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Preparation and application of asymmetric polyphenylene acetylene oligomers with ion transmembrane transport activity

A polyphenylene acetylene, asymmetric technology, applied in the field of artificial bionics, can solve the problems of limited application and low transmembrane activity

Inactive Publication Date: 2018-02-16
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, most of the artificial ion channels currently constructed are constructed by multi-molecular self-assembly. The existence of a large number of inactive monomers leads to a low overall transmembrane activity, and its EC 50 (Concentration of required channel molecules when transmembrane activity reaches 50%) values ​​are often in the 10-100 μM order, this concentration requirement greatly limits its application in the field of biomedicine

Method used

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  • Preparation and application of asymmetric polyphenylene acetylene oligomers with ion transmembrane transport activity
  • Preparation and application of asymmetric polyphenylene acetylene oligomers with ion transmembrane transport activity
  • Preparation and application of asymmetric polyphenylene acetylene oligomers with ion transmembrane transport activity

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Experimental program
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Embodiment 1

[0059] (1) Weigh 10g of hydroquinone (90mmol) and 13.8g of potassium carbonate (99mmol) into a 250mL round bottom flask, measure about 100mL of anhydrous N,N-dimethylformamide into the reaction system, and heat to 90°C, after 30 minutes of reaction, a small amount of potassium iodide was added to accelerate the reaction process. Dissolve 16mL (90mmol) bromooctane in 20mL of anhydrous N,N-dimethylformamide and slowly add it dropwise to the reaction flask, and monitor by spotting. After the reaction was completed, the pH of the reaction system was adjusted to neutral, extracted twice with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by suction filtration, and purified by column chromatography (petroleum ether: ethyl acetate = 4:1 , v / v), 18 g of yellow solid 1 was obtained, yield 90%. 1 H NMR (CDCl 3 ,400MHz): δ=6.85–6.69(m,4H),3.89(t,J=6.6Hz,2H),1.81–1.67(m,2H),1.49–1.39(m,2H),1.37– 1.24(m ,9H),0.88(t,J=6.9Hz,3H); 13 C ...

Embodiment 2

[0083] Step (1)-(10) embodiment 1 is identical, and step (11) is as follows:

[0084] (11) Synthesis of stereoregular oligomer P2:

[0085] Under anhydrous and oxygen-free conditions, take a 50mL drying tube and add compound 11 (0.06g, 0.076mmol), cuprous iodide (0.0017g, 0.0076mmol), tetrakistriphenylphosphine palladium (0.0106g, 0.0076mmol) in sequence, and pump Under argon atmosphere after vacuum, toluene (2.5 mL), triethylamine (2.5 mL) and tetrahydrofuran (2.5 mL) were injected by syringe. Freeze to remove oxygen, react at room temperature for 24 hours, the solution gradually turns bright yellow, and the upper layer shows strong green fluorescence, heat up to 60°C and react for about 72 hours; after the reaction is completed, pour into saturated sodium chloride aqueous solution to quench the reaction, two It was extracted twice with methyl chloride, dried over anhydrous magnesium sulfate, and the solvent was removed by suction filtration. The resulting bright yellow sol...

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Abstract

The invention relates to preparation and application of an asymmetric poly(phenyleneethynylene) oligomer with ion transmembrane transfer activity. The asymmetric poly(phenyleneethynylene) oligomer has a structural formula shown as the formula I (please see the formula I in the description), wherein R1 is selected from one of -CH2(CH2)4CH3, -CH2(CH2)6CH3, -CH2(CH2)8CH3, -CH2(CH2)10CH3, -OCH2CH2OCH2CH2O(CH2)5CH3 and -OCH2CH2OCH2CH2O(CH2)7CH3, R2 represents a cation recognition group or an anion recognition group, the cation recognition group is selected from one of benzo-15-crown-5, benzo-18-crown-6, hybridized nitrogen-15-crown-5, hybridized nitrogen-18-crown-6, dibenzo-15-crown-5 and dibenzo-18-crown-6, and the anion recognition group is selected from one of 2,6-pyridine diamide and isophthalic diamide. According to the asymmetric poly(phenyleneethynylene) oligomer, a single-molecule artificial ion channel is formed in a bi-layer membrane, ion transmembrane transfer is effectively achieved, a new method is sought for treating diseases related to function disorders of the ion channel, and the important application value in the field of antibacterial and anti-cancer biological medicine for treating diseases is achieved.

Description

technical field [0001] The invention belongs to the field of artificial bionic technology, in particular to the preparation and application of an asymmetric polyphenylene acetylene oligomer with ion transmembrane transport activity. Background technique [0002] Among the substances transported across the membrane, the transport of ions has attracted widespread attention from scientists because it is closely related to the occurrence and development of various life activities and many diseases, especially the ion channels that play a major role in ion transport have been widely studied. Deep research. In 2003, Roderick MacKinnon and Peter Agre were awarded the Nobel Prize in Chemistry for their pioneering work on cell membrane channels. The abnormal structure and function of ion channels caused by genetic or acquired lesions are the root causes of many diseases, such as common epilepsy, migraine, deafness, congenital myotonia, senile dementia (Alzheimer's disease), Parkinso...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D323/00C07D213/81C07C233/65C07C235/18
CPCC07C233/65C07C235/18C07D213/81C07D323/00
Inventor 包春燕汪晨曦吴芝烨陈素君林秋宁朱麟勇
Owner EAST CHINA UNIV OF SCI & TECH
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