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A method for detecting fe in vivo 2+ Two-photon fluorescent probe and its preparation method and application

A two-photon fluorescence and fluorescent probe technology, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high price, affecting the imaging effect of probes, and limitation of penetration depth, etc.

Active Publication Date: 2021-12-24
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A method for detecting fe in vivo <sup>2+</sup> Two-photon fluorescent probe and its preparation method and application
  • A method for detecting fe in vivo <sup>2+</sup> Two-photon fluorescent probe and its preparation method and application
  • A method for detecting fe in vivo <sup>2+</sup> Two-photon fluorescent probe and its preparation method and application

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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 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. The fluorescent probe is a PyFe fluorescent probe, and the structural formula of the PyFe fluorescent probe is shown in formula (I). The fluorescent probe of the present invention can accurately detect Fe in living organisms 2+ , to avoid the interference of other ionic amino acids in the cell. The probe has extremely fast response rate, high ion selectivity, can realize naked-eye detection in vitro and also has good biocompatibility. Fluorescence confocal imaging experiments show that the probe has good cell permeability and has no toxic side effects on cells and organisms. At the same time, the probe has two-photon properties, which 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 TECH UNIV
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