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Fluorescent probe as well as preparation method and application thereof

A fluorescent probe and reaction technology, applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of incapable cell fluorescence imaging, and achieve the effect of high safety

Active Publication Date: 2020-11-06
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

[0005] CN104478823A discloses a lysine-modified benzofurazan compound, which has the following structure: The compound can specifically detect copper ions, and can be used as a detection probe for neurological diseases and endocrine disorders caused by the imbalance of copper ions in cells in the human body. Ionic and cannot be used alone for fluorescence imaging of cells

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  • Fluorescent probe as well as preparation method and application thereof
  • Fluorescent probe as well as preparation method and application thereof
  • Fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] In this example, the fluorescent imaging probe BLN was prepared by the following method:

[0071] (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 separation ...

Embodiment 2

[0077] In this example, the fluorescent imaging probe BLN was prepared by the following method:

[0078] (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 condition, a...

Embodiment 3

[0082] In this example, the fluorescent imaging probe BLN was prepared by the following method:

[0083] (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 condition, a...

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Abstract

The invention provides a fluorescent probe as well as a preparation method and application thereof. The fluorescent probe has a structure represented by a formula I; according to the fluorescent probe, primary amino groups on a lysine main chain are reserved, and the binding of the molecule with nanoparticles and the like is facilitated; the fluorescence labeling of the molecule or the nano material with carboxyl at the terminal can be achieved, the fluorescent probe can be used for the fluorescence imaging of tumor cells, the beneficial help is provided for the detection and the treatment oftumor cells, and the fluorescent probe has characteristics of no toxicity to cells and high safety.

Description

technical field [0001] The invention belongs to the field of chemical imaging materials, and relates to a fluorescent probe and its preparation method and application. Background technique [0002] Fluorescence imaging is a very important imaging method, which is widely used in the field of biomedicine due to its advantages of simplicity, speed and high sensitivity. NBD (4-chloro-7-nitrobenzo-2-oxa-1,3-diazole) is a widely used fluorescent molecule, which is often used to label materials with amino functional groups at the end of proteins, nanoparticles, etc. However, it cannot be used to label molecules or nanomaterials with carboxyl groups at the end. Therefore, it is expected that more NBD fluorescent probes can be developed to meet the needs of the biomedical field in this field. [0003] CN109734709A discloses a small molecule fluorescent probe, which has the following structure: [0004] The fluorescent probe can emit strong fluorescence after being combined with ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C09K11/06G01N21/64
CPCC07D413/12C09K11/06G01N21/6428G01N21/6458C09K2211/1048C09K2211/1029C09K2211/1007
Inventor 陈春英周会鸽李佳阳郭梦雨
Owner THE NAT CENT FOR NANOSCI & TECH NCNST OF CHINA
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