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Trihydroxyimidazole-fluorescein pH fluorescent probe and preparation method thereof

A technology of trihydroxyimidazole and fluorescent probes, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, and can solve problems such as low fluorescence intensity, poor water solubility of pH fluorescent probes, and small Stokes shift changes

Active Publication Date: 2019-05-17
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The present invention aims to solve the problems of poor water solubility of existing pH fluorescent probes, low fluorescence intensity of imidazole compounds, little change in fluorescence emission wavelength after interacting with receptors, and small change in Stokes shift. Imidazole-fluorescein pH fluorescent probe and preparation method thereof

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  • Trihydroxyimidazole-fluorescein pH fluorescent probe and preparation method thereof
  • Trihydroxyimidazole-fluorescein pH fluorescent probe and preparation method thereof
  • Trihydroxyimidazole-fluorescein pH fluorescent probe and preparation method thereof

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specific Embodiment approach 1

[0035] Specific embodiment one: The structural formula of the trihydroxyimidazole-fluorescein pH fluorescent probe of the present embodiment is:

[0036]

specific Embodiment approach 2

[0037] Specific embodiment two: the preparation method of the trihydroxyimidazole-fluorescein pH fluorescent probe of specific embodiment two, carry out according to the following steps:

[0038] One, the synthesis of intermediate compound I:

[0039] Add phenanthrenequinone, 5-nitrosalicylaldehyde, aniline, and ammonium acetate into the reactor according to the material ratio of 1:1.0~2.0:1.0~2.0:2~5, then add 20~40ml of glacial acetic acid, and heat up to After stirring at 80-130°C for 4-12 hours, cool to room temperature, add water to the reactor, and then adjust the pH value to 8-10 with an alkaline solution (sodium hydroxide solution with a mass fraction of 30-40%), and pump The yellow solid was collected by filtration and dried. Ethyl acetate was recrystallized, filtered with suction, and dried to obtain (2-hydroxy-3-nitro)phenylphenanthroimidazole, an intermediate compound I, as a khaki solid.

[0040] Two, the synthesis of intermediate compound II:

[0041] Weigh 2....

specific Embodiment approach 3

[0046] Specific embodiment three: this embodiment differs from specific embodiment two in that the acidic medium described in step three is concentrated sulfuric acid with a mass fraction of 98%, concentrated hydrochloric acid, glacial acetic acid or formic acid with a mass fraction of 36-37%. Others are the same as in the second embodiment.

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Abstract

A trihydroxyimidazole-fluorescein pH fluorescent probe for pH detection and a preparation method thereof relate to the fluorescent probe and its synthesis and application. It needs to solve the problems of poor water solubility of existing pH fluorescent probes and small Stokes shift of imidazole pH fluorescent probes. The fluorescent molecular probe is a trihydroxyimidazole-fluorescein pH fluorescent probe. It is formed by condensation of fluorescein monoaldehyde and (2-hydroxy-3-amino) phenylphenanthroimidazole, with a yield of 85-95%. The fluorescent molecular probe was dissolved in N,N ‑In the mixture of dimethylformamide and HEPES buffer solution, test the absorbance value or fluorescence intensity of the sample in different pH systems to determine its detection range for pH.

Description

technical field [0001] The invention relates to a trihydroxyimidazole-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. Most of the fluorescein-based pH probes reported in the literature are mostly based on rhodamine B, and such pH probes have poor water solubility, which greatly limits their application range. In 2015, an acetyl-linked rhodamine B hydrazine-1-phenylpiperazine pH probe was repo...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06C09K2211/1044C09K2211/1088G01N21/6428
Inventor 赵冰宋波李少鑫孔凤巧刘婷阚伟王丽艳
Owner QIQIHAR UNIVERSITY