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A hypoxic fluorescent imaging probe and its preparation method and application

A fluorescent imaging and fluorescent probe technology, applied in the field of chemical imaging, can solve problems such as complex structures and achieve the effect of simple structures

Active Publication Date: 2022-01-11
THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the probe is in the form of a polymer and has a complex structure

Method used

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  • A hypoxic fluorescent imaging probe and its preparation method and application
  • A hypoxic fluorescent imaging probe and its preparation method and application
  • A hypoxic fluorescent imaging probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] In this example, the hypoxia fluorescent imaging probe PLN was prepared by the following method:

[0070] (1) Add fmoc-lysine (fmoc-lys, 184mg, 0.5mmol) and sodium carbonate (139mg, 1mmol) into a 50mL round bottom flask, add methanol 6.28mL, water 5mL, stir for about 15min, the solution became clear and fmoc-lys was completely dissolved. 4-Chloro-7nitrobenzo-2-oxa-1,3-oxadiazole (NBD, 100 mg, 0.5 mmol) was dissolved in 2 mL of methanol and added to the reaction system. Stir the reaction at room temperature for 12 hours, adjust the pH value of the reaction solution to 2 with 1M hydrochloric acid, sonicate the reaction solution to fully precipitate, filter and wash the precipitate, dissolve it with methanol and water (10 / 1, V / V), pass through 0.22 μm After filtering the membrane, use high-performance liquid phase, with 20:80 (V / V) as the initial gradient and 100:0 (V / V) as the final gradient to carry out gradient elution, and the gradient elution time is 30min as the sep...

Embodiment 2

[0075] In this example, the hypoxia fluorescent imaging probe PLN was prepared by the following method:

[0076] (1) Add fmoc-lysine (fmoc-lys, 184mg, 0.5mmol) and sodium carbonate (139mg, 1mmol) into a 50mL round bottom flask, add methanol 6.28mL, water 5mL, stir for about 15min, the solution became clear and fmoc-lys was completely dissolved. 4-Chloro-7nitrobenzo-2-oxa-1,3-oxadiazole (NBD, 100 mg, 0.5 mmol) was dissolved in 2 mL of methanol and added to the reaction system. Stir the reaction at room temperature for 12 hours, adjust the pH value of the reaction solution to 2-3 with 1M hydrochloric acid, sonicate the reaction solution to fully precipitate, filter and wash the precipitate, dissolve it with methanol and water (10 / 1, V / V), pass After the 0.22μm filter membrane, use high performance liquid phase, with 20:80 (V / V) as the initial gradient, 100:0 (V / V) as the end gradient, gradient elution is carried out, and the gradient elution time is 30min as the separation cond...

Embodiment 3

[0080] In this example, the hypoxia fluorescent imaging probe PLN was prepared by the following method:

[0081] (1) Add fmoc-lysine (fmoc-lys, 184mg, 0.5mmol) and sodium carbonate (139mg, 1mmol) into a 50mL round bottom flask, add methanol 6.28mL, water 5mL, stir for about 15min, the solution became clear and fmoc-lys was completely dissolved. 4-Chloro-7nitrobenzo-2-oxa-1,3-oxadiazole (NBD, 100 mg, 0.5 mmol) was dissolved in 2 mL of methanol and added to the reaction system. Stir the reaction at room temperature for 12 hours, adjust the pH value of the reaction solution to 2-3 with 1M hydrochloric acid, sonicate the reaction solution to fully precipitate, filter and wash the precipitate, dissolve it with methanol and water (10 / 1, V / V), pass After the 0.22μm filter membrane, use high performance liquid phase, with 20:80 (V / V) as the initial gradient, 100:0 (V / V) as the end gradient, gradient elution is carried out, and the gradient elution time is 30min as the separation cond...

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Abstract

The present invention provides a hypoxic fluorescent imaging probe and its preparation method and application. The hypoxic fluorescent imaging probe has a structure shown in formula I, named as: 1-(1-(2-nitroimidazole)-3 ‑[(4‑aminomethyl)azepine]‑2‑propanol)‑6‑(4‑nitrobenzo‑2‑oxa‑1,3‑oxadiazole)‑lysine, abbreviated PLN; the probe of the present invention can achieve specific fluorescence imaging of hypoxic cells through the nitroimidazole group of the probe to macromolecules in cells in different hypoxic environments, and the primary amino group in the molecule is beneficial Further modification of the molecule.

Description

technical field [0001] The invention belongs to the technical field of chemical imaging, and relates to a hypoxia fluorescent imaging probe, a preparation method and application thereof. Background technique [0002] Hypoxia is a common phenomenon in most solid tumors and is closely related to tumor occurrence, development, metastasis and drug resistance (J.Natl.Cancer I.2007,99(19),1441-1454.). The 2019 Nobel Prize in Physiology and Medicine was awarded to the discoverer of its related factor (HIF-1α). Therefore, how to realize the imaging of hypoxic cells is very important for tumor diagnosis and treatment. [0003] Due to the lack of oxygen competition, nitroimidazole and its derivatives can be reduced to hydroxylamine imidazole by the nitroreductase inside the hypoxic cell, and its para-position can undergo an irreversible addition reaction with macromolecules containing sulfhydryl groups inside the cell to form an adduct Substances, thereby staying inside the cell, to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/14C09K11/06G01N21/64
CPCC07D413/14C09K11/06G01N21/6402C09K2211/1029C09K2211/1044C09K2211/1048
Inventor 陈春英周会鸽李佳阳郭梦雨赵宇亮
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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