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A near-infrared II-region hypoxia fluorescent probe and a preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of fluorescent probes, can solve the problem that the emission wavelength of the probe is not greater than 1000nm.

Inactive Publication Date: 2019-03-05
SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the near-infrared second region window is rarely used for hypoxia detection, and there are no probes with emission wavelengths greater than 1000nm reported so far.

Method used

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  • A near-infrared II-region hypoxia fluorescent probe and a preparation method and application thereof
  • A near-infrared II-region hypoxia fluorescent probe and a preparation method and application thereof
  • A near-infrared II-region hypoxia fluorescent probe and a preparation method and application thereof

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preparation example Construction

[0078] The preparation method of the anoxic fluorescent probe in the near-infrared second region of the present invention can be referred to as follows: NO 2 -R 1 -R 2 -Y 1 (i) with R 3 -Y 2 (ii) mixed reaction, the target probe compound can be obtained, the preparation method is relatively convenient, and the operation is relatively simple, suitable for large-scale expanded production;

[0079] Among them, in compound (i), R 1 C5~C30 arylene, heteroarylene, substituted arylene, or substituted heteroarylene; preferably, R 1 Arylene, heteroarylene, substituted arylene, or substituted heteroarylene of C5-C15; more preferably, R 1 C5-C15 heteroarylene or substituted heteroarylene, wherein the heteroatoms in the heteroarylene or substituted heteroarylene are one or more of nitrogen, oxygen, and sulfur, and each The number of heteroatoms contained in heteroaryl or substituted heteroarylene is one or more; for example, R 1 Can be, but not limited to: furan, thiophene, pyrrol...

Embodiment 1

[0113] (1) Preparation of MZ-BOC molecules:

[0114] 2-Nitroimidazole (5g, 44.2mmol) was dissolved in 20mL DMF, and then, under stirring, K 2 CO 3 (9.15g, 66.3mmol), N-Boc-bromoethylamine (9.9g, 44.2mmol), and reacted for 18h under the protection of nitrogen;

[0115] Rotary evaporation to remove the solvent, vacuum drying, the obtained solid was dissolved in water, and then extracted with ethyl acetate, the organic phase was collected, and the solvent was removed by rotary evaporation, the obtained crude product was recrystallized with ethyl acetate to obtain a dark yellow solid product (recorded as MZ-BOC, 0.81g, 72%), and its NMR detection spectrum is as figure 1 As shown, the mass spectrometry detection spectrum is as figure 2 As shown, the specific analysis of each map is as follows:

[0116] 1 H NMR (400MHz, DMSO-d 6 )δ7.46(s, 1H), 7.14(s, 1H), 4.43(t, J=5.6Hz, 2H), 3.36(q, J=5.9Hz, 2H), 1.31(s, 9H);

[0117] HRMS (ESI + ): m / z calcd for C 10 h 16 N 4 o 4 :...

Embodiment 2

[0131] (1) Preparation of MZ-BOC molecules:

[0132] 2-Nitroimidazole (0.5g, 4.42mmol) was dissolved in 2mL DMF, and then, under stirring conditions, K 2 CO 3 (0.915g, 6.63mmol), N-Boc-bromoethylamine (0.99g, 4.42mmol), reacted overnight under nitrogen protection;

[0133] The solvent was removed by rotary evaporation, dried in vacuo, the obtained solid was dissolved in water, and then extracted with ethyl acetate, the organic phase was collected, the solvent was removed by rotary evaporation, and the obtained crude product was recrystallized from ethyl acetate to obtain a dark yellow solid product MZ-BOC (0.10 g, 89%).

[0134] (2) Preparation of MZ molecules

[0135] Dissolve MZ-BOC (0.85g, 3.3mmol) in methanol (2mL) and add 1.25M HCl in methanol (2mL) with stirring, react at room temperature for 5h;

[0136] The solvent was removed by rotary evaporation, and the obtained solid was washed with methanol, and the washing liquid was collected, the solvent was removed by rot...

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Abstract

A near-infrared II-region hypoxia fluorescent probe and a preparation method and application thereof are provided. The fluorescent probe has a nitro group as a responsive group and a near-infrared II-region dye base as a parent structure, and utilizes a strong quenching action of the nitro group on the fluorescent group and a fluorescence recovery effect after the reduction, so that the near-infrared II-region hypoxia fluorescent probe can be used for hypoxia detection, and influences of autofluorescence of biological samples on detection accuracy and precision can be avoided. The preparationmethod has the advantages that process steps are simple, the prepared fluorescent probe compound is low in toxicity, and the like.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to an oxygen-deficient fluorescent probe in the second near-infrared region and its preparation method and application. Background technique [0002] Malignant tumors are one of the diseases that seriously endanger human life and health. Among them, solid tumors account for more than 85% of clinical malignant tumors, and hypoxia is one of the important characteristics of solid tumors. Tumor hypoxic cells will change in metabolism, molecular genetics, and pathophysiology, which play a very important role in the evolution and progression of tumors, and resist chemotherapy and radiotherapy, leading to local tumor recurrence, distant metastasis and The prognosis is poor. Therefore, the research on tumor cell hypoxia is still a very hot topic. [0003] It is well known that hypoxia can lead to increased reducing stress, leading to the overexpression of nitroreductase (NTR), and the le...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07D403/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1092G01N21/6428G01N21/6486G01N2021/6432Y02P20/55
Inventor 蔡林涛孟晓青龚萍张佳丽孙枝红
Owner SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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