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A fluorescent probe for detecting cytosine and its preparation method

A technology of fluorescent probe and cytosine, applied in the field of fluorescent probe for detection of cytosine and its preparation

Inactive Publication Date: 2020-03-17
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As we all know, dimethylpyrrole BODIPY is a stable fluorescent dye, which has the characteristics of strong photochemical stability, high fluorescence intensity, and strong adaptability in various environments. It has become one of the fluorescent probes that are widely valued. Fluorescent probes are mainly used in ion detection, and there are rare reports on biological organic active molecules

Method used

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  • A fluorescent probe for detecting cytosine and its preparation method
  • A fluorescent probe for detecting cytosine and its preparation method
  • A fluorescent probe for detecting cytosine and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1. The synthetic steps of three (2-oxo-chloroethoxymethyl) propane:

[0031] Add 1.34g (0.01mol) of trihydroxypropane and 3.39g (0.03mmol) of chloroacetyl chloride into a 100mL three-neck flask filled with 25mL of dichloromethane, heat and stir under reflux for 4 hours to stop the reaction. Cool to room temperature, add 5% sodium hydroxide solution to fully wash the organic layer 3 times, separate the organic layer, dry over magnesium sulfate, filter, and evaporate the solvent under reduced pressure to obtain tris(2-oxo-chloroethoxymethyl) Propane solid, yield 85%.

[0032] 2. The synthesis steps of three BODIPY:

[0033] In a three-necked flask equipped with 50 mL of acetonitrile, add 0.363 g (0.001 mmol) of tris(2-oxo-chloroethoxymethyl) propane, 1.02 g of hydroxy BODIPY (0.003 mmol), and 1.0 g of potassium carbonate (0.007 mol) and potassium iodide 0.1g (0.0006mol), heated and stirred under reflux for 10 hours, and TLC detected that the raw material point disappear...

Embodiment 2

[0052] 1. The synthetic steps of three (2-oxo-chloroethoxymethyl) propane:

[0053] Add 1.34g (0.01mol) of trihydroxypropane and 5.65g (0.05mmol) of chloroacetyl chloride into a 100mL three-necked flask filled with 30mL of dichloromethane, heat and stir under reflux for 10 hours to stop the reaction. Cool to room temperature, add 5% sodium hydroxide solution to fully wash the organic layer 3 times, separate the organic layer, dry over magnesium sulfate, filter, and evaporate the solvent under reduced pressure to obtain tris(2-oxo-chloroethoxymethyl) Propane solid, yield 88%.

[0054] 2. The synthesis steps of three BODIPY:

[0055] In a three-necked flask equipped with 60mL of acetonitrile, add 0.363g (0.001mmol) tris(2-oxo-chloroethoxymethyl)propane, 1.36g (0.004mmol) of hydroxy BODIPY, 2.0g (0.014mol) of potassium carbonate and potassium iodide 0.2g (0.0012mol), heated and stirred under reflux for 12 hours, and TLC detected that the raw material point disappeared. Stop th...

Embodiment 3

[0057] 1. The synthetic steps of three (2-oxo-chloroethoxymethyl) propane:

[0058] Add 1.34g (0.01mol) of trihydroxypropane and 6.78g (0.06mmol) of chloroacetyl chloride into a 100mL three-necked flask filled with 40mL of dichloromethane, heat and stir under reflux for 5 hours to stop the reaction. Cool to room temperature, add 5% sodium hydroxide solution to fully wash the organic layer 3 times, separate the organic layer, dry over magnesium sulfate, filter, and evaporate the solvent under reduced pressure to obtain tris(2-oxo-chloroethoxymethyl) Propane solid, 82% yield.

[0059] 2. The synthesis steps of three BODIPY:

[0060] In a three-necked flask equipped with 50mL of acetonitrile, add 0.363g (0.001mmol) tris(2-oxo-chloroethoxymethyl)propane, 2.04g (0.006mmol) of hydroxy BODIPY, 3.0g (0.021mol) of potassium carbonate and potassium iodide 0.2g (0.0012mol), heated and stirred under reflux for 20 hours, and TLC detected that the raw material point disappeared. Stop the...

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Abstract

The invention relates to a fluorescent probe for detecting cytosine and a preparation method of the fluorescent probe. The fluorescent probe is a high fluorescence derivative containing three dimethylpyrrole BODIPY primitives. The fluorescent probe is of a structure making the three dimethyl pyrrole BODIPY primitives connected to the same alkyl carbon, and the chemical name is tri-([4-(acetoxyphenyl]-(4,4-difluoro-1,3,5,7-tetramethyl-4-boron-3a,4a-bipyrrole))oxygen methylene propane. The tri BODIPY shows bright yellow in the solution state, very strong fluorescence-emission is achieved at 510nm, the tri BODIPY fluorescence quantum yield reaches 0.97, fluorescence is obviously enhanced after complexation is conducted with cytosine, fluorescence enhancement and cytosine concentration are in linear relation, the minimum detection limit reaches 8.2 micrometer, interference of other biomolecules is small, and the fluorescent probe is an ideal rapid cytosine detection sensing probe.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and analytical chemistry, and in particular relates to a fluorescent probe for detecting cytosine and a preparation method thereof. Background technique [0002] Due to the high selectivity and sensitivity of fluorescent probes, they have been widely used in the detection of various ions and small molecules. Proper chemical modification of the probe can adapt to different detection substrates and monitoring environments. As we all know, dimethylpyrrole BODIPY is a stable fluorescent dye, which has the characteristics of strong photochemical stability, high fluorescence intensity, and strong adaptability in various environments. It has become one of the fluorescent probes that are widely valued. Fluorescent probes are mainly used in ion detection, and are rarely reported for bioorganic active molecules. [0003] Cytosine, whose scientific name is 4-amino-2-carbonylpyrimidine, is one of ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1029C09K2211/1055G01N21/6486
Inventor 杨发福周文超严祯曦郭红玉
Owner FUJIAN NORMAL UNIV
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