F3506
N-Formyl-Met-Leu-Phe
≥97% (HPLC)
동의어(들):
Chemotactic peptide, N-Formyl-L-methionyl-L-leucyl-L-phenylalanine, fMLF, fMLP (misnomer but widely used)
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크기 선택
제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C21H31N3O5S
CAS 번호:
Molecular Weight:
437.55
UNSPSC Code:
12352200
NACRES:
NA.32
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2315783
form
powder
InChI key
PRQROPMIIGLWRP-BZSNNMDCSA-N
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
assay
≥97% (HPLC)
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
Quality Level
Gene Information
human ... FPR1(2357)
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General description
N-Formyl-Met-Leu-Phe is a chemotactic peptide, which functions on polymorphonuclear leukocytes (PMN), neutrophils etc.
Research area: Cell signaling
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.
저장 등급
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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.
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
Ildefonso M De la Fuente et al.
Nature communications, 10(1), 3690-3690 (2019-08-17)
Associative memory is the main type of learning by which complex organisms endowed with evolved nervous systems respond efficiently to certain environmental stimuli. It has been found in different multicellular species, from cephalopods to humans, but never in individual cells.
John A L Meeuwsen et al.
Cells, 9(2) (2020-02-23)
: Introduction: Preeclampsia (PE) represents a hypertensive pregnancy disorder that is associated with increased cardiovascular disease (CVD) risk. This increased risk has been attributed to accelerated atherosclerosis, with inflammation being a major contributor. Neutrophils play an important role in the
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