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Preparation method and application of fluorescent probe

A fluorescent probe and reaction technology, applied in the field of medicine, can solve problems such as unseen and achieve good tracking effect

Inactive Publication Date: 2019-12-20
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Applicants envision, however, that non-Michael acceptor type probes may be more biocompatible
So far, there have been no reports on the introduction of aryl sulfides into the electron-deficient 4-position of 1,8-naphthoimide fluorophores, nor have there been reports on the use of the resulting compounds as fluorescent probes for tracking endogenous sulfides in living cells. Reports on Sexual GSH Fluctuation

Method used

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  • Preparation method and application of fluorescent probe
  • Preparation method and application of fluorescent probe
  • Preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the preparation of compound shown in formula (II)

[0037] Prepare compound shown in formula (II) according to following synthetic route:

[0038]

[0039] Concrete preparation method comprises the following steps:

[0040] 1) Add 4-chloro-1,8-naphthalic anhydride (2.32g, 10mmol), DMF (30mL, 28.35g), NaHCO to a 250mL round bottom flask in turn under electromagnetic stirring 3 (0.84g) and p-fluorothiophenol (1.59mL, 15mmol), heated to reflux for 10h (TLC monitoring reaction, developer: V EA :V PE =1:4). Cool, remove the solvent under reduced pressure, acidify with 5% HCl solution to obtain a yellow precipitate, filter, and recrystallize with ethanol to obtain 1.62g of compound 2, with a yield of 69.8%;

[0041] 2) Add compound 2 (0.30g, 0.93mmol) and 1.5 equivalents of m-CBPA (purity 85%, 0.28g, 1.40mmol) to a round bottom flask filled with DCM (10mL) solvent and react at room temperature under electromagnetic stirring 5h (TLC monitoring reaction, d...

Embodiment 2

[0048] Embodiment 2: Preparation of compound (i.e. probe NA-21) shown in formula (I)

[0049] Add the compound (0.27g, 0.59mmol) shown in formula (II) and N,N-dimethylethylenediamine (0.12mL, 0.71mmol) successively to the round bottom flask filled with ethanol (20mL) under electromagnetic stirring , normal temperature reaction 2h (TLC monitoring reaction, developer: V EA :V MeOH =4:1), the solvent was removed under reduced pressure, and silica gel column chromatography (eluent: V EA :V MeOH =10:1), 0.21 g of a light yellow solid was obtained, and the yield was 77.8%.

[0050] The light yellow solid obtained in this example was analyzed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance and electrospray mass spectrometry, and the data were as follows:

[0051] 1 H NMR (500MHz, CDCl3) δ8.75(d, J=7.7Hz, 1H), 8.62(d, J=7.3Hz, 1H), 8.48(dd, J=8.0, 4.5Hz, 2H), 7.80(t ,J=7.6Hz,1H),7.69(dd,J=8.7,5.0Hz,2H),7.12(t,J=8.4Hz,2H),4.31(t,J=6.8Hz,2H),2.64(t ,J=6.8H...

Embodiment 3

[0056] Embodiment 3: the preparation of compound shown in formula (I)

[0057] Repeat Example 2, the difference is:

[0058] Use N,N-dimethylformamide instead of ethanol, change the reaction time to 1h, and change the eluent to V EA :V MeOH =6:1, the rest of the reaction conditions remain unchanged. 0.08 g of pale yellow solid was obtained, the yield was about 29.6%.

[0059] The pale yellow solid obtained in this example was analyzed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance and electrospray mass spectrometry, and it was determined to be the target compound.

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Abstract

The invention discloses a preparation method and application of a fluorescent probe. The fluorescent probe has the structure shown in the formula (I), and experiments show that the fluorescent probe is capable of reacting with reduced glutathione in tumor cells and well tracking the reduced glutathione level in cells. The preparation method of the fluorescent probe mainly comprises the following steps of putting the compound shown in the formula (II) and N,N-dimethyl ethylene diamine into an organic solvent for reaction, and recovering the solvent after the reaction is finished to obtain a crude product of fluorescent probe.

Description

technical field [0001] The invention relates to a preparation method of a fluorescent probe and the application of the fluorescent probe, belonging to the technical field of medicine. Background technique [0002] Cancer is the number one killer that seriously threatens human health, with a high incidence and a high mortality rate. Chemotherapy is an important means of treating malignant tumors, but chemotherapeutic drugs form oxygen free radicals to damage normal cells by interfering with cell metabolism. Reduced glutathione (GSH) can remove oxygen free radicals formed during chemotherapy, or combine with chemotherapeutic drugs and Its metabolites form low-toxic products to protect or restore damaged cells or damaged organ functions. However, for tumor cells, the presence of GSH can easily make them resistant to chemotherapy drugs. Increased levels of GSH over their drug-sensitive counterparts were observed in various multidrug-resistant cells. GSH may be involved in che...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06G01N21/6486G01N21/6428C09K2211/1029C09K2211/1007
Inventor 张国海李平平彭艳潘成学曾淑兰
Owner GUANGXI NORMAL UNIV