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Fluorescent probe based on resorufin dye specific response ONOO<->, and preparation method and application thereof

A fluorescent probe and resorufin technology, applied in the field of fluorescent probes, can solve the problems of lack of imaging applications, short fluorescence emission wavelength, low selectivity, etc., and achieve the effects of obvious detection signal, low cytotoxicity, and simple synthesis method

Active Publication Date: 2021-03-30
上海安能健生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the reported fluorescent probes can realize the detection of ONOO ‒ detection, but there are still some limitations, such as low selectivity (some ONOO ‒ Probes may also be sensitive to H 2 o 2 and NaClO), the fluorescence emission wavelength is short (in the ultraviolet-visible region) and the imaging application in vivo is scarce, so the construction of ONOO ‒ Research on novel long-wavelength fluorescent probes with high specificity and imaging of cells and in vivo is still urgent

Method used

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  • Fluorescent probe based on resorufin dye specific response ONOO&lt;-&gt;, and preparation method and application thereof
  • Fluorescent probe based on resorufin dye specific response ONOO&lt;-&gt;, and preparation method and application thereof
  • Fluorescent probe based on resorufin dye specific response ONOO&lt;-&gt;, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The preparation steps of the probe are as follows:

[0041] (1) Preparation of Compound 1

[0042] ;

[0043] N 2 Under the protection of an ice-water bath, dissolve p-hydroxybenzyl alcohol in a mixed solvent, then add diphenylphosphinyl chloride, react at room temperature for 1-2 hours, quench with ice water, extract with dichloromethane, and separate by column chromatography to obtain compound 1;

[0044] (2) Preparation of Compound 2

[0045] ;

[0046] Dissolve the compound 1 prepared in step (1) in dichloromethane, then add carbon tetrabromide and triphenylphosphine into the above system according to the ratio of equivalent 1:1~2, stir and react at room temperature for 1~2 hours, and then The solvent was removed under reduced pressure, and the compound 2 was obtained by column chromatography;

[0047] (3) Preparation of probe RFP

[0048] ;

[0049]First dissolve resorufin and potassium carbonate in N,N-dimethylformamide at a ratio of 1:2 equivalent, a...

Embodiment 2

[0052] The preparation steps of the probe are as follows:

[0053] (1) Preparation of Compound 1

[0054] N 2 Under the protection of ice-water bath, triethylamine was added into the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and p-hydroxybenzoic acid oxime ester and diphenylphosphinoyl chloride were dissolved in the mixed solvent according to the ratio of equivalent of 1:1.5, and reacted at room temperature for 2 hours, quenched with ice water, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0055] (2) Preparation of Compound 2

[0056] Dissolve compound 1 in dichloromethane, add carbon tetrabromide and triphenylphosphine in an equivalent ratio of 1:1.5, stir at 25°C for 1-1.5h, then remove the solvent under reduced pressure, and separate by column chromatography to obtain compound 2;

[0057] (3) Preparation of compound 3

[0058] First dissolve resorufin and potassium carbonate in N,N-dimethylformamide in...

Embodiment 3

[0060] The preparation steps of the probe are as follows:

[0061] (1) Preparation of Compound 1

[0062] N 2 Under the protective ice-water bath, triethylamine was added into the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and p-hydroxybenzyl alcohol and diphenylphosphinoyl chloride were dissolved in the mixed solvent in a ratio of 1:2 in equivalent, and reacted at room temperature for 2 hours, and the Quenched with water, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0063] (2) Preparation of Compound 2

[0064] Dissolve compound 1 in dichloromethane, add carbon tetrabromide and triphenylphosphine in an equivalent ratio of 1:2, stir at 25°C for 1-1.5h, then remove the solvent under reduced pressure, and separate by column chromatography to obtain compound 2;

[0065] (3) Preparation of compound 3

[0066] First dissolve resorufin and potassium carbonate in N,N-dimethylformamide at a ratio of 1:2 equivalen...

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Abstract

The invention provides a fluorescent probe based on resorufin dye specific response ONOO<->, and a preparation method and application thereof. The structural formula of the probe is shown in the specification. According to the probe, a resorufin dye is selected as a fluorophore, and diphenyl phosphinic acid ester is selected as a recognition group. A detection mechanism comprises that ONOO<-> anddiphenyl phosphinic acid ester are subjected to an oxidation reaction, then a one-step self-elimination reaction is carried out, and fluorophores are released to cause fluorescence signal change. Theprobe is used for detecting ONOO<-> through ultraviolet and fluorescence spectrometers without being interfered by active nitrogen and active oxygen, the detection process is simple, convenient, rapidand sensitive, and the detection limit is 238 nM. More importantly, the probe can be used for detecting ONOO<-> in cells and living bodies, and has a good application prospect in the field of biological monitoring.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a resorufin dye-based specific response ONOO ‒ Fluorescent probes, preparation and application. Background technique [0002] As a short-lived and highly reactive reactive nitrogen species (RNS), peroxynitrite (ONOO ‒ ) is composed of nitric oxide (NO) and superoxide anion (O2˙ ‒ ) are produced in mitochondria by a free diffusion reaction. Due to its extremely strong transmembrane diffusion, it can penetrate various biological membranes through anion channels and act on macromolecules such as enzymes, proteins, and DNA, and participate in various physiological and pathological processes of the body. So far, there is increasing evidence that excess ONOO ‒ May cause diseases such as inflammation, neurodegenerative diseases, Alzheimer's disease, Parkinson's disease, cardiovascular, ischemia-reperfusion injury and cancer. Therefore, the development of a detection cell ONOO ‒ I...

Claims

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Application Information

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IPC IPC(8): C07F9/6533C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07F9/65335C09K11/06C09K2211/1007C09K2211/1014C09K2211/1033G01N21/6428
Inventor 王佳敏张健苏慧慧王瀚王楠楠陶远芳岳金磊赵伟利
Owner 上海安能健生物医药科技有限公司
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