V2255

[β-Mercapto-β,β-cyclopentamethylenepropionyl¹, O-me-Tyr², Arg⁸]-Vasopressin

≥97% (HPLC)

• 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

Properties

• 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)

Description

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.

Safety Information

• Pictograms: 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