Two-photon fluorescence probe for detecting peroxynitrite as well as preparation method and application of two-photon fluorescence probe

A technology of peroxynitrite and two-photon fluorescence, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means, which can solve the problem of fewer fluorescent probes and reduce self-absorption and yield High, highly sensitive and selective effects

Active Publication Date: 2018-06-15
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, at present, the two-photon properties are good and have near-infrared fluorescence emission, which is beneficial to ONOO - Fewer sensitive fluorescent probes

Method used

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  • Two-photon fluorescence probe for detecting peroxynitrite as well as preparation method and application of two-photon fluorescence probe
  • Two-photon fluorescence probe for detecting peroxynitrite as well as preparation method and application of two-photon fluorescence probe
  • Two-photon fluorescence probe for detecting peroxynitrite as well as preparation method and application of two-photon fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0046] Example: Synthesis of fluorescent probe

[0047] Under the protection of argon, the compound TPNIR-NH 2 (160 mg, 0.5 mmol) was dissolved in 10 mL of anhydrous dichloromethane, and triethylamine (58 μL, 2.0 mmol) was added, and stirred at room temperature for 5.0 min. Subsequently, compound 1 (1.06 g, 5.0 mmol) was dissolved in 5.0 mL of dichloromethane, added dropwise to the above mixture, and stirring was continued for 1.5 h at room temperature. After the completion of the reaction, the solvent was concentrated and spin-dried, and the solid was separated by column chromatography (eluent: dichloromethane: methanol 200:1, V / V) to obtain 174 mg of purple black solid (yield 70%).

[0048] Nuclear magnetic and mass spectrometry characterization:

[0049] 1 H NMR(400MHz, DMSO-d 6 ): δ11.42(s,1H),8.69(s,1H), 8.40(d,J=8.9Hz,2H), 8.34(d,J=8.9Hz,2H), 8.25(d,J=9.4Hz ,1H),7.95(s,2H),7.93(s,1H),7.47(dd,J=9.4,2.2Hz,1H),7.30(d,J=1.9Hz,1H),3.70(q,J= 7.0Hz, 4H), 3.08 (br s, 4H), 1.26 (t, J...

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Abstract

The invention discloses a two-photon fluorescence probe for detecting peroxynitrite as well as a preparation method and application of the two-photon fluorescence probe. The two-photon fluorescence probe has the structural formula as shown in the description. The two-photon fluorescence probe is named as TPNIR-FP. The two-photon fluorescence probe adopts a Nile red derivative as a fluorescent group and an alpha-keto-amide functional group as an ONOO-reaction group, can rapidly respond to ONOO- (within 10 seconds), and in addition is high in sensitivity and good in selectivity. The two-photon fluorescence probe can be applied to imaging research on ONOO- in antharcycline antibiotic induced cardiac muscle cell and cardiac muscle tissue damage.

Description

Technical field [0001] The invention belongs to the technical field of synthesis and detection, and specifically relates to a two-photon fluorescent probe for detecting peroxynitrite and a preparation method and application thereof. Background technique [0002] In organisms, peroxynitrite (ONOO - ) Is generated by the reaction of superoxide radical anions and nitric oxide, which can simultaneously represent the levels of oxidative stress and nitrification stress. As one of the most reactive endogenous toxins, ONOO - It can regulate cell signaling pathways by oxidizing or nitrifying biomolecules, and induce cell apoptosis or necrosis, leading to tissue and organ dysfunction. Research shows that ONOO - It is closely related to the onset and progression of many diseases, including neurodegenerative diseases, diabetes, and cancer. In addition, in the pathological process of anthracycline-induced cardiotoxicity, ONOO - Plays a very critical role. However, ONOO - Under physiological...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/78C09K11/06G01N21/64
CPCC07D311/78C09K11/06C09K2211/1007C09K2211/1088G01N21/6486
Inventor 唐波解希雷唐福艳王栩焦晓云
Owner SHANDONG NORMAL UNIV
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