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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)

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About This Item

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
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Quality Level

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)

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX7635
MKCX0763
MKCV7798
MKCS7331
MKCR6637

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Carlos José Correia Santana et al.
Biomolecules, 10(5) (2020-05-24)
In recent years, the number of new antimicrobial drugs launched on the market has decreased considerably even though there has been an increase in the number of resistant microbial strains. Thus, antimicrobial resistance has become a serious public health problem.
E Krump et al.
The Journal of biological chemistry, 272(2), 937-944 (1997-01-10)
Activation of polymorphonuclear leukocytes (PMN) by chemotactic peptides initiates a series of functional responses that serve to eliminate pathogens. The intermediate steps that link engagement of the chemoattractant receptor to the microbicidal responses involve protein kinases that have yet to
P M Lad et al.
Proceedings of the National Academy of Sciences of the United States of America, 82(3), 869-873 (1985-02-01)
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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