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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

Fórmula empírica (notación de Hill):
C52H74N14O12S2
Número de CAS:
73168-24-8
Peso molecular:
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

signalword

Warning

hcodes

H332

Hazard Classifications

Acute Tox. 4 Inhalation

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

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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
Ada C Felix-Ortiz et al.
PloS one, 7(5), e37313-e37313 (2012-05-23)
Valproic acid (VPA) has been used clinically as an anticonvulsant medication during pregnancy; however, it poses a neurodevelopmental risk due to its high teratogenicity. We hypothesized that midgestational (GD) exposure to VPA will lead to lasting deficits in social behavior
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).
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
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
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