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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

Fórmula empírica (Notação de Hill):
C53H75N13O11S2
Número CAS:
77453-01-1
Peso molecular:
1134.37
Número MDL:
MFCD00076752
Código UNSPSC:
51111800
ID de substância PubChem:
329829049
NACRES:
NA.32

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fonte biológica

synthetic (organic)

Nível de qualidade

200

Ensaio

≥97% (HPLC)

Formulário

powder

solubilidade

water: 1 mg/mL, clear, colorless

Condições de expedição

ambient

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

SDFJYGJKEXYVCG-ZZTMPEIHSA-N

Informações sobre genes

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]

Aplicação

[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.[1]The product was also be used for visualizing cell surface V1a receptors in rat hepatocytes by using high-affinity fluorescent linear antagonist, Rhm8 -PVA.[2]

Ações bioquímicas/fisiológicas

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.[3]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.[4]

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H332

Declarações de precaução

P261 - P271 - P304 + P340 + P312

Classificações de perigo

Acute Tox. 4 Inhalation

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
0000267635
SLCQ8849
0000267635
SLCQ5706
031M1823V

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L B Kinter et al.
The Journal of pharmacology and experimental therapeutics, 241(3), 797-803 (1987-06-01)
Vasopressin antagonism and water diuresis (aquaresis) is demonstrated after i.p. or i.v. administration of vasopressin antagonists in a primate species, the squirrel monkey (Saimiri sciureus). Antagonism of vasopressin-stimulated renal medullary adenylate cyclase activity was evaluated in vitro; the most potent
D Tran et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 47(3), 401-410 (1999-02-20)
To visualize cell surface V1a vasopressin receptors in rat hepatocytes in the absence of receptor-mediated endocytosis, we used a high-affinity fluorescent linear antagonist, Rhm8-PVA. Epifluorescence microscopy (3CCD camera) and fluorescence spectroscopy were used. Rhm8-PVA alone did not stimulate Ca2+ signals
W Y Chan et al.
Experimental physiology, 85 Spec No, 7S-18S (2000-05-05)
Synthetic oxytocin and vasopressin agonists and antagonists have become important tools for research and were instrumental in the identification of the four known receptor subtypes, V1a, V2, V1b (V3) and oxytocin, of these peptide hormones. However, the relative lack of
M Manning et al.
Journal of medicinal chemistry, 38(10), 1762-1769 (1995-05-12)
We report the solid-phase synthesis of the D-Cys6 analogues of arginine-vasopressin (AVP), peptide 1, of the selective AVP vasopressor (V1a receptor) antagonist [1-(beta-mercapto-beta,beta-pentamethylenepropionic acid),2-O-methyltyrosine]arginine-vasopressin (d(CH2)5[Tyr(Me)2]-AVP, (A)), peptide 2, of the three nonselective antidiuretic/vasopressor (V2/V1a receptor) AVP antagonists d(CH2)5[Tyr(Et)2]VAVP (B), d(CH2)5[D-Tyr(Et)2]VAVP
D Tran et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 47(5), 601-616 (1999-04-28)
In freshly isolated rat hepatocyte multiplets, Ca2+ signals in response to vasopressin are highly organized. In this study we used specific probes to visualize, by fluorescence and confocal microscopy, the main signaling molecules involved in vasopressin-mediated Ca2+ responses. V1a receptors
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