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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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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
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
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
Megan Gray et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 37(12), 2712-2719 (2012-07-26)
Previous studies suggest that central arginine vasopressin (AVP) signaling can inhibit the hypothalamic-pituitary-adrenal (HPA) axis. To test a role for the AVP V1A receptor in stress HPA axis habituation, adult male rats were exposed to 5 consecutive days of 3
L Wang et al.
Journal of neuroendocrinology, 24(4), 664-673 (2011-10-13)
Synaptic activity in magnocellular neurosecretory neurones is influenced by the retrograde (i.e. somatodendritic) release of vasopressin, oxytocin and cannabinoids (CBs). For oxytocin neurones, oxytocin exerts constitutive effects on pre-synaptic activity through its ability to release CBs post-synaptically. In the present
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