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Near-infrared fluorescent compound for specific detection of hydrazine and preparation method of near-infrared fluorescent compound

A fluorescent compound and detection method technology, applied in the field of organic small molecule fluorescent probes, can solve problems such as time-consuming operation and complexity

Pending Publication Date: 2020-10-23
ANHUI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods are time-consuming and complicated to operate

Method used

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  • Near-infrared fluorescent compound for specific detection of hydrazine and preparation method of near-infrared fluorescent compound
  • Near-infrared fluorescent compound for specific detection of hydrazine and preparation method of near-infrared fluorescent compound
  • Near-infrared fluorescent compound for specific detection of hydrazine and preparation method of near-infrared fluorescent compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Preparation of Near Infrared Fluorescent Compounds for Hydrazine Detection

[0073] The near-infrared fluorescent compound of the present invention is (E)-2-(2-(3-(dicyanomethylene)-5,5-dimethylcyclohex-1-en-1-yl) vinyl )-5-(diethylamino)phenyl 4-bromobutanoic acid (DCDB), the specific preparation process is as follows:

[0074]

[0075] (1) Under nitrogen protection, DHDM (1.0g, 2.8mmol), triethylamine (1.0mL) and anhydrous dichloromethane (50mL) were mixed and added to a 100mL three-necked flask, cooled to 0 with an ice bath ℃.

[0076] (2) Under ice-bath conditions, then slowly add 4-bromobutyryl chloride (0.62mg, 3.3mmol) dropwise into the three-necked flask containing the mixture in step (1), and stir at room temperature for 10-12 hours. The progress of the reaction was monitored using thin layer chromatography (TLC) during the reaction.

[0077] (3) After the reaction was completed, the mixture was poured into 50 mL of ice water at 0° C., stirred and mixed, ...

Embodiment 2

[0090] Selective detection of hydrazine in solution system

[0091] (1) The buffer solution for the near-infrared fluorescent compound prepared in Example 1 is prepared into a near-infrared fluorescent compound solution with a concentration of 10 μM, and the buffer solution is composed of phosphate buffered saline (PBS) with a volume ratio of 1:1 and Dimethyl sulfoxide (DMSO) is prepared, and the pH value of the buffer is 7.4;

[0092] (2) hydrazine in the solution is selectively detected with a 10 μM near-infrared fluorescent compound solution;

[0093] Take 81 parts of 3mL near-infrared fluorescent compound solution with a concentration of 10μM, and add 120μL of a concentration of 5×10 -5 mol / L of analytes to be measured, there are 27 kinds of analytes to be measured, and each analyte to be measured is composed of 3 parallel units to form a group, and a total of 81 reactants are obtained; 27 kinds of analytes to be measured are 200 μ M hydrazine ( N 2 h 4 ), 200 μM magne...

Embodiment 3

[0097] Detection Sensitivity of Near-infrared Fluorescent Compounds to Hydrazine in Solution System

[0098] (1) The buffer solution for the near-infrared fluorescent compound prepared in Example 1 is prepared into a near-infrared fluorescent compound solution with a concentration of 10 μM, and the buffer solution is composed of phosphate buffered saline (PBS) with a volume ratio of 1:1 and Dimethyl sulfoxide (DMSO) is prepared, and the pH value of the buffer is 7.4;

[0099] (2) Use 10 μM near-infrared fluorescent compound solution to test hydrazine at different concentrations (0 μM, 10 μM, 20 μM, 30 μM, 40 μM, 50 μM, 60 μM, 70 μM, 80 μM, 90 μM, 100 μM, 110 μM, 120 μM, 130 μM, 140 μM, 150 μM) Fluorescence detection;

[0100] (3) Add different concentrations (0 μM, 10 μM, 20 μM, 30 μM, 40 μM, 50 μM, 60 μM, 70 μM, 80 μM, 90 μM, 100 μM, 110 μM, 120 μM to 48 prepared 3 mL near-infrared fluorescent compound solutions with a concentration of 10 μM, respectively. , 130 μM, 140 μM,...

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Abstract

The invention discloses a novel near-infrared fluorescent compound for specific detection of hydrazine, wherein the near-infrared fluorescent compound is (E)-2-(2-(3-(dicyanomethylene)-5,5-dimethylcyclohexyl-1-ene-1-yl)vinyl)-5-(diethylamino)phenyl 4-bromobutyric acid and is capable of specifically detecting hydrazine in an organism. The near-infrared fluorescent compound is simple in preparationprocess, readily available in raw materials, low in cost and stable in structure, has relatively good cell membrane permeability and relatively low cytotoxicity, can enter living cells and animal tissues and react with exogenous hydrazine to generate strong red fluorescence which can be distinguished by naked eyes; ultraviolet absorption and fluorescence spectrophotometry analysis shows that the near-infrared fluorescent compound has excellent selectivity to hydrazine under various interferents and has quite strong anti-interference capability to common biomolecules; the novel near-infrared fluorescent compound not only can selectively recognize exogenous hydrazine, but also can quantitatively detect hydrazine with high sensitivity in the growth environment of various living cells, and issuccessfully applied to imaging of living cells and zebra fishes.

Description

technical field [0001] The invention belongs to the technical field of organic small molecule fluorescent probes, in particular to (E)-2-(3-(4-(diethylamino)-2-hydroxystyryl)-5,5-dimethylcyclohexyl -2-en-1-yl)malononitrile is a fluorescent chemical compound for the specific detection of environmental pollutant hydrazine as a fluorescent matrix and its application. Background technique [0002] Inorganic pollutants in the environment have a wide range of sources and complex types, most of which will enter the human body. When the concentration of these pollutants in the environment exceeds the safe threshold, it may pose a threat to the environment and human health. Hydrazine (N 2 h 4 ) is an important inorganic compound with certain reducibility, which has been widely used in pesticide production, aerospace, chemical industry and other fields. Not only that, but hydrazine is also a volatile and possibly carcinogenic environmental pollutant. Due to its wide application a...

Claims

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Application Information

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IPC IPC(8): C07C255/43C07C253/30C09K11/06G01N21/64
CPCC07C255/43C09K11/06G01N21/6428G01N21/643G01N21/6458C07C2601/16C09K2211/1007Y02A20/20
Inventor 王毅朱美庆赵宗元凡福港吴祥为花日茂
Owner ANHUI AGRICULTURAL UNIVERSITY
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