Aggregation-induced emission fluorescent molecule as well as preparation method and fluorescent dye composition, and application of aggregation-induced emission fluorescent molecule and fluorescent dye composition in mitochondria dyeing

A technology for aggregation-induced luminescence and fluorescent molecules, which is applied in the fields of aggregation-induced luminescence fluorescent molecules and their preparation, fluorescent dye compositions and their application in mitochondrial staining, which can solve the problems of large mitochondrial toxicity, cytotoxicity, and poor dyeing stability , to achieve the effect of low toxicity and good luminescence stability

Inactive Publication Date: 2014-05-14
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] However, the above-mentioned commonly used fluorescent probes for mitochondrial staining have di

Method used

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  • Aggregation-induced emission fluorescent molecule as well as preparation method and fluorescent dye composition, and application of aggregation-induced emission fluorescent molecule and fluorescent dye composition in mitochondria dyeing
  • Aggregation-induced emission fluorescent molecule as well as preparation method and fluorescent dye composition, and application of aggregation-induced emission fluorescent molecule and fluorescent dye composition in mitochondria dyeing
  • Aggregation-induced emission fluorescent molecule as well as preparation method and fluorescent dye composition, and application of aggregation-induced emission fluorescent molecule and fluorescent dye composition in mitochondria dyeing

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preparation example Construction

[0045] In another aspect, the present invention provides a method for preparing the aggregation-induced luminescent fluorescent molecule, wherein the method comprises: in the presence of an organic solvent and a basic substance catalyst, a compound having the structure shown in formula II or a compound such as The compound with the structure shown in formula IV is mixed with the compound with the structure shown in formula III and heated to reflux to generate a product containing the aggregation-induced luminescent fluorescent molecule as claimed in claim 1;

[0046]

[0047] Among them, R 1 selected from -O-(CH 2 ) n-OH, -OC n h 2n+1 、-C n h 2n+1 and any of -H; R 2 and R 4 each independently -O-(CH 2 ) n-OH, -OC n h 2n+1 、-C n h 2n+1 , -H and Any of them; R 3 selected from -CHO, -O-(CH 2 ) n-OH, -OC n h 2n+1 、-C n h 2n+1 , -H and Any one of them, n is an integer of 1-10; X - Selected from halogen anions, ClO 4 - 、PF 6 - 、CF 3 - , BF 4 - Any on...

Embodiment 1

[0071] 1. Synthesis of Probe 1

[0072]

[0073] (1) Mix 200mg (0.66mmol) of compound 2 and 239mg (0.66mmol) of compound 3, mix well, add 20mL of ethanol to the mixture, and add 52.8mg of sodium hydroxide as a catalyst and mix well to form a reaction mixture.

[0074] (2) The reaction mixture was heated to reflux in a reflux heating device for 6 hours, and then the heating was stopped to obtain a product.

[0075] (3) Cool the product to 25°C, add 100 mg of anhydrous magnesium sulfate to the cooled organic phase and dry it for 3 hours, then filter the dried product to remove the desiccant.

[0076] (4) The product from which the desiccant was removed was vacuum distilled to remove the solvent in a fully automatic vacuum distillation device to obtain 350 mg of red pure product 1, namely probe 1.

[0077] 2. Synthesis of probe 4

[0078]

[0079] (1) Mix 602mg (2mmol) of compound 2 and 388mg (1mmol) of compound 5, mix well, add 65mL ethanol to the mixture, and add 294mg ...

Embodiment 2

[0118] 1. Cytotoxicity test of probes 1, 4, 6, 9, 11 and rhodamine 123

[0119] Seed Hela cells in 96-well plates at 37°C, 5% CO by volume 2 Incubate in the cell culture incubator for 12 hours under the condition of , and replace with fresh medium. Then, dyeing probes 1, 4, 6, 9, 11 and rhodamine 123 at different concentrations (0, 50 μM and 500 μM) were added to the 96-well plate at 37°C, 5% CO by volume. 2 and cultured at pH 7.4 for 6 hours, washed the 96-well plate and added fresh cell culture medium, carried out the CCK-8 cell activity detection experiment according to the instructions of the CCK-8 detection kit, and detected the optical density with a microplate reader, and measured the optical density with light Density indicates the activity of the cells. The activity of the cells without fluorescent probes is 100%. When the concentrations of probes 1, 4, 6, 9, 11 and rhodamine 123 are 50 μM, the activity of the cells is 89.08%, 83.72%, 87.54%, 89.48%, 83.25%, 79.63%;...

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Abstract

The invention provides an aggregation-induced emission fluorescent molecule as well as a preparation method of the aggregation-induced emission fluorescent molecule. Furthermore, the invention provides a fluorescent dye composition containing the aggregation-induced emission fluorescent molecule. In addition, the invention provides application of the aggregation-induced emission fluorescent molecule and the fluorescent dye composition in mitochondria dyeing. The aggregation-induced emission fluorescent molecule (fluorescent probe) disclosed by the invention is low in cytotoxicity and luminescence stability, and the fluorescent molecule can effectively dye mitochondria and can simultaneously indicate membrane potential of the mitochondria; the fluorescent molecule can be used for marking and tracking mitochondria in cell for a long time, and can be used for detecting membrane potential of the mitochondria.

Description

technical field [0001] The invention relates to an aggregation-induced luminescent fluorescent molecule, a preparation method thereof, a fluorescent dye composition and their application in mitochondrial staining. Background technique [0002] Mitochondria are highly active organelles in cells and the main site of ATP production, and play a key role in life activities such as oxidative phosphorylation, iron homeostasis, superoxide generation, and apoptosis. Mitochondrial dysfunction is closely related to many acute and chronic diseases, such as cancer, diabetes, and neurodegenerative diseases. [0003] Therefore, the evaluation of intracellular mitochondria is particularly important. At present, the evaluation of intracellular mitochondria is mainly performed by staining them with fluorescent dyes, and then observing the stained mitochondria. Among them, related observations on mitochondria, detection of mitochondrial membrane potential (fluorescent dyes will accumulate in ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/08C07D209/12C07D487/04C09B67/22G01N21/64C12Q1/02
Inventor 蒋兴宇张璐黄显虹刘文文王卓张关心张德清
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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