F3506

N-Formyl-Met-Leu-Phe

≥97% (HPLC)

• Sinónimos: Chemotactic peptide, N-Formyl-L-methionyl-L-leucyl-L-phenylalanine, fMLF, fMLP (misnomer but widely used)
• Fórmula empírica (notación de Hill): C₂₁H₃₁N₃O₅S
• Número de CAS: 59880-97-6
• Peso molecular: 437.55
• Beilstein: 2315783
• Número MDL: MFCD00036780
• Código UNSPSC: 12352200
• ID de la sustancia en PubChem: 24894846
• NACRES: NA.32

Propiedades

• Ensayo: ≥97% (HPLC)
• Formulario: powder
• mol peso: 437.55
• condiciones de almacenamiento: (Keep container tightly closed in a dry and well-ventilated place)
• técnicas: activity assay: suitable
• solubilidad: acetic acid: 20 mg/mL, clear, colorless
• temp. de almacenamiento: −20°C
• cadena SMILES: 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
• Clave InChI: PRQROPMIIGLWRP-BZSNNMDCSA-N
• Información sobre el gen: human ... FPR1(2357)

Descripción

Amino Acid Sequence

NFor-Met-Leu-Phe

Descripción general

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

Research area: Cell signaling

Aplicación

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]

Acciones bioquímicas o fisiológicas

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.

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Gloves, type N95 (US)