All Photos(4)

F3506

Sigma-Aldrich

N-Formyl-Met-Leu-Phe

≥97% (HPLC)

Synonym(s):
Chemotactic peptide, fMLP (misnomer but widely used), fMLF, N-Formyl-L-methionyl-L-leucyl-L-phenylalanine
Empirical Formula (Hill Notation):
C21H31N3O5S
CAS Number:
Molecular Weight:
437.55
Beilstein:
2315783
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥97% (HPLC)

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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Amino Acid Sequence

NFor-Met-Leu-Phe

General description

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

Application

N-Formyl-Met-Leu-Phe has been used for:
  • creating gradients in Zigmond chamber chemotaxis assay performed on neutrophils
  • use in neutrophil chemotaix assay and
  • 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.

Packaging

50, 100, 500 mg in glass bottle
5, 10 mg in glass insert

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.
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.
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.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

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
Michael Hannigan et al.
Proceedings of the National Academy of Sciences of the United States of America, 99(6), 3603-3608 (2002-03-21)
Confocal imaging and time-lapsed videomicroscopy were used to study the directionality, motility, rate of cell movement, and morphologies of phosphoinositide 3-kinase gamma (PI3K)gamma(-/-) neutrophils undergoing chemotaxis in Zigmond chambers containing N-formyl-Met-Leu-Phe gradients. Most of the PI3Kgamma(-/-) neutrophils failed to translocate
Masoud Nasri et al.
Haematologica, 105(3), 598-609 (2019-06-30)
A Autosomal-dominant ELANE mutations are the most common cause of severe congenital neutropenia. Although the majority of congenital neutropenia patients respond to daily granulocyte colony stimulating factor, approximately 15 % do not respond to this cytokine at doses up to

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