,7-bis(4-vinylpyridine)-9-fluorenone salt-based two-photon fluorescent cell nucleus localization probe material and its preparation method and application
  • 2,7-bis(4-vinylpyridine)-9-fluorenone salt-based two-photon fluorescent cell nucleus localization probe material and its preparation method and application

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specific Embodiment approach 1

[0028] Specific embodiment 1: The structural formula of the 2,7-bis(4-vinylpyridine)-9-fluorenone salt-based two-photon fluorescent cell nucleus localization probe material in this embodiment is as follows:

[0029]

[0030] Among them, R is CH 3 、C 2 h 5 or C 4 h 9 .

[0031] The 2,7-bis(4-vinylpyridine)-9-fluorenone salt-based two-photon fluorescent cell nucleus localization probe material of this embodiment uses a two-photon femtosecond laser in the near-infrared band (biological optical window) of 800-860 nm Under excitation, the probe materials can produce strong fluorescence. And in the process of two-photon fluorescence imaging, the probe material can accurately mark the nuclear staining area, and the nuclear localization is clear and obvious. The fluorescence under the continuous excitation of the femtosecond laser is stable and long-lasting, and the real-time continuous observation time can reach more than 3000 seconds.

specific Embodiment approach 2

[0032] Specific embodiment two: The preparation method of the 2,7-bis(4-vinylpyridine)-9-fluorenone salt-based two-photon fluorescent nucleus localization probe material of this embodiment is carried out according to the following steps:

[0033] 1. Weigh 23-26% of 2,7-dibromo-9-fluorenone, 24-27% of 4-vinylpyridine, 5-9% of tri-o-tolylphosphine, 1-3% Palladium acetate, 38-42% anhydrous potassium carbonate, and 15-20ml of N-methylpyrrolidone were added at the same time. Mix the above materials evenly and add them into a closed reaction vessel. Under the protection of an inert gas, gradually raise the temperature to 125-135°C and keep the temperature for 20-24 hours. After the reaction, the mixture was fully extracted with dichloromethane, and the crude product was distilled under reduced pressure. Two eluents of ethyl acetate:petroleum ether=2-4:1 and acetonitrile:dichloromethane=4-6:1 were used for silica gel column chromatography to obtain a red intermediate product.

[0...

specific Embodiment approach 3

[0038] Specific embodiment three: the difference between this embodiment and specific embodiment two is that: 24.5% of 2,7-dibromo-9-fluorenone and 26.5% of 4-vinyl Pyridine, 8.5% tri-o-tolylphosphine, 1.5% palladium acetate, 39% anhydrous potassium carbonate and 15 ml of N-methylpyrrolidone.

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Abstract

Provided is a 2,7-bis(4-vinylpyridine)-9-fluorenone salt two-photon fluorescent cell nucleus positioning probe material. The structural formula of the positioning probe material is shown in the specification, wherein R represents CH3 or C2H5 or C4H9. A preparation method of the positioning probe material comprises the steps that reactants such as 2,7-dibromo-9-fluorenone and 4-vinylpyridine are put in a mixture which takes palladium acetate as a catalyst, adopts anhydrous potassium carbonate to provide an alkaline environment and takes N-methyl pyrrolidinone as solvent, a heck reaction is conducted in a sealed container in a nitrogen protection mode under the conditions of certain temperature and pressure, and then a final product is obtained after iodoalkane salinization is conducted. According to the 2,7-bis(4-vinylpyridine)-9-fluorenone salt two-photon fluorescent cell nucleus positioning probe material and the preparation method and application thereof, long-time real-time continuous observation capacity is embodied in cell nucleus dyeing marking and two-photon fluorescent imaging, a biological optical window (800-860 nm), located in a near-infrared band, of light is excited, and Rayleigh scattering of exciting light is effectively reduced. The 2,7-bis(4-vinylpyridine)-9-fluorenone salt two-photon fluorescent cell nucleus positioning probe material can be applied to the field of two-photon three-dimensional bioluminescent imaging.

Description

technical field [0001] The invention relates to a two-photon fluorescent cell nucleus localization probe material and its preparation method and application, specifically a 2,7-bis(4-vinylpyridine)-9-fluorenone salt two-photon fluorescent cell nucleus localization probe Materials and their preparation methods and applications. Background technique [0002] With the continuous development of life sciences, bioluminescent imaging technology has been widely used in the selective localization and labeling of living tissues. In particular, a new class of biomarkers with bioluminescent probe materials as the main research object is currently a research hotspot in the imaging field of life science. Compared with the traditional single-photon fluorescent probes that use the ultraviolet band as the excitation light source, their application as fluorescent labeling dyes is limited due to the defects of large cell damage, low imaging resolution and inability to perform three-dimension...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D213/50C12Q1/02
Inventor 迟书恒李亮吴谊群王阳
Owner SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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