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Fluorescent probe for detecting peroxynitrite and its preparation method and application

A peroxynitrite, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, material analysis by optical means, etc. Limitation, increase the difficulty of designing new probes, etc., to achieve the effect of good staining effect, high sensitivity and selectivity, and low cost

Active Publication Date: 2020-09-29
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently reported detection of ONOO - The fluorescent probes generally have the following problems: (1) the recognition group does not have universal applicability, and it is difficult to extend to other fluorescent groups, which increases the difficulty of designing new probes; (2) the chemical structure of the probe is complex and the synthetic route is difficult. Long, difficult to synthesize, unable to achieve large-scale production
These problems caused the existing ONOO - The practical application of fluorescent probes has been greatly limited, which is not conducive to large-scale promotion and application. Therefore, it is necessary to develop new ones for the detection of ONOO - Fluorescent probe and preparation method thereof

Method used

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  • Fluorescent probe for detecting peroxynitrite and its preparation method and application
  • Fluorescent probe for detecting peroxynitrite and its preparation method and application
  • Fluorescent probe for detecting peroxynitrite and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Three methods for preparing fluorescent probes for detecting peroxynitrite based on formamide recognition groups, the reaction equations are respectively:

[0045]

[0046]

[0047] Among them, compound 1 represents benzothiazole-aminonaphthalene, compound 2 represents naphthalimide, and compound 3 represents benzophenoxazine.

[0048] Specifically, the preparation steps of the above three fluorescent probes in this embodiment are as follows:

[0049] (1) Mix 1 mmol of compound 1 or 2 or 3 (274 mg or 268 mg or 263 mg respectively) with 3 mL of formic acid;

[0050] (2) Then the three mixed solutions obtained in step (1) were all heated up to 80° C., and reacted for 5 hours;

[0051] (3) After the reaction is completed, the three reaction solutions are cooled to room temperature, then concentrated and spin-dried to dry the solvent, and the obtained solids are separated by column chromatography to obtain three product solids: BT-FAP, NA-FAP, NR -FAP, which is a fl...

Embodiment 2

[0054] Three kinds of preparation methods of fluorescent probes based on formamide recognition groups to detect peroxynitrite, the reaction equation / principle are the same as in Example 1, and the specific preparation steps are:

[0055] (1) Mix 1.2mmol of compound 1 or 2 or 3 with 5mL formic acid respectively;

[0056] (2) Then the three mixed solutions obtained in step (1) were all heated up to 60° C., and reacted for 6 hours;

[0057] (3) After the reaction is completed, the three reaction solutions are cooled to room temperature, then concentrated and spin-dried to dry the solvent, and the obtained solids are separated by column chromatography to obtain three product solids: BT-FAP, NA-FAP, NR -FAP, which is a fluorescent probe for the detection of peroxynitrite based on the formamide recognition group; wherein, the volume ratios of dichloromethane and methanol used for the purification of the three reaction products of compound 1, 2 or 3 and formic acid are respectively ...

Embodiment 3

[0060] Three kinds of preparation methods of fluorescent probes based on formamide recognition groups to detect peroxynitrite, the reaction equation / principle are the same as in Example 1, and the specific preparation steps are:

[0061] (1) Mix 1.5mmol of compound 1 or 2 or 3 with 4mL of formic acid respectively;

[0062] (2) Then, the three mixed solutions obtained in step (1) were all heated up to 85° C., and reacted for 4.5 hours;

[0063] (3) After the reaction is completed, the three reaction solutions are cooled to room temperature, then concentrated and spin-dried to dry the solvent, and the obtained solids are separated by column chromatography to obtain three product solids: BT-FAP, NA-FAP, NR -FAP, which is a fluorescent probe for the detection of peroxynitrite based on the formamide recognition group; wherein, the volume ratios of dichloromethane and methanol used for the purification of the three reaction products of compound 1, 2 or 3 and formic acid are respecti...

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Abstract

The invention belongs to the technical field of synthesis and detection, and particularly relates to a fluorescent probe for detecting peroxynitrite and a preparation method and application thereof. The invention provides a universal identification group for detecting peroxy nitrite, and three new fluorescent probes which are respectively named as BT-FAP, NA-FAP and NR-FAP are formed by connectingthe universal identification group with common fluorophores, wherein aminonaphthalene (BT), naphthalimide (NA) and benzophenoxazine (NR) are the fluorophores, and formamide (FAP) is the identification group to achieve the instant reaction with ONOO (all 4s), the fluorescent probe has high sensitivity and good selectivity, and is very suitable for ONOO fluorescence imaging studies in cells.

Description

technical field [0001] The invention belongs to the technical field of synthesis and detection, and in particular relates to a fluorescent probe based on a formamide recognition group, which can be used for detecting peroxynitrite, and a preparation method and application thereof. Background technique [0002] In vivo, peroxynitrite (ONOO - ) is an important reactive nitrogen species, which is produced by the reaction of superoxide radical anion and nitric oxide, and can represent the level of oxidative stress and nitrification stress at the same time. Moreover, existing studies have shown that ONOO - It is closely related to the occurrence and development of many diseases, including neurodegenerative diseases, diabetes, cancer, etc. ONOO - The short half-life and extremely low steady-state concentration under physiological conditions allow the detection of ONOO in living cells and tissues - become very difficult. Fluorescence assays based on fluorescent probes enable r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/66C07D221/14C07D265/38C09K11/06G01N21/64
CPCC07D221/14C07D265/38C07D277/66C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037G01N21/6428
Inventor 唐波解希雷刘光照王栩焦晓云
Owner SHANDONG NORMAL UNIV