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(diphenyl amino) phenyl flavonoid fluorescent probe for detecting cysteine and preparation method of (diphenyl amino) phenyl flavonoid fluorescent probe

A technology of diphenylamino and cysteine, which can be used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of complicated operation, expensive equipment, long detection time, etc., and achieve the effect of good application prospects.

Pending Publication Date: 2022-08-02
NANJING FORESTRY UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] There are many methods for the detection of cysteine ​​have been reported, mainly including high performance liquid chromatography, atomic absorption spectrometry, gas chromatography, methylene blue method and electrochemical analysis, etc., but these methods have complex sample pretreatment, expensive equipment, The operation is cumbersome and the detection takes a long time, which has certain limitations

Method used

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  • (diphenyl amino) phenyl flavonoid fluorescent probe for detecting cysteine and preparation method of (diphenyl amino) phenyl flavonoid fluorescent probe
  • (diphenyl amino) phenyl flavonoid fluorescent probe for detecting cysteine and preparation method of (diphenyl amino) phenyl flavonoid fluorescent probe
  • (diphenyl amino) phenyl flavonoid fluorescent probe for detecting cysteine and preparation method of (diphenyl amino) phenyl flavonoid fluorescent probe

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Effect test

Embodiment 1

[0031] The preparation of (diphenylamino) phenylflavonoids, the reaction formula is:

[0032]

[0033] Specific steps are as follows:

[0034] 1) Preparation of 4-(diphenylamino)phenyl-2-hydroxyacetophenone:

[0035] 10mmol of 4-bromo-2-hydroxyacetophenone, 12mmol of 4-(diphenylamino)phenylboronic acid, 40mmol of sodium carbonate and 1mmol of tetrakis(triphenylphosphine) palladium were successively added to the dry three-necked flask, and then 50mL of diphenylphosphine was added. Oxane and 15 mL of water were dissolved, heated to 90°C under nitrogen protection and reacted overnight, followed and monitored by TLC method, and the reaction was stopped when the reaction was complete; the reaction solution was distilled under reduced pressure to remove dioxane and water, and then ethyl acetate was added. Ester, washed with saturated brine to neutrality, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to obtain 4-(diphenylamino)phenyl-2-hydro...

Embodiment 2

[0041] 6-(4-(Diphenylamino)phenyl)-2-(furan-2-yl)-3-hydroxychromone acrylate and Cys, GSH, Hcy, Gly, Arg, Asp, Ala, His, Lys, Glu, Ser, Val, Tyr, F - , Cl - , Br - , I - , NO 3 - , CO 3 2- , SO 4 2- , HSO 3 - , SO 3 2- , Mg 2+ , Na + , Cu 2+ , Ca 2+ , Ag + , K + 28 different analytes were respectively dissolved in DMSO / PBS (v / v=6 / 4) buffer to prepare a concentration of 1.0×10 -6 Probe solution and concentration of M is 1.0 × 10 -5 28 different analyte solutions of M were used to measure the fluorescence spectrum of the solution using a fluorescence spectrometer, and the results were as follows figure 1 shown. figure 1 It shows that the addition of cysteine ​​makes the fluorescence intensity of the system change from colorless to orange-red under ultraviolet light at 365 nm, and by adding other interfering substances GSH, Hcy, Gly, Arg, Asp, Ala, His, Lys, Glu, Ser, Val, Tyr, F - , Cl - , Br - , I - , NO 3 - , CO 3 2- , SO 4 2- , HSO 3 - , SO ...

Embodiment 3

[0043] 6-(4-(Diphenylamino)phenyl)-2-(furan-2-yl)-3-hydroxychromone acrylate was formulated to a concentration of 1.0×10 -5 M in DMSO / PBS (v / v=6 / 4) buffer solution, also dissolve cysteine ​​in DMSO / PBS (v / v=6 / 4) buffer solution to make the concentration of 0, 3, 6, 9 , 12, 15, 18, 21, 24, 27, 30, 33, 36, 40 μM solutions. The effect of different concentrations of cysteine ​​on the fluorescence spectrum of 6-(4-(diphenylamino)phenyl)-2-(furan-2-yl)-3-hydroxychromone acrylate by titration , the result is figure 2 shown. figure 2 It shows that with the continuous increase of cysteine ​​concentration in the system, the fluorescence intensity at 575nm gradually increases, which indicates that the compound can detect cysteine ​​sensitively.

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Abstract

The invention discloses a (diphenylamino) phenyl flavonoid fluorescent probe for detecting cysteine and a preparation method of the (diphenylamino) phenyl flavonoid fluorescent probe. 4-bromo-2-hydroxyacetophenone is used as a raw material and is subjected to a coupling reaction with 4-(diphenylamino) phenylboronic acid to obtain 4-(diphenylamino) phenyl-2-hydroxyacetophenone, and then the 4-(diphenylamino) phenyl-2-hydroxyacetophenone and furfural are subjected to aldol condensation and cyclization reaction to obtain 6-(4-(diphenylamino) phenyl)-2-(furan-2-yl)-3-hydroxychromone; and then carrying out esterification reaction with acryloyl chloride to obtain the 6-(4-(diphenylamino) phenyl)-2-(furan-2-yl)-3-hydroxychromone acrylate. The compound can rapidly and specifically react with cysteine at room temperature, so that the fluorescence color of a solution is changed from colorless to orange red, and the lowest detection limit is 9.76 * 10 <-8 > M. The probe can be used as a fluorescent probe for detecting cysteine and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a (diphenylamino)phenylflavonoid fluorescent probe for detecting cysteine ​​and a preparation method thereof. Background technique [0002] Cysteine ​​(Cys), homocysteine ​​(Hcy), and glutathione (GSH) are major thiol-containing amino acids that play important roles in many biological processes. Among them, Cys is directly related to many important cellular functions, such as antioxidant defense, cell growth, detoxification and metabolism, etc. Therefore, abnormal levels of Cys in cells are also associated with various diseases. Cys deficiency can lead to slow growth, decreased hematopoiesis, skin damage, hair depigmentation, decreased body weight ratio, plasma albumin levels, leukopenia, liver damage, and Parkinson's disease; conversely, excessive Cys may lead to severe neurotoxicity, Alzheimer's disease Haimer's disease and cardiovascular disease. Therefore, it ...

Claims

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Application Information

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IPC IPC(8): C07D407/04C09K11/06G01N21/64
CPCC07D407/04C09K11/06G01N21/6428C09K2211/1088C09K2211/1014C09K2211/1007Y02P20/55
Inventor 王石发秦阿慧巩帅张燕王忠龙李明新杨益琴徐徐
Owner NANJING FORESTRY UNIV
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