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Merck
CN

E6877

[Ala1,3,11,15]-Endothelin 1

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About This Item

Empirical Formula (Hill Notation):
C109H163N25O32S
CAS Number:
121204-87-3
Molecular Weight:
2367.67
NACRES:
NA.32
PubChem Substance ID:
329799000
UNSPSC Code:
12352200
MDL number:
MFCD00143562

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InChI

1S/C109H163N25O32S/c1-16-56(9)87(107(163)128-79(109(165)166)43-64-47-113-68-28-22-21-27-67(64)68)134-108(164)88(57(10)17-2)133-102(158)78(46-85(143)144)126-98(154)73(40-54(5)6)122-100(156)76(44-65-48-112-52-114-65)121-90(146)59(12)116-96(152)74(41-62-25-19-18-20-26-62)124-99(155)75(42-63-30-32-66(138)33-31-63)127-106(162)86(55(7)8)132-92(148)61(14)115-93(149)70(34-35-83(139)140)119-94(150)69(29-23-24-37-110)118-101(157)77(45-84(141)142)125-95(151)71(36-38-167-15)120-97(153)72(39-53(3)4)123-104(160)82(51-137)131-105(161)81(50-136)130-91(147)60(13)117-103(159)80(49-135)129-89(145)58(11)111/h18-22,25-28,30-33,47-48,52-61,69-82,86-88,113,135-138H,16-17,23-24,29,34-46,49-51,110-111H2,1-15H3,(H,112,114)(H,115,149)(H,116,152)(H,117,159)(H,118,157)(H,119,150)(H,120,153)(H,121,146)(H,122,156)(H,123,160)(H,124,155)(H,125,151)(H,126,154)(H,127,162)(H,128,163)(H,129,145)(H,130,147)(H,131,161)(H,132,148)(H,133,158)(H,134,164)(H,139,140)(H,141,142)(H,143,144)(H,165,166)/t56-,57-,58-,59-,60-,61-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,86-,87-,88-/m0/s1

SMILES string

CC[C@H](C)[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](C)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](C)N)C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](Cc4c[nH]c5ccccc45)C(O)=O

InChI key

NRTWVLDGYXCWHD-IGKRDWOESA-N

storage temp.

−20°C

Quality Level

200

Gene Information

human ... EDNRB(1910)
mouse ... EDNRB(13618)
rat ... EDNRB(50672)

General description

[Ala1,3,11,15]-Endothelin 1 is a linear endothelin (ET)-1 analogue, and acts as an ETB receptor agonist. ET-1 is a peptide that acts as both, a vasodilator and a vasoconstrictor. It is a ligand for ET receptor, which is of two types, ETA and ETB. ETB receptor is found in the vascular endothelial cells of cardiovascular tissues.

Application

[Ala1,3,11,15]-Endothelin 1 may be used to assess the effects of endothelin-1 and [Ala1,3,11,15]-endothelin 1 produced by ETA and ETB receptors, in the presence of BQ-123, in anaesthetized rat.

Biochem/physiol Actions

Selective agonist for ETB endothelin receptors.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCM0326
SLBX4339
SLBX4340
SLBW7775
SLBV7734

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P S Widdowson et al.
British journal of pharmacology, 118(8), 2126-2130 (1996-08-01)
1. We performed radioligand binding experiments on rat cerebellar homogenates using [125I]-endothelin-1 ¿[1251]-ET-1¿ and [125I]-BQ3020 to examine the pharmacology of endothelin receptors in rat brain. Saturation experiments demonstrated a single population of binding sites with high affinity for both radioligands
J Green
International journal of peptide and protein research, 41(5), 492-498 (1993-05-01)
[Ala1,3,11,15]-Endothelin-1, a linear analogue of endothelin-1 in which alanines replace the cystine residues, has been prepared by solid-phase synthesis in approximately 17% yield. Fmoc amino acids were coupled using an economical modified double-coupling (symmetrical anhydride followed by O-benzotriazolyl ester) procedure
H De León et al.
Regulatory peptides, 60(1), 1-8 (1995-12-07)
Endothelin (ET) increases renal vascular resistance by constriction of post- and preglomerular vessels in the rat. However, ET receptor subtypes in renal microvessels have not been clearly defined. Radioligand binding experiments were performed in isolated arcuate and interlobular arteries as
M D Randall et al.
British journal of pharmacology, 98(2), 685-699 (1989-10-01)
1. The effects of endothelin-1 and of three analogues in which alanyl residues had been substituted in place of cysteinyl residues were studied in the rat, isolated, Krebs-Henseleit-perfused mesenteric bed and the in situ, blood-perfused, mesenteric and hindquarters circulations of
S Topouzis et al.
British journal of pharmacology, 98(2), 669-677 (1989-10-01)
1. The aim of the present study was to examine the contractile responses evoked by the recently characterized vasoactive peptide endothelin-1 (ET-1) and by two of its structural analogues, [Ala3,11]ET-1 and [Ala1,15]ET-1 in endothelium-denuded rat isolated aorta, and also to
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