A kind of bispyrene compound and its fluorescent nano-aggregate and application

A technology of fluorescent nanometers and compounds, applied in the direction of condensation preparation of carbonyl compounds, chemical instruments and methods, luminescent materials, etc., can solve the problems of poor optical stability, rare research reports, poor anti-bleaching performance, etc., and achieve excellent anti-photobleaching properties, high chemical stability, effect of good optical stability

Active Publication Date: 2016-12-28
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In practical applications, small molecular compounds have limitations in their use: some small molecular fluorescent molecules are not water-soluble, which limits their application in life sciences, medicine and other fields, and small molecular fluorescent molecules have some disadvantages. , For example, the fluorescence is easily quenched in aqueous solution, and the anti-bleaching performance is poor (poor optical stability), which limits its application and development
The fluorescent nanoaggregates that gather and emit light in aqueous solution are a good substitute for small molecule fluorescent materials, which overcome the above-mentioned shortcomings of small molecule fluorescent materials, but research reports in this area are still relatively rare, and new types of fluorescent materials need to be developed. Fluorescent nanoaggregates for biological applications

Method used

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  • A kind of bispyrene compound and its fluorescent nano-aggregate and application
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  • A kind of bispyrene compound and its fluorescent nano-aggregate and application

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preparation example Construction

[0047] 2 Preparation of nanoaggregates

[0048] Dissolve 5 mg of compound (a) in 10 mL of DMSO solvent, quickly inject this solution into 90 mL of ultrapure water with a syringe, and sonicate for 30 minutes to obtain a fluorescent nano-aggregate dispersion. image 3 It is a transmission electron micrograph of the nano-aggregates prepared in this embodiment.

[0049] 3 Lysosome co-localization

[0050] KB cells were cultured in DMEM (Invitrogen) with 10% PBS (Invitrogen). The day before the confocal fluorescence imaging experiment, the cells were seeded in a dedicated cell confocal culture dish. The next day, 25 μM of compound (a) nanofluorescent aggregates were added thereto, and kept at 37 °C and 5% CO 2 Under conditions, incubate for 3 hours, and then wash 3 times with phosphate buffer solution. Then add 10 μM lysosome probe compound LysoTracker Red (Beiyuntian) and keep it at 37°C and 5% CO 2 Incubate for 1 hour, and then wash with phosphate buffer solution 3 times, th...

Embodiment 2

[0051] Embodiment 2 is with R structure as as an example

[0052] 1 Synthesis of bispyrene compounds

[0053] Friedel-Crafts acylation reaction of pyrene: Dissolve 10mmol pyrene (2g) in 30mL carbon disulfide and put it in a 50mL single-necked bottle, add 7.5mmol 2,6-pyridine dicarboxylic acid chloride (1.53g), and cool to 0 in an ice bath ℃, add 20mmol aluminum oxide (2.64g), heat and reflux for 12 hours, pour the product into 100mL ice water and stir for 2 hours after cooling, separate the liquid with dichloromethane, dry and filter the organic phase through anhydrous magnesium sulfate, and then recrystallize. 1.88 g of the product (b) was obtained as yellow flaky crystals, and the yield was 71%. Figure 5 It is the nuclear magnetic spectrum (1H NMR) of the bispyrene compound prepared in this embodiment; Image 6 is the nuclear magnetic spectrum (13C NMR) of the bispyrene compound prepared in this example.

[0054] 2 Preparation of nanoaggregates

[0055] Dissolve 5 mg ...

Embodiment 4

[0063] Embodiment 4 is with R structure as as an example

[0064] 1 Synthesis of bispyrene compounds

[0065] Friedel-Crafts acylation reaction of pyrene: 10mmol pyrene (2g) was dissolved in 30mL carbon disulfide, and placed in a 50mL single-necked bottle, and 25mmol of (5.125g), cooled to 10°C in an ice bath, added 20mmol aluminum oxide (2.64g), heated and refluxed for 20 hours, cooled the product and poured it into 100mL ice water and stirred for 8 hours, separated with dichloromethane, organic The phase was dried and filtered through anhydrous magnesium sulfate, and then recrystallized to obtain 4.5 g of product (b) as yellow flaky crystals, with a yield of 83%.

[0066] 2 Preparation of nanoaggregates

[0067] Dissolve 2 mg of compound (c) in 10 mL of acetone solvent, inject this solution into 90 mL of ultrapure water with a syringe, and sonicate for 60 minutes to obtain a fluorescent nano-aggregate dispersion.

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Abstract

The invention relates to a bis-pyrene compound. The bis-pyrene compound is a compound expressed by a general formula (I) as shown in the specification or a salt thereof, wherein R is selected from aromatic ring structures. The compound is prepared by use of a simple Friedel-Crafts acylation reaction. The bis-pyrene compound prepared by use of the method can be used for preparing a nano-aggregate by use of a quick precipitation method; the dimension of the nano-aggregate is at nano-scale, and the nano-aggregate has high fluorescent quantum yield and high chemical stability. The nano-aggregate is capable of serving as a fluorescent dye to mark the lysosomes of cells; and compared with a traditional dye, the nano-aggregate dye has higher chemical stability in cells and more excellent photobleaching resistance, and can be applied to marking the lysosomes of cells.

Description

technical field [0001] The invention relates to the field of biology, in particular, the invention relates to a bispyrene compound and its fluorescent nano-aggregate and application. Background technique [0002] Organic fluorescent materials have a wide range of applications. It can not only be used as fluorescent pigments, fluorescent whitening agents, etc. in traditional industries such as plastics, paper, synthetic detergents, synthetic fibers, inks, etc., but it is also widely used in a variety of emerging fields, such as organic fluorescent materials, Organic Field Effect Transistors, Light Harvesting Systems, Logic Gates, Fluorescent Labels, Fluorescent Probes, and more. With the development of science and the progress of society, people's demand for organic fluorescent materials with special purposes is further increasing, so it is of great significance to develop new organic fluorescent functional materials with special functions. [0003] As a fluorescent sensor,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/788C07C45/46C07D213/50C07D277/24C07D239/26C09K11/06G01N33/52
Inventor 王浩王磊李微
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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