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Irreversible rhodamine-based ClO<-> fluorescent probe and synthetic method thereof

A technique for fluorescent probes and synthesis methods, applied in the field of irreversible rhodamine-based ClO-fluorescent probes and their synthesis, capable of solving problems such as poor sensitivity, complicated synthesis steps of fluorescent probes, and short excitation wavelengths, achieving high sensitivity and high yield High, easy-to-operate effect

Inactive Publication Date: 2018-10-12
QUANGANG PETROCHEM RES INST OF FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to solve the problems of complex synthetic steps, poor sensitivity, and short excitation wavelength of the above-mentioned fluorescent probes, the present invention provides an irreversible rhodamine-based ClO - Fluorescent probe and its synthesis method

Method used

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  • Irreversible rhodamine-based ClO&lt;-&gt; fluorescent probe and synthetic method thereof
  • Irreversible rhodamine-based ClO&lt;-&gt; fluorescent probe and synthetic method thereof
  • Irreversible rhodamine-based ClO&lt;-&gt; fluorescent probe and synthetic method thereof

Examples

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Embodiment 1

[0029] A Rhodamine 110 ClO - Fluorescent probe, synthetic group R1, R2, R3, R4 is H, n is 2 rhodamine 110 ClO - fluorescent probe.

[0030] A Rhodamine 110 ClO - The synthetic method of fluorescent probe, prepare above-mentioned Rhodamine 110 ClO - Fluorescent probe, its synthetic method is as follows:

[0031] Step 1: Synthesize rhodamine 110 lactam intermediate, weigh 2g rhodamine 110 dye, dissolve it in acetonitrile solvent, then add ethylenediamine solution dropwise to rhodamine 110 solution, heat to 50°C, and reflux for 6h , during the reaction process, the solution turns from maroon red to orange yellow, and the rhodamine 110 lactam intermediate is obtained;

[0032] Step 2: Synthesis of Rhodamine 110 ClO -Fluorescent probe, weigh 1mmol rhodamine 110 lactam, dissolve it in acetonitrile solvent, then add 1.2mmol dansyl chloride solution dropwise to rhodamine 110 lactam solution, heat to 80°C, reflux, thin layer The analysis was followed until the end of the reaction...

Embodiment 2

[0034] A tetramethylrhodamine ClO - Fluorescent probe, synthetic groups R1 and R2 are CH 3 , group R3 and R4 are H, n is 2 tetramethylrhodamine ClO - fluorescent probe.

[0035] A tetramethylrhodamine ClO - The synthetic method of fluorescent probe, prepares above-mentioned tetramethylrhodamine ClO - Fluorescent probe, its synthetic method is as follows:

[0036] Step 1: In the middle of synthesizing tetramethylrhodamine lactam, weigh 2g of tetramethylrhodamine dye, dissolve it in acetonitrile solvent, then add ethylenediamine solution dropwise into the tetramethylrhodamine solution, and heat to 50°C, reflux reaction for 6 hours, during the reaction, the solution changed from maroon red to orange yellow, and tetramethylrhodamine lactam intermediate was obtained;

[0037] Step 2: Synthesis of Tetramethylrhodamine ClO - Fluorescent probe, weigh 1mmol tetramethylrhodamine lactam, dissolve it in acetonitrile solvent, then add 1.2mmol dansyl chloride solution dropwise to the ...

Embodiment 3

[0039] A Rhodamine B ClO - Fluorescent probe, synthetic group R1 and R2 are C 2 h 5 , group R3 and R4 are H, n is 2 irreversible rhodamine group Fe 3+ fluorescent probe.

[0040] A Rhodamine B ClO - The synthetic method of fluorescent probe, prepares above-mentioned rhodamine B ClO - Fluorescent probe, its synthetic method is as follows:

[0041] Step 1: Synthesize rhodamine B lactam intermediate, weigh 2g of rhodamine B dye, dissolve it in acetonitrile solvent, then add ethylenediamine solution dropwise into rhodamine B solution, heat to 50°C, and reflux for 6h , the solution changes from maroon red to orange yellow during the reaction process, and the rhodamine B lactam intermediate is obtained;

[0042] Step 2: Synthesis of Rhodamine B ClO - Fluorescent probe, weigh 1mmol rhodamine B lactam, dissolve it in acetonitrile solvent, then add 1.2mmol dansyl chloride solution dropwise to rhodamine B lactam solution, heat to 80°C, reflux, thin layer The analysis was followe...

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Abstract

The invention belongs to the field of biological cell diagnosis and specifically relates to an irreversible rhodamine-based ClO<-> fluorescent probe and a synthetic method thereof. A structural formula of the irreversible rhodamine-based ClO<-> fluorescent probe is as shown in a figure in the specification. The irreversible rhodamine-based ClO<-> fluorescent probe contains a rhodamine fluorophorewith high sensitivity, good light stability, high fluorescent quantum yield and long wavelength. A certain amount of rhodamine lactam and dansyl chloride are subjected to a condensation reaction undercertain conditions to obtain the irreversible rhodamine-based ClO<-> fluorescent probe with a special structure. A synthetic process has simple and easily-available raw materials, mild reaction conditions and simple operation, the obtained rhodamine fluorescent probe can quickly detect ClO<-> in biological cells in an aquatic environment, is free from interference of other ions, belongs to response type identification in combination with the ClO<-> and has irreversibility.

Description

technical field [0001] The invention belongs to the field of biological cell diagnosis, in particular to an irreversible rhodamine-based ClO - Fluorescent probes and methods for their synthesis. Background technique [0002] In recent years, the detection of inorganic anions in the environment, in biological systems and even in medicine has attracted much attention. Active oxygen compounds in inorganic anions play an important role in physiological and pathological processes. Hypochlorite (ClO - ) is a common non-nucleophilic oxidant, the main component of detergents and antibacterial agents widely used in industry and daily life, and the most critical reactive oxygen species (ROS) for the immune system of organisms. In living organisms, hypochlorite (ClO - ) is involved in intracellular redox reactions and various signal transduction processes, including vasodilation, myocardial contraction, neurotransmission, and insulin secretion. And when intracellular hypochlorite ...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6428
Inventor 陈登龙白欣刘金玲陈嘉炼刘志鹏陈敏
Owner QUANGANG PETROCHEM RES INST OF FUJIAN NORMAL UNIV
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