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Mitochondrial-targeting 3,4,9,10-perylenetetracarboxylic dianhydride fluorescent probe, synthesis method and applications thereof

A technology of fluorescent probe and synthesis method, which is applied in the field of targeted mitochondrial perylene anhydride fluorescent probe and its synthesis, can solve the problems of high cytotoxicity, weak localization ability, poor photostability, etc., achieve good water solubility, and solve the problem of targeting The effect of poor stability and excellent photostability

Inactive Publication Date: 2019-04-16
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as far as the current mitochondrial fluorescent probes are concerned, most of the probes have disadvantages such as weak localization ability, poor photostability, high cytotoxicity, and poor permeability.

Method used

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  • Mitochondrial-targeting 3,4,9,10-perylenetetracarboxylic dianhydride fluorescent probe, synthesis method and applications thereof
  • Mitochondrial-targeting 3,4,9,10-perylenetetracarboxylic dianhydride fluorescent probe, synthesis method and applications thereof
  • Mitochondrial-targeting 3,4,9,10-perylenetetracarboxylic dianhydride fluorescent probe, synthesis method and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] A fluorescent probe targeting mitochondrial perylene anhydride, characterized in that its structural formula is:

[0055]

[0056] The molecular formula of the fluorescent probe targeting mitochondrial perylene anhydride is C 112 h 151 o 34 N 7 P 1 S 1 , the molar mass is 2201.26g / mol.

[0057] Spectral properties of fluorescent probes targeting mitochondrial perylene anhydride:

[0058] In order to study the UV-vis absorption and fluorescence properties of the probe, it was dissolved in PBS at a concentration of 1 × 10 -5 mol / L, the result is as figure 1 and figure 2 As shown, the ultraviolet maximum absorption wavelengths of the fluorescent probe targeting mitochondrial perylene anhydride are 532nm and 534nm, the fluorescence excitation and emission wavelengths are 559nm and 621nm, and the measured fluorescence quantum yield is 43%.

Embodiment 2

[0060] A method for synthesizing the fluorescent probe targeting mitochondrial perylene anhydride, the synthesis route of the fluorescent probe targeting mitochondrial perylene anhydride is:

[0061]

[0062] Instrumentation and Reagents All chemicals used in the synthesis were analytical grade reagents and were used as received. Fluorescence spectra were measured using a Tsushima RF-5301PC fluorescence spectrophotometer, and UV-Vis spectra were measured using a Tsushima UV-3600 UV-Vis spectrophotometer. Fluorescent images of cells were acquired on a LSM 880 confocal laser scanning microscope using an objective lens (×63 Oil). Fluorescence analysis and cell cycle analysis were performed using a BD FACS Calibur flow cytometer. Compounds were efficiently synthesized following the synthetic method shown in Scheme 1.

[0063] Synthesis of compound Ⅰ

[0064] Weigh perylene anhydride (12.00g, 30.59mmol), measure 98mL of 98% concentrated sulfuric acid, add it to a 1000mL two-n...

Embodiment 3

[0072] An application of the fluorescent probe targeting mitochondrial perylene anhydride in a reagent for monitoring the shape and quantity of mitochondria in living cells.

[0073] cell culture

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Abstract

The invention discloses a mitochondrial-targeting 3,4,9,10-perylenetetracarboxylic dianhydride fluorescent probe, which has a molecular formula of C112H151O34N7P1S1, and has a molar mass of 2201.26 g / mol. According to the present invention, the mitochondrial-targeting 3,4,9,10-perylenetetracarboxylic dianhydride fluorescent probe easily enters cells, and has characteristics of high cell loading rate, good cell permeability, no cytotoxicity and high photostability. The invention further discloses a synthesis method of the mitochondrial-targeting 3,4,9,10-perylenetetracarboxylic dianhydride fluorescent probe so as to provide the theoretical and practical basis for the smooth synthesis of the mitochondrial-targeting 3,4,9,10-perylenetetracarboxylic dianhydride fluorescent probe. The inventionfurther discloses applications of the mitochondrial-targeting 3,4,9,10-perylenetetracarboxylic dianhydride fluorescent probe in reagents for monitoring the shape and the number of the mitochondrial in living cells.

Description

technical field [0001] The invention relates to the technical fields of functional polymer technology, analytical chemistry and bioanalytical chemistry, in particular to a fluorescent probe targeting mitochondrial perylene anhydride and its synthesis method and application. Background technique [0002] Mitochondria, as energy conversion organelles in eukaryotic cells, is the main place for cells to carry out aerobic respiration, participates in numerous metabolic processes, and has an independent genetic system, known as the "power factory" of cells. Mitochondria play an important role in eukaryotic cells, for example, mitochondria use glycolysis, glutamine and fatty acids to generate ATP to meet the energy needs of cells, in addition, through Ca in the mitochondrial matrix 2+ For the regulation of concentration and release of reactive oxygen species (ROS), mitochondria are regarded as signaling organelles. Abnormal mitochondrial function is closely related to many disease...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561C09K11/06G01N21/64
CPCC07F9/65618C09K11/06C09K2211/1007C09K2211/1029G01N21/6428
Inventor 刘红梅刘恺孙竹兴吕树芳王佳高保祥
Owner HEBEI UNIVERSITY