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F3506

Sigma-Aldrich

N-Formyl-Met-Leu-Phe

≥97% (HPLC)

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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:
Molecular Weight:
437.55
Beilstein/REAXYS Number:
2315783
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

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)

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P1319S6135F5135
N-Formyl-Met-Leu-Phe ≥97% (HPLC)

F3506

N-Formyl-Met-Leu-Phe

Thyrotropin releasing hormone ≥98% (HPLC), powder

P1319

Thyrotropin releasing hormone

Somatostatin 28 ≥97% (HPLC)

S6135

Somatostatin 28

technique(s)

activity assay: suitable

technique(s)

activity assay: suitable

technique(s)

activity assay: suitable

technique(s)

-

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

-

Gene Information

human ... FPR1(2357)

Gene Information

human ... TRH(7200), TRHR(7201)
mouse ... Trhr(22045)

Gene Information

human ... SST(6750)

Gene Information

mouse ... Prkcq(18761)

storage condition

(Keep container tightly closed in a dry and well-ventilated place)

storage condition

(Keep container tightly closed in a dry and well-ventilated place)

storage condition

(Keep container tightly closed in a dry and well-ventilated place)

storage condition

-

Amino Acid Sequence

NFor-Met-Leu-Phe

General description

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

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
  • 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.
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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Pertussis toxin inhibits the N-formyl-Met-Leu-Phe (fMet-Leu-Phe) mediated human neutrophil functions of enzyme release, superoxide generation, aggregation, and chemotaxis. As pertussis toxin modifies the GTP binding receptor-regulatory protein "Ni," the association of the fMet-Leu-Phe receptor with such a protein was further

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