Labelling agent, and composition for labelling a protein, method for labelling a protein, and method for detecting a protein

Patent metadata

Field	Value
Publication number	US-9822164-B2
Application number	US-201514927942-A
Country	US
Kind code	B2
Filing date	Oct 30, 2015
Priority date	Oct 31, 2014
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

Provided are a labelling agent including a compound of the following Formula 1, a labelling composition, a method of labelling a protein with the labelling agent, and a method of detecting the protein using the labelling agent:

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 8 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl, R 7 is H or —NR 9 R 10 , R 9 and R 10 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl, X is —NR 11 , —O, or S, R 11 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl, Y is —OR 12 or —NR 13 R 14 , R 12 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl, and R 13 and R 14 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl.

First claim

What is claimed is:

1. A labelling composition comprising a compound of the following Formula 2 or 3;

wherein R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
X is —NR 22 , —O, or S, R 22 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
Y is —OR 23 or —NR 24 R 25 , R 23 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl, and R 24 and R 25 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl; and
R 26 , R 27 , R 28 , R 29 , R 30 , and R 32 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
R 31 is —NR 32 R 33 , R 32 and R 33 are independently H, substituted or unsubstituted —C 1 - 10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl, X is —NR 34 H, —O, or S, R 34 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
Y is —CR 35 or —NR 36 R 37 , R 35 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl, and R 36 and R 37 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl.

2. The composition of claim 1 , wherein the composition is selected from the group consisting of

and combinations thereof.

3. A method of labelling a protein, the method comprising:
contacting a protein with a labelling agent represented by the following Chemical Formula 1; and
irradiating light to the labelling agent:

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 8 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
R 7 is H or —NR 9 R 10 , R 9 and R 10 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
X is —NR 11 , —O, or S, R 11 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
Y is —OR 12 or —NR 13 R 14 , R 12 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl, and R 13 and R 14 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl.

4. The method of claim 3 , wherein the irradiating light causes a radical reaction of the labelling agent to form a complex of the labelling agent and the protein.

5. A method of detecting a protein, the method comprising:
contacting a protein with a labelling agent represented by the following Chemical Formula 1; and
irradiating light to the labelling agent:

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 8 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
R 7 is H or —NR 9 R 10 , R 9 and R 10 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
X is —NR 11 , —O, or S, R 11 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl,
Y is —OR 12 or —NR 13 R 14 , R 12 is H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl, and R 13 and R 14 are independently H, substituted or unsubstituted —C 1-10 -alkyl-, —C 2-10 -alkenyl, or —C 2-10 -alkynyl.

Assignees

• Korea Inst Sci & Tech

Inventors

• Dhiraj Murale
• Hong Seong Cheol
• Yun Ji Hyeon
• Yoon Chang No
• Lee Jun Seok

Classifications

• C07D263/57

  Aryl or substituted aryl radicals · CPC title

• G01N33/58 Primary

  involving labelled substances (G01N33/53 takes precedence) · CPC title

• G01N21/17

  Systems in which incident light is modified in accordance with the properties of the material investigated (where the material investigated is optically excited causing a change in wavelength of the incident light G01N21/63) · CPC title

• C07D235/14

  Radicals substituted by nitrogen atoms (by nitro radicals C07D235/10) · CPC title

• C07D277/66 Primary

  with aromatic rings or ring systems directly attached in position 2 · CPC title