US 12,173,087 B2
Melanocortin 1 receptor ligands and methods of use
Robert J. Gillies, Tampa, FL (US); David L. Morse, Tampa, FL (US); Natalie M. Barkey, Tampa, FL (US); Kevin N. Sill, Tampa, FL (US); Josef Vagner, Tucson, AZ (US); Narges K. Tafreshi, Tampa, FL (US); Jonathan L. Sessler, Austin, TX (US); Christian Preihs, Austin, TX (US); and Victor J. Hruby, Tucson, AZ (US)
Assigned to H. Lee Moffitt Cancer Center and Research Institute, Inc., Tampa, FL (US); Intezyne Technologies Inc., Tampa, FL (US); Arizona Board of Regents on Behalf of The University of Arizona, Tuscon, AZ (US); and Board of Regents, The University of Texas System, Austin, TX (US)
Filed by H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC., Tampa, FL (US); INTEZYNE TECHNOLOGIES INC., Tampa, FL (US); ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA, Tucson, AZ (US); and BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM, Austin, TX (US)
Filed on Jan. 24, 2022, as Appl. No. 17/582,368.
Application 17/582,368 is a continuation of application No. 16/450,382, filed on Jun. 24, 2019, granted, now 11,230,568.
Application 16/450,382 is a continuation of application No. 15/263,028, filed on Sep. 12, 2016, granted, now 10,329,326, issued on Jun. 25, 2019.
Application 15/263,028 is a continuation of application No. 14/117,949, granted, now 9,441,013, issued on Sep. 13, 2016, previously published as PCT/US2012/038425, filed on May 17, 2012.
Claims priority of provisional application 61/618,144, filed on Mar. 30, 2012.
Claims priority of provisional application 61/531,357, filed on Sep. 6, 2011.
Claims priority of provisional application 61/487,239, filed on May 17, 2011.
Claims priority of provisional application 61/487,245, filed on May 17, 2011.
Prior Publication US 2023/0167154 A1, Jun. 1, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07K 14/00 (2006.01); A61K 47/64 (2017.01); A61K 47/69 (2017.01); A61K 49/00 (2006.01); A61K 49/10 (2006.01); A61K 49/18 (2006.01); C07K 5/117 (2006.01); C07K 7/08 (2006.01); C07K 14/68 (2006.01); C07K 14/72 (2006.01); A61K 38/34 (2006.01)
CPC C07K 5/1024 (2013.01) [A61K 47/64 (2017.08); A61K 47/6907 (2017.08); A61K 49/0056 (2013.01); A61K 49/101 (2013.01); A61K 49/1809 (2013.01); C07K 7/08 (2013.01); C07K 14/68 (2013.01); C07K 14/723 (2013.01); A61K 38/34 (2013.01)] 18 Claims
 
1. A method of imaging a melanoma tumor of a subject, comprising:
administering an MC1R peptide ligand-micelle complex to the subject, wherein the MC1R peptide ligand-micelle complex comprises a MC1R peptide ligand and a micelle comprising an inner core, outer core and hydrophilic shell, wherein the MC1R peptide ligand is linked to the shell of the micelle by a linker, wherein a contrast agent is present within the inner core of the micelle, and wherein the MC1R peptide ligand-micelle complex concentrates in the tumor, and observing a signal from the contrast agent by an imaging device;
wherein the MC1R peptide ligand comprises:
4-phenylbutyryl-His-DPhe-Arg-Trp-Gly-Lys(hex-5-ynoyl)-NH2 (SEQ ID NO:3);
H-Lys(hex-5-ynoyl)-Tyr-Val-Nle-Gly-His-DNal(2′)-Arg-DTrp-Asp-Arg-Phe-Gly-NH2 (SEQ ID NO:4); or
H-Lys(hex-5-ynoyl) Tyr-Val-Nle-Gly-His-DNal(2′)-Arg-DPhe-Asp-Arg-Phe-Gly-NH2 (SEQ ID NO:5).