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Merck
CN

SML2084

[Pyr1]-Apelin-13 trifluoroacetate salt

≥96% (HPLC), APJ agonist, powder

Synonym(s):

5-Oxo-L-prolyl-L-arginyl-L-prolyl-L-arginyl-L-leucyl-L-seryl-L-histidyl-L-lysylglycyl-L-prolyl-L-methionyl-L-prolyl-L-phenylalanine TFA, Pyroglutamated apelin-13, Pyroglutaminated apelin-13, Pyroglutamyl apelin-13, [Glp1]-Apelin-13, [Pyr-1]-apelin-13, [Pyr]-apelin-13, [pGlu1]-apelin-13, pERPRLSHKGPMPF TFA, pGlu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe, TFA

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About This Item

Empirical Formula (Hill Notation):
C69H108N22O16S · xC2HF3O2
CAS Number:
217082-60-5
Molecular Weight:
1533.80 (free base basis)
UNSPSC Code:
51111800
NACRES:
NA.77

Key Documents

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Product Name

[Pyr1]-Apelin-13 trifluoroacetate salt, ≥96% (HPLC)

SMILES string

S(CC[C@H](NC(=O)[C@H]3N(CCC3)C(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]5N(CCC5)C(=O)[C@@H](NC(=O)[C@H]6NC(=O)CC6)CCCN\C(=N/[H])\N)CCCN\C(=N/[H])\N)CC(C)C)CO)Cc4nc[nH]c4)CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](Cc2ccccc

InChI

1S/C69H108N22O16S/c1-39(2)32-47(85-57(96)43(17-9-26-76-68(71)72)82-63(102)52-20-12-29-90(52)65(104)45(18-10-27-77-69(73)74)83-58(97)44-22-23-54(93)80-44)59(98)88-50(37-92)61(100)86-48(34-41-35-75-38-79-41)60(99)81-42(16-7-8-25-70)56(95)78-36-55(94)89-28-11-19-51(89)62(101)84-46(24-31-108-3)66(105)91-30-13-21-53(91)64(103)87-49(67(106)107)33-40-14-5-4-6-15-40/h4-6,14-15,35,38-39,42-53,92H,7-13,16-34,36-37,70H2,1-3H3,(H,75,79)(H,78,95)(H,80,93)(H,81,99)(H,82,102)(H,83,97)(H,84,101)(H,85,96)(H,86,100)(H,87,103)(H,88,98)(H,106,107)(H4,71,72,76)(H4,73,74,77)/t42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-/m0/s1

InChI key

GGMAXEWLXWJGSF-PEWBXTNBSA-N

assay

≥96% (HPLC)

form

powder

color

white to beige

shipped in

wet ice

storage temp.

−20°C

Related Categories

Biochem/physiol Actions

(Pyr1)-Apelin-13, the major apelin form in human plasma and heart, corresponds to Apelin-13 with posttranslationally modified pyroglutamyl (pGlu, pE) at the N-terminus instead of glutamine (Gln, Q). (Pyr1)-Apelin-13 exhibits higher APJ agonist potency than Apelin-13 (EC50 = 0.30 vs. 0.37 nM, respectively; acidification induction in human APJ-expresing CHO cell cultures). (Pyr1)-Apelin-13 is reactive toward human, murine, rat, and bovine species, and widely used for studyinhg APJ-mediated cellular and physiological functions both in cultures and in animals in vivo (via intraperitoneal, intravenous, intrathecal injection).
Posttranslationally modified pyroglutamyl (pGlu) form of Apelin-13 with higher APJ agonist potency and stability.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000515870
0000515870
0000506588
0000506588
0000476960

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Eugene Y Zhen et al.
Analytical biochemistry, 442(1), 1-9 (2013-07-23)
Apelin is emerging as an important hormone regulator of cardiovascular homoeostasis and an important biomarker for heart failure. Apelin concentrations have historically been measured by immunoassays; however, reported apelin concentrations measured in healthy volunteers show a large disparity from a
Alexandre Murza et al.
Organic & biomolecular chemistry, 15(2), 449-458 (2016-12-08)
Apelin is the endogenous ligand for the G protein-coupled receptor APJ and exerts a key role in regulating cardiovascular functions. We report herein a novel series of macrocyclic analogues of apelin-13 in which the N- and C-terminal residues as well
K Tatemoto et al.
Biochemical and biophysical research communications, 251(2), 471-476 (1998-10-30)
In the search for an endogenous ligand of the orphan G protein-coupled receptor APJ, the presence of the ligand in various tissue extracts was examined by measuring the increase in extracellular acidification rate of the cells expressing the APJ receptor

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