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Application of heptamethine indocyanine organic dye as mitochondria fluorescent probe

A technology of heptamethine indocyanines and organic dyes, which is applied in the direction of organic dyes, methine/polymethine dyes, fluorescence/phosphorescence, etc., which can solve the disadvantages of near-infrared light observation, low fluorescence quantum yield, and lack of observation Near-infrared fluorescence and other problems, to achieve excellent targeting effect, high fluorescence quantum yield, and improve the effect of imaging quality

Active Publication Date: 2017-12-01
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the fluorescence emitted by such dyes is usually in the near-infrared band and the fluorescence quantum yield is low, and most fluorescence microscopes on the market do not have the ability to observe near-infrared fluorescence, and near-infrared light is not conducive to direct observation by human eyes

Method used

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  • Application of heptamethine indocyanine organic dye as mitochondria fluorescent probe
  • Application of heptamethine indocyanine organic dye as mitochondria fluorescent probe
  • Application of heptamethine indocyanine organic dye as mitochondria fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The synthetic process of the mitochondrial fluorescent probe (hereinafter referred to as IR825-Cl) is as follows:

[0030]

[0031] Step 1: Using toluene as a solvent, 2,3,3-trimethyl-4,5-benzo-3H-indole reacted with benzyl bromide in the dark under the protection of nitrogen, and refluxed for 12 hours; where 2,3, The molar ratio of 3-trimethyl-4,5-benzo-3H-indole to benzyl bromide is 1:1, and the resulting reaction product is recrystallized from isopropanol to obtain compound 1;

[0032] Step 2: dichloromethane as solvent, N,N-dimethylformamide (DMF) as reagent and solvent, cyclohexanone and POCl 3 Vilsmeimer-Haack formylation reaction takes place, reacts for 4 hours; Wherein cyclohexanone: POCl 3 : The molar ratio of DMF is 1:2.3:5.4; The obtained product obtains compound 2 through ethyl acetate recrystallization;

[0033] Step 3: The above two products 1 and 2 obtained above are co-dissolved in acetic anhydride with anhydrous sodium acetate, and reacted under ni...

Embodiment 2

[0035] Measure the fluorescence spectrum of the IR825-Cl that embodiment 1 makes in water and ethanol, and its method is as follows:

[0036] Dissolve IR825-Cl in dimethyl sulfoxide to prepare a 50mg / mL stock solution, and then dilute the stock solution with water and ethanol to a 10μg / mL working solution. The fluorescence properties of the two solutions were characterized by fluorescence spectrometer. see results figure 1 .

[0037] As shown in the figure, the IR825-Cl prepared in Example 1 has almost no fluorescence in water, but emits strong red fluorescence at around 610 nm in ethanol.

Embodiment 3

[0039] Measure the fluorescence spectrum of the IR825-Cl that embodiment 1 makes in the liposome solution of different concentrations, its method is as follows:

[0040] Dissolve IR825-Cl in dimethyl sulfoxide to prepare a 50 mg / mL stock solution, and then dilute the stock solution with phosphate buffered solution (PBS) to a 20 μg / mL working solution. Weigh 4 mg of palmitoyloleoylphosphatidylcholine (POPC), add 1 mL of PBS for hydration, and then prepare a liposome solution of POPC by ultrasonic method. The liposome solution was diluted with PBS to solutions with concentrations of 20, 100 and 400 μg / mL, respectively, and then mixed with the above-mentioned IR825-Cl working solution in equal volume to prepare the final sample. The fluorescence properties of these three samples were characterized by fluorescence spectrometer. see results figure 2 .

[0041] As shown in the figure, as the concentration of the liposome solution increases, the red fluorescence of the IR825-Cl p...

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Abstract

The invention discloses an application of a heptamethine indocyanine organic dye as a mitochondria fluorescent probe. The structural formula of the heptamethine indocyanine organic dye is as follows: the formula is as shown in the specification. The fluorescent probe has excellent mitochondria targeting capacity, and is capable of emitting red fluorescence of which the reflection wavelength is 610nm after being combined with mitochondria. Meanwhile, the probe also has the advantages of being high in fluorescence quantum yield, long in imaging time, high in signal-noise ratio and low in cytotoxicity, and can be used as a novel mitochondria imaging reagent.

Description

technical field [0001] The invention relates to the application of a heptamethine indocyanine organic dye in mitochondrial fluorescence imaging, and belongs to the field of biotechnology. Background technique [0002] Mitochondria are one of the most important organelles in cells. It is the site of oxidative metabolism in eukaryotes and the main place for energy production and release. In addition, mitochondria are also responsible for regulating many biological behaviors including apoptosis, calcium ion balance, free radical production, cell growth and differentiation. In recent years, a large number of studies have shown that abnormal mitochondrial function is closely related to the occurrence of various human diseases, and this pathological change is usually manifested as changes in the size, number and shape of mitochondria at the cellular level. For example, the number of mitochondria in the cells of people with Alzheimer's disease is reduced. Therefore, the imaging ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B23/08G01N21/64
CPCC09B23/086C09K11/06C09K2211/1029G01N21/6486
Inventor 吴富根贾浩然潘光玉
Owner SOUTHEAST UNIV
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