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E6877

Sigma-Aldrich

[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
MDL number:
MFCD00143562
UNSPSC Code:
12352200
PubChem Substance ID:
329799000
NACRES:
NA.32

storage temp.

−20°C

Quality Level

200

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

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

InChI key

NRTWVLDGYXCWHD-IGKRDWOESA-N

Gene Information

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

Amino Acid Sequence

Ala-Ser-Ala-Ser-Ser-Leu-Met-Asp-Lys-Glu-Ala-Val-Tyr-Phe-Ala-His-Leu-Asp-Ile-Ile-Trp

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 Code

11 - 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

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Certificates of Analysis (COA)

Lot/Batch Number
SLCM0326
SLBX4339
SLBX4340
SLBW7775
SLBV7734

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Robert K Fitzgerald et al.
Pediatric critical care medicine : a journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies, 5(6), 571-577 (2004-11-09)
To investigate the hemodynamic effects of tezosentan in the intact lamb both at rest and during acute and chronic pulmonary hypertension. Prospective, randomized experimental study. University-based research laboratory. Lambs with and without pulmonary hypertension. Six newborn lambs were instrumented to
G Thibault et al.
Circulation research, 74(3), 460-470 (1994-03-01)
Endothelin (ET), a potent vasoconstrictor peptide, is known to enhance the secretion of atrial natriuretic factor (ANF) by the heart. In the present study, we investigated the potency of ET isopeptides to stimulate ANF and brain natriuretic peptide (BNP) secretion
M Bigaud et al.
British journal of pharmacology, 107(4), 912-918 (1992-12-01)
1. The influence of BQ-123 (a selective ETA-receptor antagonist) on the haemodynamic response elicited by endothelin-1 (ET-1) and [Ala1,3,11,15]ET-1 (a selective ETB-receptor agonist) was studied in anaesthetized rats instrumented with ultrasonic Doppler flow probes on the carotid, coeliac, mesenteric, renal
T Saeki et al.
Biochemical and biophysical research communications, 179(1), 286-292 (1991-08-30)
A linear peptide analog of endothelin (ET)-1, [Ala1,3,11,15]ET-1 (4AlaET-1), and its truncated peptide analogs were synthesized to study the structural requirements of ET-1 for the recognition of ETs-nonselective ETB receptors. ET-1 exhibited sub-nanomolar binding to two distinct ET receptor subtypes
Q D Wang et al.
Cardiovascular research, 29(1), 44-49 (1995-01-01)
The local myocardial overflow and tissue content of endothelin-like immunoreactivity (ET-LI) during ischaemia and reperfusion as well as the coronary vascular effects of endothelin were characterised in anaesthetised pigs. Ischaemia was induced by ligation of the left anterior descending coronary
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