[Pyr1]-Apelin-13

Product Name: [Pyr1]-Apelin-13

Sequence One Letter Code: Pyr-RPRLSHKGPMPF-OH

Sequence Three Letter Code: Pyr-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe-OH

Cas No: 217082-60-5

Chemical Formula:C69H108N22O16S

Molecular Weight: 1533.9

Purity: 95%

Form: Lyophilized

Storage Conditions: - 20 °C

Research Area: Cardiovascular Disease Research

SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N2CCC[C@H]2C(=O)N[C@@H](CCSC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H]5CCCN5C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H]6CCC(=O)N6

IUPAC: (2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-1-[2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-1-[(2S)-5-(diaminomethylideneamino)-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]-4-methylsulfanylbutanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid

INCHIKEY: GGMAXEWLXWJGSF-PEWBXTNBSA-N

INCHI:

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

Source / Species: human, mouse, bovine, rat

Conjugation: Unconjugated

Code Nacres: NA.26

Application: [Pyr¹]-Apelin-13 is a pyroglutamylated form of apelin-13, a biologically active peptide derived from the apelin precursor and a high-affinity endogenous ligand of the APJ receptor. The N-terminal pyroglutamyl modification enhances peptide stability and contributes to improved receptor interaction and resistance to enzymatic degradation. Apelin signaling plays a critical role in cardiovascular physiology, influencing cardiac contractility, vascular tone, and fluid homeostasis. Because of its strong receptor affinity and biological activity, [Pyr¹]-Apelin-13 is widely used in receptor binding studies, signaling pathway analysis, and pharmacological research focused on the apelin–APJ signaling axis. The peptide is particularly valuable in investigations of cardiovascular function, including studies of heart performance, vascular regulation, and the molecular mechanisms underlying cardiovascular disease.

Current Research: The apelin signaling system has gained significant attention in recent years due to its important role in cardiovascular regulation, metabolic control, and fluid balance. Central to this pathway is apelin, an endogenous peptide ligand that binds to the APJ receptor (APLNR), a class A G protein–coupled receptor widely expressed in the heart, blood vessels, brain, and other tissues. Among the different bioactive fragments derived from the apelin precursor, apelin-13 is considered one of the most potent and biologically active forms. A particularly important variant of this peptide is [Pyr¹]-Apelin-13, a modified form in which the N-terminal glutamine residue undergoes cyclization to form pyroglutamate (pGlu). This pyroglutamyl modification enhances peptide stability and resistance to enzymatic degradation while maintaining strong affinity for the APJ receptor. Because of these properties, [Pyr¹]-Apelin-13 has become a widely used tool in research investigating the apelin–APJ signaling axis, especially in studies related to cardiovascular physiology and disease mechanisms. The Apelin–APJ Signaling System The apelinergic system consists primarily of the apelin peptides and the APJ receptor, which together regulate several physiological processes. APJ is a G protein–coupled receptor structurally related to the angiotensin receptor family and is distributed in many organs, including the cardiovascular system, central nervous system, and kidneys. When apelin peptides bind to APJ, they activate intracellular signaling pathways that influence multiple physiological responses, including: Regulation of cardiac contractility Control of vascular tone Maintenance of fluid homeostasis Modulation of metabolic processes Because of its widespread biological effects, the apelin–APJ pathway has become an important subject of study in cardiovascular biology and metabolic research. Apelin-13: A Potent Bioactive Fragment Apelin peptides originate from a larger precursor protein that is processed enzymatically into several shorter fragments, including apelin-36, apelin-17, and apelin-13. Among these forms, apelin-13 is widely recognized for its high receptor potency and strong physiological activity. Apelin-13 has been shown in experimental systems to produce significant cardiovascular effects, particularly through interactions with APJ receptors located in cardiac and vascular tissues. Reported biological activities include: Positive inotropic effects, increasing the strength of cardiac contraction Vasodilatory activity, influencing blood vessel diameter and blood pressure Endothelial signaling modulation, supporting vascular function These properties highlight the central role of apelin-13 in maintaining cardiovascular homeostasis. Pyroglutamyl Modification and Peptide Stability In [Pyr¹]-Apelin-13, the N-terminal amino acid is converted into pyroglutamate, a cyclic derivative formed through intramolecular modification of glutamine or glutamic acid residues. This structural change offers several advantages for peptide stability. The pyroglutamyl modification can: Improve resistance to aminopeptidase degradation Increase structural stability of the peptide Maintain or enhance receptor binding affinity As a result, [Pyr¹]-Apelin-13 often displays greater stability in biological systems compared with non-modified peptides, making it particularly useful in experimental studies that require reliable receptor activation. Applications in Receptor Binding and Signaling Research Because of its stability and strong receptor interaction, [Pyr¹]-Apelin-13 is frequently used in receptor binding experiments and signaling pathway studies. Researchers utilize the peptide to examine how activation of the APJ receptor influences intracellular signaling networks. Experimental studies often investigate pathways such as: G protein–mediated signaling β-arrestin recruitment ERK/MAPK signaling cascades PI3K/Akt pathway activation By studying these pathways, scientists can better understand how apelin peptides regulate physiological processes at the cellular and molecular levels. Relevance to Cardiovascular Physiology One of the most important research areas involving [Pyr¹]-Apelin-13 is cardiovascular physiology. The apelin–APJ system is highly expressed in cardiac tissue and vascular endothelium, where it contributes to regulation of heart performance and vascular function. Research involving [Pyr¹]-Apelin-13 has explored several aspects of cardiovascular biology, including: Regulation of cardiac output and contractile function Control of vascular tone and blood pressure Endothelial signaling and vascular health Cellular mechanisms involved in cardiovascular stress responses These studies provide insight into how peptide signaling pathways contribute to the maintenance of normal cardiovascular function. A Valuable Tool for Pharmacological Research In addition to physiological studies, [Pyr¹]-Apelin-13 is also valuable in pharmacological and receptor biology research. The peptide allows scientists to explore ligand–receptor interactions and evaluate how modifications to peptide structure influence signaling outcomes. Research applications commonly include: Investigation of APJ receptor pharmacology Analysis of structure–activity relationships within apelin peptides Characterization of receptor signaling dynamics Development of experimental models for cardiovascular signaling pathways Through these studies, [Pyr¹]-Apelin-13 contributes to a deeper understanding of peptide-mediated receptor signaling. Conclusion [Pyr¹]-Apelin-13 is a pyroglutamylated form of apelin-13 that combines strong receptor affinity with enhanced stability against enzymatic degradation. As an active ligand of the APJ receptor, it plays a valuable role in research focused on the apelin signaling pathway. Its ability to reliably activate APJ signaling makes it widely used in studies investigating cardiovascular physiology, vascular regulation, receptor pharmacology, and peptide signaling mechanisms. As interest in the apelin–APJ system continues to expand, [Pyr¹]-Apelin-13 remains an important research peptide for exploring the molecular and physiological processes that govern cardiovascular function.