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Indole hydrogen peroxide fluorescent probe and preparation method thereof

A technology of indole hydrogen peroxide and fluorescent probes, applied in the field of biological fluorescent probes, can solve the problems of poor stability, low quantum yield, complex synthesis process, etc., achieve low cost, simple synthesis method, fluorescent quantum production high rate effect

Active Publication Date: 2020-09-15
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a highly sensitive fluorescence-enhanced near-infrared hydrogen peroxide fluorescent probe to solve the complex synthesis process of the organic small molecule hydrogen peroxide fluorescent probe in the prior art, low quantum yield and stable gender issues

Method used

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  • Indole hydrogen peroxide fluorescent probe and preparation method thereof
  • Indole hydrogen peroxide fluorescent probe and preparation method thereof
  • Indole hydrogen peroxide fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Weigh 1 g of 2,3,3-trimethylindole into a 100 ml flask, and add 20 ml of dry acetonitrile. After dissolving, 1.17 g of iodoacetic acid was added, and the mixture was reacted at 60° C. under reflux for 4 hours. After the reaction was completed, most of the acetonitrile was removed under vacuum distillation, and the product was dropped into anhydrous ether, and a black solid was precipitated. After suction filtration, the filter cake was washed three times with anhydrous ether to obtain the pure product iodo-1-carboxymethyl-2,3,3-trimethylindole with a yield of 85%.

[0034] (2) Weigh 1.5 g of 4-formylphenylboronic acid and 1.18 g of pinacol in a 500 ml flask, and add 150 ml of toluene. The mixture was reacted at 80°C under reflux for 8 hours. After the reaction was completed, the solvent toluene was removed under reduced pressure distillation, and white 4-formylphenylboronic acid pinacol ester was precipitated, which was directly used for the next reaction.

[003...

Embodiment 2

[0038] (1) Weigh 1 g of 2,3,3-trimethylindole into a 100 ml flask, and add 20 ml of dry acetonitrile. After dissolving, 0.86 g of bromoacetic acid was added, and the mixture was reacted under reflux at 100° C. for 4 hours. After the reaction was completed, most of the acetonitrile was removed under vacuum distillation, and the product was dropped into anhydrous ether, and a black solid was precipitated. After suction filtration, the filter cake was washed three times with anhydrous ether to obtain the pure bromo-1-carboxymethyl-2,3,3-trimethylindole with a yield of 88%.

[0039](2) Weigh 1.5 g of 4-formylphenylboronic acid and 1.18 g of pinacol in a 500 ml flask, and add 150 ml of toluene. The mixture was reacted at 120° C. under reflux for 8 hours. After the reaction was completed, the solvent toluene was removed under reduced pressure distillation, and white 4-formylphenylboronic acid pinacol ester was precipitated, which was directly used for the next reaction.

[0040] ...

Embodiment 3

[0043] (1) Weigh 1 g of 2,3,3-trimethylindole into a 100 ml flask, and add 20 ml of dry acetonitrile. After being dissolved, 1.17 g of iodoacetic acid was added, and the mixture was reacted at 60° C. under reflux for 12 hours. After the reaction was completed, most of the acetonitrile was removed under vacuum distillation, and the product was dropped into anhydrous ether, and a black solid was precipitated. After suction filtration, the filter cake was washed three times with anhydrous ether to obtain the pure product iodo-1-carboxymethyl-2,3,3-trimethylindole with a yield of 85%.

[0044] (2) Weigh 1.5 g of 4-formylphenylboronic acid and 1.18 g of pinacol in a 500 ml flask, and add 150 ml of toluene. The mixture was reacted at 120° C. under reflux for 16 hours. After the reaction was completed, the solvent toluene was removed under reduced pressure distillation, and white 4-formylphenylboronic acid pinacol ester was precipitated, which was directly used for the next reactio...

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Abstract

The invention provides an indole hydrogen peroxide fluorescent probe and a preparation method thereof, and belongs to the field of organic dye synthesis. The indole hydrogen peroxide probe prepared bythe method is a black solid in appearance, and the melting point is within the range of 180-300 DEG C. The fluorescent probe has the advantages of novel structure, high sensitivity, good selectivity,high molar extinction coefficient, good light stability and the like; besides, the fluorescence emission wavelength of the hydrogen peroxide probe is 500-650 nm, biological background fluorescence interference can be effectively avoided, the hydrogen peroxide probe has excellent penetrability to the environment and biological tissues, and a sensitive tool is provided for detection and research oforganisms and trace hydrogen peroxide in the environment.

Description

technical field [0001] The invention belongs to the technical field of biological fluorescent probes, and specifically designs a near-infrared fluorescent probe for detecting the concentration of trace hydrogen peroxide and a preparation method thereof. Background technique [0002] Hydrogen peroxide is one of the important representatives of reactive oxygen species (ROS). Signals such as hormones, as well as biotic and abiotic stress stimuli can induce intracellular H 2 0 2 production and accumulation. Hydrogen peroxide has relatively stable chemical properties, long life span, high transmembrane permeability and the ability to rapidly diffuse between cells, and external stimuli can rapidly stimulate its synthesis and decomposition. These characteristics allow hydrogen peroxide to interact with other signaling molecules such as hormones, and affect the production and participation of a series of downstream signaling molecules such as protein kinases and protein phosphatas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06G01N21/643C09K2211/1029C09K2211/1007C09K2211/1096
Inventor 王琦吴铭敏马振祥范志伟褚修余龚莹
Owner NANTONG UNIVERSITY
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