Fluorescent probe sensing tyrosine kinase and use thereof

Patent metadata

Field	Value
Publication number	US-9958434-B2
Application number	US-201414888883-A
Country	US
Kind code	B2
Filing date	Mar 10, 2014
Priority date	May 10, 2013
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

A fluorescent probe for detecting a tyrosine kinase using a compound having an ortho-hydroxy-benzaldehyde structure, and use thereof are provided. The fluorescent probe can show a change in fluorescence when the compound binds with a tyrosine kinase. The compound can be readily synthesized and has high stability and low cytotoxicity in vivo. The fluorescent probe can be used to image cells or tissues overexpressing the tyrosine kinase, the fluorescent probe can be effectively used in a composition for imaging the tissues and a method of imaging the tissues. Also, the fluorescent probe can be used to image cancer cells or tissues since the fluorescent probe can exhibit fluorescence when the fluorescent probe binds to the cancer cells or tissues overexpressing the tyrosine kinase.

First claim

What is claimed is:

1. A method of detecting a tyrosine kinase in a biological sample, the method comprising:
a) contacting the biological sample with an effective amount of a compound represented by the following Formula 1

b) measuring fluorescence from the sample that the compound has contacted; and
c) at least based on measured fluorescence relative to one or more controls, determining either or both of the existence and a level of a tyrosine kinase in the sample.

2. The method of claim 1 , wherein the compound comprises an intramolecular hydrogen bond in an ortho-hydroxy-benzaldehyde structure thereof, wherein the compound exhibits changes in fluorescence when the intramolecular hydrogen bond breaks as the compound and the tyrosine kinase bind with each other.

3. The method of claim 1 , wherein the tyrosine kinase is selected from the group consisting of ABL1 (T315I), BRAF, PDGFRa, RSK2, TYK2, and Src.

4. The method of claim 1 , wherein measuring the fluorescence is performed using at least one apparatus selected from the group consisting of a confocal fluorescence microscope, a two-photon fluorescence microscope, and an optical coherence tomograph.

5. The method of claim 1 , wherein the biological sample comprises cancer cells and tissues.

6. The method of claim 1 , wherein the biological sample is a biopsy sample comprising cells and/or tissues from a subject, and wherein the cells and/or tissues of the biological sample are contacted with the compound of Formula 1 in vivo by administering the compound to a subject.

Assignees

• Postech Acad Ind Found
• Postech Academy Found

Inventors

• Ahn Kyo Han
• Kim Dokyoung
• Kim Sungjee
• Kim Ki Hean

Classifications

• G01N33/575

  for cancer · CPC title

• G01N2500/10

  involving cells · CPC title

• G01N2333/9121

  with an alcohol group as acceptor (2.7.1), e.g. general tyrosine, serine or threonine kinases · CPC title

• C07C223/06 Primary

  having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• C12Q1/485

  involving kinase · CPC title