Phenanthroimidazole-fluorescein pH fluorescent probe containing two hydroxyl groups and preparation method of phenanthroimidazole-fluorescein pH fluorescent probe

A technology of phenanthroimidazole and fluorescent probe, which is applied in the field of phenanthroimidazole-fluorescein pH fluorescent probe and its preparation, can solve the problem of single structure, few modification sites of pH fluorescent probe, no clear response site, etc. problem, to achieve the effect of stable structure, high sensitivity and high selectivity

Inactive Publication Date: 2017-06-30
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The present invention aims to solve the technical problems of the existing fluorescein-based pH fluorescent probes, which have few modification sites, single structure, no clear response site, and cannot quantitatively detect the pH value, and provide a phenanthroimidazole containing two hydroxyl groups. - Fluorescein pH fluorescent probe and preparation method thereof

Method used

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  • Phenanthroimidazole-fluorescein pH fluorescent probe containing two hydroxyl groups and preparation method of phenanthroimidazole-fluorescein pH fluorescent probe
  • Phenanthroimidazole-fluorescein pH fluorescent probe containing two hydroxyl groups and preparation method of phenanthroimidazole-fluorescein pH fluorescent probe
  • Phenanthroimidazole-fluorescein pH fluorescent probe containing two hydroxyl groups and preparation method of phenanthroimidazole-fluorescein pH fluorescent probe

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specific Embodiment approach 1

[0034] Embodiment 1: The structural formula of the phenanthrene imidazole-fluorescein pH fluorescent probe containing two hydroxyl groups in this embodiment is:

[0035]

specific Embodiment approach 2

[0036] Specific embodiment two: the preparation method of the phenanthroimidazole-fluorescein pH fluorescent probe containing two hydroxyl groups described in specific embodiment one is carried out according to the following steps:

[0037] One, the synthesis of intermediate compound I:

[0038] Add phenanthrenequinone, m-nitrobenzaldehyde, aniline, and ammonium acetate into the reactor according to the ratio of 1:(1.0~2.0):(1.0~2.0):(2~5) substance amount, and then add glacial acetic acid as As a solvent, heat up to 80-130°C and stir for 4-12 hours, then cool to room temperature, add water to the reactor, adjust the pH value to 8-10, filter with suction, collect the yellow solid, dry it, and reconstitute it with ethyl acetate. Crystallization, after suction filtration and drying, intermediate compound I 2-(3-nitrophenyl)phenanthroimidazole was obtained;

[0039] Two, the synthesis of intermediate compound II:

[0040] Take intermediate compound I, Raney nickel and mass perc...

specific Embodiment approach 3

[0045] Embodiment 3: This embodiment is different from Embodiment 2 in that the reaction temperature in step 1 is 95-100° C., and the reaction time is 10-12 hours. Others are the same as in the second embodiment.

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Abstract

The invention provides a phenanthroimidazole-fluorescein pH fluorescent probe containing two hydroxyl groups and a preparation method of the phenanthroimidazole-fluorescein pH fluorescent probe, relates to fluorescein pH fluorescent probes and preparation methods thereof and aims to solve the technical problems that the conventional fluorescein pH fluorescent probes have fewer modification sites and single structures and have no clear response sites and pH values cannot be detected quantitatively. The structural formula of the phenanthroimidazole-fluorescein pH fluorescent probe containing the two hydroxyl groups is shown in the specification. The preparation method comprises the following steps: 1, an intermediate compound I is prepared from phenanthrenequinone, m-nitrobenzaldehyde, aniline and ammonium acetate as raw materials and glacial acetic acid as a solvent; 2, an intermediate compound II is synthesized from the intermediate compound I, Raney nickel and a hydrazine hydrate solution; 3, an intermediate compound III is synthesized from fluorescein, a methanol solution, a sodium hydroxide solution and chloroform; 4, the pH fluorescent probe is synthesized from the intermediate compound II and the intermediate compound III as raw materials and an acid medium as a solvent. The pH fluorescent probe can be used for detecting and monitoring the pH values.

Description

technical field [0001] The invention relates to a phenanthroimidazole-fluorescein pH fluorescent probe and a preparation method thereof. Background technique [0002] The pH value is an important indicator of organisms, and a specific pH value plays a very important role in many physiological and pathological processes. Intracellular pH plays an important role in many physiological and pathological processes. Excessive acidity or alkalinity can cause cell dysfunction, lead to heart, lung disease or neurological diseases, and even life-threatening in severe cases. Therefore, monitoring changes in intracellular pH can provide important information for studying physiological and pathological processes. Fluorescein pH probes are widely used due to their non-destructive and high sensitivity. In 2011, a series of fluorescein pH fluorescent probes with electron donors (Study on various fluorescein derivatives as pHsensors) were reported in Tetrahedron letters. This series of fl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06C09K2211/1044C09K2211/1088G01N21/643
Inventor 阚伟李少鑫程鸿博周雪然王丽艳宋波赵冰陈书文
Owner QIQIHAR UNIVERSITY
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