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Fe<3+> fluorescent probe containing amino acid and synthetic method thereof

A technique for fluorescent probes and synthesis methods, applied in the field of fluorescent probe materials and their preparation, can solve problems such as poor water solubility, strong professionalism, and expensive instruments, and achieve the effects of mild reaction conditions, simple and easy-to-obtain raw materials, and simple operations

Inactive Publication Date: 2018-07-17
QUANGANG PETROCHEM RES INST OF FUJIAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In order to solve the problems of expensive, professional, time-consuming, and destructive to samples and the problems of irreversibility, poor specificity, and poor water solubility of current fluorescent probes, the present invention provides an amino acid-containing Fe 3+ Fluorescent probe and its synthesis method

Method used

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  • Fe&lt;3+&gt; fluorescent probe containing amino acid and synthetic method thereof
  • Fe&lt;3+&gt; fluorescent probe containing amino acid and synthetic method thereof
  • Fe&lt;3+&gt; fluorescent probe containing amino acid and synthetic method thereof

Examples

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Effect test

Embodiment 1

[0031] An amino acid-containing Fe 3+Fluorescent probe, synthetic group R1, R2, R3, R4 is H, n is 2 rhodamine 110Fe 3+ fluorescent probe.

[0032] An amino acid-containing Fe 3+ The synthetic method of fluorescent probe, prepare above-mentioned rhodamine 110Fe 3+ Fluorescent probe, its synthetic method is as follows:

[0033] Step 1: Synthesize rhodamine 110 lactam intermediate, weigh 2g rhodamine 110 dye, dissolve it in ethanol 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;

[0034] Step 2: Synthesis of Rhodamine 110Fe 3+ Fluorescent probe, weigh 1mmol rhodamine 110 lactam, dissolve it in ethanol solvent, then add 1.2mmol serine solution dropwise to the rhodamine 110 lactam solution, heat to 80°C, reflux, TLC tracking To the end of the reaction, the target compound was o...

Embodiment 2

[0036] An amino acid-containing Fe 3+ Fluorescent probe, synthetic groups R1 and R2 are CH 3 , group R3 and R4 are H, n is 2 tetramethylrhodamine Fe 3+ fluorescent probe.

[0037] An amino acid-containing Fe 3+ The synthetic method of fluorescent probe, prepares above-mentioned tetramethylrhodamine Fe 3+ Fluorescent probe, its synthetic method is as follows:

[0038] Step 1: In the middle of synthesizing tetramethylrhodamine lactam, weigh 2g of tetramethylrhodamine dye, dissolve it in ethanol 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;

[0039] Step 2: Synthesis of Fe containing amino acids 3+ Fluorescent probe, weigh 1mmol tetramethylrhodamine lactam, dissolve it in ethanol solvent, then add 1.2mmol serine solution dropwise into the tetramethyl...

Embodiment 3

[0041] An amino acid-containing Fe 3+ Fluorescent probe, synthetic group R1 and R2 are C 2 h 5 , group R3 and R4 are H, n is 2 amino acid-containing Fe 3+ fluorescent probe.

[0042] An amino acid-containing Fe 3+ The synthetic method of fluorescent probe, prepares above-mentioned rhodamine B Fe 3+ Fluorescent probe, its synthetic method is as follows:

[0043] Step 1: Synthesize rhodamine B lactam intermediate, weigh 2g rhodamine B dye, dissolve it in ethanol solvent, then add ethylenediamine solution dropwise to rhodamine B solution, heat to 50°C, and reflux for 6h , the solution changes from maroon red to orange yellow during the reaction process to obtain the rhodamine B lactam intermediate;

[0044] Step 2: Synthesis of Fe containing amino acids 3+ Fluorescent probe, weigh 1mmol rhodamine B lactam, dissolve it in ethanol solvent, then add 1.2mmol serine solution dropwise to rhodamine B lactam solution, heat to 80°C, reflux, TLC tracking To the end of the reaction,...

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Abstract

The invention belongs to the fields of a fluorescent probe material and a preparation method, and concretely relates to a Fe<3+> fluorescent probe containing amino acid and a synthetic method thereof.A structural formula is shown as a graph, sensitivity is high, light stability is good, fluorescence quantum yield is high, a rhodamine fluorophore with long wavelength, serine with good water solubility, a certain amount of rhodamine lactamide and serine are subjected to a condensation reaction under certain conditions to obtain the amino acid-containing Fe<3+> fluorescent probe having a specialstructure, a synthesis process has the advantages of simple and easily available raw material, mild reaction condition, and simple operation, the rhodamine fluorescent probe can rapidly detect Fe<3+>in biological cells under water environment, is capable of performing coordination-type recognition for combination of Fe<3+>, and has reversibility.

Description

technical field [0001] The invention belongs to the field of fluorescent probe materials and preparation thereof, in particular to an amino acid-containing Fe 3+ Fluorescent probes and methods for their synthesis. Background technique [0002] The human body is rich in iron, with an average of 3-5g per adult, and the concentration in the whole cell is about 50-100μΜ (Epsztejn, S., Glickstein, H., Picard, V., Slotki, I.N., Breuer, W., Beaumont, C., Cabantchik, Z.I. H-ferritin subunit overexpression in erythroid cells reduces the oxidative stress response and induces multidrug resistance property [J]. Blood 1999, 94(10), 3593-3603). Iron is involved in most cellular processes in the human body, such as metabolism, electron transfer and DNA synthesis. Usually iron exists in the human body in two ionic forms namely Fe 2+ and Fe 3+ , the two ions will be in a certain equilibrium state during the physiological process of cells. Therefore, it is necessary to control the conten...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6486
Inventor 陈登龙陈嘉炼刘志鹏白欣刘金玲陈敏
Owner QUANGANG PETROCHEM RES INST OF FUJIAN NORMAL UNIV
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