Boron dipyrromethene fluorescent probe, preparation method and application thereof in viscosity detection

A fluoroboron dipyrrole and fluorescent probe technology is applied in the field of analytical chemistry to achieve the effects of good biocompatibility, simple preparation and wide range

Active Publication Date: 2020-12-15
GUANGDONG UNIV OF PETROCHEMICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, based on the structure of fluoroborate dipyrrole, the fluorescent small molecule derived in the middle position has not been reported as a probe for viscosity measurement in mitochondria. It is necessary to design such a structure and prepare a viscosity fluorescent probe with excellent performance.

Method used

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  • Boron dipyrromethene fluorescent probe, preparation method and application thereof in viscosity detection
  • Boron dipyrromethene fluorescent probe, preparation method and application thereof in viscosity detection
  • Boron dipyrromethene fluorescent probe, preparation method and application thereof in viscosity detection

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of fluorescent probes

[0024] Compound B-1 used in the present invention is prepared by a conventional method, and the specific preparation process refers to the document Dalton Transactions, 48(23), 8488-8501; 2019.

[0025] The synthetic chemical reaction formula of fluorescent probe of the present invention is:

[0026]

[0027] In a round bottom flask equipped with a distillation dehydration device, add 2,5-dihydroxybenzaldehyde (65mg, 0.47mmol), glacial acetic acid (0.5mL), piperidine (0.4mL) and compound B-1 (136mg, 0.43mmol), the mixture was dissolved in absolute ethanol (15mL), and then refluxed for 6 hours under the protection of argon. After the reaction was complete, the solvent was removed by rotary evaporation, and the residue was extracted with 100 mL of ethyl acetate, washed successively with saturated brine (30 mL×3) and ultrapure water (30 mL×3). The resulting organic phase was dried over anhydrous sodium sulfate, then filtered and conce...

Embodiment 2

[0032] Fluorometric determination of viscosity

[0033] Dissolve the BV-1 probe in absolute ethanol to give a concentration of 1 x 10 -3 M stock solution, and then prepare different volume ratios of PBS 7.4 buffer and glycerol mixture (100:0, 99:1, 95:5, 90:10, 80:20, 70:30, 60:40, 50:50 , 20:80, 1:99) as a solvent. Before adding BV-1 stock solution (10 μL each time) to solutions (2 mL) with different ratios of water and glycerol, use a viscometer as a control to measure the viscosity of the solution. The resulting solution of BV-1 was sonicated in an ultrasonic cleaner for 5 minutes to eliminate air bubbles. Then, under the constant temperature condition of 25°C, use 480nm excitation wavelength and 500nm / min scan rate to record the fluorescence spectrum in the range of 500-700nm to measure the solution, such as Figure 4 shown. For the test method of other species, the fluorescent probe is dissolved in PBS 7.4 buffer, and then the species to be tested is added to make the...

Embodiment 3

[0035] cell imaging

[0036] First, A549 cells were cultivated in DMEM alkaline medium at 37°C and in a humidified environment of 5% CO2 (The First Affiliated Hospital of Anhui Medical University). Subsequently, BV-1 (5 μM) was added to the culture medium, the cells were incubated for 30 min, washed three times with phosphate buffered saline (PBS), and then imaged with a fluorescent confocal microscope. Firstly, the localization characteristics of the fluorescent probes in the cells were studied, and the above-mentioned fluorescent probes were incubated with the mitochondrial localization dye Mito-Tracker Green (Thermo Fisher), and the coincidence coefficient of the fluorescent probes and the dyes was investigated. Such as Figure 7 As shown, the region where the probe is located in the cell can well overlap with the dye, indicating that the probe can accurately locate the position of mitochondria in the cell. In order to evaluate the ability of BV-1 to detect the viscosity ...

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Abstract

The invention relates to a boron dipyrromethene fluorescent probe and a preparation method and application thereof in viscosity detection, and in particular relates to a method for measuring intracellular viscosity by using a fluorescent molecular probe based on a boron dipyrromethene structure. The fluorescence of the fluorescent probe is very weak in a low-viscosity system, the fluorescence of the fluorescent probe is enhanced in a high-viscosity solvent system such as glycerol, and meanwhile, a certain degree of emission spectrum red shift phenomenon is accompanied; therefore, the probe canbe used for detecting the viscosity in different solvent systems; and meanwhile, the probe has good biocompatibility and low toxicity, can be used for detecting viscosity change in cells, and has specific positioning performance on mitochondria.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and relates to an application of a boron fluoride dipyrrole fluorescence probe for viscosity analysis and testing, in particular to an application of a boron fluoride dipyrrole structure fluorescent molecular probe in viscosity detection. Background technique [0002] Viscosity plays an important physiological and pathological role by affecting the metabolic process in the cell microenvironment, such as the transmission of substances and signals in the cytoplasm, and the interaction between biomolecules. Abnormal viscosity values ​​in cells will affect the activity of membrane-bound proteins. Inhibition of insulin synthesis, leading to the occurrence of related diseases. Increased viscosity during mitochondrial swelling has been linked to many diseases such as neurodegeneration, Parkinson's disease, Alzheimer's disease and atherosclerosis. It is reported that the viscosity of normal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/6428C09K2211/1055C09K2211/1007
Inventor 孙明泰王素华
Owner GUANGDONG UNIV OF PETROCHEMICAL TECH
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