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Functionalized bilateral column [5] arene sensor molecule and synthesis and application thereof

A bilateral column, functionalized technology, applied in chemical instruments and methods, separation/purification of carboxylic acid compounds, preparation of organic compounds, etc., can solve problems such as waste water, death, liver failure, etc.

Active Publication Date: 2020-08-11
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, high concentrations of this therapeutic agent can cause seizures, liver failure and even death
On the other hand, depending on the patient's medical condition, 20% to 70% of the drug dose can be excreted in the urine and end up in wastewater like other antibiotics, which can lead to the emergence of dangerous resistant strains of bacteria such as

Method used

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  • Functionalized bilateral column [5] arene sensor molecule and synthesis and application thereof
  • Functionalized bilateral column [5] arene sensor molecule and synthesis and application thereof
  • Functionalized bilateral column [5] arene sensor molecule and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1, the synthesis of isoniazid sensor molecule ZW

[0042] (1) Add acetonitrile (50mL), bromine-functionalized double-sided column[5]arene (ZE, 0.523g, 0.5mmol, synthesized according to the method of DOI: 10.1039 / C9SM01385G), p-hydroxybenzene, respectively, into a 100mL round bottom flask. Methyl formate (2.4mmol, 0.4g), KI (10mmol, 1.66g), K 2 CO 3 (8mmol, 1.0g), nitrogen protection 80 ℃ oil bath reflux stirring for 10~12 hours. After the reaction, add silica gel to mix the sample, spin dry, and purify by column chromatography (petroleum ether: ethyl acetate: dichloroethane = 100: 25: 1), and the white product obtained is methyl p-hydroxybenzoate functionalization Bilateral pillar[5]arenes in 75% yield.

[0043] (2) Weigh the double-sided column[5]arene functionalized with methyl hydroxybenzoate (1.16 g, 1 mmol) and dissolve it in 100 mL of DMF, add 4 mL of NaOH aqueous solution with a concentration of 1 mol / L to the system, and oil at 120 °C The bath was...

Embodiment 2

[0046] Embodiment 2, ZW solution detects isoniazid

[0047] Pipette 0.5mL of 40% water-containing ZW solution (2×10 -4 mol L -1 ) in a series of 10mL colorimetric tubes, with DMSO / H 2 O=6:4 (v / v) to 5mL, add isoniazid, benzohydrazide, phenylhydrazine, hydrazine hydrate in DMSO / H 2 O solution (2×10 -4 mol L -1 ) 0.5 mL. At this time, the concentration of ZW is 2×10 -5 mol L -1 , the concentration of each molecule is 10 times the concentration of ZW, and the response of the sensor molecule ZW to each molecule is observed. Under ultraviolet light (365 nm), the ZW solution added with isoniazid showed green fluorescence, and the ZW solution added with other molecules did not change. It shows that the sensor molecule ZW can specifically and selectively recognize isoniazid.

Embodiment 3

[0048] Embodiment 3, synthesis and application of isoniazid detection test paper

[0049] Cut the test paper into a rectangle and soak it in the solution containing ZW for 10 minutes, so that ZW is fully adsorbed on the filter paper, and then take it out to dry. The filter paper has no fluorescence under the 365nm ultraviolet lamp. Add the solutions of isoniazid, benzohydrazide, phenylhydrazine and hydrazine hydrate dropwise to the filter paper respectively. If the fluorescence of the filter paper increases and turns green, it means that isoniazid is added dropwise; if the fluorescence of the filter paper does not change, it means that It's not isoniazid.

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Abstract

The invention provides a functionalized bilateral column [5] arene sensor molecule. The sensor molecule forms a supramolecular self-assembly system through intermolecular hydrogen bond interaction ina binary solution of DMSO and H2O, and the system hardly has fluorescence. When a DMSO-H2O solution of isoniazid, benzoyl hydrazine, phenylhydrazine and hydrazine hydrate is added, fluorescence of thesolution can be opened to become green only by adding isoniazid so that isoniazid can be identified by fluorescence selectivity, the identification process is not interfered by other molecules, and the detection speed is high. The prepared isoniazid fluorescence detection test paper can be used for conveniently and quickly detecting isoniazid based on the result.

Description

technical field [0001] The present invention relates to a sensor molecule based on a functionalized bilateral column [5] aromatic hydrocarbon, in particular to a chemical sensor molecule based on a functionalized p-hydroxybenzoic acid bilateral column [5] aromatic hydrocarbon and its synthesis. The present invention also relates to the The application of sensor molecular fluorescence detection of isoniazid belongs to the field of chemical synthesis and the technical field of drug molecule detection. Background technique [0002] Isoniazid (IA) as a bacteriostatic agent has been used alone or in combination with other drugs (mainly rifampicin) in the chemotherapy of tuberculosis. Because of its good biofilm penetration, good curative effect, low toxicity, low price, and convenient oral administration, it is listed as the first choice for anti-tuberculosis drugs. The product easily passes through the blood-brain barrier and is suitable for various types of tuberculosis, such ...

Claims

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Application Information

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IPC IPC(8): C07C65/21C07C51/367C07C51/43C09K11/06G01N21/64
CPCC07C65/21C07C51/367C07C51/43C09K11/06G01N21/643C07C2603/92C09K2211/1011
Inventor 魏太保赵琪林奇曲文娟姚虹张有明
Owner NORTHWEST NORMAL UNIVERSITY
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