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ONOO<-> fluorescent probe as well as preparation method and application thereof

A fluorescent probe and reaction technology, applied in the field of fluorescent probes, can solve problems such as inability to realize large-scale synthesis, poor selectivity, complex chemical structure, etc., and achieve good promotion and application value, obvious colorimetric changes, and high sensitivity effects

Active Publication Date: 2021-02-12
SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First, some recognition groups have poor selectivity and can cross-react with endogenous substances such as hydrogen peroxide and hypochlorous acid
Second, the currently reported probes often have complex and delicate chemical structures, require lengthy multi-step reaction preparations, and have low yields, making it impossible to achieve large-scale synthesis, which severely limits the biological applications of probes

Method used

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  • ONOO&lt;-&gt; fluorescent probe as well as preparation method and application thereof
  • ONOO&lt;-&gt; fluorescent probe as well as preparation method and application thereof
  • ONOO&lt;-&gt; fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1. ONOO - Preparation of fluorescent probe L-1

[0039] 4-(N,N-diethylamino) salicylaldehyde (0.193g, 1mmol) and 2-hydrazinopyridine (0.109g, 1mmol) were stirred and reacted at 40°C for 24h in absolute ethanol (20ml) to form a precipitate. After filtering and washing with absolute ethanol (10ml*3), the product was dried to obtain a light yellow solid with a yield of 55%.

[0040] Prepared ONOO - Fluorescent probes were characterized as follows: 1 H NMR (300MHz, CDCl 3 ):δ=10.73(s,1H),8.13(d,J=5.1Hz,1H),7.88(s,1H),7.71–7.60(m,1H),7.11–6.97(m,2H), 6.79( dd,J=6.7,5.5Hz,1H),6.27(dq,J=4.9,2.5Hz,2H),3.41(q,J=7.1Hz,4H), 2.16(s,2H),1.22(t,J =7.1Hz,6H). 13 C NMR (75MHz, CDCl 3 ):δ=159.19,155.91, 149.98,147.17,144.67,138.60,131.24,115.34,106.91,106.62,103.75,98.27,44.47,12.66.LC-MS:m / z[M+H] + calcd for [C 16 h 20 N 4 O+H] + :285.1710, found 285.1594.

[0041] Prepare the ONOO - The reaction equation of the fluorescent probe is:

[0042]

[0043] 2. Preparation o...

Embodiment 2

[0052] The research of embodiment 2 ultraviolet absorption and fluorescence spectrum

[0053] Monitoring the response of fluorescent probe L-1 to various concentrations of ONOO by titration experiments - (0-50μM) analytical capability. in the absorption spectrum figure 1 a, with ONOO - The concentration of the fluorescent probe L-1 increased from 0 μM to 50 μM, and the main absorption peak of the fluorescent probe L-1 showed a blue shift, moving from 360nm to 350nm; at the same time figure 1 b, The weak fluorescence emission of the free probe at about 450 nm weakens, a new emission band appears at 525 nm, and the fluorescence intensity increases accordingly. With ONOO - Concentrations increase from 0 to 25 μM ONOO - Within the concentration range, the fluorescence intensity (525nm) and ONOO - There is an excellent linear relationship between concentrations (R 2 = 0.9870). When ONOO in solution - When the concentration is greater than 25μM, the fluorescence intensity t...

Embodiment 3

[0054] The influence of embodiment 3pH and reaction time on the response of fluorescent probe L-1

[0055] The fluorescent probe L-1 itself does not change significantly in a wide range (pH=5-10), which indicates that the pH value has almost no effect on the fluorescence emission of L-1. When fluorescent probe L-1 and ONOO - In response, L-1 to ONOO - After the response, the fluorescence intensity reached the maximum at pH = 7, which indicated that the probe L-1 was neutral to ONOO - Fluorescence changes in response are most pronounced. In order to simulate the detection environment in vivo, physiological pH (pH=7.4) was selected as the working pH in the following experiments. Afterwards, the response time, as an important factor to evaluate the actual sensing performance of the probe, was also investigated. Such as figure 2 As shown in a, without ONOO - In the case of , almost no change in the fluorescence of probe L-1 was observed. Such as figure 2 b, when applying...

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PUM

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Abstract

The invention discloses an ONOO<-> fluorescent probe as well as a preparation method and application thereof, and belongs to the technical field of fluorescent probes. The structural formula of the ONOO<-> fluorescent probe is shown in the specification, and the ONOO<-> fluorescent probe is high in sensitivity and good in selectivity, can quickly respond to ONOO<-> and has good popularization andapplication value.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, and specifically provides an ONOO - Fluorescent probes, preparation methods and applications. Background technique [0002] Peroxynitrite (ONOO - ) as a well-recognized highly reactive oxygen species has attracted extensive attention due to its signal transduction and antibacterial activities in biological systems. ONOO - Nitric oxide (NO) and superoxide anion radicals (O 2 ·- ) is generated by free radical coupling reaction, and the reaction rate is extremely fast (k=0.4-1.9×10 10 m -1 S -1 ), so when NO and O 2 ·- When the two coexist, they will quickly react to generate ONOO - . In 1990, ONOO - It was discovered for the first time that it can be used as an endogenous oxidant, with instability and high reactivity. ONOO - It can not only undergo two-electron oxidation with biomolecules to generate sulfenic acid derivatives; it can also directly oxidize cytochrome C throu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/76C09K11/06A61K49/00G01N21/64
CPCC07D213/76C09K11/06A61K49/0032G01N21/6428G01N21/6456C09K2211/1029G01N2021/6439Y02A50/30
Inventor 王延风刘媛媛路文娟张平平魏永春何咏琪罗春宇
Owner SHANDONG FIRST MEDICAL UNIV & SHANDONG ACADEMY OF MEDICAL SCI
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