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Peroxynitrite fluorescent probe, preparation method and application thereof

A peroxynitrite, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, material analysis by optical means, etc., can solve the problems of insufficient sensitivity and specificity of fluorescent probes, and achieve A stable effect

Pending Publication Date: 2020-12-15
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are multiple detection ONOO - Fluorescent probes have been reported, but the sensitivity and specificity of current fluorescent probes are not good enough. Therefore, better fluorescent probes should be developed to detect ONOO - of great significance

Method used

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  • Peroxynitrite fluorescent probe, preparation method and application thereof
  • Peroxynitrite fluorescent probe, preparation method and application thereof
  • Peroxynitrite fluorescent probe, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation process of peroxynitrite fluorescent probe.

[0031]

[0032] Step (1): In a 250mL single-necked round bottom flask, add 150mL of dichloromethane, then add pyridine-4-carbaldehyde (4.5mmol, 0.48g) and 2,4-dimethylpyrrole (9.7mmol, 0.92g) , a drop of trifluoroacetic acid was added as a catalyst, N 2 Protected, stirring rapidly overnight, rotary evaporation to remove the solvent, and then adding chloranil (4.5mmol, 1.1g) to continue the treatment for 30min.

[0033] Step (2): Add 7.5 mL of triethylamine to the product of step (1), and stir for 15 min. Add 7.5mL boron trifluoride diethyl ether at 0°C, and stir at room temperature for 3h. React at 0°C for 2 hours, react at room temperature for 3 hours, wash with saturated sodium hydrogen acid acid solution, separate the organic phase, and dry with anhydrous magnesium sulfate to obtain compound b, whose structural formula is: Step (3): Add compound b (0.09mmol, 0.03g) into a 100mL single-necked round b...

Embodiment 2

[0035] Embodiment 2: the peroxynitrite fluorescent probe (10 equivalents) gained in embodiment 1 is dissolved in the PBS buffer solution (10%), does not handle, finds that the fluorescence of this probe self is very weak even does not have fluorescence, to OCl was added to the solution - , ROO , OH, NO, H 2 o 2 、 O 2 - , t-BuOO· did not cause any change in fluorescence, but the addition of ONOO - Fluorescence changes were caused after that, indicating that the probe was ONOO - Recognition that exhibits high selectivity, see figure 1 .

[0036] Example 2:

[0037] The peroxynitrite fluorescent probe of the present invention changes with different equivalents of ONOO - Add the change of fluorescence spectrogram, in the present invention, when ONOO - When the equivalent weight of is 10, the fluorescence intensity of the formed compound A is the largest, see figure 2 .

Embodiment 3

[0039] The fluorescence intensity of the peroxynitrite fluorescent probe itself in the present invention is very little or even no fluorescence, see image 3 . When with ONOO - The compound A formed during the action has a strong fluorescence. In order to prove the formation of the compound A, it was characterized by mass spectrometry, see Figure 4, draw the mechanism of the present invention is that fluorescent probe and ONOO - The effect forms the conclusion of the new compound A.

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Abstract

The invention relates to a peroxynitrite fluorescent probe, a preparation method and application thereof. The structural formula of the probe is shown as the specification. The probe can recognize ONOO<-> with high sensitivity and high selectivity and perform accurate detection. The probe has very weak fluorescence, when the probe is combined with ONOO<->, a compound A with strong fluorescence isobtained, the property is stable, and detection of ONOO<-> (in vivo / in vitro) in an actual sample is facilitated.

Description

technical field [0001] The invention relates to a peroxynitrite fluorescent probe, a preparation method and application thereof. Background technique [0002] ONOO - is NO·with O 2 · - .interactive product, ONOO - Can cause DNA damage, enzyme inhibition, cell death and bacterial poisoning and can cause a range of diseases. by ONOO - The detection research can help us better explain the cause of the disease, and thus take effective preventive measures to reduce the damage to the body. [0003] Currently measured ONOO - The methods mainly include electron spin resonance, electron paramagnetic resonance, high performance liquid chromatography, chemiluminescence, fluorescence and electrochemical methods. However, due to ONOO in vivo - The half-life is very short and the steady-state concentration is low, so it is really suitable for ONOO in living organisms - There are still few methods, which urgently requires relevant scientific researchers to develop methods for ONOO...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/643C09K2211/1029C09K2211/1055
Inventor 程洁崔雷孔艳萍李春举
Owner SHANGHAI UNIV
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