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A kind of environmentally sensitive dye based on benzofurazan and its preparation method and application

An environmentally sensitive, benzofurazan technology, applied in methine/polymethine dyes, organic dyes, chemical instruments and methods, etc., can solve the problem of high fluorescence background, achieve fluorescence enhancement, easy visualization, and improve signal-to-noise ratio Effect

Active Publication Date: 2020-10-02
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The biggest problem with this design strategy is the high fluorescence background and the need for complex cleaning procedures before cell imaging

Method used

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  • A kind of environmentally sensitive dye based on benzofurazan and its preparation method and application
  • A kind of environmentally sensitive dye based on benzofurazan and its preparation method and application
  • A kind of environmentally sensitive dye based on benzofurazan and its preparation method and application

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example 1

[0048] Synthesis of BDI, BDB, BDP

[0049]

[0050] Reagents and conditions: (a) dimethylamine hydrochloride, ethanol, triethylamine, 150°C (b) phosphorus oxychloride, N,N-dimethylformamide, 0°C, (c) acetonitrile, iodine Methane, reflux, (d) 2, piperidine, ethanol, reflux (e) acetonitrile, methyl iodide, reflux (f) toluene, methyl iodide, reflux,

[0051] Intermediate 1: N,N-Dimethylbenzo[c][1,2,5]oxadiazol-4-amine

[0052] Weigh 4-chlorobenzofurazan (6.0g, 0.039mol) in a 100mL vacuum-sealed tube, add 50mL ethanol to dissolve it completely, add dimethylamine hydrochloride (18g, 0.22mol), and then add triethylamine dropwise Amine (36mL), quickly capped the self-sealing tube, and stirred at 150°C for 48h. After the reaction was completed, it was cooled to room temperature, and the solvent was distilled off under reduced pressure. Sodium hydroxide solution (2M, 100mL) was added, extracted with ethyl acetate (60mL×3), the organic phase was washed with concentrated brine, dri...

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Abstract

The invention provides an environmentally sensitive material based on Benzofuroxan as well as a preparation method and an application thereof. The environmentally sensitive material has a structural formula as shown in the specification, wherein R1 is selected from one out of 1,4-dimethyl pyridine or 1,2,3,3-methylindole or 1,1,2,3-tetramethyl benzoindoles; functional transformation is further performed on a dye so as to derive a dye intermediate containing carboxyl; and recognition groups of different proteins are combined with an environmentally sensitive material by carboxyl so as to prepare a probe for detecting intra-cellular o-bithiol protein and an application of the probe in detecting o-bithiol protein and bioimaging. Fluorescence is greatly enhanced when the probe molecule prepared by using the environmentally sensitive material based on Benzofuroxan disclosed by the invention is combined with o-bithiol protein, thus easily realizing visualization of receptor proteins, increasing the signal-to-voice ratio, avoiding the tedious washing step and greatly saving time.

Description

technical field [0001] The invention belongs to the field of organic biology technology, and in particular relates to a benzofurazan-based environment-sensitive dye and a preparation method and application thereof. Background technique [0002] Environmentally sensitive probes are a new class of probes whose fluorescence intensity changes with changes in the external microenvironment (for example: polarity, viscosity, molecular ordering, etc.), and the fluorescent background of environmentally sensitive dyes is low. It is often used in the detection of proteins in order to develop new environmentally sensitive dyes. We tried to transform the traditional nitro-substituted benzofurazan dye, which is a commonly used environmentally sensitive dye, but it only emits green fluorescence with a short wavelength, which often interferes with the autofluorescence of the cell or tissue itself, and These short-wavelength light has poor penetrating power and cannot effectively penetrate ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/06C09B23/10C07F9/80C07F9/82C09K11/06G01N21/64
CPCC07D413/06C07F9/80C07F9/82C09B23/105C09K11/06C09K2211/1007C09K2211/1048C09K2211/1096G01N21/6428
Inventor 蒋健晖唐丽娟刘锋汪凤林
Owner HUNAN UNIV
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