Publication number: 20240123099
Abstract: There is provided peptidic compounds of Formula I, A or B(Rradn6-[linker]-RL-Xaa1-Xaa2-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7-Xaa8-?-Xaa9-NH2). Xaa1 is D-Phe, Cpa, D-Cpa, Nal, D-Nal, 2-Nal, or D-2-Nal; Xaa2 is Asn, Gln, Hse, Cit or His. Xaa3 is Trp, Bta, Trp(Me), Trp(7-Me), Trp(6-Me), Trp(5-Me), Trp(4-Me), Trp(2-Me), Trp(7-F), Trp(6-F), Trp(5-F), Trp(4-F), Trp(5-OH), or ?Me-Trp. Xaa4 is Ala or Ser. Xaa5 is Val, Cpg, or Tle. Xaa6 is Gly, NMe-Gly, or D-Ala. Xaa7 is His or NMe-His. Xaa8 is Leu or Phe. Xaa9-NH2 is a C-terminally amidated amino acid residue selected from Pro, 4-oxa-L-Pro, Me2 Thz, or Thz. ? represents a peptide bond or reduced peptide bond joining Xaa8 to Xaa9. Rradn6 is 1-5 radiolabeling groups. There is also provided the use of such compounds as imaging agents or therapeutic agents.
Type:
Application
Filed:
November 17, 2023
Publication date:
April 18, 2024
Inventors:
Kuo-Shyan LIN, François BÉNARD, Lei WANG, Zhengxing ZHANG, Ivica BRATANOVIC, Chengcheng ZHANG
Patent number: 11395857
Abstract: A compound is provided comprising a melanocortin 1 receptor (MC1R) targeting peptide (MC1RTP), a radiolabeling group, and a linker joining the MC1RTP to the radio labeling group. The MC1RTP is linear or cyclized, and comprises a sequence of Formula I or Formula II: Xaa1-Xaa2a-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7a (I) or Xaa1-Xaa2b-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7b (II). Xaa1 is L-/D-Nle, L-/D-Nle, L-/D-Ala, L-/D-Leu, L-/D-Ile, D-Ile, L-/D-Cys, L-/D-Met, L-/D-Phe, L-/D-Trp, L-/D-Val, L-/D-Nal, L-/D-2-Nal, Gly, L-/D-?-aminobutryic acid, L-/D-norvaline, or L-/D-homonorleucine. Xaa2a and Xaa7b are L-/D-Cys, L-/D-Asp, L-/D-Glu, L-/D-2-Aad, L-/D-3-Aad, L-/D-Pra, L-/D-Hpg, or L-/D-Bpg. Xaa2b and Xaa7a are L-/D-Cys, L-/D-Lys, L-/D-Orn, L-/D-Dab, L-/D-Dap, L-/D-Lys(N3), L-/D-Orn(N3), L-/D-Dab(N3), L-/D-Dap(N3), L-/D-2-(5?-azidopentyl)alanine, or L-/D-2-(6?-azidohexyl)alanine. Xaa3 is L-/D-His, Pro, beta-(1,2,3-triazol-4-yl)-L-alanine, beta-(1,2,3-triazol-4-yl)-D-alanine, 1,2,4-triazole-3-alanine, or 1,2,4-triazole-3-D-alanine.
Type:
Grant
Filed:
October 5, 2021
Date of Patent:
July 26, 2022
Assignee:
PROVINCIAL HEALTH SERVICES AUTHORITY
Inventors:
François Bénard, Kuo-Shyan Lin, Chengcheng Zhang, Zhengxing Zhang
Publication number: 20220040340
Abstract: A compound is provided comprising a melanocortin 1 receptor (MC1R) targeting peptide (MC1RTP), a radiolabeling group, and a linker joining the MC1RTP to the radiolabeling group. The MC1RTP is linear or cyclized, and comprises a sequence of Formula I or Formula II: Xaa1-Xaa2a-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7a (I) or Xaa1-Xaa2b-Xaa3-Xaa4-Xaa5-Xaa6-Xaa7b (II). Xaa1 is L-/D-Nle, L-/D-Nle, L-/D-Ala, L-/D-Leu, L-/D-Ile, D-Ile, L-/D-Cys, L-/D-Met, L-/D-Phe, L-/D-Trp, L-/D-Val, L-/D-Nal, L-/D-2-Nal, Gly, L-/D-?-aminobutyric acid, L-/D-norvaline, or L-/D-homonorleucine. Xaa2a and Xaa7b are L-/D-Cys, L-/D-Asp, L-/D-Glu, L-/D-2-Aad, L-/D-3-Aad, L-/D-Pra, L-/D-Hpg, or L-/D-Bpg. Xaa2b and Xaa7a are L-/D-Cys, L-/D-Lys, L-/D-Orn, L-/D-Dab, L-/D-Dap, L-/D-Lys(N3), L-/D-Orn(N3), L-/D-Dab(N3), L-/D-Dap(N3), L-/D-2-(5?-azidopentyl)alanine, or L-/D-2-(6?-azidohexyl)alanine. Xaa3 is L-/D-His, Pro, beta-(1,2,3-triazol-4-yl)-L-alanine, beta-(1,2,3-triazol-4-yl)-D-alanine, 1,2,4-triazole-3-alanine, or 1,2,4-triazole-3-D-N alanine.
Type:
Application
Filed:
October 5, 2021
Publication date:
February 10, 2022
Inventors:
François BÉNARD, Kuo-Shyan LIN, Chengcheng ZHANG, Zhengxing ZHANG, Jutta ZEISLER