F3681

2-Furoyl-LIGRLO-amide trifluoroacetate salt

≥97% (HPLC)

• Synonym(s): 2-Fly, 2-Furoyl-Leu-Ile-Gly-Arg-Leu-Orn-NH2 trifluoroacetate salt, 2-f-LIGRLO-NH2, 2-fAP, 2fLI, f-LIGRLO-NH2
• Empirical Formula (Hill Notation): C₃₆H₆₃N₁₁O₈ · xC₂HF₃O₂
• CAS Number: 729589-58-6
• Molecular Weight: 777.95 (free base basis)
• MDL number: MFCD03821022
• UNSPSC Code: 51111800
• PubChem Substance ID: 329799702
• NACRES: NA.32

Properties

• assay: ≥97% (HPLC)
• form: lyophilized powder
• color: white
• storage temp.: −20°C
• SMILES string: Cc1cc(C)c2c(N)c(sc2n1)C(=O)NCc3ccc(Cl)cc3
• InChI: 1S/C17H16ClN3OS/c1-9-7-10(2)21-17-13(9)14(19)15(23-17)16(22)20-8-11-3-5-12(18)6-4-11/h3-7H,8,19H2,1-2H3,(H,20,22)
• InChI key: FPRULFHDSFKYBV-UHFFFAOYSA-N

Description

General description

2-Furoyl-LIGRLO-amide trifluoroacetate salt is a peptide that acts as a proteinase-activated receptor-2 (PAR₂) agonist, and contains a furoyl group addition at its N-terminal.

Application

2-Furoyl-LIGRLO-amide trifluoroacetate salt may be used as a protease-activated receptor 2 (PAR2) agonist in endothelial progenitor cells (EPCs) and in transient receptor potential cation channel subfamily V member (TRPV4)-transfected HEK293t cells.

Biochem/physiol Actions

2-Furoyl-LIGRLO-amide is a potent and selective protease-activated receptor 2 (PAR2) agonist. PAR-2 activation is associated with increases in cAMP and intracellular Ca(2+). Immunoblot analysis revealed increases in phosphorylation of epidermal growth factor (EGF) receptor (EGFR) tyrosine kinase, Src, Pyk2, cRaf, and ERK1/2 in response to PAR-2 activation. 2-Furoyl-LIGRLO-amide is nearly 100-fold more potent than SLIGRL-NH2 (Cat. No. S9317). 2-Furoyl-LIGRLO-amide caused both an endothelium-dependent relaxation and an endothelium-independent contraction. It produced delayed (6 hours later) facilitation of capsaicin-evoked visceral nociception, an effect being much more potent than SLIGRL-NH2. Such effects were mimicked by i.col. trypsin. 2-f-LIGRL-NH2, coadministered repeatedly with caerulein six times in total, abolished the caerulein-evoked abdominal hyperalgesia/allodynia in WT, but not PAR2-KO, mice. Repeated doses of 2-f-LIGRL-NH2 moderately attenuated the severity of caerulein-induced pancreatitis in WT animals. It induced a similar dose-dependent increase in Ca2 levels in the presence and absence of b-arrestins.

2-Furoyl-LIGRLO-amide trifluoroacetate salt is a highly potent agonist of proteinase-activated receptor-2 (PAR₂). In KNRK cells with high number of PAR₂ receptors, this agonist causes elevation of intracellular Ca²⁺ levels. Studies on rat show that it causes the relaxation of aorta rings in an endothelium-dependent manner.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves