NIR fluorescent probe for labeling mitochondria

Patent metadata

Field	Value
Publication number	US-11359096-B2
Application number	US-201916403041-A
Country	US
Kind code	B2
Filing date	May 3, 2019
Priority date	Aug 2, 2018
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

Disclosed is a fluorescent probe specifically labeling mitochondria, which can exhibit high transmittance by virtue of light emission in the NIR range and in which nonspecific fluorescence absorption in biomolecules can be avoided, making it possible to observe fluorescence images in deep tissue.

First claim

What is claimed is:

1. A compound represented by Chemical Formula 1 below

2. A fluorescent probe for labeling mitochondria, represented by Chemical Formula 1 below

3. A method of detecting mitochondria using the compound represented by Chemical Formula 1 of claim 1 , comprising:
preparing a solution by dissolving the compound represented by Chemical Formula 1 in a solvent; and
adding the solution to a sample including cells.

4. The method of claim 3 , further comprising:
applying light at a predetermined wavelength to the sample added with the compound represented by Chemical Formula 1; and
measuring a fluorescence emitted from the sample.

5. A method of preparing a compound for labeling mitochondria, the method comprising forming a compound represented by Chemical Formula 1 below by reacting a compound represented by Chemical Formula 4 below, acetonitrile and methyl iodide,

6. The method of claim 5 , wherein the compound represented by Chemical Formula 4 is formed by dissolving a compound represented by Chemical Formula 3 below, 2-pyridine carbaldehyde, pyrrolidine and acetic acid in acetonitrile and carrying out a reaction with addition of a molecular sieve,

7. The method of claim 6 , wherein the compound represented by Chemical Formula 3 is formed by reacting a compound represented by Chemical Formula 2 below, hydrazine and Pd/C in ethanol, removing Pd/C through celite, performing purification to give a powder, dissolving the powder in a mixed solution of hydrochloric acid and methanol, carrying out a reaction with addition of a sodium nitrite solution, and carrying out a reaction with addition of a sodium azide solution,

8. The method of claim 7 , wherein the compound represented by Chemical Formula 2 is formed by dissolving 2,4-dimethylpyrrole and 4-nitrobenzaldehyde in dichloromethane, carrying out a reaction with addition of trifluoroacetic acid, carrying out a reaction with addition of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone dissolved in dichloromethane, carrying out a reaction with addition of diisopropylethylamine, and carrying out a reaction with addition of boron trifluoride etherate.

Assignees

• Korea Inst Sci & Tech

Inventors

• Lee Jun-Seok
• Murale Dhiraj P
• Hong Seong-Cheol
• Hong Kyung-Tae
• Kim Yun-Kyung
• Lee Seok

Classifications

• C07F5/027 Primary

  Organoboranes and organoborohydrides · CPC title

• C09B23/04 Primary

  one >CH- group, e.g. cyanines, isocyanines, pseudocyanines · CPC title

• C09K2211/1022

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• G01N2021/6439

  with indicators, stains, dyes, tags, labels, marks · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title