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Application of compound containing oxygen positive ions in preparation of fluorescent molecular probe for detecting peroxynitrite ions

A technology of peroxynitroso and fluorescent molecular probes, which is applied in the application field of ratiometric fluorescent probes, can solve problems such as inaccurate detection results, false signals, and probe appearance, and achieve good selectivity and broad application prospects , the effect of fast detection speed

Active Publication Date: 2021-03-09
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the strong oxidizing and nucleophilic properties of peroxynitrite ions, on the one hand, many ONOO - The selectivity of the probe is not good, on the other hand, it will lead to false signals of the probe during the detection process, which will eventually lead to inaccurate detection results

Method used

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  • Application of compound containing oxygen positive ions in preparation of fluorescent molecular probe for detecting peroxynitrite ions
  • Application of compound containing oxygen positive ions in preparation of fluorescent molecular probe for detecting peroxynitrite ions
  • Application of compound containing oxygen positive ions in preparation of fluorescent molecular probe for detecting peroxynitrite ions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 1 equivalent of ONOO to the prepared probe I-1 solution in PBS (pH=7.4) buffer with a micro-syringe - and 50 equivalents of H 2 o 2 ,HClO, 1 o 2 ,TBHP, · OH,t-BuOO · ,H 2 o 2 ,HClO, 1 o 2 ,TBHP, · OH,t-BuOO · ,S 2- ,S 2 o 3 2- ,SCN - ,Cys,Hcy,GSH,NO,NO 2 - , Hydrazine hydrate, SO 4 2- ,CH 3 COO - ,CO 3 2- , Na + , K + , Ca 2+ ,Mg 2+ ,Zn 2 + , Fe 2+ ,Cu 2+ Aqueous solution, place for 10 minutes after the fluorescence spectrophotometry test, shows that the probe I-1 for ONOO - with good selectivity, see figure 1 . Join ONOO - After that, the fluorescence emission wavelength at around 620nm is obviously reduced, while the fluorescence emission wavelength at around 485nm is obviously enhanced, which has a very good response, see image 3 .

Embodiment 2

[0024] Add 1 equivalent of ONOO to the prepared probe I-2 solution in PBS (pH=7.4) buffer with a micro-syringe - and 50 equivalents of H 2 o 2 ,HClO, 1 o 2 ,TBHP, · OH,t-BuOO · ,H 2 o 2 ,HClO, 1 o 2 ,TBHP, · OH,t-BuOO· ,S 2- ,S 2 o 3 2- ,SCN - ,Cys,Hcy,GSH,NO,NO 2 - , Hydrazine hydrate, SO 4 2- ,CH 3 COO - ,CO 3 2- , Na + ,K + , Ca 2+ ,Mg 2+ ,Zn 2 + , Fe 2+ ,Cu 2+ Aqueous solution, after standing for 10 minutes, carry out fluorescence spectrophotometry test, show that probe I-2 is for ONOO - with good selectivity, see figure 2 . Join ONOO - After that, the fluorescence emission wavelength at around 620nm is obviously reduced, while the fluorescence emission wavelength at around 485nm is obviously enhanced, which has a very good response, see Figure 4 .

Embodiment 3

[0026] Intracellular fluorescence imaging test:

[0027] HepG2 cells were divided into three control groups A, B, and C, which were treated with different methods.

[0028] Control group A: HepG2 cells were cultured for 30 minutes in cell culture medium with probe I-1 (5 μM); Control group B: HepG2 cells were cultured with probe I-1 (5 μM) and peroxynitroso initiator Sin -1 (1mM) cell culture medium was co-incubated for 1h; control group C: HepG2 cells were incubated with peroxynitroso initiator Sin-1 (1mM) for 1h, and then added with peroxide scavenger UA (100μM) for 3h, Finally, probe I-1 (5 μM) was added and incubated for 30 minutes.

[0029] Fluorescent confocal microscopy showed that probe I-1 penetrated into the cells, and the cells in control group A had red fluorescence, but no blue fluorescence; in control group B, the red fluorescence disappeared after adding Sin-1, and obvious blue fluorescence appeared; C has red fluorescence after adding Sin-1 and UA, but no blu...

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Abstract

The invention discloses an application of a compound containing oxygen positive ions in preparation of a ratiometric fluorescent probe for selectively detecting peroxynitrite ions. The structural formula of the compound is shown as a formula I in the specification. The fluorescent probe prepared by the invention has good water solubility, high fluorescence quantum yield, large Stokes shift, extremely high selectivity on ONOO-, short response time and low detection limit, and can realize high-sensitivity and high-selectivity detection on ONOO- in an aqueous solution or cells. The probe realizesthe detection of ONOO- in the living cell level, can be applied to the field of biological ONOO- detection as a novel probe, and has a wide application prospect.

Description

【Technical field】 [0001] The invention belongs to the field of fluorescent probes for detecting peroxynitrite ions, in particular to the application of a compound containing oxycations in the preparation of a ratio fluorescent probe for selectively detecting peroxynitrite ions. 【Background technique】 [0002] Inflammation and drug-induced liver injury have been considered to be a serious health problem in recent years, so highly sensitive and selective detection of biomarkers in the process of inflammation and drug-induced liver injury will help people gain a deeper understanding of these diseases The occurrence and development mechanism of the disease should be timely prevented and targeted treatment. Peroxynitrite anion (ONOO - ) is a known biomarker of drug-induced liver injury, but due to ONOO - It is extremely unstable and has a short half-life, so the commonly used detection methods are difficult to detect peroxynitrite anion, and it is necessary to develop a rapid q...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/94C07D311/78C09K11/06G01N21/64
CPCC07D311/94C07D311/78C09K11/06G01N21/6428G01N21/643C09K2211/1088
Inventor 王鲲鹏陈汝星房颖张琦陈绍晋胡志强
Owner QINGDAO UNIV OF SCI & TECH
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