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(Phenylac1,D-Tyr(Et)2,Lys6,Arg8,des-Gly9)-Vasopressin

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

(Phenylac1,D-Tyr(Et)2,Lys6,Arg8,des-Gly9)-Vasopressin is a selective and highly potent antagonist of V1 receptor (antivasopressor) with an antiantidiuretic/antivasopressor ED ratio of about 570.

Category

Peptide Inhibitors

Catalog number

BAT-015213

CAS number

129520-65-6

Molecular Formula

C54H76N14O11

Molecular Weight

1097.27

(Phenylac1,D-Tyr(Et)2,Lys6,Arg8,des-Gly9)-Vasopressin

Specification
Reference Reading

IUPAC Name

(2S)-N-[(2S)-4-amino-1-[[(2S)-6-amino-1-[(2S)-2-[[(2S)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-1,4-dioxobutan-2-yl]-2-[[(2S)-2-[[(2R)-3-(4-ethoxyphenyl)-2-[(2-phenylacetyl)amino]propanoyl]amino]-3-phenylpropanoyl]amino]pentanediamide

Synonyms

Phenylac-D-Tyr(Et)-Phe-Gln-Asn-Lys-Pro-Arg-NH2; benzylcarbonyl-D-Tyr(Et)-Phe-Gln-Asn-Lys-Pro-Arg-NH2; N-(benzylcarbonyl)-O4-ethyl-D-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparagyl-L-lysyl-L-prolyl-L-argininamide; L-Argininamide, O-ethyl-N-(phenylacetyl)-D-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-lysyl-L-prolyl-

Appearance

White Powder

Purity

≥95% by HPLC

Density

1.39±0.1 g/cm3 (Predicted)

Sequence

Phenylac-D-Y(Et)-FQNKPR-NH2

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C54H76N14O11/c1-2-79-36-22-20-35(21-23-36)30-40(62-46(71)31-34-15-7-4-8-16-34)49(74)66-41(29-33-13-5-3-6-14-33)50(75)64-38(24-25-44(56)69)48(73)67-42(32-45(57)70)51(76)65-39(17-9-10-26-55)53(78)68-28-12-19-43(68)52(77)63-37(47(58)72)18-11-27-61-54(59)60/h3-8,13-16,20-23,37-43H,2,9-12,17-19,24-32,55H2,1H3,(H2,56,69)(H2,57,70)(H2,58,72)(H,62,71)(H,63,77)(H,64,75)(H,65,76)(H,66,74)(H,67,73)(H4,59,60,61)/t37-,38-,39-,40+,41-,42-,43-/m0/s1

InChI Key

PBPXAIJQDPORTG-ZRBRQIMBSA-N

Canonical SMILES

CCOC1=CC=C(C=C1)CC(C(=O)NC(CC2=CC=CC=C2)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)N)C(=O)NC(CCCCN)C(=O)N3CCCC3C(=O)NC(CCCN=C(N)N)C(=O)N)NC(=O)CC4=CC=CC=C4

1. Oestrogen inhibits salt-dependent hypertension by suppressing GABAergic excitation in magnocellular AVP neurons

Eun-Hwa Hong, Yoon Sik Kim, Hyung Kyung Kang, Woong Bin Kim, Xiangyan Jin, Christopher S Colwell, Young-Beom Kim, Won Woo Jung, Wan Joo Shim, Hee Chul Han, Yang In Kim, Mi-Na Kim Cardiovasc Res . 2021 Aug 29;117(10):2263-2274. doi: 10.1093/cvr/cvaa271.

Aims:Abundant evidence indicates that oestrogen (E2) plays a protective role against hypertension. Yet, the mechanism underlying the antihypertensive effect of E2 is poorly understood. In this study, we sought to determine the mechanism through which E2 inhibits salt-dependent hypertension.Methods and results:To this end, we performed a series of in vivo and in vitro experiments employing a rat model of hypertension that is produced by deoxycorticosterone acetate (DOCA)-salt treatment after uninephrectomy. We found that E2 prevented DOCA-salt treatment from inducing hypertension, raising plasma arginine-vasopressin (AVP) level, enhancing the depressor effect of the V1a receptor antagonist (Phenylac1,D-Tyr(Et)2,Lys6,Arg8,des-Gly9)-vasopressin, and converting GABAergic inhibition to excitation in hypothalamic magnocellular AVP neurons. Moreover, we obtained results indicating that the E2 modulation of the activity and/or expression of NKCC1 (Cl- importer) and KCC2 (Cl- extruder) underpins the effect of E2 on the transition of GABAergic transmission in AVP neurons. Lastly, we discovered that, in DOCA-salt-treated hypertensive ovariectomized rats, CLP290 (prodrug of the KCC2 activator CLP257, intraperitoneal injections) lowered blood pressure, and plasma AVP level and hyperpolarized GABA equilibrium potential to prevent GABAergic excitation from emerging in the AVP neurons of these animals.Conclusion:Based on these results, we conclude that E2 inhibits salt-dependent hypertension by suppressing GABAergic excitation to decrease the hormonal output of AVP neurons.