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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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Stephanie J Gutzler et al.
The European journal of neuroscience, 31(9), 1655-1663 (2010-06-09)
Arginine-vasopressin (AVP) is critical for the expression of a variety of social behaviors in many species. Previous studies have demonstrated that AVP regulates behaviors such as social communication and aggression in Syrian hamsters through the V1a receptor subtype. In male
Ronald G Oldfield et al.
Physiology & behavior, 102(3-4), 296-303 (2010-11-30)
The nonapeptides arginine vasopressin (AVP; including its non-mammalian homolog arginine vasotocin, AVT) and oxytocin (OT; including its non-mammalian homologs mesotocin, MT, and isotocin, IT) regulate social behavior, including aggression and reproduction, via receptors conserved across vertebrates. In monogamous prairie voles
Zoe R Donaldson et al.
Behavioral neuroscience, 124(1), 159-163 (2010-02-10)
The neuropeptide arginine vasopressin (AVP) modulates a variety of species-specific social behaviors. In socially monogamous male prairie voles, AVP acts centrally via vasopressin V1a receptor (V1aR) to facilitate mating induced partner preferences. The display of a partner preference requires at
L Katay et al.
Neurochemical research, 23(6), 831-836 (1998-05-08)
Ion and water homeostasis in the CNS is subjected to a neuroendocrine control exerted by neuropeptides formed within the brain. In order to gain information on this neuroendocrine control of Cl- homeostasis, 36Cl- uptake was measured in cultured Type-I astrocytes
M Carrillo et al.
Neuroscience, 185, 85-96 (2011-04-05)
In the latero-anterior hypothalamus (LAH) increased glutamate and vasopressin (AVP) activity facilitate anabolic androgenic steroid (AAS)-induced offensive aggression. In addition, adolescent AAS treatment increases the strength of glutamate-mediated connections between the LAH and the brain nucleus of stria terminalis (BNST).
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