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O6887

Sigma-Aldrich

[β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Me-Tyr2, Orn8]-Oxytocin

≥93% (HPLC), solid

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About This Item

Empirische Formel (Hill-System):
C48H74N12O12S2
CAS-Nummer:
77327-45-8
Molekulargewicht:
1075.30
MDL-Nummer:
MFCD00135712
UNSPSC-Code:
51111800
PubChem Substanz-ID:
329818919
NACRES:
NA.32

Qualitätsniveau

200

Assay

≥93% (HPLC)

Form

solid

Lagertemp.

−20°C

SMILES String

CC[C@H](C)C1NC(=O)[C@H](Cc2ccc(OC)cc2)NC(=O)CC3(CCCCC3)SSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CCCN)C(=O)NCC(N)=O

InChI

1S/C48H74N12O12S2/c1-4-27(2)40-46(70)56-31(16-17-36(50)61)42(66)57-33(23-37(51)62)43(67)58-34(47(71)60-21-9-11-35(60)45(69)55-30(10-8-20-49)41(65)53-25-38(52)63)26-73-74-48(18-6-5-7-19-48)24-39(64)54-32(44(68)59-40)22-28-12-14-29(72-3)15-13-28/h12-15,27,30-35,40H,4-11,16-26,49H2,1-3H3,(H2,50,61)(H2,51,62)(H2,52,63)(H,53,65)(H,54,64)(H,55,69)(H,56,70)(H,57,66)(H,58,67)(H,59,68)/t27-,30-,31-,32-,33-,34-,35-,40-/m0/s1

InChIKey

ZWVZXPFUQHTUKV-SZQHDTAUSA-N

Angaben zum Gen

human ... OXT(5020) , OXTR(5021)
rat ... OXT(18429) , OXTR(18430)

Amino Acid Sequence

β-Mercapto-β,β-Cyclopentamethylenepropionyl-MeTyr-Ile-Gln-Asn-Cys-Pro-Orn-Gly-NH2 [Disulfide Bridge: 1-6]

Anwendung

[β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Me-Tyr2, Orn8]-Oxytocin has been used as an oxytocin receptor antagonist:
  • to study the influence of blockading the oxytocin receptors in the anterior cingulate cortex on helping behavior
  • to determine the receptors that mediate vasopressin-stimulated anion secretion across cultured porcine vas deferens epithelial cell monolayers
  • to study the influence of oxytocin receptors inhibition on intravenous and in situ oxytocin effects on the urinary bladder and cardiovascular activities in sham rats

Biochem./physiol. Wirkung

Potent oxytocin antagonist.
[β-Mercapto-β,β-cyclopentamethylenepropionyl1, O-Me-Tyr2, Orn8]-also acts as an arginine vasopressin receptor 1A (AVPR1A) antagonist.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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2-Mercaptoethanol for molecular biology, suitable for electrophoresis, suitable for cell culture, BioReagent, 99% (GC/titration)

Sigma-Aldrich

M3148

2-Mercaptoethanol

2-Mercaptoethanol ≥99.0%

Sigma-Aldrich

M6250

2-Mercaptoethanol

R C Lambert et al.
Neuroscience, 57(4), 1027-1038 (1993-12-01)
During suckling, the periodic and synchronous bursting activity of oxytocin neurons has been shown to be facilitated by oxytocin itself, acting via several target sites, including the magnocellular nuclei. To investigate the role of the endogenous oxytocin released within the
M Mayntz et al.
Physiology & behavior, 65(1), 151-156 (1998-11-12)
This experiment was to test the hypothesis that suckling behavior in Bos taurus is related to milk ejection. Intra-gland milk transport was manipulated by applying four different treatments to four cow-calf pairs: T1, injection of oxytocin during the post-stimulation period;
R J Windle et al.
The Journal of endocrinology, 152(2), 257-264 (1997-02-01)
The effect of three oxytocin receptor antagonists on the renal actions of oxytocin and vasopressin was investigated in conscious male rats infused with hypotonic saline. Infusion of oxytocin at 100 pg/min produced plasma concentrations of 12.7 +/- 3.3 pmol/l and
M R Melis et al.
European journal of pharmacology, 294(1), 1-9 (1995-12-27)
In order to provide further support for a role of central nitric oxide as a mediator of penile erection and yawning, the nitric oxide donors sodium nitroprusside, hydroxylamine, isoamyl nitrite and S-nitroso-N-acetyl-penicillamine were injected into the lateral ventricles (i.c.v.) or
M R Melis et al.
European journal of pharmacology, 328(2-3), 115-123 (1997-06-11)
A dose of N-methyl-D-aspartic acid (NMDA, 50 ng) that induces penile erection and yawning when injected into the paraventricular nucleus of the hypothalamus, increased the concentration of NO2- from 1.10 +/- 0.28 microM to 7.32 +/- 1.12 microM and of
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