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Modified conjugated polymer, and preparation method and application thereof

A conjugated polymer and modified technology, applied in the field of biomedicine, can solve the problems of unstable cell membrane structure binding and poor biocompatibility.

Active Publication Date: 2017-12-05
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the problems of poor biocompatibility and inability to stably combine with the cell membrane structure existing in the prior art, to provide modified conjugated polymers and their preparation methods and applications, and to prepare modified conjugated polymers. Conjugated polymers have both the biocompatibility of phospholipids and the fluorescent properties and ability to generate reactive oxygen species of conjugated polymers

Method used

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  • Modified conjugated polymer, and preparation method and application thereof
  • Modified conjugated polymer, and preparation method and application thereof
  • Modified conjugated polymer, and preparation method and application thereof

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[0037] The second aspect of the present invention provides the preparation method of the above-mentioned modified conjugated polymer, the method comprises: under the condition that solvent and catalyst exist, the conjugated polymer and the compound shown in formula (III) or formula (IV) Carry out click chemistry synthesis reaction,

[0038]

[0039] Among them, R 4 for C 2 -C 20 straight-chain alkyne group.

[0040] In a specific embodiment of the present invention, the R 4 Can be but not limited to: propynyl, butynyl or pentynyl. In preferred cases, the R 4 For butynyl.

[0041] In a specific embodiment of the present invention, in the presence of a solvent and a catalyst, the conjugated polymer and the compound represented by formula (III) are subjected to click chemical synthesis to prepare the modified compound represented by formula (I). Conjugated polymers.

[0042] In another specific embodiment of the present invention, in the presence of a solvent and a cat...

Embodiment 1

[0071] (1) Preparation of conjugated polymer

[0072] (1a) Synthesis of (E)-1-bromo-4-(4-bromoethylstyryl)benzene

[0073] Diethyl 4-bromobenzylphosphonate (purchased from Bailingwei Company, batch number 377896) (2.0g, 6.5mmol), sodium tert-butoxide (NaO t Bu) (0.69g, 7.2mmol) and 40mL of anhydrous tetrahydrofuran (THF) were successively added into a 100mL Schlenk flask, after alternate freezing, evacuation and thawing and degassing for 3 times, the solution containing 4-(methyl bromide) was added dropwise. (1.29 g, 6.5 mmol) in 10 mL of degassed and dried THF, and the above mixture was kept stirring at 0° C. for 30 minutes. After removing the ice bath, the reaction mixture was stirred at room temperature for 24 hours. The reaction was quenched with water and extracted with dichloromethane. Subsequently, the organic layer was washed with brine, washed with Na 2 SO 4 Dry and spin dry the organic phase. The crude product was purified by column chromatography (petroleum et...

Embodiment 2

[0142] (1) Preparation of conjugated polymer

[0143] (1a) 9,9-bis(6′-bromohexyl)-2,7-dibromofluorene

[0144] 1,6-dibromohexane (97.6g, 400mmol) was added in 100ml of 50% potassium hydroxide solution, 1.28g of phase transfer catalyst tetrabutylammonium bromide (TBAB) was added, and the temperature of the reaction solution was raised to 75°C , then added 2,7-dibromofluorene (12.96 g, 40 mmol) and stirred for 15 min. After the reaction was stopped and cooled to room temperature, dichloromethane extracted (100ml, performed 3 times), the organic phases were combined, washed with 1M hydrochloric acid solution and distilled water, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was separated and purified by silica gel column chromatography, and the developing solvent was dichloromethane / petroleum ether (v / v=1 / 9) to obtain product V as a white solid (mass 21.4 g, yield 82%).

[0145] The hydrogen spectrum data of V is: 1 H-NMR: (300MHz, CDCl ...

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Abstract

The invention relates to the field of biomedical science, and discloses a modified conjugated polymer, and a preparation method and an application thereof. The modified conjugated polymer comprises a compound represented by formula (I) or formula (II) shown in the description; and in the formula (I) or formula (II), R1 is a group having a conjugated structure unit, R2 is a C2-C25 linear alkyl group, and R3 is a hydrophilic group. The modified conjugated polymer has the biocompatibility of phospholipid, and also has the fluorescence property of the conjugated polymer. The modified conjugated polymer is interlaced to the membrane structure of cells through the strong hydrophobic effect of the modified conjugated polymer and the natural phospholipid, so the fluorescence property of the conjugated polymer can realize the imaging of the intracellular membrane structure; and active oxygen generated under an illuminating condition can effectively oxidize adjacent unsaturated phospholipid to realize the controlled release of drugs. The modified conjugated polymer has application values in the fields of self-assembling, cell imaging, cell membrane permeability adjustment and drug controlled release.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a modified conjugated polymer and its preparation method and application. Background technique [0002] The cell membrane plays an extremely important role in maintaining the homeostasis of the cell, regulating and selecting substances in and out of the cell, and cell metabolism. The introduction of various antibodies, ligands, probes and other functional molecules on the cell membrane through the method of cell membrane engineering has greatly promoted the development of life sciences, and has important significance in cell imaging, detection, tumor treatment, etc. . Regulating and visualizing the activities involved in cell membranes is an important purpose of cell membrane engineering, and has received extensive attention in the field of basic biomedicine and clinical diagnosis. At present, the fluorescent materials widely used in cell imaging are mainly quantum dots and small mol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6518C08G61/10C09K11/06G01N21/84A61K47/34A61K47/24
CPCA61K47/24A61K47/34C07F9/6518C08G61/10C08G2261/124C08G2261/143C08G2261/147C08G2261/228C08G2261/3142C08G2261/354C08G2261/72C09K11/06C09K2211/1059C09K2211/1466G01N21/84
Inventor 王树陈艳艳刘礼兵吕凤婷
Owner INST OF CHEM CHINESE ACAD OF SCI
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