Boron-based dual imaging probes, compositions and methods for rapid aqueous F-18 labeling, and imaging methods using same

Patent metadata

Field	Value
Publication number	US-9987380-B2
Application number	US-201213549309-A
Country	US
Kind code	B2
Filing date	Jul 13, 2012
Priority date	Jul 15, 2011
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

A composition useful as a PET and/or fluorescence imaging probe a compound a compound of Formula I, including salts, hydrates and solvates thereof:

wherein R 1 -R 7 may be independently selected from hydrogen, halogen, hydroxy, alkoxy, nitro, substituted and unsubstituted amino, cycloalkyl, carboxy, carboxylic acids and esters thereof, cyano, haloalkyl, aryl, X is selected from the group consisting of C and N; and A is selected of hydrogen, halogen, hydroxy, alkoxy, nitro, substituted and unsubstituted amino, alkyl, cycloalkyl, carboxy, carboxylic acids and esters thereof, cyano, haloalkyl, aryl, including phenyl and aminophenyl, and heteroaryl.

First claim

We claim:

1. A composition having an imaging probe therein comprising:
the lewis acid SnCl 4 ; and
at least one compound selected from the group consisting of compounds of Formula I, including salts, hydrates and solvates thereof:

the compounds of Formula X, including salts, hydrates and solvates thereof

the compounds of Formula XII, including salts, hydrates and solvates thereof

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 may be independently selected from one or more of the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitro, substituted and unsubstituted amino, cycloalkyl, carboxy, carboxylic acids and esters thereof, cyano, haloalkyl, aryl, including phenyl and aminophenyl, azide, alkyne and heteroaryl;
X is selected from the group consisting of C and N;
A is selected from one or more of the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitro, and substituted and unsubstituted amino, alkyl, cycloalkyl, carboxy, carboxylic acids and esters thereof, cyano, haloalkyl, aryl, including phenyl and aminophenyl, and heteroaryl.

2. The composition according to claim 1 , wherein the composition comprises at least one compound of Formula I, including salts, hydrates and solvates thereof:

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 may be independently selected from one or more of the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitro, substituted and unsubstituted amino, cycloalkyl, carboxy, carboxylic acids and esters thereof, cyano, haloalkyl, aryl, including phenyl and aminophenyl, azide, alkyne and heteroaryl;
X is selected from the group consisting of C and N;
A is selected from one or more of the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitro, and substituted and unsubstituted amino, alkyl, cycloalkyl, carboxy, carboxylic acids and esters thereof, cyano, haloalkyl, aryl, including phenyl and aminophenyl, and heteroaryl.

3. The composition according to claim 2 , wherein the composition comprises at least one compound selected from the group consisting of Formulas IV and VI, including salts, hydrates and solvates thereof:

4. The composition according to claim 3 , further comprising at least one compound selected from the group consisting of:

wherein at least one of the fluorines in a B—F bond in the compound is 18 F.

5. The composition according to claim 1 , wherein the compound is conjugated to a targeting moiety.

6. The composition according to claim 5 , wherein the compound is a compound according to Formula 1, including salts, hydrates and solvates thereof:

7. The composition according to claim 6 , wherein the targeting moiety is a peptide.

8. The composition according to claim 7 , wherein the targeting moiety is an RGD peptide.

9. The composition according to claim 8 , wherein the targeting moiety is a cyclic RGD peptide.

10. The composition according to claim 7 , wherein the peptide is selected from the group consisting of:

Assignees

• Li Zibo
• Gabbai Francois P
• Conti Peter S
• Hudnall Todd W
• Lin Tzu Pin
• Liu Shuanglong
• Huang Chiun Wei
• Univ Southern California

Inventors

• Li Zibo
• Gabbai Francois P
• Conti Peter S
• Hudnall Todd W
• Lin Tzu-Pin
• Liu Shuanglong
• Huang Chiun-Wei

Classifications

• A61K49/0021

  the fluorescent group being a small organic molecule · CPC title

• A61K51/0446 Primary

  having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil · CPC title

• A61K51/0455

  having six-membered rings with one nitrogen as the only ring hetero atom · CPC title

• C07F5/022

  without C-boron linkages · CPC title

• A61K49/0002

  General or multifunctional contrast agents, e.g. chelated agents · CPC title