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V2257

Sigma-Aldrich

[deamino-Cys1, D-3-Pyridyl-Ala2, Arg8]-Vasopressin

≥97% (HPLC)

Synonym(s):

D3PVP

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About This Item

Empirical Formula (Hill Notation):
C45H63N15O11S2
CAS Number:
136105-89-0
Molecular Weight:
1054.21
MDL number:
MFCD00214667
UNSPSC Code:
51111800
PubChem Substance ID:
24900730

Assay

≥97% (HPLC)

form

solid

shipped in

ambient

storage temp.

−20°C

SMILES string

NC(=N)NCCCC(NC(=O)C1CCCN1C(=O)C2CSSCCC(=O)NC(Cc3cccnc3)C(=O)NC(Cc4ccccc4)C(=O)NC(CCC(N)=O)C(=O)NC(CC(N)=O)C(=O)N2)C(=O)NCC(N)=O

InChI

1S/C45H63N15O11S2/c46-34(61)13-12-28-39(66)58-31(21-35(47)62)42(69)59-32(44(71)60-17-6-11-33(60)43(70)56-27(10-5-16-52-45(49)50)38(65)53-23-36(48)63)24-73-72-18-14-37(64)54-29(20-26-9-4-15-51-22-26)40(67)57-30(41(68)55-28)19-25-7-2-1-3-8-25/h1-4,7-9,15,22,27-33H,5-6,10-14,16-21,23-24H2,(H2,46,61)(H2,47,62)(H2,48,63)(H,53,65)(H,54,64)(H,55,68)(H,56,70)(H,57,67)(H,58,66)(H,59,69)(H4,49,50,52)

InChI key

KEAHYTRPVNOHKL-UHFFFAOYSA-N

Gene Information

human ... AVPR1B(553)
mouse ... AVPR1B(26361)
rat ... AVPR1B(29462)

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Amino Acid Sequence

Mpa-(3-Pyridyl)-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2 [Disulfide Bridge: 1-6]

Application

[Deamino-Cys1, D-3-Pyridyl-Ala2, Arg8]-Vasopressin is a V1b specific receptor agonist was used to examine vasopressin receptor types involved in regulation of COX expression in BB rats.

Biochem/physiol Actions

[Deamino-Cys1, D-3-Pyridyl-Ala2, Arg8]-Vasopressin also referred to as D3PVP is a selective and potent vasopressor agent that stabilizes the cardiocirculatory function in normal human as well as in patients suffering from catecholamine-resistant vasodilatory shock. It stimulates three acid-base transporters and hence increases the capability of the cell to regulate pHi.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H332

Hazard Classifications

Acute Tox. 4 Inhalation

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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M Sobocinska et al.
Peptides, 16(3), 389-393 (1995-01-01)
A number of analogues of vasopressin, incorporating the substitution of D-3'-(pyridyl)-alanine in position 2, were synthesized and tested for antidiuretic (V2), vasoconstrictor (V1a) and ACTH secretory (V1b; pituitary) activities. One analogue, deamino-[D-3'-(pyridyl)-alanine2]arginine-vasopressin (abbreviated d[D-3Pal]VP) was a potent pituitary agonist, weaker
J Schwartz et al.
Endocrinology, 129(2), 1107-1109 (1991-08-01)
The biological activity of a new synthetic analog of vasopressin, deamino[D-3-(3'-pyridyl)-Ala2, Arg8] vasopressin, was assessed in a number of assays. Antidiuretic (V2) and vasoconstrictor (V1), agonist and antagonist activities were assessed in rats in vivo. Corticotropin-releasing activity was assessed with
M Saito et al.
European journal of pharmacology, 401(3), 289-296 (2000-08-11)
Vasopressin V(2) receptors at high-density and V(1B) receptors are candidates for the V(2)-like receptor, which evokes an increase in [Ca(2+)](i) when stimulated by the vasopressin V(2) receptor agonist 1-desamino-8-D-arginine vasopressin (dDAVP) in kidney inner medullary collecting duct. We compared the
Ming-Zhi Zhang et al.
Endocrinology, 145(3), 1402-1409 (2003-12-20)
The antagonism between prostaglandin and vasopressin represents a classic negative feedback loop. It is not clear whether cyclooxygenase (COX)-2 and/or COX-1 expression is involved in elevated prostaglandin production stimulated by vasopressin in vivo. In the present study, we explored vasopressin
S Lundin et al.
Peptides, 15(5), 809-814 (1994-01-01)
The gastrointestinal absorption of a series of vasopressin (VP) analogues with enhanced enzymatic stability was determined in chronically catheterized, conscious rats. The following peptides were used: [Mpa1,D-Arg8]vasopressin (dDAVP), [Mpa1,Asn4,D-Arg8]VP, [Mpa1,Val4,D-Arg8]VP, [Mpa1,(CH3)3Ala4,D-Arg8]VP, [Mpa1,Tyr(ethyl)2,D-Arg8]VP, and [Mpa1,D-Tyr(ethyl)2,Ile3,Val4,D-Arg8]VP. The peptides were administered by gavage
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