N-Formyl-Met-Leu-Phe
SIGMA/F3506 - ≥97% (HPLC)
Synonym: Chemotactic peptide; N-Formyl-L-methionyl-L-leucyl-L-phenylalanine; fMLF; fMLP (misnomer but widely used)
CAS Number: 59880-97-6
Empirical Formula (Hill Notation): C21H31N3O5S
Molecular Weight: 437.55
MDL Number: MFCD00036780
Linear Formula: C21H31N3O5S
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: F3506-100MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: F3506-500MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: F3506-50MG
| assay | ≥97% (HPLC) |
| form | powder |
| InChI | 1S/C21H31N3O5S/c1-14(2)11 |
| InChI key | PRQROPMIIGLWRP-BZSNNMDCSA |
| mol wt | 437.55 |
| Quality Level | 100  |
| SMILES string | CSCC[C@H](NC=O)C(=O)N[C@@ |
| solubility | acetic acid: 20 mg/mL, clear, colorless |
| storage condition | (Keep container tightly closed in a dry and well-ventilated place) |
| storage temp. | −20°C |
| technique(s) | activity assay: suitable |
| Amino Acid Sequence: | NFor-Met-Leu-Phe |
| Application: | N-Formyl-Met-Leu-Phe has been used for: • creating gradients in Zigmond chamber chemotaxis assay performed on neutrophils • neutrophil chemotaxis assay • 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. |
| 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. It acts as an inflammatory agent and activates polymorphonuclear leukocytes (PMNs) without the formation of 5-hydroxyicosatetraenoic acid (5-HETE) and leukotriene B4 (LTB4). Its effects on neutrophils and the inhibition of adenylate cyclase are inhibited by pertussis toxin. |
| Biochem/physiol Actions: | 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. |
| Biochem/physiol Actions: | 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. |
| General description: | N-Formyl-Met-Leu-Phe is a chemotactic peptide, which functions on polymorphonuclear leukocytes (PMN), neutrophils etc. Research area: Cell signaling |
| Packaging: | 5, 10 mg in glass insert |
| Packaging: | 50, 100, 500 mg in glass bottle |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥97% (HPLC) |
| Storage Temp. | −20°C |
| UNSPSC | 12352200 |