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Mitochondrial fluorescent probe with dual fluorescence emission and its preparation method and application

A fluorescent probe, mitochondrial technology, applied in fluorescence/phosphorescence, color-changing fluorescent materials, chemical instruments and methods, etc., can solve the problems of further improvement of photostability, complex structure, high price, etc., and achieve efficient mitochondrial specific identification Ability, good water solubility, low cost effect

Inactive Publication Date: 2018-05-22
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few types of mitochondrial fluorescent probes on the market, the price is relatively expensive, and the photostability needs to be further improved
In recent years, some novel mitochondrial fluorescent probes have been reported one after another, but the reported mitochondrial fluorescent probes still generally have shortcomings such as complex structures and difficult synthesis.

Method used

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  • Mitochondrial fluorescent probe with dual fluorescence emission and its preparation method and application
  • Mitochondrial fluorescent probe with dual fluorescence emission and its preparation method and application
  • Mitochondrial fluorescent probe with dual fluorescence emission and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the synthesis of intermediate perylene benzyl bromide

[0030]

[0031] Add phosphorus tribromide (0.49 g) to a solution of perylene benzyl alcohol (0.42 g) in carbon tetrachloride (50 mL) at room temperature. The temperature was raised to reflux, and the reaction was stopped after 2 hours of reaction. After removing carbon tetrachloride, the resulting solid was washed with methanol (40 mL), filtered with suction and dried in vacuo to obtain the orange target perylenebenzyl bromide (0.37 g, 73%).

Embodiment 2

[0032] Embodiment 2: the synthesis of intermediate perylene benzyl chloride

[0033]

[0034] Add thionyl chloride (0.4 mL) to a solution of perylene benzyl alcohol (0.3 g in toluene (9 mL) at room temperature. After continuing the reaction for 24 hours, stop the reaction. Remove excess thionyl chloride under reduced pressure, leaving The target compound was obtained as a light yellow solid (0.31 g, 97%) after washing with water, suction filtration and vacuum drying.

Embodiment 3

[0035] Embodiment 3: the synthesis of target tributyl (3-perylene benzyl) phosphorus bromide

[0036]

[0037] Under nitrogen, perylenebenzyl bromide (0.69 g), tributylphosphine (0.75 mL) and ethyl acetate (15 mL) were added to the reaction flask. After heating up to 80 ºC for 8 hours, the reaction was stopped. After suction filtration, the solid was washed with ethyl acetate to obtain the target compound tributyl(3-pyrenebenzyl)phosphorus bromide as a yellow solid (0.90 g, 82%).

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Abstract

The invention discloses a mitochondria fluorescent probe as well as a preparation method and application thereof, belonging to the field of functional materials. The mitochondria fluorescent probe has a double fluorescence emission function and is a quaternary phosphonate compound with a structural formula shown by formula I. In the formula I, R is alkyl or aryl, and the anion X is halogen ion. The fluorescent probe disclosed by the invention has very efficient mitochondria specificity recognition ability, and the fluorescent probe molecule presents a double fluorescence emission phenomenon under the excitation of different lights so as to realize precise double fluorescence labeling of mitochondria. In the invention, the fluorescent probe molecule also has excellent light stability, experiences relatively little influence of the charge change on the mitochondria surface, and can realize real-time tracking of the mitochondria distribution and form in a living cell. Moreover, the mitochondria fluorescent probe disclosed by the invention has the advantages of high water solubility, simple synthesis path, simple after-treatment, batch production, relatively low cost and the like and shows a broad market prospect.

Description

technical field [0001] The invention belongs to the field of functional materials, and in particular relates to a mitochondrial fluorescent probe with dual fluorescence emission and its preparation method and application. technical background [0002] Organelles play an extremely important role in the functional expression of normal cells as well as in the development of diseases. Mitochondria is an important eukaryotic organelle and an important place for cells to carry out aerobic respiration. In addition to supplying energy to cells, mitochondria are also involved in physiological processes such as cell information transmission, cell differentiation, cell apoptosis, and regulation of cell growth and cell cycle. Therefore, developing a class of mitochondria-specific fluorescent probes to track the shape and distribution of mitochondria in cells will help us study some important cellular physiological processes. [0003] Due to its high spatial and temporal resolution, fl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/54C09K9/02G01N21/64
CPCC07F9/5456C09K9/02C09K2211/1011G01N21/6486
Inventor 李高参王云兵杨立
Owner SICHUAN UNIV
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