[Orn5]-URP
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[Orn5]-URP

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[Orn5]-URP is a urotensin-II (UT) receptor pure antagonist (pEC50 = 7.24) that displays no agonist activity unlike other U-II/URP analogs. [Orn5]-URP has been shown to inhibit the action of U-II in the rat aorta ring assay.

Category
Peptide Inhibitors
Catalog number
BAT-010249
CAS number
782485-03-4
Molecular Formula
C48H62N10O10S2
Molecular Weight
1003.2
[Orn5]-URP
IUPAC Name
(2S)-2-[[(4R,7S,10S,13S,16S,19R)-19-[[(2S)-2-aminopropanoyl]amino]-10-(3-aminopropyl)-16-benzyl-7-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]amino]-3-methylbutanoic acid
Appearance
White Lyophilized Solid
Purity
>98%
Density
1.4±0.1 g/cm3
Boiling Point
1426.1±65.0°C at 760 mmHg
Sequence
ACFWXYCV
Storage
Store at -20°C
InChI
InChI=1S/C48H62N10O10S2/c1-26(2)40(48(67)68)58-47(66)39-25-70-69-24-38(56-41(60)27(3)50)46(65)54-35(20-28-10-5-4-6-11-28)43(62)55-37(22-30-23-51-33-13-8-7-12-32(30)33)45(64)52-34(14-9-19-49)42(61)53-36(44(63)57-39)21-29-15-17-31(59)18-16-29/h4-8,10-13,15-18,23,26-27,34-40,51,59H,9,14,19-22,24-25,49-50H2,1-3H3,(H,52,64)(H,53,61)(H,54,65)(H,55,62)(H,56,60)(H,57,63)(H,58,66)(H,67,68)/t27-,34-,35+,36-,37-,38-,39-,40-/m0/s1
InChI Key
BPLKRLYKWHXTMO-YRQLXXDMSA-N
Canonical SMILES
CC(C)C(C(=O)O)NC(=O)C1CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CC2=CC=C(C=C2)O)CCCN)CC3=CNC4=CC=CC=C43)CC5=CC=CC=C5)NC(=O)C(C)N
1.Structure-activity relationships and structural conformation of a novel urotensin II-related peptide.
Chatenet D;Dubessy C;Leprince J;Boularan C;Carlier L;Ségalas-Milazzo I;Guilhaudis L;Oulyadi H;Davoust D;Scalbert E;Pfeiffer B;Renard P;Tonon MC;Lihrmann I;Pacaud P;Vaudry H Peptides. 2004 Oct;25(10):1819-30.
Urotensin II (UII) has been described as the most potent vasoconstrictor peptide and recognized as the endogenous ligand of the orphan G protein-coupled receptor GPR14. Recently, a UII-related peptide (URP) has been isolated from the rat brain and its sequence has been established as H-Ala-Cys-Phe-Trp-Lys-Tyr-Cys-Val-OH. In order to study the structure-function relationships of URP, we have synthesized a series of URP analogs and measured their binding affinity on hGPR14-transfected cells and their contractile activity in a rat aortic ring bioassay. Alanine substitution of each residue of URP significantly reduced the binding affinity and the contractile activity of the peptides, except for the Ala8-substituted analog that retained biological activity. Most importantly, D-scan of URP revealed that [D-Trp4]URP abrogated and [D-Tyr6]URP partially suppressed the UII-evoked contractile response. [Orn5]URP, which had very low agonistic efficacy, was the most potent antagonist in this series. The solution structure of URP has been determined by 1H NMR spectroscopy and molecular dynamics. URP exhibited a single conformation characterized by an inverse gamma-turn comprising residues Trp-Lys-Tyr which plays a crucial role in the biological activity of URP.
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