Water-soluble cationic biphenyl aromatic hydrocarbon as well as inclusion compound and preparation method thereof

A technology for water-soluble cationic and biphenyl aromatic hydrocarbons, which is applied in the field of its inclusion complex and its synthesis, and the water-soluble cationic biphenyl aromatic hydrocarbons of the supramolecular macrocyclic main body, and achieves the effects of mild reaction conditions and easy operation.

Active Publication Date: 2018-10-02
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The host-guest complexation between water-soluble cation 2,2’-biphenyl[n]arene and ATP has not been reported so far

Method used

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  • Water-soluble cationic biphenyl aromatic hydrocarbon as well as inclusion compound and preparation method thereof
  • Water-soluble cationic biphenyl aromatic hydrocarbon as well as inclusion compound and preparation method thereof
  • Water-soluble cationic biphenyl aromatic hydrocarbon as well as inclusion compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044]Example 1: Preparation and characterization of novel 2,2'-bromoethoxybiphenyl[n]arenes:

[0045] Dissolve 2,2'-bromoethoxybiphenyl: paraformaldehyde: boron trifluoride ether in 1,2-dichloroethane at a molar ratio of 1:2:2 to 1:2:3. The mixture was stirred at room temperature for 0.5 h, the reaction solution gradually changed from colorless to light red, until wine red, the reaction process was monitored by spot plate, quenched with 50 ml of water after 0.5 h, and the whole reaction was carried out at room temperature. The organic phase was sequentially washed with saturated NaHCO 3 aqueous solution, saturated NaCl aqueous solution for washing and extraction, and then the organic phase was washed with anhydrous NaCl 2 SO 4 Dry processing. Then the sample was mixed and spin-dried to pack the column. Adjust the volume ratio of developing agent sherwood oil and methylene chloride by column chromatography from 1:1.5 to 1:2.5 and pass through the column successively to obt...

Embodiment 2

[0046] Embodiment 2: the preparation of novel water-soluble cationic biphenyl arene:

[0047] The preparation of the following novel water-soluble cationic biphenyl aromatic hydrocarbons takes water-soluble cationic biphenyl[4] aromatic hydrocarbons as an example. The preparation method of other water-soluble cationic biphenyl aromatic hydrocarbons is similar to that of water-soluble cationic biphenyl[4] aromatic hydrocarbons. The specific steps are:

[0048] Get BrBP4 (500mg, 0.3mmol) and add among 25ml absolute ethanol, then add the ethanol solution of 2.5ml trimethylamine (33%) wherein, in N 2 Heating to reflux for 24 hours under the protection of the atmosphere, the reaction solution gradually changed from turbid to clear and transparent. After the reaction is complete, the reaction liquid is cooled to room temperature, the solvent is removed by vacuum rotary evaporation, the residue is dissolved in deionized water, filtered, most of the water is removed by vacuum rotary e...

Embodiment 3

[0050] Preparation and characterization of embodiment 3ATP and AWB4 clathrate:

[0051] Accurately weigh 23.55mgATP (0.05mmol) and 105.62mgAWB4 (0.05mmol) and mix together to dissolve in 10ml of water and mix evenly. The filtrate can be vacuum freeze-dried to obtain the saturate of ATP and AWB4. At the same time, we prepared a separate host AWB4 (2mM) and a separate guest ATP (2mM) in D 2 O, through 1 It can be seen from the HNMR spectrum that ATP is wrapped in the main body AWB4 as Figure 9 .

[0052] Depend on Figure 9 It can be clearly seen that when ATP is included by AWB4, its chemical shift value changes obviously, and the proton peak obviously broadens and moves to the high field. This indicates that ATP molecules enter the cavity of AWB4 to produce a shielding effect, which makes the hydrogen spectrum peak of ATP molecules move to the high field. The broadening of the peak shape indicates that it is caused by shielding the NMR signal completely in the cavity of ...

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Abstract

The invention relates to a water-soluble cationic biphenyl aromatic hydrocarbon as well as an inclusion compound and a preparation method thereof. The compound has a structural formula as shown in thedescription, wherein n is equal to 4-7. The inclusion compound is molecular aggregate formed by the steps: taking water-soluble cationic biphenyl [4] aromatic hydrocarbon as a macrocyclic host compound, taking an ATP molecule (Adenosine Triphosphate) as an individual guest molecule, enabling the ATP molecule to enter a cavity of the water-soluble cationic biphenyl [4] aromatic hydrocarbon, and forming the aggregate by virtue of electrostatic interaction and pi-pi interaction. A molar ratio of the water-soluble cationic biphenyl [4] aromatic hydrocarbon to the ATP molecule is 1 to 1. A bindingconstant measured by a thermostatic calorimetric titration experiment (ITC) experiment is (1.05+/-0.07)*10<4>M<-1>. The method has the advantages of being simple in operation and mild in reaction conditions, improves the biological stability of the ATP, and provides a new thought for reducing multidrug resistance (MDR) produced by tumor cells to anticancer drugs.

Description

technical field [0001] The invention relates to a water-soluble cationic biphenyl aromatic hydrocarbon, its clathrate and a preparation method thereof, in particular to a water-soluble cationic biphenyl aromatic hydrocarbon with a supramolecular macrocyclic main body, its clathrate compound and a synthesis method thereof. Background technique [0002] Adenosine triphosphate is composed of 1 molecule of adenine, 1 molecule of ribose and 3 molecules of phosphate groups, also known as adenosine triphosphate, or ATP for short. It is white powdery crystal, molecular formula, C 10 h 16 N 5 o 12 P 3 , Molecular weight: 491.00, the structural formula is as follows: [0003] [0004] ATP is an unstable high-energy phosphate compound. Under the action of ATP hydrolase, the "~" (high-energy phosphate bond) farthest from A (adenosine) of ATP is broken, and ATP is hydrolyzed into ADP+Pi (free phosphate group) + energy. When the ATP molecule is hydrolyzed, it actually refers to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07C213/02C07C217/16A61K47/69
CPCA61K47/6949C07C41/30C07C43/225C07C213/02C07C217/16
Inventor 钱田鑫李春举贾学顺
Owner SHANGHAI UNIV
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