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Urantide

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Urantide is a selective and competitive urotensin-II (UT) receptor antagonist (pKB = 8.3) that blocks hU-II induced contractions in thoracic aorta ex vivo. Urantide has no effect on noradrenaline or endothelin 1-induced contraction or on acetylcholine-induced relaxation. Urantide also exhibits partial agonist activity in a calcium mobilization assay (in CHO cells expressing hUT receptors).

Category
Peptide Inhibitors
Catalog number
BAT-010272
CAS number
669089-53-6
Molecular Formula
C51H66N10O12S2
Molecular Weight
1075.26
Urantide
IUPAC Name
(2S)-2-[[(4R,7S,10S,13R,16S,19R)-19-[[(2S)-2-amino-3-carboxypropanoyl]amino]-10-(3-aminopropyl)-16-benzyl-7-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-20,20-dimethyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]amino]-3-methylbutanoic acid
Synonyms
L-Valine, L-α-aspartyl-3-mercapto-L-valyl-L-phenylalanyl-D-tryptophyl-L-ornithyl-L-tyrosyl-L-cysteinyl-, cyclic (2→7)-disulfide; H-Asp-Pen(1)-Phe-D-Trp-Orn-Tyr-Cys(1)-Val-OH; L-alpha-aspartyl-L-penicillamyl-L-phenylalanyl-D-tryptophyl-L-ornithyl-L-tyrosyl-L-cysteinyl-L-valine (2->7)-disulfide acetic acid; (S)-4-(((4R,7S,10S,13R,16S,19R)-13-((1H-indol-3-yl)methyl)-10-(3-aminopropyl)-16-benzyl-4-(((S)-1-carboxy-2-methylpropyl)carbamoyl)-7-(4-hydroxybenzyl)-20,20-dimethyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl)amino)-3-amino-4-oxobutanoic acid
Related CAS
705261-07-0 (D-val)
Appearance
White Lyophilized Solid
Purity
≥95%
Density
1.42±0.1 g/cm3
Boiling Point
1465.2±65.0°C at 760 mmHg
Sequence
DXFWXYCV (Modifications: X-2 = Pen, X-5 = Orn, Trp-4 = D-Trp, Disulfide bridge between Pen2-Cys7)
Storage
Store at -20°C
Solubility
Soluble in Water
InChI
InChI=1S/C51H66N10O12S2/c1-27(2)41(50(72)73)60-48(70)39-26-74-75-51(3,4)42(61-43(65)33(53)24-40(63)64)49(71)58-37(21-28-11-6-5-7-12-28)45(67)57-38(23-30-25-54-34-14-9-8-13-32(30)34)47(69)55-35(15-10-20-52)44(66)56-36(46(68)59-39)22-29-16-18-31(62)19-17-29/h5-9,11-14,16-19,25,27,33,35-39,41-42,54,62H,10,15,20-24,26,52-53H2,1-4H3,(H,55,69)(H,56,66)(H,57,67)(H,58,71)(H,59,68)(H,60,70)(H,61,65)(H,63,64)(H,72,73)/t33-,35-,36-,37-,38+,39-,41-,42+/m0/s1
InChI Key
VXLUBANOZQJZFE-MSYIYWSESA-N
Canonical SMILES
CC(C)C(C(=O)O)NC(=O)C1CSSC(C(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(CC(=O)O)N)(C)C
1.Urotensin II-induced hypotensive responses in Wistar-Kyoto (Wky) and spontaneously hypertensive (Shr) rats.
Gendron G;Gobeil F Jr;Bélanger S;Gagnon S;Regoli D;D'Orléans-Juste P Peptides. 2005 Aug;26(8):1468-74.
Human urotensin II (hU-II) is a potent vasoactive peptide which modulates some of the functions of the cardiovascular and other systems. The in vivo mechanism of action by which hU-II may influence blood pressure in developmental and pathological conditions, is poorly understood. Herein, the blood pressure effects of hU-II (0.1-10 nmol/kg) injected intravenously (i.v.) were studied on ketamine/xylazine anesthetized male WKY and SHR rats aged 4 and 8 weeks. hU-II elicited dose-dependent decreases in mean arterial pressure in both strains of animals. The hypotensive responses to hU-II were, however, significantly higher in SHR rats, independently of age. Four-week-old SHR rats (which are normotensive) were, however, less responsive than their hypertensive 8-week-old counterparts. A series of pharmacological inhibitors were used to identify putative endogenous (endothelial) factors that might account for the hU-II-mediated hypotension in 8-week-old SHR. These include the non-selective nitric oxide synthase inhibitor L-NAME (5 micromol/kg), the non-selective cyclooxygenase inhibitor meclofenamate (16 micromol/kg), the voltage-sensitive and ATP-sensitive K+-channel inhibitors, 4-aminopyridine (5 micromol/kg) and glybenclamide (10 micromol/kg), the cytochrome P450 CYP2C9 inhibitor sulfaphenazole (15 micromol/kg), the cytoskeletal fixation agent phalloidin (15 micromol/kg), the endothelin ETB receptor antagonist BQ-788(35 micromol/kg), the bradykinin B2 receptor antagonist HOE 140 (0.
2.Urotensin II receptor (UTR) exists in hyaline chondrocytes: a study of peripheral distribution of UTR in the African clawed frog, Xenopus laevis.
Konno N;Fujii Y;Imae H;Kaiya H;Mukuda T;Miyazato M;Matsuda K;Uchiyama M Gen Comp Endocrinol. 2013 May 1;185:44-56. doi: 10.1016/j.ygcen.2013.01.015. Epub 2013 Feb 8.
Urotensin II (UII) and UII-related peptide (URP) exhibit diverse physiological actions including vasoconstriction, locomotor activity, osmoregulation, and immune response through UII receptor (UTR), which is expressed in the central nervous system and peripheral tissues of fish and mammals. In amphibians, only UII has been identified. As the first step toward elucidating the actions of UII and URP in amphibians, we cloned and characterized URP and UTR from the African clawed frog Xenopus laevis. Functional analysis showed that treatment of UII or URP with Chinese hamster ovary cells transfected with the cloned receptor increased the intracellular calcium concentration in a concentration-dependent manner, whereas the administration of the UTR antagonist urantide inhibited UII- or URP-induced Ca(2+) mobilization. An immunohistochemical study showed that UTR was expressed in the splenocytes and leukocytes isolated from peripheral blood, suggesting that UII and URP are involved in the regulation of the immune system. UTR was also localized in the apical membrane of the distal tubule of the kidney and in the transitional epithelial cells of the urinary bladder. This result supports the view that the UII/URP-UTR system plays an important role in osmoregulation of amphibians.
3.Enhanced renal sensitivity of the spontaneously hypertensive rat to urotensin II.
Abdel-Razik AE;Balment RJ;Ashton N Am J Physiol Renal Physiol. 2008 Oct;295(4):F1239-47. doi: 10.1152/ajprenal.90374.2008. Epub 2008 Aug 13.
Urotensin II (UII) has been implicated widely in cardiovascular disease. The mechanism(s) through which it contributes to elevated blood pressure is unknown, but its emerging role as a regulator of mammalian renal function suggests that the kidney might be involved. The aim of this study was to determine the effect of UII on renal function in the spontaneously hypertensive rat (SHR). UII infusion (6 pmol.min(-1).100 g body wt(-1)) in anesthetized SHR and control Wistar-Kyoto (WKY) rats produced marked reductions in glomerular filtration rate (DeltaGFR WKY, n=7, -0.3+/-0.1 vs. SHR, n=7, -0.6+/-0.1 ml.min(-1).100 g body wt(-1), P=0.03), urine flow, and sodium excretion rates, which were greater in SHR by comparison with WKY rats. WKY rats also showed an increase in fractional excretion of sodium (DeltaFE(Na); +0.6+/-0.1%, P=0.02) in contrast to SHR in which no such change was observed (DeltaFE(Na) -0.6+/-0.2%). Blockade of the UII receptor (UT), and thus endogenous UII activity, with urantide evoked an increase in GFR which was greater in SHR (+0.3+/-0.1) compared with WKY rats (+0.1+/-0.1 ml.min(-1).100 g body wt(-1), P=0.04) and was accompanied by a diuresis and natriuresis. UII and UT mRNA expression were greater in the renal medulla than the cortex of both strains; however, expression levels were up to threefold higher in SHR tissue.
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