Near-infrared aggregation-induced emission membrane probe molecule, and preparation method and application thereof

A technology of aggregation-induced luminescence and probe molecules, which is applied in the field of optical probes, can solve the problems of optical probe quenching, inability to trace fluorescence, and fluorescence quenching, etc., and achieve increased residence time, good water solubility, and fast dyeing Effect

Active Publication Date: 2021-12-14
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Existing optical probes usually have aggregation fluorescence quenching and significant photobleaching properties, and complex biological systems are prone to aggregation and fluorescence quenching, so they cannot be used for long-term fluorescence tracking

Method used

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  • Near-infrared aggregation-induced emission membrane probe molecule, and preparation method and application thereof
  • Near-infrared aggregation-induced emission membrane probe molecule, and preparation method and application thereof
  • Near-infrared aggregation-induced emission membrane probe molecule, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1, the synthesis of single charge big steric hindrance salt

[0044] Dissolve 1,4-diazidobicyclo[2.2.2]octane (2.24g, 20mmol) in 100mL acetone, add 1,3-dibromopropane (2.02mL, 20mmol), stir overnight at room temperature, a white solid precipitates . Pour off the liquid on the upper part of the precipitation, wash with acetone by decantation, repeat 3 to 4 times to remove unreacted raw materials, spin dry the solid under reduced pressure and vacuum at 40°C, and seal it for storage.

Embodiment 2

[0045] Embodiment 2, the synthesis of two charge big steric hindrance salt

[0046] Dissolve single-charge bulky hindered salt (1.57g, 5mmol) in 50mL ethanol, vacuumize, fill with nitrogen, add 4-methylpyridine (4.866mL, 50mmol), heat to reflux at 80°C for 48h. The solution gradually darkened from clear and transparent, and finally turned brownish yellow. After the reaction, spin the ethanol to dryness, add a large amount of acetone and a small amount of ethanol (used to remove the raw material salt) mixed solution to the crude product, heat and reflux for 1 hour, pour off the supernatant after cooling, repeat the operation 3 to 4 times, use a developing Agent EA:PE=1:5 to climb the plate, judge whether the 4-picoline is completely removed, after the removal, the solid is dried under reduced pressure and vacuum at 40°C, and then sealed and stored to obtain a brown-yellow solid.

Embodiment 3

[0047] The synthesis of embodiment 3,4-hexyloxydiphenylamine

[0048] Add cesium carbonate (7.78g, 23.88mmol) to 30mL of dry DMF, vacuumize, fill with nitrogen, add 4-hydroxydiphenylamine (2.65g, 14.32mmol), and add hexyl bromide (1.68mL, 11.94 mmol), reacted at 100°C for 6h. After the reaction, the solution was brownish black, extracted with ethyl acetate, the organic layer was washed 3 times with water and dried with anhydrous sodium sulfate, the sample was mixed with silica gel powder and spin-dried, EA:PE=1:30 was passed through the column, and a white solid was obtained. Visibly fluorescent.

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Abstract

The invention discloses a near-infrared aggregation-induced emission membrane probe molecule, and also discloses a preparation method of the probe molecule. The preparation method comprises the following steps: S1, adding ethanol into a three-necked flask, conducting vacuumizing, filling nitrogen, sequentially adding two-charge large-steric-hindrance salt, a triphenylamine skeleton and piperidine, and conducting refluxing; S2, after a reaction is finished, subjecting a solution to spin-drying until a small amount of ethanol is left, adding a large amount of ethyl acetate into a formed system, separating red solids out, carrying out standing, and pouring an upper-layer solution away; S3, completely removing a triphenylamine skeleton; S4, washing a solid obtained in the step 3 with acetone to remove ethyl acetate with a high boiling point; and S5, performing reduced-pressure vacuum spin-drying on the solid obtained in the step S4, and carrying out sealing and storing to obtain red solid powder. According to the invention, a water-soluble near-infrared fluorescent molecular probe is synthesized by taking triphenylamine as a skeleton and is used for cell membrane imaging, and a group with relatively large steric hindrance and a long alkyl chain are introduced into the probe to prolong membrane retention time.

Description

technical field [0001] The invention relates to the technical field of optical probes, in particular to a near-infrared aggregation-induced luminescent film probe molecule, a preparation method and an application. Background technique [0002] The cell membrane is a glycerophospholipid bilayer located at the periphery of the cell, which plays an important role in the cell, such as controlling the entry and exit of substances, protecting the cell, and maintaining the stability of the intracellular environment. The bilayer structure of the cell membrane is mainly composed of lipids and proteins. Phospholipid molecules are the major lipid components of cell membranes and have hydrophobic alkyl chains and hydrophilic polar groups. These molecules spontaneously assemble into continuous membranes in aqueous media, forming the basic skeleton of cell membranes. Unraveling the biological functions of cell membranes is crucial for various applications such as drug screening, early d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/08C09K11/06G01N21/64
CPCC07D487/08C09K11/06G01N21/6428G01N21/6458C09K2211/1029C09K2211/1044C09K2211/1007C09K2211/1014
Inventor 钱兆生丰慧张晓晓
Owner ZHEJIANG NORMAL UNIVERSITY
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