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Two-photon fluorescent probe for detecting Fe < 2 + > in living body as well as preparation method and application of two-photon fluorescent probe

A two-photon fluorescence, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of high price, unclear probe detection limit and disease application model data, penetration depth, etc. restrictions, etc.

Active Publication Date: 2021-11-16
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to related reports, these probes have been able to detect Fe2+ in vivo and in vitro, but they are expensive (1300 yuan / 50 μg or 2480 yuan / 24 μg), and due to the characteristics of single-photon excitation, these probes The penetration depth of the needle in biological tissue will be limited, which will also affect the imaging effect of the probe in vivo
At the same time, data such as detection limits and disease application models of these probes are still unclear

Method used

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  • Two-photon fluorescent probe for detecting Fe &lt; 2 + &gt; in living body as well as preparation method and application of two-photon fluorescent probe
  • Two-photon fluorescent probe for detecting Fe &lt; 2 + &gt; in living body as well as preparation method and application of two-photon fluorescent probe
  • Two-photon fluorescent probe for detecting Fe &lt; 2 + &gt; in living body as well as preparation method and application of two-photon fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] A novel method for detecting Fe in living organisms 2+ The preparation method of the two-photon fluorescent probe is as follows:

[0044] 1. Preparation of pyrimidin-based dye DEt

[0045] Dissolve 4-fluorobenzaldehyde, potassium carbonate, diethylamine, and Aliquat-336 in DMF, and stir at 95°C for 12h. The reacted solution was dissolved in ethyl acetate and washed with water. Anhydrous sodium sulfate was used to remove water, and purified by silica gel chromatography to obtain DEt-a.

[0046] Dissolve DEt-a in ethanol, ultrasonically dissolve the solid, stir and add concentrated hydrochloric acid, and reflux at 95°C for 24h. After the reaction, the solution was poured into ice water and neutralized by adding sodium bicarbonate. use CH 2 Cl 2 After extracting twice, dry the organic phase with anhydrous sodium sulfate, remove anhydrous sodium sulfate and organic solvent, and obtain the dye DEt by silica gel chromatography.

[0047] 2. Preparation of probe PyFe

...

Embodiment 2

[0052] A novel method for detecting Fe in living organisms 2+ The preparation method of the two-photon fluorescent probe is as follows:

[0053] 1. Preparation of pyrimidin-based dye DEt

[0054] Dissolve 4-fluorobenzaldehyde, potassium carbonate, diethylamine, and Aliquat-336 in DMF, and stir at 95°C for 14h. The reacted solution was dissolved in ethyl acetate and washed with water. Anhydrous sodium sulfate was used to remove water, and purified by silica gel chromatography to obtain DEt-a.

[0055] Dissolve DEt-a in ethanol, ultrasonically dissolve the solid, add concentrated hydrochloric acid with stirring, and reflux overnight at 95°C. After the reaction, the solution was poured into ice water and neutralized by adding sodium bicarbonate. use CH 2 Cl 2 After extracting twice, dry the organic phase with anhydrous sodium sulfate, remove anhydrous sodium sulfate and organic solvent, and obtain the dye DEt by silica gel chromatography.

[0056] 2. Preparation of probe P...

Embodiment 3

[0061] A novel method for detecting Fe in living organisms 2+ The preparation method of the two-photon fluorescent probe is as follows:

[0062] 1. Preparation of pyrimidin-based dye DEt

[0063] Dissolve 4-fluorobenzaldehyde, potassium carbonate, diethylamine, and Aliquat-336 in DMF, and stir at 95°C for 20h. The reacted solution was dissolved in ethyl acetate and washed with water. Anhydrous sodium sulfate was used to remove water, and purified by silica gel chromatography to obtain DEt-a.

[0064] Dissolve DEt-a in ethanol, ultrasonically dissolve the solid, stir and add concentrated hydrochloric acid, and reflux at 95°C for 24h. After the reaction, the solution was poured into ice water and neutralized by adding sodium bicarbonate. use CH 2 Cl 2 After extracting twice, dry the organic phase with anhydrous sodium sulfate, remove anhydrous sodium sulfate and organic solvent, and obtain the dye DEt by silica gel chromatography.

[0065] 2. Preparation of probe PyFe

...

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Abstract

The invention relates to a pyrimidyl dye-based two-photon fluorescent probe capable of rapidly and sensitively detecting Fe < 2 + > in a living body through light regulation and control, and belongs to the field of organic fluorescent probes. The fluorescent probe is a PyFe fluorescent probe, and the structural formula of the PyFe fluorescent probe is as shown in formula (I). The fluorescent probe provided by the invention can accurately detect Fe < 2 + > in a living body and avoid interference of other ionic amino acids in cells. The probe has an extremely high response rate and very high ion selectivity, can realize in-vitro naked eye detection, and also has very good biocompatibility. Fluorescence confocal imaging experiments show that the probe has good cell permeability, has no toxic or side effect on cells and organisms, has two photons and can realize deep imaging of living animals or tissues.

Description

technical field [0001] The invention relates to a pyrimidine-based dye that can rapidly and sensitively detect Fe in living organisms through light regulation. 2+ A two-photon fluorescent probe belongs to the field of organic fluorescent probes. Background technique [0002] Iron is a transition metal ubiquitously distributed in the biosphere and is essential to maintain normal cellular functions due to its ability to participate in electron transfer reactions, however excess iron, especially the redox-active Fe 2+ , may also generate toxic reactive oxygen species (ROS), thereby damaging the body. Studies have shown that oxidative stress caused by abnormal iron metabolism is closely related to some diseases such as Parkinson's disease (PD). Based on the important role of iron in these diseases, rapid and accurate detection of intracellular Fe 2+ It is of great significance for studying the pathogenesis of PD and other diseases and effectively monitoring the occurrence and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/34C09K11/06G01N21/64
CPCC07D239/34C09K11/06G01N21/6428C09K2211/1044
Inventor 张承武陆瑶李林吴越徐家佳王延宾黄维
Owner NANJING UNIV OF TECH
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