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A ratiometric two-photon fluorescent probe and its preparation method and application

A two-photon fluorescence, ratiometric technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of strong photobleaching and phototoxicity, low detection accuracy, poor imaging effect, etc. Needle concentration, accurate and reliable test results, small damage effect

Active Publication Date: 2022-05-13
SHANDONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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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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  • A ratiometric two-photon fluorescent probe and its preparation method and application
  • A ratiometric two-photon fluorescent probe and its preparation method and application
  • A ratiometric two-photon fluorescent probe and its preparation method and application

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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 fluorescent probe and its preparation method and application. The preparation method of the fluorescent probe is: reacting hydroxytetraphenylethylene with hexamethylenetetramine to obtain Compound 1, compound 1 reacts with o-aminothiophenol to obtain compound 2, adding trifluoromethanesulfonyl chloride to compound 2 to generate the final product, which is the ratio-type two-photon fluorescent probe TPE-BT-TF; the fluorescent probe is applied For the detection of superoxide anion, the concentration of superoxide anion can be determined, and the selectivity is strong; the fluorescent probe has two-photon excitation characteristics, and can use two-photon confocal microscopy to perform ratiometric double-photon detection of superoxide anion in samples such as cells. Photon fluorescence imaging detection, the imaging effect is good.

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 Patents(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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