F3506

N-Formyl-Met-Leu-Phe

≥97% (HPLC)

• Synonym(s): Chemotactic peptide, N-Formyl-L-methionyl-L-leucyl-L-phenylalanine, fMLF, fMLP (misnomer but widely used)
• Empirical Formula (Hill Notation): C₂₁H₃₁N₃O₅S
• CAS Number: 59880-97-6
• Molecular Weight: 437.55
• UNSPSC Code: 12352200
• NACRES: NA.32
• PubChem Substance ID: 24894846
• MDL number: MFCD00036780
• Beilstein/REAXYS Number: 2315783

Properties

• Quality Segment: 100
• assay: ≥97% (HPLC)
• form: powder
• mol wt: 437.55
• storage condition: (Keep container tightly closed in a dry and well-ventilated place)
• technique(s): activity assay: suitable
• solubility: acetic acid: 20 mg/mL, clear, colorless
• storage temp.: −20°C
• SMILES string: CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(O)=O
• InChI: 1S/C21H31N3O5S/c1-14(2)11-17(23-19(26)16(22-13-25)9-10-30-3)20(27)24-18(21(28)29)12-15-7-5-4-6-8-15/h4-8,13-14,16-18H,9-12H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)(H,28,29)/t16-,17-,18-/m0/s1
• InChI key: PRQROPMIIGLWRP-BZSNNMDCSA-N
• Gene Information: human ... FPR1(2357)

Description

General description

N-Formyl-Met-Leu-Phe is a chemotactic peptide, which functions on polymorphonuclear leukocytes (PMN), neutrophils etc.[1][2]

Research area: Cell signaling

Application

N-Formyl-Met-Leu-Phe has been used for:

• creating gradients in Zigmond chamber chemotaxis assay performed on neutrophils
• neutrophil chemotaxis assay[3]
• determination of the involvement of MAPK-activating protein kinase-2 (MAPKAPK-2) and/or p38, in the signaling pathway of human polymorphonuclear leukocytes (PMNs) stimulated by N-Formyl-Met-Leu-Phe.[1]

Biochem/physiol Actions

N-Formyl-Met-Leu-Phe induced chemotaxis in phosphoinositide 3-kinase γ (PI3K)γ^-/- neutrophils, and promotes adhesion, polymerization of F-actin, Fcγ receptor-mediated phagocytosis and intracellular Ca²⁺ release.[2] It acts as an inflammatory agent and activates polymorphonuclear leukocytes (PMNs) without the formation of 5-hydroxyicosatetraenoic acid (5-HETE) and leukotriene B₄ (LTB₄).[4] Its effects on neutrophils and the inhibition of adenylate cyclase are inhibited by pertussis toxin.[3]

Potent chemotactic peptide. Induces a metabolic burst in macrophages accompanied by an increase in respiratory rate, secretion of lysosomal enzymes, and production of superoxide anion.

Potent inducer of leucocyte chemotaxis and macrophage activator. Receptors that bind formylpeptides are found on phagocytic neutrophils and have recently been identified on cells of the intestinal mucosa.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)