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V2013

Sigma-Aldrich

[deamino-Cys1, Val4, D-Arg8]-Vasopressin

≥95%

Synonyme(s) :

Val4−dDAVP

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About This Item

Formule empirique (notation de Hill):
C46H65N13O11S2
Poids moléculaire :
1040.22
Numéro MDL:
MFCD00080166
Code UNSPSC :
51111800
ID de substance PubChem :
329829030
Nomenclature NACRES :
NA.32

Source biologique

synthetic (organic)

Niveau de qualité

200

Stérilité

non-sterile

Pureté

≥95%

Forme

powder

Solubilité

50% acetic acid: soluble 1 mg/mL, clear, colorless

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

CC(C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)CCSSC[C@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N4CCC[C@H]4C(=O)N[C@H](CCCNC(N)=N)C(=O)NCC(N)=O

InChI

1S/C46H65N13O11S2/c1-25(2)38-44(69)56-32(22-35(47)61)41(66)57-33(45(70)59-18-7-11-34(59)43(68)54-29(10-6-17-51-46(49)50)39(64)52-23-36(48)62)24-72-71-19-16-37(63)53-30(21-27-12-14-28(60)15-13-27)40(65)55-31(42(67)58-38)20-26-8-4-3-5-9-26/h3-5,8-9,12-15,25,29-34,38,60H,6-7,10-11,16-24H2,1-2H3,(H2,47,61)(H2,48,62)(H,52,64)(H,53,63)(H,54,68)(H,55,65)(H,56,69)(H,57,66)(H,58,67)(H4,49,50,51)/t29-,30+,31+,32+,33+,34+,38+/m1/s1

Clé InChI

KEBRFHAVFOSSOX-WSFLLCRESA-N

Informations sur le gène

human ... AVPR2(554)
mouse ... AVPR2(12000)
rat ... AVPR2(25108)

Amino Acid Sequence

Mpa-Tyr-Phe-Val-Asn-Cys-Pro-Arg-Gly-NH2

Application

[Deamino-Cys1, Val4, D-Arg8]-Vasopressin was used to prepare sample for qualitative detection of desmopressin in plasma by using liquid chromatography-electrospray tandem mass spectrometry.

Actions biochimiques/physiologiques

[Deamino-Pen1, O-Me-Tyr2, Arg8]-Vasopressin is a V1 antagonist that stabilizes the cardiocirculatory function in normal human as well as in patients suffering from catecholamine-resistant vasodilatory shock.It can also stimulate three acid-base transporters and hence increases the capability of the cell to regulate pHi.

Notes préparatoires

[deamino-Cys1, Val4, D-Arg8]-Vasopressin dissolves in water at 1 mg/ml to yield a clear, colorless solution.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Ana Pena et al.
Journal of medicinal chemistry, 50(4), 835-847 (2007-02-16)
The neurohypophyseal peptides arginine vasopressin (AVP) and oxytocin (OT) mediate a wide variety of peripheral and central physiological and behavioral effects by acting on four different G-protein coupled receptors, termed V1a (vascular), V1b (pituitary), V2 (renal), and OT (uterine). We
Simone Esposito et al.
Analytical and bioanalytical chemistry, 402(9), 2789-2796 (2012-02-10)
This work describes a liquid chromatography-electrospray tandem mass spectrometry method for detection of desmopressin in human plasma in the low femtomolar range. Desmopressin is a synthetic analogue of the antidiuretic hormone arginine vasopressin and it might be used by athletes
G Croiset et al.
Brain research, 759(1), 18-23 (1997-06-06)
Subcutaneously (s.c.) administered [Arg8]vasopressin (AVP) potentiated seizures induced by intracerebroventricular (i.c.v.) injection of 1.95 mg pilocarpine (a muscarinic cholinergic agonist). A bell-shaped relation between dose and effect was found. I.c.v. pretreatment with a V1, V2 or oxytocin receptor antagonist was
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
Martin W Dünser et al.
Circulation, 107(18), 2313-2319 (2003-05-07)
Vasodilatory shock is a potentially lethal complication of severe disease in critically ill patients. Currently, catecholamines are the most widely used vasopressor agents to support blood pressure, but loss of catecholamine pressor effects is a well-known clinical dilemma. Arginine vasopressin
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