A9486

AG-09/1

≥98% (HPLC)

• Synonym(s): 2-[(6-methoxy-1H-benzimidazol-2-yl)thio]-N-(4-nitrophenyl)-acetamide
• Empirical Formula (Hill Notation): C₁₆H₁₄N₄O₄S
• CAS Number: 356776-32-4
• Molecular Weight: 358.37
• MDL number: MFCD02321063
• UNSPSC Code: 12352202
• PubChem Substance ID: 329771051
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• color: yellow to brown
• solubility: DMSO: ≥30 mg/mL
• storage temp.: 2-8°C
• SMILES string: COc1ccc2[nH]c(SCC(=O)Nc3ccc(cc3)[N+]([O-])=O)nc2c1
• InChI: 1S/C16H14N4O4S/c1-24-12-6-7-13-14(8-12)19-16(18-13)25-9-15(21)17-10-2-4-11(5-3-10)20(22)23/h2-8H,9H2,1H3,(H,17,21)(H,18,19)
• InChI key: LYQDSNOFTIZWAX-UHFFFAOYSA-N

Description

Biochem/physiol Actions

AG-09/1 is a selective formyl peptide receptor 1 (FPR1) agonist; it activates chemotaxis in human neutrophils. Formyl peptide recetors (FPRs) are GPCRs mainly expressed in phagocytic leukocytes but with lower expression in many other cell types. Formyl peptides, act as Alarmins and are released from bacteria and damaged mitochondria, serving as chemoattractants for phagocyte recruitment to sites of inflammation, resulting in immune response. Because the endogenous ligands for FPRs are peptides and arachidonic acid metabolites, there are few small molecule tools for these receptors. A recent HTS of commercially available libraries yielded several FPR-1 selective agonists, of which AG-091 was the most potent. AG-091 induced intracellular calcium flux in FPR-1- but not FPR-2-expressing cells. It also caused chemotaxis and intracellular calcium flux in human leukocytes. AG-091 is a valuable tool for studying FPR1 function in immune and other disease states.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H318
• Precautionary Statements: P280 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable