Novel selective human melanocortin-3 receptor ligands: Use of the 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one (Aba) scaffold

Date

2007

Authors

Ballet, Steven
Mayorov, Alexander V.
Cai, Minying
Tymecka, Dagmara
Chandler, Kevin B.
Palmer, Erin S.
Van Rompaey, Karolien
Misicka, Aleksandra
Tourwe, Dirk
Hruby, Victor J.

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Bioorganic & Medicinal Chemistry Letters , 2007; 17(9):2492-2498

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Abstract

In search of new selective antagonists and/or agonists for the human melanocortin receptor subtypes hMC1R to hMC5R to elucidate the specific biological roles of each GPCR, we modified the structures of the superagonist MT-II (Ac-Nle-c[Asp-His-D-Phe-Arg-Trp-Lys]-NH₂) and the hMC3R/hMC4R antagonist SHU9119 (Ac-Nle-c[Asp-His-D-Nal(2')-Arg-Trp-Lys]-NH₂) by replacing the His-D-Phe and His-D-Nal(2') fragments in MT-II and SHU9119, respectively, with Aba-Xxx (4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one-Xxx) dipeptidomimetics (Xxx = D-Phe/pCl-D-Phe/D-Nal(2')). Employment of the Aba mimetic yielded novel selective high affinity hMC3R and hMC3R/hMC5R antagonists.

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School of Chemistry and Physics : Chemistry

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