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Trihydroxy imidazole-fluorescein pH fluorescent probe and preparation method thereof

A fluorescent probe, hydroxyimidazole technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of poor water solubility of pH fluorescent probes, low fluorescence intensity, and little change in the fluorescence emission wavelength.

Active Publication Date: 2017-05-31
QIQIHAR UNIVERSITY
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  • 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

Method used

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  • Trihydroxy imidazole-fluorescein pH fluorescent probe and preparation method thereof
  • Trihydroxy imidazole-fluorescein pH fluorescent probe and preparation method thereof
  • Trihydroxy imidazole-fluorescein pH fluorescent probe and preparation method thereof

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specific Embodiment approach 1

[0041] Specific embodiment 1: The structural formula of the trihydroxyimidazole-fluorescein pH fluorescent probe of this embodiment is:

[0042]

specific Embodiment approach 2

[0043] Specific embodiment two: The preparation method of the trihydroxyimidazole-fluorescein pH fluorescent probe of specific embodiment two is carried out according to the following steps:

[0044] 1. Intermediate compounds Synthesis:

[0045] Add phenanthrenequinone, 5-nitrosalicylic aldehyde, aniline, and ammonium acetate into the reactor at a ratio of 1: 1.0~2.0: 1.0~2.0: 2~5, then add 20~40 ml of glacial acetic acid, and increase the temperature. After stirring for 4-12 hours at 80~130℃, cool to room temperature, add water to the reactor, and adjust the pH value to 8~10 with alkaline solution (30~40% sodium hydroxide solution) , Suction filtration, collect the yellow solid, and dry. Ethyl acetate was recrystallized, filtered and dried to obtain an ocher solid (2-hydroxy-3-nitro)phenylphenanthrimidazole, an intermediate compound .

[0046] 2. Intermediate compounds Synthesis:

[0047] Weigh 2.0 mmol intermediate compound Add 0.08~0.22 g Raney nickel to the reactor, then add...

specific Embodiment approach 3

[0052] Specific embodiment three: This embodiment is different 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 with a mass fraction of 36 to 37%, glacial acetic acid or formic acid. Others are the same as the second embodiment.

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Abstract

The invention discloses a trihydroxy imidazole-fluorescein pH fluorescent probe for pH detection and a preparation method thereof and relates to a fluorescent probe and synthesis and application thereof. The invention aims at solving the problems of low water solubility of the existing pH fluorescent probe and little Stokes displacement of the imidazole pH fluorescent probe. The fluorescent molecular probe is a trihydroxy imidazole-fluorescein pH fluorescent probe. The trihydroxy imidazole-fluorescein pH fluorescent probe is prepared through condensation of fluorescein single aldehyde and (2-hydroxy-3-amino)phenyl benzimidazole, and the yield is 85-95%. The fluorescent molecular probe is dissolved in the mixed liquid of N,N-dimethyl formamide and HEPES buffer solution, and the pH detection range is determined by testing the absorbance value or fluorescence intensity change of a sample in different pH systems.

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 the organism, 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, leading to heart and lung diseases or neurological diseases, and even life-threatening in severe cases. Therefore, monitoring the changes of 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 rhodamine B, and this type of pH probe has poor water solubility, which greatly limits its application range. In 2015, an acetyl-linked rhodamine B hydrazine-1-phenylpiperazine pH probe (The...

Claims

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Application Information

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