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V2255

Sigma-Aldrich

[β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-me-Tyr2, Arg8]-Vasopressin

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C52H74N14O12S2
CAS Number:
73168-24-8
Molecular Weight:
1151.36
MDL number:
MFCD00076747
UNSPSC Code:
51111800
PubChem Substance ID:
329829034
NACRES:
NA.32

Quality Level

200

Assay

≥97% (HPLC)

solubility

H2O: soluble 1 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

COc1ccc(C[C@@H]2NC(=O)CC3(CCCCC3)SSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](Cc4ccccc4)NC2=O)C(=O)N5CCC[C@H]5C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(N)=O)cc1

InChI

1S/C52H74N14O12S2/c1-78-32-16-14-31(15-17-32)25-35-46(73)63-36(24-30-10-4-2-5-11-30)47(74)61-34(18-19-40(53)67)45(72)64-37(26-41(54)68)48(75)65-38(29-79-80-52(27-43(70)60-35)20-6-3-7-21-52)50(77)66-23-9-13-39(66)49(76)62-33(12-8-22-58-51(56)57)44(71)59-28-42(55)69/h2,4-5,10-11,14-17,33-39H,3,6-9,12-13,18-29H2,1H3,(H2,53,67)(H2,54,68)(H2,55,69)(H,59,71)(H,60,70)(H,61,74)(H,62,76)(H,63,73)(H,64,72)(H,65,75)(H4,56,57,58)/t33-,34-,35-,36-,37-,38-,39-/m0/s1

InChI key

QVQOGNOOAMQKCE-ZTYVOHGWSA-N

Gene Information

human ... AVPR1A(552)
mouse ... AVPR1A(54140)
rat ... AVPR1A(25107)

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Amino Acid Sequence

(1-Mercaptocyclohexyl)acetyl-Tyr-OMet-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide Bridge: 1-6]

Application

[Beta-Mercapto-beta,beta-cyclopentamethylenepropionyl1, O-me-Tyr2, Arg8]-Vasopressin was used to block Vasopressin (V1a) receptors and study the role of endothelin, vasopressin and angiotensin in regulating arterial pressure during anaesthesia in dogs. The product was used as a test compound for studying the impact of arginine vasopressin and atriopeptin on chloride uptake in cultured Type-I astrocytes.

Biochem/physiol Actions

[Beta-Mercapto-beta,beta-cyclopentamethylenepropionyl1, O-me-Tyr2, Arg8]-Vasopressin is a V1a vasopressin receptor antagonist also referred to as “Manning compound”. Vasopressin can stimulate three acid-base transporters and hence increases the capability of the cell to regulate pHi. It induces reversible translocation of aquaporin-CD water channels from intracellular vesicles to apical plasma membrane, which increases the water permeability of collecting duct cells.

Preparation Note

[Beta-Mercapto-beta,beta-cyclopentamethylenepropionyl1, O-me-Tyr2, Arg8] vasopressin dissolves in water at 1 mg/ml to yield a clear, colorless solution.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H332

Precautionary Statements

P261 - P271 - P304 + P340 + P312

Hazard Classifications

Acute Tox. 4 Inhalation

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fan Yan-Hong et al.
Journal of cardiovascular pharmacology, 55(5), 489-495 (2010-02-19)
Differentiation of cardiac fibroblasts (CFs) into myofibroblasts is a critical event in the initiation of myocardial fibrosis (MF). Previous studies have shown that arginine vasopressin (AVP) facilitates MF. However, the effects of AVP on CFs-myofibroblasts transformation, and its possible mechanisms
D G Shirley et al.
Nephron. Physiology, 117(3), p21-p26 (2010-11-13)
Although it is known that moderate-to-high doses of the neurohypophysial hormones oxytocin and vasopressin are natriuretic, doubts remain over the identity of the receptors responsible. To address this issue, we have used highly selective antagonists of oxytocin and vasopressin receptors
Shuang-Yu Lv et al.
Peptides, 33(1), 132-138 (2011-11-24)
Apelin, the novel identified peptide, is the endogenous ligand for the APJ. Previous studies have reported the effect of apelin on food intake, however the action of acute central injected apelin on food intake in mice remains unknown. The present
Nick Santangelo et al.
Brain, behavior and evolution, 75(4), 282-291 (2010-08-10)
The neuropeptide arginine vasotocin (AVT) is well known to modulate both aggression and affiliation, yet few studies relate individual behavioral state to a quantitative assessment of AVT distribution in the brain. Here, using a wild population of beaugregory damselfish, Stegastes
N Cotte et al.
European journal of biochemistry, 267(13), 4253-4263 (2000-06-24)
Despite their opposite effects on signal transduction, the nonapeptide hormone arginine-vasopressin (AVP) and its V1a receptor-selective cyclic peptide antagonist d(CH2)5[Tyr(Me)2]AVP display homologous primary structures, differing only at residues 1 and 2. These structural similarities led us to hypothesize that both
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