IP Library Granted Patent US 11,311,637
Granted Patent B2
US 11,311,637 · App. 16/870,776 · Granted Apr 26, 2022

Positron emitting radionuclide labeled peptides for human uPAR PET imaging

Inventors: Andreas Kjaer (Frederiksberg, DK); Morten Persson (Copenhagen, DK); Jacob Madsen (Copenhagen, DK)
Assignee: Curasight A/S
A61K51/088A61K38/08A61K51/08A61K51/083
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Quick Facts
Patent No.
US 11,311,637
App. No.
16/870,776
Granted
Apr 26, 2022
Kind
B2
Abstract

There is provided a positron-emitting radionuclide labelled peptide for non-invasive PET imaging of the Urokinase-type Plasminogen Activator Receptor (uPAR) in humans. More specifically the invention relates to human uPAR PET imaging of any solid cancer disease for diagnosis, staging, treatment monitoring and especially as an imaging biomarker for predicting prognosis, progression and recurrence.

Claims (57)

1. A method of generating images of uPAR expression in a human by diagnostic imaging of uPAR expressing tumors involving administering an imaging agent to said human, and generating an image of at least a part of said body to which said imaging agent is administered;

wherein the imaging agent is a positron-emitting radionuclide labelled peptide conjugate, said conjugate comprising a uPAR binding peptide coupled via the chelating agent DOTA to a 64 Cu radionuclide;

wherein the conjugate is to be administered in a dose of 100-500 MBq followed by PET scanning ½-24h after the conjugate has been administered, and quantification through SUVmax and/or SUVmean.

wherein the peptide is selected from the group consisting of:

(D-Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-

(D-Ser)-(D-Arg)-(Tyr)-(Leu)-(Trp)-(Ser),

(Ser)-(Leu)-([beta]-cyclohexyl-L-alanine)-(Phe)-

(D-Ser)-(Gln)-(Tyr)(Leu)-(Trp)-(Ser),

(D-Glu)-([beta]-cyclohexyl-L-alanine)-(Phe)-

(D-Ser)-(D-Tyr)-(Tyr)-(Leu)-(Trp)-(Ser),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-

(D-Ser)-(D-Arg)-(Tyr)-(Leu)-(Trp)-(Ser),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-(Ser)-

(D-Arg)-(Tyr)-Leu)-(Trp)-(Ser),

(D-Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-(Ser)-

(D-Arg)-(Tyr)-Leu)-(Trp)-(Ser),

(D-Thr)-([beta]-cyclohexyl-L-alanine)-(Phe)-

(D-Ser)-(D-Arg)-(Tyr)-(Leu)-(Trp)-(Ser),

(D-Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-

(D-Ser)-(D-Arg)-(Tyr)-(Leu)-([beta]-2-naphthyl-

L-alanine)-(Ser),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-(D-Ser)-

(Arg)-(Tyr)-(Leu)-(Trp)-(Ser),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-(D-Ser)-

(D-Arg)-(Tyr)-(Leu)([beta]-1-naphthyl-L-alanine)-

(Ser),

(D-Glu)-([beta]-cyclohexyl-L-alanine)-(Phe)-

(D-Ser)-(Tyr)-(Tyr)-(Leu)-(Trp)-(Ser),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-(D-Ser)-

(D-Arg)-(Leu)-(Leu)-(Trp)-(D-His),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-(D-Ser)-

(D-Arg)-([beta]-cyclohexyl-L-alanine)-(Leu)-(Trp)-

(Ile),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-(D-Ser)-

(D-Arg)-(Tyr)-(Leu)([beta]-1-naphthyl-L-alanine)-

(D-His),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-(D-Ser)-

(D-Arg)-(N-(2,3-dimethoxybenzyl)glycine)-(D-Phe)-

(N-(3-indolylethyl)glycine)-(N-

(2-methoxyethyl)glycine),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-(D-Ser)-

(D-Arg)-(N-(2,3-dimethoxybenzyl)glycine)-(D-Phe)-

(N-benzylglycine)-(N-(2[beta]thoxyethyl)glycine),

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-

(D-Ser)-(D-Arg)-(N-(2,3-dimethoxybenzyl)glycine)-

(D-Phe)-(N-(methylnaphthalyl)glycine)-(N-

(2-methoxyethyl)glycine), and

(Asp)-([beta]-cyclohexyl-L-alanine)-(Phe)-

(D-Ser)-(D-Arg)-(N-(2,3-dimethoxybenzyl)glycine)-

(D-Phe)-(N-(2,3-dimethoxybenzyl)glycine)-(Ile),   

wherein the C-terminal is either a carboxylic

acid or an amide.

2. The method according to claim 1 , wherein the peptide is (D-Asp)-([beta]- cyclohexyl-L-alanine)-(Phe)-(D-Ser)-(D-Arg)-(Tyr)-(Leu)-(Trp)-(Ser).

3. The method according to claim 1 , having the formula:

4. The method according to claim 1 , wherein the cancer is selected from prostate, breast, pancreatic, lung, brain and colorectal cancer.

5. The method according to claim 1 , wherein the conjugate is administered in a dose of 200-400 MBq.

6. The method according to claim 1 , wherein the imaging agent is provided in a pharmaceutical composition comprising the imaging agent, together with one or more pharmaceutical acceptable adjuvants, excipients or diluents.

Assignments (1)
CHANGE OF NAME Recorded Jul 22, 2021
From: CURASIGHT APS
To: CURASIGHT A/S
Reel/Frame 057624/0385 →
Priority Claims (1)
DK PA 2012 70751 · Dec 3, 2012 · national
Continuity (4)
Division 15832371 · Dec 5, 2017
Division 14649113
Provisional Application 61732443 · Dec 3, 2012
Related Publication 20200268914A1 · Aug 27, 2020
Cited By (2)
US 12,409,240 US 12,589,171