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Novel fluorescence probe for detecting hydrogen peroxide in alkaline environment and preparation method and biological application thereof

A fluorescent probe and alkaline environment technology, applied in the field of organic small molecule fluorescent probes, can solve the problems of few types of probes, insufficient sensitivity of detection signals, lack of fluorescent probes, etc., and achieve obvious phenomena, simple preparation methods, and detection highly sensitive effect

Inactive Publication Date: 2015-10-28
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The current fluorescent probes for hydrogen peroxide still have the disadvantages of fewer types of probes and insufficient sensitivity of the detection signal. Near-infrared luminescent fluorescent probes for detecting hydrogen peroxide in alkaline environments cannot realize the detection of hydrogen peroxide in alkaline environments in organisms such as mitochondria, bile, and pancreatic juice by adjusting the acidity and alkalinity of fluorescence

Method used

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  • Novel fluorescence probe for detecting hydrogen peroxide in alkaline environment and preparation method and biological application thereof
  • Novel fluorescence probe for detecting hydrogen peroxide in alkaline environment and preparation method and biological application thereof
  • Novel fluorescence probe for detecting hydrogen peroxide in alkaline environment and preparation method and biological application thereof

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Embodiment 1

[0038] Preparation of compound 1

[0039] React m-N-diethylaminophenol (0.50 g, 3.03 mmol) with phthalic anhydride (0.49 g, 3.33 mmol) in 180 mL of benzene at 60°C for 24 hours to obtain a white solid, then add the white solid to 20 mL of 98 wt% concentrated sulfuric acid containing 6 ml of cyclohexanone was reacted at 50°C for 3 hours, and the solid was recrystallized from ethanol to obtain compound 1 (0.22 g, 0.45 mmol).

[0040] The synthetic route is as follows:

Embodiment 2

[0042] Preparation of a Novel Fluorescent Probe for Detecting Hydrogen Peroxide in Alkaline Environment

[0043] The reaction scheme is as follows:

[0044]

[0045] The preparation process comprises steps as follows:

[0046] Compound 1 (0.377 g, 1.0 mmol) and p-borate benzaldehyde (0.157 g, 1.2 mmol) were reacted in 20 ml of acetic acid at 50 °C for 12 h to obtain a dark solution, and the solvent was removed by rotary distillation. Chloromethane was dissolved, and the mixed solvent of dichloromethane and methanol was separated by column chromatography to obtain the target compound CS-BOH ; Yield: 50%. 1 H NMR (400 MHz, DMSO-d6) δ 8.16 (m, 2H), 8.06 (s, 1H), 7.86 (t, J = 7.2, 2H), 7.72 (d, J = 8.4 , 1H), 7.51 (s, 2H), 7.35 (d, J = 7.6 , 1H), 6.8 (m, 2H), 3.58 (q, J = 6.4 , 4H ), 2.8 (m, 2H), 2.07 (m, 1H), 1.67 (m, 3H), 1.23 (t, J = 6.8 , 6H ). 13 C NMR (101 MHz, CDCl3) δ 169.94, 152.38, 152.09, 149.39, 146.29, 142.08, 134.56, 133.47, 131.95, 129.98, 129.38, 128....

Embodiment 3

[0048] The preparation method of hydrogen peroxide fluorescent probe as described in embodiment 2, difference is:

[0049] The amount of p-borate benzaldehyde was 3 mmol, acetic acid was replaced by acetic anhydride, the amount of acid was 20 mL, the reaction temperature was 60 °C, and the reaction time was 12 h.

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Abstract

The invention discloses a novel fluorescence probe for detecting hydrogen peroxide in an alkaline environment and a preparation method thereof, and belongs to the technical field of molecular probes. The structural formula of the probe is as follow (please see the formula in the specification), and the preparation method of the hydrogen peroxide fluorescence probe is simple. The probe detects the hydrogen peroxide in the mode of fluorescence enhancement and obvious color change and can recognize the hydrogen peroxide high selectively in a water system or an organic solvent system or an organism; the fluorescence of the probe itself is weaker, an obtained solution is purple after the probe is added in water or organic solvent, and the fluorescence of the solution is obviously enhanced and the color of the solution is changed into green after the probe acts with the hydrogen peroxide. The selectivity to hydrogen peroxide detection is high, the detection sensitivity is high, and a phenomenon is obvious and convenient to recognize.

Description

technical field [0001] The invention relates to a novel fluorescent probe for detecting hydrogen peroxide in an alkaline environment and its preparation method and biological application. The fluorescent probe can efficiently identify hydrogen peroxide in an alkaline environment and belongs to the field of organic small molecule fluorescent probes . Background technique [0002] Hydrogen peroxide chemical formula H 2 o 2 , with a relative molecular mass of 34.01, is a weakly acidic colorless transparent liquid. It is a strong oxidizing agent with oxidizing and bleaching properties. As an important inorganic chemical raw material and fine chemical product, hydrogen peroxide has important application value in the fields of industry, food and medical care. First of all, as an important oxidant, hydrogen peroxide can generate hydroxyl radicals and other substances under the action of catalysts and other conditions, thereby rapidly and thoroughly degrading organic matter in w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F5/02G01N21/64
Inventor 林伟英刘克印尚慧明
Owner UNIV OF JINAN
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