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SML2084

Sigma-Aldrich

[Pyr1]-Apelin-13 trifluoroacetate salt

≥96% (HPLC)

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

Assay

≥96% (HPLC)

form

powder

color

white to beige

shipped in

wet ice

storage temp.

−20°C

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

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).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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

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