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A kind of onoo-fluorescent probe, preparation method and application thereof

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

Active Publication Date: 2022-08-09
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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  • A kind of onoo-fluorescent probe, preparation method and application thereof
  • A kind of onoo-fluorescent probe, preparation method and application thereof
  • A kind of onoo-fluorescent probe, 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-hydrazinepyridine (0.109g, 1mmol) were stirred in absolute ethanol (20ml) at 40°C for 24h to form a precipitate, and the mixture was extracted. Filtered and washed with absolute ethanol (10ml*3), and the product was dried to obtain a pale yellow solid with a yield of 55%.

[0040] Prepared ONOO - The 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] Preparation of the ONOO - The reaction equation of the fluorescent...

Embodiment 2

[0052] Example 2 Study of UV Absorption and Fluorescence Spectra

[0053] Monitoring Fluorescent Probe L-1 to Various Concentrations of ONOO by Titration Experiments - (0-50 μM) analytical power. in the absorption spectrum figure 1 a, with ONOO - The concentration of L-1 increased from 0 μM to 50 μM, the main absorption peak of the fluorescent probe L-1 showed a blue shift from 360 nm to 350 nm; figure 1 b, The weak fluorescence emission of the free probe at about 450 nm is weakened, a new emission band appears at 525 nm, and the fluorescence intensity increases accordingly. With ONOO - Increase in concentration at 0 to 25 μM ONOO - Concentration range, fluorescence intensity (525nm) and ONOO - There is an excellent linear relationship between the concentrations (R 2 =0.9870). When ONOO in solution - When the concentration is greater than 25 μM, the fluorescence intensity tends to be stable. The detection limit (S / N=3) of the fluorescent probe L-1 was determined to b...

Embodiment 3

[0054] Example 3 Effects of pH and reaction time on the response of fluorescent probe L-1

[0055] The fluorescent probe L-1 itself did not change significantly in a wide range (pH=5-10), which indicated that the pH value had almost no effect on the fluorescence emission of L-1. When the fluorescent probe L-1 and ONOO - In response, L-1 responds to ONOO - After the response, the fluorescence intensity reached the maximum value at pH=7, which indicated that the probe L-1 was sensitive to ONOO under neutral conditions. - The fluorescence change in response is the most pronounced. In order to simulate the in vivo detection environment, 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. like figure 2 a, in the absence of ONOO - In the case of , almost no fluorescence change of probe L-1 was observed. like ...

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Abstract

The invention discloses an ONOO ‑ A fluorescent probe, a preparation method and an application thereof belong to the technical field of fluorescent probes. ONOO of the present invention ‑ The structural formula of the fluorescent probe is: ONOO of the invention ‑ Fluorescent probes have high sensitivity and selectivity, and can detect ONOO ‑ Quick response, with good promotion and application value.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, and specifically provides an ONOO - Fluorescent probe, preparation method and application thereof. Background technique [0002] peroxynitrite (ONOO - ), as a recognized highly reactive oxygen species, has attracted widespread attention due to its signal transduction and antibacterial activities in biological systems. ONOO - from nitric oxide (NO) and superoxide anion radicals (O 2 ·- ) is formed 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 react quickly to generate ONOO - . 1990, ONOO - For the first time, it was found to be an endogenous oxidant with instability and high reactivity. ONOO - It can undergo two-electron oxidation with biomolecules to generate sulfenic acid derivatives; it can also directly oxidize cytochrome C through single-electron oxidation,...

Claims

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Application Information

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Patent Type & Authority Patents(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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