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V4253

Sigma-Aldrich

[β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Et-Tyr2, Val4, Arg8]-Vasopressin

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C53H75N13O11S2
CAS Number:
77453-01-1
Molecular Weight:
1134.37
MDL number:
MFCD00076752
UNSPSC Code:
51111800
PubChem Substance ID:
329829049
NACRES:
NA.32

biological source

synthetic (organic)

Quality Level

200

Assay

≥97% (HPLC)

form

powder

solubility

water: 1 mg/mL, clear, colorless

shipped in

ambient

storage temp.

−20°C

SMILES string

CCOc1ccc(C[C@@H]2NC(=O)CC3(CCCCC3)SSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc4ccccc4)NC2=O)C(C)C)C(=O)N5CCC[C@H]5C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(N)=O)cc1

InChI

1S/C53H77N13O11S2/c1-4-77-34-19-17-33(18-20-34)26-36-46(71)62-37(25-32-13-7-5-8-14-32)48(73)65-44(31(2)3)50(75)63-38(27-41(54)67)47(72)64-39(30-78-79-53(28-43(69)60-36)21-9-6-10-22-53)51(76)66-24-12-16-40(66)49(74)61-35(15-11-23-58-52(56)57)45(70)59-29-42(55)68/h5,7-8,13-14,17-20,31,35-40,44H,4,6,9-12,15-16,21-30H2,1-3H3,(H2,54,67)(H2,55,68)(H,59,70)(H,60,69)(H,61,74)(H,62,71)(H,63,75)(H,64,72)(H,65,73)(H4,56,57,58)/t35-,36-,37-,38-,39-,40-,44-/m0/s1

InChI key

SDFJYGJKEXYVCG-ZZTMPEIHSA-N

Gene Information

human ... AVPR1A(552) , AVPR2(554) , OXT(5020) , OXTR(5021)
mouse ... AVPR1A(54140) , AVPR2(12000)
rat ... AVPR1A(25107) , AVPR2(25108) , OXT(18429) , OXTR(18430)

Amino Acid Sequence

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

Application

[Beta-Mercapto-beta, beta-cyclopentamethylenepropionyl1, O-Et-Tyr2, Val4, Arg8]-Vasopressin is a potent V1a and V2 vasopressin receptor anatgonist, used for examining the impact of vasopressin V1receptor blockade in rats.The product was also be used for visualizing cell surface V1a receptors in rat hepatocytes by using high-affinity fluorescent linear antagonist, Rhm8 -PVA.

Biochem/physiol Actions

Vasopressin also known as antidiuretic hormone (ADH) or argipressin can stimulate three acid-base transporters and hence increases the capability of the cell to regulate pHi.ADH can induce reversible translocation of aquaporin-CD water channels from intracellular vesicles to apical plasma membrane, which in turn increases the water permeability of collecting duct cells.

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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M Manning et al.
Journal of peptide science : an official publication of the European Peptide Society, 3(1), 31-46 (1997-01-01)
We report the solid-phase synthesis and some pharmacological properties of 12 position three modified analogues (peptides 1-12) of the potent non-selective antagonist of the antidiuretic (V2-receptor), vasopressor (V1a-receptor) responses to arginine vasopressin (AVP) and of the uterine contracting (OT-receptor) responses
M Bosch-Marcé et al.
Gastroenterology, 109(1), 217-223 (1995-07-01)
It has recently been described that kappa-opioid receptor agonists inhibit antidiuretic hormone secretion and promote water excretion in humans and experimental animals. The aim of this study was to evaluate the aquaretic efficacy of the kappa-opioid receptor agonist RU 51599
J Filep et al.
The American journal of physiology, 253(5 Pt 2), F952-F958 (1987-11-01)
To investigate the role of arginine vasopressin (AVP) in the maintenance of blood pressure in deoxycorticosterone (DOC)-salt hypertension, the effects of specific pressor and antidiuretic antagonists of AVP were studied in conscious, freely moving rats with established malignant DOC-salt hypertension.
H Tsushima et al.
Japanese journal of pharmacology, 66(2), 241-246 (1994-10-01)
We investigated the effects of angiotensin II (Ang II), microinjected into the supraoptic (SON) and paraventricular (PVN) nuclei of rats, on the urine outflow rate and underlying mechanisms. Ang II produced antidiuretic effects in a dose-dependent manner with ED50 values
M K Sun et al.
European journal of pharmacology, 304(1-3), 63-71 (1996-05-23)
We examined whether vasomotor neurons in the rostroventrolateral reticular nucleus of the medulla oblongata might be responsible for an acute increase in arterial pressure, elicited by application of angiotensin II in the central nervous system, as suggested by others. In
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