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Bodipy compound and application thereof

A technology of fluoroboropyrrole and compound, which is applied in the field of fluorescent probes for detecting nitrosyl hydrogen, can solve the problems of probe interference, interference detection, lack of sensitive and specific detection, etc., to reduce interference and improve detection accuracy Effect

Active Publication Date: 2015-11-04
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this type of probe is still susceptible to the interference of endogenous reducing agents in cells, and NO may seriously interfere with the detection
Although each of the above methods is feasible under certain conditions, the bottleneck encountered in the study of HNO in living organisms is the lack of sensitive and specific detection tools for detecting changes in the target concentration of HNO in living systems. It can be seen that the development of a new biomedical tool that can realize the targeted detection of HNO levels in the living body will be a breakthrough in this research field.

Method used

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  • Bodipy compound and application thereof
  • Bodipy compound and application thereof
  • Bodipy compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1. Preparation of fluoroborate pyrrole compound:

specific Embodiment

[0045] Fluoropyrrole compounds shown in general formula I react with commercially available p-hydroxyacetophenone and benzaldehyde to synthesize the corresponding fluorophore BODIPY, and then modify different positioning groups on the corresponding positions of the fluorophore. Finally, the fluorophore modifying the positioning group is reacted with 2-(diphenylphosphine)benzoic acid in dichloromethane solvent to generate the corresponding fluoroboryrrole compound by DMAP and EDC catalysis. Specific examples are as follows:

[0046] Preparation of a compound of formula:

[0047]Under argon protection, BODIPY fluorophore (52.9mg, 0.1mmol) and 2-(diphenylphosphine) benzoic acid (61.2mg, 0.2mmol), DMAP (24.4mg, 0.2mmol), EDCI (19.2mg, 0.1 mmol) was dissolved in a 50ml flask filled with 20ml of dry dichloromethane, stirred at room temperature for 24h, followed by TLC. The crude product was neutralized by hydrobromic acid, washed with a saturated NaBr solution until neutral, extra...

Embodiment 2

[0061] The prepared compound of formula two is used as a probe in water system, simulated physiological environment and intracellular to detect HNO, simulated physiological conditions, the following experiments are all carried out under the condition of pH=7.4 (HEPES buffer solution, concentration is 40mM ), and the probe concentration was 10 μM.

[0062] The spectral response of the compound of Formula 2 prepared above to HNO; add 10 μM of the compound of Formula 2 to a 10 ml colorimetric tube, then add 40 mM HEPES, then add 10 μM of HNO, dilute the volume to 10 ml with ultrapure water, shake the solution to balance for 10 minutes, and then The above working solution was added into a fluorescent dish to measure the fluorescence spectrum. The fluorescence spectrum changes as figure 1 shown. Depend on figure 1 The compound shown can be used to realize the detection of HNO in vivo. At the same time, the structure of the product after the reaction of the probe provided in the...

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Abstract

The invention relates to a fluorescent probe for detecting nitroxyl (HNO), in particular to a bodipy compound and application thereof. The bodipy compound is as shown in general formula I and serves as the fluorescent probe for HNO. The corresponding fluorescence intensity of the compound serving as the fluorescent probe for HNO is varied in the presence of HNO, and the compound can be used for HNO detection, can greatly reduce the interference of external detection conditions and improve detection accuracy. The compound serving as the fluorescent probe can be used for detecting the level of HNO inside and outside cells, not only is of great scientific significance for illuminating the HNO intracellular in-situ generation mechanism, but also lays the theoretical basis for discovering new drugs for treating cardiac failure, and provides feasible selection for cardiac failure treatment. The general formula I is as follows.

Description

technical field [0001] The invention relates to a fluorescent probe for detecting nitrosyl hydrogen (HNO), in particular to a fluoroboron pyrrole compound and application thereof. Background technique [0002] Nitroxyl (HNO) is a one-electron reduced and protonated derivative of nitric oxide (NO), but its biological and pharmacological characteristics are quite different from NO. Nitrosyl hydrogen can directly react with the intracellular antioxidant scavenger thiol, inhibit the activity of acetaldehyde dehydrogenase; it can activate the voltage-controlled K in the mammalian vascular system + Channel; the latest research shows that HNO can increase the contractility of the myocardium in normal and heart failure (cardiac failure), and at the same time improve the myocardial diastolic function. Heart failure is mainly characterized by decreased myocardial contractility, and there is still a lack of ideal therapeutic drugs in clinic. Therefore, the potential pharmacological ac...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1022C09K2211/1029G01N21/64
Inventor 于法标陈令新景晓彤高敏陈浩
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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