L-glucose derivatives having fluorescent chromophore

Patent metadata

Field	Value
Publication number	US-9958450-B2
Application number	US-201514614854-A
Country	US
Kind code	B2
Filing date	Feb 5, 2015
Priority date	Aug 8, 2008
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

An object of the present invention is to provide a method for accurately evaluating the specific incorporation of D-glucose into cells. The present invention as a means for achieving the object is characterized by comprising contacting a D-glucose derivative that has a fluorescent chromophore in the molecule and is specifically incorporated into cells and an L-glucose derivative that has a fluorescent chromophore in the molecule with different cells in the same cell strain to be evaluated, respectively, comparing the fluorescence emitted by the D-glucose derivative that has a fluorescent chromophore in the molecule and is specifically incorporated into cells with the fluorescence emitted by the L-glucose derivative that has a fluorescent chromophore in the molecule, and evaluating the specific incorporation of D-glucose into cells relative to L-glucose by taking the difference between the two kinds of fluorescence intensities.

First claim

The invention claimed is:

1. An L-glucose derivative, characterized by having a fluorescent chromophore in the molecule, wherein the fluorescent chromophore is selected from the group consisting of an N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino group, a 7-(N,N-dimethylaminosulfonyl)benz-oxa-1,3-diazol-4-yl)amino group and sulforhodamine.

2. A method of producing an L-glucose derivative that has a fluorescent chromophore in the molecule, comprising the step of:
linking a fluorescent chromophore to the amine group of L-glucosamine.

3. An L-glucose derivative according to claim 1 , wherein the fluorescent chromophore is an N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino group.

4. An L-glucose derivative according to claim 1 , wherein the fluorescent chromophore is sulforhodamine.

5. An L-glucose derivative according to claim 1 , wherein the L-glucose derivative has a fluorescent chromophore attached to the 2-position.

6. An L-glucose derivative according to claim 1 , wherein the L-glucose derivative is selected from the group consisting of 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-L-glucose, 2-[N-(7-(N′,N′-dimethylaminosulfonyl)benz-oxa-1,3-diazol-4-yl)amino]-2-deoxy-L-glucose, and an L-glucose derivative having sulforhodamine attached to the 2-position thereof.

7. An L-glucose derivative according to claim 1 , wherein the L-glucose derivative is 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-L-glucose.

8. An L-glucose derivative according to claim 1 , wherein the L-glucose derivative is an L-glucose derivative having sulforhodamine attached to the 2-position thereof.

9. An L-glucose derivative according to claim 1 , wherein the L-glucose derivative is 6-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-6-deoxy-L-glucose.

Assignees

• Univ Hirosaki

Inventors

• Yamada Katsuya
• Teshima Tadashi
• Yamamoto Toshihiro

Classifications

• G01N33/533

  with fluorescent label · CPC title

• C12Q1/54

  involving glucose or galactose · CPC title

• G01N33/582 Primary

  with fluorescent label · CPC title

• C12Q1/02

  involving viable microorganisms · CPC title

• G01N33/5005

  involving human or animal cells (immunoassay G01N33/56966; immunoassays of protozoa G01N33/56905; protozoa in screening assays C12Q1/025) · CPC title