Lanthanide ion complexes and imaging method

Patent metadata

Field	Value
Publication number	US-9783554-B2
Application number	US-201615186984-A
Country	US
Kind code	B2
Filing date	Jun 20, 2016
Priority date	Dec 16, 2008
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

A lanthanide complex, method of forming and method of using the lanthanide complex as a near-infrared luminescent material are described. The complex includes at least one lanthanide ion and at least one polydentate ligand derived from a molecule having the general formula of Structure 2:

where: E represents a heteroatom or heteroatom-containing group and R 1 -R 8 are independently selected from H, —OH, —NH 2 , —SO 3 H, —CO 2 H, halides, optionally substituted organic groups; and conjugated linking groups which link two of the polydentate ligands of Structure 2 together.

First claim

The invention claimed is:

1. A polydentate ligand of Structure 2:

where:
E is a heteroatom or heteroatom-containing group; and
R 1 and R 4 -R 8 are independently selected from the group consisting of H, —OH, —NH 2 , and X, where X is a halide, —SO 3 H—CO 2 H, optionally substituted organic groups, or conjugated linking groups which link two of the polydentate ligands of Structure 2 together; R 2 is a substituted organic group, wherein the substituted organic group of R 2 is a heterocyclic group; R 3 is an —OH group; and at least one of R 1 and R 5 is a chelating group independently selected from the group consisting of —CO 2 H, a dipicolyl amino group, and polyaminocarboxylic acid group, the dipicolyl amino group or polyaminocarboxylic acid group being linked through a carbon-containing bridge of from 0-2 carbon atoms.

2. The polydentate ligand of claim 1 , where the heterocyclic group R 2 is

wherein R 10 is an optionally substituted C 1 -C 15 group selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, and alkylaryl groups.

3. The polydentate ligand of claim 1 , wherein at least one of R 1 and R 5 is independently selected from the group consisting of:

4. The polydentate ligand of claim 1 , wherein E is selected from the group consisting of O, S, P, Si, B, and N—R, where R is selected from H, alkyl, and aryl groups.

5. The polydentate ligand of claim 1 , where the polydentate ligand defined by the following formula:

where R 12 and R 6 are each individually selected from the group consisting of —H and —C(CH 3 ) 3 , and R 5 is selected from the group consisting of

6. The polydentate ligand of claim 5 , where R 12 is —C(CH 3 ) 3 .

7. The polydentate ligand of claim 5 , where R 6 is —H.

8. The polydentate ligand of claim 5 , where R 5 is

9. The polydentate ligand of claim 5 , where R 12 is —C(CH 3 ) 3 , R 6 is —H, and R 5 is

Assignees

• Pang Yi
• Chu Qinghui
• Univ Akron

Inventors

• Pang Yi
• Chu Qinghui

Classifications

• A61K49/0021

  the fluorescent group being a small organic molecule · CPC title

• C07F5/003 Primary

  without C-Metal linkages · CPC title

• C09K2211/182

  of the rare earth metals, i.e. Sc, Y or lanthanide · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1033

  with oxygen · CPC title