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Novel near infrared ratio fluorescence probe for detecting hydrogen peroxide as well as preparation method and application of probe

A ratiometric fluorescent probe and hydrogen peroxide technology, applied in the field of analytical chemistry, can solve the problem of fewer probes, achieve high selectivity, simple synthesis, and easy post-processing

Inactive Publication Date: 2018-12-28
HEZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although ratiometric probes offer clear advantages over fluorescence-increasing or decreasing probes for accurate quantitation, such probes have been few and far between.

Method used

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  • Novel near infrared ratio fluorescence probe for detecting hydrogen peroxide as well as preparation method and application of probe
  • Novel near infrared ratio fluorescence probe for detecting hydrogen peroxide as well as preparation method and application of probe
  • Novel near infrared ratio fluorescence probe for detecting hydrogen peroxide as well as preparation method and application of probe

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Embodiment 1

[0053] A novel near-infrared ratiometric fluorescent probe for detecting hydrogen peroxide of the present invention, named 2-[2-[2-[[4-(4,4,5,5-tetramethyl-1,3,2 -dioxoborolan-2-yl)benzyloxycarbonyl]benzylamino]-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indole-2-ylidene Base) ethylidene]-1-cyclohexen-1-yl]vinyl]-1,3,3-trimethylindolium iodide, the molecular formula is C 53 h 61 BIN 3 o 4 , the structural formula is shown in formula (1):

[0054]

[0055] The preparation method of the novel near-infrared ratiometric fluorescent probe for detecting hydrogen peroxide in the above-mentioned present embodiment, its synthetic route is as follows: figure 1 shown, including the following steps:

[0056] (1) Synthesis of 1,2,3,3-tetramethyl-3H-iodoindole as shown in formula (5):

[0057]

[0058] The reaction formula is as formula (2):

[0059]

[0060] The specific process is: dissolve 2,3,3-trimethyl-3H-indole (1.59g, 10mmol) in nitromethane (30mL), then add iodomethane (2.1...

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Abstract

The invention discloses a novel near infrared ratio fluorescence probe for detecting hydrogen peroxide as well as a preparation method and an application of the probe. The probe is 2-[2-[2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxycarbonyl]benzylamino]-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethylindolium iodide. The preparation method comprises steps as follows: 1,2,3,3-tetramethyl-3H-iodoindole and 2-chloro-1-formyl-3-hydroxymethylcyclohexene are subjected to a dehydration condensation reaction; obtained 2-[2-[2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethylindolium iodide and benzylamine react; obtained 2-[2-[2-benzylamino-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethylindolium iodide and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbobenzoxy chloride react, and the novel fluorescence probe is obtained. The probe shows higher selectivity for detection of hydrogen peroxide.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a novel near-infrared ratio fluorescent probe for detecting hydrogen peroxide, a preparation method and application thereof. Background technique [0002] Hydrogen peroxide (H 2 o 2 ) is a metabolic by-product of reactive oxygen species, excessive production and accumulation in cells can lead to oxidative stress and a series of serious health problems. Therefore, fluorescence imaging techniques for the visualization of intracellular hydrogen peroxide have attracted increasing attention. More and more studies have shown that hydrogen peroxide is not only closely related to the occurrence of various diseases in organisms, but also an important information transduction molecule in the normal physiological process of cells. The design and development of hydrogen peroxide fluorescent probes with high sensitivity and good selectivity will provide a powerful ...

Claims

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Application Information

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IPC IPC(8): C07F5/04C09K11/06G01N21/3577G01N21/64
CPCC07F5/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1096G01N21/3577G01N21/643G01N2021/6432
Inventor 朱东建任爱山蔡文段振华
Owner HEZHOU UNIV
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