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Application of tetralone as near-infrared fluorescent probe in lipid droplet imaging

A technology of tetralone and fluorescent probes, which is applied in the field of analytical chemistry, can solve problems such as unfavorable lipid droplet biological processes, and achieve the effects of increasing photostability, simple molecular structure, and simple methods

Active Publication Date: 2022-07-26
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, most of the reported fluorescent probes for detecting lipid droplets are concentrated in the ultraviolet-visible (UV / Vis) range, which is not conducive to the study of biological processes of lipid droplets in organisms.

Method used

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  • Application of tetralone as near-infrared fluorescent probe in lipid droplet imaging
  • Application of tetralone as near-infrared fluorescent probe in lipid droplet imaging
  • Application of tetralone as near-infrared fluorescent probe in lipid droplet imaging

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Experimental program
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Embodiment 1

[0017] 1. Synthesis of Tetralone

[0018]

[0019] (1) Phosphorus oxychloride (6.0 mL, 0.06 mol) was slowly added dropwise to a round-bottomed flask filled with 10.0 mL DMF, the mixture was stirred and reacted at 0°C for 30 min, and then compound 1 (1.0 g, 6 mmol) was dissolved In 5.0 mL of DMF, and slowly added dropwise to the flask, the mixture was stirred and reacted at 90 ° C for 5 h. After the reaction was completed, the mixture was poured into 50.0 mL of ice water, and the precipitated precipitate was collected by filtration, washed with ice water, and dried. Thus, compound 2 (953.0 mg, 72% yield) was obtained as a brown solid. 1 H NMR (400MHz, DMSO-d 6 )δ10.24-10.15(s, 1H), 7.79-7.67(s, 1H), 6.98-6.86(s, 2H), 3.85-3.80(s, 3H), 2.83-2.76(d, J=7.8, 2H) ),2.53-2.48(s,2H); 13 C NMR (101MHz, DMSO-d 6 )δ190.19,162.50,145.16,141.81,130.08,128.46,124.45,114.20,114.04,56.04,27.09,21.75.HRMS(ESI):m / z C 12 H 11 ClO 2 [M+Na] + The theoretical value is 245.0345, and the m...

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Abstract

The invention discloses an application of tetralone as a near-infrared fluorescent probe in lipid droplet imaging, the structural formula of tetralone is shown in the specification, the compound as the probe is sensitive to environmental viscosity change, has excellent brightness and light stability, can quickly penetrate cells and is enriched in lipid droplets to realize no-wash fluorescence imaging of the lipid droplets, and the application range is wide. The fluorescence imaging of the lipid droplets in the cells is realized by virtue of a confocal fluorescence microscope, the dynamic distribution of the lipid droplets in the zebra fish body can be monitored, and the method has a wide application prospect in cell biology research.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, in particular to the application of tetralone as a near-infrared fluorescent probe in lipid droplet imaging. Background technique [0002] Lipid droplets (LDs) are the main storage sites of intracellular neutral fat, with obvious size differences ranging from 40 nm to 100 μm in diameter. It consists of pure organic neutral lipid cores (ie triacylglycerols and sterol esters). Lipid droplets play important roles in lipid metabolism and storage, membrane transport, protein degradation, and signal transduction. [0003] In recent years, fluorescence imaging has emerged as one of the most powerful techniques for monitoring targets and biological processes in the context of living systems. However, most fluorescent probes have absorption and emission in the ultraviolet-visible (UV / Vis) range, light in this wavelength region is easily absorbed by biomolecules (such as water and hemoglobin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06G01N21/64A61K49/00
CPCC09K11/06G01N21/6428G01N21/6458A61K49/0021G01N2021/6439C09K2211/1007C09K2211/1011Y02A40/81
Inventor 吴少平吴雷李斌史光耀李奕衡周洁宇董泳仪
Owner NORTHWEST UNIV(CN)
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