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Benzopyrylium-based aβ monomer, so 2 and h 2 o 2 Fluorescent probes and their preparation and application

A technology of benzopyrylium and fluorescent probes, which is applied in the field of organic small molecule fluorescent probes and biosensing, to achieve the effect of simple probe synthesis, easy operation and rapid identification

Active Publication Date: 2020-06-05
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, there is no program to identify and sense Aβ, SO 2 and H 2 o 2 Fluorescent probes have been reported

Method used

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  • Benzopyrylium-based aβ monomer, so <sub>2</sub> and h <sub>2</sub> o <sub>2</sub> Fluorescent probes and their preparation and application
  • Benzopyrylium-based aβ monomer, so <sub>2</sub> and h <sub>2</sub> o <sub>2</sub> Fluorescent probes and their preparation and application
  • Benzopyrylium-based aβ monomer, so <sub>2</sub> and h <sub>2</sub> o <sub>2</sub> Fluorescent probes and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis of probe (I), the steps are as follows:

[0036] Add 4-diethylaminosalicylaldehyde (0.5 mmol, 96 mg) and p-dimethylaminoacetophenone (0.5 mmol, 81 mg) to a round bottom flask, H 2 SO 4 (3.0 mL). The resulting mixture was stirred at 90 °C for 2 h and cooled to room temperature. Then, the reaction mixture was poured into ice (30 g) and 70% perchloric acid (0.5 mL) was added. The resulting precipitate was collected by filtration, washed with water and dried to give crude product. Chromatography on silica gel (CH 2 Cl 2 / CH 3 OH = 20:1) to obtain probe (I).

Embodiment 2

[0038] The synthesis of probe (I), the steps are as follows:

[0039] Add 4-diethylaminosalicylaldehyde (0.75 mmol, 121.5 mg) and p-dimethylaminoacetophenone (0.5 mmol, 81 mg) to a round bottom flask, H 2 SO 4 (3.0 mL). The resulting mixture was stirred at 100 °C for 3 h and cooled to room temperature. Then, the reaction mixture was poured into ice (30 g) and 70% perchloric acid (0.5 mL) was added. The resulting precipitate was collected by filtration, washed with water and dried to give crude product. Chromatography on silica gel (CH 2 Cl 2 / CH 3 OH = 20:1) to obtain probe (I).

Embodiment 3

[0041] The synthesis of probe (I), the steps are as follows:

[0042] Add 4-diethylaminosalicylaldehyde (1.0 mmol, 193 mg) and p-dimethylaminoacetophenone (0.5 mmol, 81 mg) to a round bottom flask, H 2 SO 4 (3.0 mL). The resulting mixture was stirred at 80 °C for 1 h and cooled to room temperature. Then, the reaction mixture was poured into ice (30 g) and 70% perchloric acid (0.4 mL) was added. The resulting precipitate was collected by filtration, washed with water and dried to give crude product. Chromatography on silica gel (CH 2 Cl 2 / CH 3 OH = 20:1) to obtain probe (I).

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PUM

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Abstract

The invention provides an Abeta monomer, SO2 and H2O2 fluorescent probe based on benzopyrylium as well as a preparation method and application thereof. The structural formula is as shown in formula (I) in the description. The preparation method comprises the following steps: dissolving 4-diethylamino salicylaldehyde and p-methylamino acetophenone into concentrated sulfuric acid, stirring the mixture for 1 to 3 hours at 80 to 100 DEG C, and cooling to room temperature; and then pouring the reaction mixture into ice, adding 70 percent of perchloric acid, filtering, collecting to obtain precipitates, and further purifying to obtain the fluorescent probe with the structural formula of formula (I). By adopting the Abeta monomer, SO2 and H2O2 fluorescent probe, the specificity detection and rapid identification of the Abeta monomer can be realized, and the Abeta monomer and Abeta polymers can be better distinguished; and the far-infrared and near-infrared fluorescent probes based on anthocyanidin derivatives of the invention can simultaneously or sequentially identify and sense Abeta, SO2 and H2O2, and provide an effective tool for the pathogenesis, early diagnosis and new drug researchand development of AD.

Description

technical field [0001] The invention relates to the technical field of organic small molecule fluorescent probes and biosensing, in particular to a benzopyrylium-based Aβ monomer, SO 2 and H 2 o 2 Fluorescent probes and their preparation and applications. Background technique [0002] Alzheimer's disease (AD) seriously threatens the life and health of the elderly and imposes a heavy burden on patients, families and society. β-Amyloid (Aβ) is a disease marker of AD. In different stages of AD disease, Aβ exists in different forms such as monomers, dimers and oligomers, as well as fibers, aggregates and plaques. There are different forms of Aβ protein, and the toxicity caused by it is also very different. In the early stage of AD, Aβ generally exists in the form of monomers, so the development of fluorescent probes for the specific detection of Aβ monomers is of great significance for the early diagnosis of AD. Sulfur dioxide (SO 2 ) is a common air pollutant that can pr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/04C09K11/06G01N21/64
CPCC07D311/04C09K11/06C09K2211/1007C09K2211/1088G01N21/6486
Inventor 孙远强陈晓岚李朝辉姬丹阳张自强何山
Owner ZHENGZHOU UNIV