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Preparation method of amphipathic asymmetric double-ion perylene bisimide dye and application thereof in marking cell membranes

A perylene imide, asymmetric technology, applied in the field of biomarkers, can solve the problems of poor stability and short action time, and achieve the effects of low toxicity, low biological toxicity and economical raw materials

Active Publication Date: 2017-06-06
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the poor stability and short action time of the current commercialized cell membrane dyes, it is of great significance to develop a specific labeling fluorescent dye with good stability, longer labeling action time and the ability to dynamically monitor the cell membrane.

Method used

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  • Preparation method of amphipathic asymmetric double-ion perylene bisimide dye and application thereof in marking cell membranes
  • Preparation method of amphipathic asymmetric double-ion perylene bisimide dye and application thereof in marking cell membranes
  • Preparation method of amphipathic asymmetric double-ion perylene bisimide dye and application thereof in marking cell membranes

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Experimental program
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Effect test

Embodiment 1

[0036] 1. Dissolve 527mg (1mmol) of 3,4,9,10-perylenetetracarboxylic dianhydride and 130mg (1mmol) of octylamine in 15ml of methanol, add it to a 50mL three-necked bottle, and then seal the system with a rubber stopper. Under protection, stir magnetically for 30 minutes, heat up to 85°C and reflux. After 12h of reaction. After the reactant was concentrated, it was washed with ethanol to obtain a precipitate. After concentration and vacuum drying, a dark red solid was obtained.

[0037] Add the above dark red solid, 10g of imidazole, 106mg of N,N-dimethylethylenediamine (1.2mmol about 132ul) into a three-necked flask, then seal the system with a rubber stopper, and raise the temperature to 120°C for reflux reaction under the protection of nitrogen . After 12h of reaction. After the reactant was concentrated, it was filtered to obtain a precipitate, washed with a large amount of water, and separated by column chromatography on a silica gel column to obtain the second point, ...

Embodiment 2

[0045] 1. Dissolve 530mg (1mmol) of 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride and 130mg (1mmol) of octylamine in 15ml of toluene, and add it to a 50mL three-necked bottle 106mg (1.2mmol about 132ul) of N,N-dimethylethylenediamine was added to the system with a micro-injector, and then the system was sealed with a rubber stopper. Under the protection of nitrogen, magnetic stirring was carried out for 30min, and the temperature was raised to 105°C for reflux. . After 12h of reaction. After the reactant was concentrated, the second point was separated by column chromatography on a silica gel column, and the eluent was dichloromethane / n-hexane (v / v=1 / 1). After concentration and vacuum drying, 278 mg of product 2 was obtained (39% yield).

[0046]

[0047] 2. Add 46mg (0.05mmol) of the above product into the polymerization tube, then add 10ml of dichloromethane, stir in a water bath at room temperature, then add 4uL 1,3-propane sultone 5.5mg (about 0.04...

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Abstract

The invention discloses amphipathic asymmetric double-ion perylene bisimide dye, a preparation method thereof and application thereof in a living cell membrane mark fluorescence imaging aspect and belongs to the technical field of biomarker. According to the preparation method, sea island position chlorine or bromine-substitution perylene tetracarboxylic dicarboxylic anhydride or sea island position unmodified perylene tetracarboxylic dianhydride is utilized as fluorophore, and a hydrophobic alkyl chain and a hydrophilic double-ion radical are respectively led into two ends to obtain the amphipathic asymmetric double-ion perylene bisimide dye. By means of leading into the double-ion radical, water solubility and biocompatibility of a whole structure are improved, and cellular poison of the whole structure is reduced. The dye can be applied to external and internal cell membrane mark fluorescence imaging. As perylene with good photochemical stability and near-infrared emission wavelength is utilized as the fluorophore, effective marking time is greatly improved in a biological living cell membrane imaging process through an electrostatic force effect between a double-ion structure and a membrane structure, and time duration can be 72 hours or more.

Description

technical field [0001] The invention belongs to the technical field of biomarkers, and in particular relates to an amphiphilic asymmetric diionic peryleneimide dye, a preparation method thereof, and an application in live cell membrane labeling fluorescence imaging. Background technique [0002] In the field of biological and medical research, bioluminescent imaging is widely used in physiological and pathological research due to its advantages of mature detection instruments, high sensitivity, high contrast, high resolution, intuitive imaging, fast imaging speed and non-destructive detection. Bioluminescent imaging relies on the development of optical molecular probes, especially non-toxic, long-acting fluorescent dye molecules that do not affect biological functions. An intuitive and clear static or dynamic image can be used to analyze the characteristics and state of a cell or a specific area of ​​an organism, and even the expression and distribution of specific molecules...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B5/62C09K11/06G01N21/64
CPCC09B5/62C09K11/06C09K2211/1029G01N21/6486
Inventor 尹梅贞叶勇冀辰东沈杰郑洋
Owner BEIJING UNIV OF CHEM TECH
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