Ratio type two-photon fluorescent probe as well as preparation method and application thereof

A two-photon fluorescence and ratiometric technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low accuracy of detection results, strong photobleaching and phototoxicity, poor imaging effect, etc., and achieve detection results Accurate and reliable, eliminate probe concentration, effect with little damage

Active Publication Date: 2020-11-03
SHANDONG NORMAL UNIV
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Problems solved by technology

The inventors found that currently reported superoxide anion fluorescent probes mainly have the following disadvantages: on the one hand, they are mainly fluorescence-enhanced probes based on a single wavelength. Compared with ratiometric probes, these probes are easier to detect. Interference with probe concentration, laser efficiency and other factors leads to low accuracy of detection results; on the other hand, it is mainly single-photon fluorescent probes. Shallow, strong photobleaching and phototoxicity, poor imaging effect

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  • Ratio type two-photon fluorescent probe as well as preparation method and application thereof
  • Ratio type two-photon fluorescent probe as well as preparation method and application thereof
  • Ratio type two-photon fluorescent probe as well as preparation method and application thereof

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preparation example Construction

[0026] In one embodiment of the present invention, a method for preparing a ratiometric two-photon fluorescent probe is provided. The preparation method includes the following steps: reacting hydroxytetraphenylethylene with hexamethylenetetramine to obtain a product, and preparing the product React with o-aminothiophenol, and finally add trifluoromethanesulfonyl chloride to generate the final product, which is the ratiometric two-photon fluorescent probe for detecting superoxide anion;

[0027] The reaction process of the preparation method is as follows:

[0028]

[0029] In a specific embodiment, the steps of the preparation method are as follows:

[0030] (1) Add hexamethylenetetramine to the solvent system of hydroxytetraphenylethylene, and heat to reflux to obtain compound 1;

[0031] (2) adding o-aminothiophenol to the solvent system of compound 1 to obtain compound 2;

[0032] (3) Add trifluoromethanesulfonyl chloride to the solvent system of compound 2 to obtain a...

Embodiment 1

[0045] A preparation method of a ratiometric two-photon fluorescent probe for detecting superoxide anions:

[0046] (1) Dissolve hydroxytetraphenylethylene (348mg) and hexamethylenetetramine (700mg) in a mixed solvent of glacial acetic acid (3mL) and trifluoroacetic acid (3mL), heat to reflux for 3-4h, then wash with 30mL water Quench the reaction, extract 3 times with dichloromethane (3 × 20mL), spin dry, and separate with a chromatographic column, the eluent ratio is V 二氯甲烷 :V 石油醚 =1:1, spin-dried to obtain compound 1.

[0047] (2) Add compound 1 (150 mg) and o-aminothiophenol (65 μL) into a mixed solvent of dichloromethane (1.5 mL) and methanol (2.5 mL) to react at room temperature for 6 h, spin dry, separate with a chromatographic column, and elute agent is V 二氯甲烷 :V 石油醚 =1:5, spin-dried to obtain compound 2.

[0048] (3) Compound 2 (48 mg) was dissolved in dichloromethane (3 mL), and trifluoromethanesulfonyl chloride (53 μL) was added to react for 2 h under stirring ...

Embodiment 2

[0054] A preparation method of a ratiometric two-photon fluorescent probe for detecting superoxide anions:

[0055] (1) Dissolve hydroxytetraphenylethylene (450mg) and hexamethylenetetramine (900mg) in a mixed solvent of glacial acetic acid (4mL) and trifluoroacetic acid (4mL), heat to reflux for 3-4h, then wash with 30mL water Quench the reaction, extract 3 times with dichloromethane (3 × 20mL), spin dry, and separate with a chromatographic column, the eluent ratio is V 二氯甲烷 :V 石油醚 =1:1, spin-dried to obtain compound 1.

[0056] (2) Compound 1 (200 mg) and o-aminothiophenol (84 μL) were added to a mixed solvent of dichloromethane (2 mL) and methanol (3.5 mL) to react at room temperature for 6 hours, spin dry, and separate with a chromatographic column. for V 二氯甲烷 :V 石油醚 =1:5, spin-dried to obtain compound 2.

[0057] (3) Compound 2 (24 mg) was dissolved in dichloromethane (2 mL), and trifluoromethanesulfonyl chloride (30 μL) was added to react for 2 h under stirring at r...

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Abstract

The invention belongs to the technical field of synthesis and fluorescence detection, and discloses a ratio type two-photon fluorescence probe as well as a preparation method and application thereof.The preparation method of the fluorescent probe comprises the following steps: reacting hydroxyl tetraphenyl ethylene with hexamethylenetetramine to obtain a compound 1, reacting the compound 1 with o-aminothiophenol to obtain a compound 2, and adding trifluoromethanesulfonyl chloride into the compound 2 to generate a final product, namely the ratio type two-photon fluorescent probe TPEBTTF. Whenthe fluorescent probe is applied to detection of superoxide anions, the concentration of the superoxide anions can be determined, and the selectivity is high; in addition, the fluorescent probe has atwo-photon excitation characteristic, can perform ratio two-photon fluorescence imaging detection on superoxide anions in samples such as cells by means of a two-photon confocal microscope, and has agood imaging effect.

Description

technical field [0001] The invention relates to the technical field of synthesis and fluorescence detection, in particular to a ratio-type two-photon fluorescent probe and its preparation method and application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Superoxide anion (O 2 ·- ) is the most important type of reactive oxygen species, which can be converted into other reactive oxygen species through enzymatic or non-enzymatic reactions, is the origin or precursor of other reactive oxygen species, and is an important marker of oxidative stress. The concentration level of superoxide anion is closely related to physiological and pathological processes such as cell oxi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06G01N21/6428C09K2211/1007C09K2211/1037G01N2021/6417
Inventor 解希雷苏幸幸唐波王栩
Owner SHANDONG NORMAL UNIV
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