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NTR-1 response type fluorescent probe based on benzoindole as well as preparation method and application thereof

A technology of benzindole and fluorescent probes, which is applied in the field of preparation and fluorescent probes, can solve the problems of low sensitivity, low fluorescence quantum yield, and poor stability, and achieve high-sensitivity detection, significant fluorescence enhancement, and good stability Effect

Active Publication Date: 2021-04-09
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although in recent years, a series of organic small molecule fluorescent probes for the detection of NTR have been developed, but these probes still have disadvantages such as poor stability, low sensitivity, low fluorescence quantum yield, and great influence on the cell's own conditions. , so it is still of great significance to develop new organic small molecule fluorescent probes with novel structure and better performance

Method used

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  • NTR-1 response type fluorescent probe based on benzoindole as well as preparation method and application thereof
  • NTR-1 response type fluorescent probe based on benzoindole as well as preparation method and application thereof
  • NTR-1 response type fluorescent probe based on benzoindole as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The synthesis of embodiment 1 probe NFP-1:

[0037] 1. Synthesis of 1-ethyl-2-methylbenzo[cd]indole-1-chloride (EMC)

[0038] 1,8-Naphtholactam (8.03g, 47.4mmol) was dissolved in 100mL DMF, and sodium hydride (3.528g, 150mmol) was added slowly at 0°C. After the system was warmed up to room temperature, ethyl iodide (7.403 g, 50 mmol) was added dropwise and stirred at room temperature for 1 h. The reaction mixture was extracted with ethyl acetate (150mL×2), the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained solid was subjected to silica gel column chromatography (petroleum ether: ethyl acetate=10 : 1) Separation and purification to obtain 1-ethylbenzo[cd]indol-2(1H)-one 3 (7.762g yellow solid, yield 83%), which was directly used in the next reaction.

[0039] 3 (1.972 g, 10 mmol) was dissolved in 40 mL of anhydrous THF (40 mL), and methylmagn...

Embodiment 2

[0044] Spectral properties of embodiment 2 probe NFP-1:

[0045] All UV-Vis absorption and fluorescence spectra of probe NFP-1 were recorded in solution DMSO-PBS (1:9 v / v, 10 mM, pH=7.4). at lambda ex =420nm collects the fluorescence emission of the solution at 430nm-700nm, the excitation and emission slit width is 5nm / 5nm. NFP-1 was prepared as 1 mM stock solution in DMSO and then diluted for use. NTR was dissolved in ultrapure water to prepare a 100 μg / mL stock solution for later use. Unless otherwise specified, 500 μM NADH was added to all reactions.

[0046] NADH (500 μM) was added to NFP-1 (10 μM), and then incubated with different concentrations of NTR (0-10 μg / mL) at 37°C for 30 min, and the UV-visible absorption spectrum and fluorescence spectrum were recorded. In the selectivity study, NFP-1 (10 μM) was incubated with NTR (5 μg / mL), reactive oxygen species (500 μM), some metal ions (1 mM), amino acids (1 mM) at 37 ° C for 30 min, and then recorded their fluorescen...

Embodiment 3

[0052] The kinetic response of embodiment 3 probe NFP-1:

[0053] In order to study the kinetic response of probe NFP-1 to NTR, the fluorescence intensity I 490nm The change. Such as figure 2shown. The results showed that the stability of the probe NFP-1 was better, and the I of the probe after adding NTR 490nm It increased with increasing response time and reached a plateau at 25 minutes. The above analysis indicated that the probe NFP-1 could completely react with NTR within 25 min. To ensure that the reaction proceeded completely, a reaction time of 30 min was chosen in all response experiments.

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Abstract

The invention discloses an NTR-1 response type fluorescent probe based on benzoindole as well as a preparation method and application of the NTR-1 response type fluorescent probe. The structure of the NTR-1 response type fluorescent probe is as defined in the specification. The method comprises the following steps: subjecting p-hydroxybenzaldehyde to reacting with p-nitrobenzyl bromide to synthesize a stable intermediate NFP-1-M connected through ether bonds, and condensing 1-ethyl-2-methylbenzo[cd]indole-1-chloride with the intermediate NFP-1-M to generate the probe NFP-1. The probe can be used for measuring the hypoxia degree of a cell, and is beneficial to early diagnosis of tumors and the like.

Description

technical field [0001] The invention relates to a fluorescent probe, a preparation method and use, in particular to a benzindole-based NTR-1 responsive fluorescent probe, a preparation method and a use. Background technique [0002] Nitroreductase (NTR) belongs to flavin enzymes, usually containing flavin mononucleotide units or flavin adenine dinucleotide units. In the presence of NADPH or NADH, nitroreductase can reduce the nitro group on the nitro-substituted heterocycle and aromatic ring to generate the corresponding nitrite, hydroxylamine or amino derivatives. Studies have shown that NTR activity is related to intracellular oxygen content. In hypoxic cells or tissues, overexpression of NTR can be observed. Hypoxia is an important pathological process for the rapid proliferation of tumor cells, and has become the main feature of solid tumors. The hypoxic microenvironment plays an important role in tumorigenesis and metastasis, and can promote malignant biological beha...

Claims

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Application Information

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IPC IPC(8): C07D209/80C09K11/06G01N21/64A61K49/00
CPCC07D209/80C09K11/06G01N21/6428G01N21/6486A61K49/0021C09K2211/1029C09K2211/1014
Inventor 蔡进吉民杨敏黄铭琪王雨红陈茜茜
Owner SOUTHEAST UNIV
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