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Urotensin II((4-11)) Azasulfuryl Peptides: Synthesis and Biological Activity.

Abstract : Cyclic azasulfuryl (As) peptide analogs of the urotensin II (UII, 1, H-Glu-Thr-Pro-Asp-c[Cys-Phe-Trp-Lys-Tyr-Cys]-Val-OH) fragment 4-11 were synthesized to explore the influences of backbone structure on biological activity. N-Aminosulfamides were inserted as surrogates of the Trp(7) and Lys(8) residues in the biologically relevant Trp-Lys-Tyr triad. A combination of solution- and solid-phase methods were used to prepare novel UII((4-11)) analogs 6-11 by routes featuring alkylation of azasulfuryl-glycine tripeptide precursors to install various side chains. The pharmacological profiles of derivatives 6-11 were tested in vitro using a competitive binding assay and ex vivo using a rat aortic ring bioassay. Although the analogs exhibited weak affinity for the urotensin II receptor (UT) without agonistic activity, azasulfuryl-UII((4-11)) derivatives 7-9 reduced up to 50% of the effects of UII and urotensin II-related peptide (URP) without affecting their potency.
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Contributor : Michel Courcelles Connect in order to contact the contributor
Submitted on : Wednesday, August 3, 2016 - 5:45:04 PM
Last modification on : Wednesday, November 30, 2022 - 4:14:07 PM




Francesco Merlino, Ali M Yousif, Étienne Billard, Julien Dufour-Gallant, Stéphane Turcotte, et al.. Urotensin II((4-11)) Azasulfuryl Peptides: Synthesis and Biological Activity.. Journal of Medicinal Chemistry, 2016, 59 (10), pp.4740-52. ⟨10.1021/acs.jmedchem.6b00108⟩. ⟨pasteur-01351481⟩



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