For-Met-Leu-Phe-OH

Modify Date: 2024-01-09 20:13:57

For-Met-Leu-Phe-OH Structure
For-Met-Leu-Phe-OH structure
 Common Name For-Met-Leu-Phe-OH
CAS Number 59880-97-6 Molecular Weight 437.553
Density 1.2±0.1 g/cm3 Boiling Point 783.5±60.0 °C at 760 mmHg
Molecular Formula C21H31N3O5S Melting Point 271-274 °C(lit.)
MSDS USA Flash Point 427.6±32.9 °C

 Use of For-Met-Leu-Phe-OH


N-Formyl-Met-Leu-Phe (fMLP; N-Formyl-MLF) is a chemotactic peptide and a specific ligand of N-formyl peptide receptor (FPR). N-Formyl-Met-Leu-Ph is reported to inhibit TNF-alpha secretion.

 Names

Name N-formyl-L-methionyl-L-leucyl-L-phenylalanine
Synonym More Synonyms

 For-Met-Leu-Phe-OH Biological Activity

Description N-Formyl-Met-Leu-Phe (fMLP; N-Formyl-MLF) is a chemotactic peptide and a specific ligand of N-formyl peptide receptor (FPR). N-Formyl-Met-Leu-Ph is reported to inhibit TNF-alpha secretion.
Related Catalog
Target

TNF-alpha[1]
In Vitro Binding of N-Formyl-Met-Leu-Phe to its specific cell surface receptor, N-formyl peptide receptor (FPR), triggers different cascades of biochemical events, eventually leading to cellular activation. FPR is a chemoattractant receptor belonging to the G protein-coupled receptor family. N-Formyl-Met-Leu-Phe promotes osteoblastic commitment and suppresses adipogenic commitment under osteoblastic differentiation conditions. N-Formyl-Met-Leu-Phe stimulates osteogenesis is associated with increased expression of osteogenic markers and mineralization. N-Formyl-Met-Leu-Phe inhibits expression of peroxisome proliferator-activated receptor-γ1. N-Formyl-Met-Leu-Phe-stimulated osteogenic differentiation is mediated via FPR1-phospholipase C/phospholipase D-Ca2+-calmodulin-dependent kinase II-ERK-CREB signaling pathways[1]. N-Formyl-Met-Leu-Phe, a bacterial-derived peptide, induced proinflammatory cytokine gene expression in human peripheral blood monocytes. Bacterial products LPS and N-Formyl-Met-Leu-Phe synergistically induce inflammatory response via multiple signaling pathways. TLR4, IKKβ-IκBα, and NF-κB signaling pathways are involved in the synergistic induction of TNF-α via p65 nuclear translocation-dependent mechanisms[2].
In Vivo N-Formyl-Met-Leu-Phe promotes bone formation in zebrafish and rabbits. Extensive skeletal development is evident at 5 dpf in over 80% of N-Formyl-Met-Leu-Phe-treated zebrafish. Treatment with N-Formyl-Met-Leu-Phe results in increased expression of Runx2. Bone marrow spaces are widely formed, and connective tissue covering bone is dense, like periosteum, in N-Formyl-Met-Leu-Phe-treated calvaria[1]. N-Formyl-Met-Leu-Phe mediate release of calprotectin from PMN in vitro. It induces release of calprotectin from PMN in a dose dependent manner. A minimum of 10% of total PMN calprotectin is retained at concentrations of 0.1-10.0 nM of N-Formyl-Met-Leu-Phe[3].
Cell Assay Cells are cotransfected with either a dominant negative form of IκBα or a dominant negative form of IKKβ together with the NF-κB-dependent luciferase reporter plasmid. The plasmid pCMVβ is used as a control for transfection efficiency and this is monitored via the expression of β-galactosidase. Cells are transiently transfected with plasmids using DEAE-dextran. The transfected cells are cultivated for 48 h before a 6-h incubation in medium ±N-Formyl-Met-Leu-Phe, LPS, or N-Formyl-Met-Leu-Phe/LPS. Luciferase activity is determined by using the luciferase assay kit and a Monolight 3010 luminometer[2].
Animal Admin Mice: N-Formyl-Met-Leu-Phe is prepared in sterile PBS. Under the anesthesia, mice are intranasally treated with LPS (0.3 mg/kg) or N-Formyl-Met-Leu-Phe (0.5 mg/kg) or N-Formyl-Met-Leu-Phe and LPS in 50 μL of sterile PBS (control), BAL is performed by cannulating the trachea with sterilized PBS, and cells from BAL fluid are stained with Wright-Giemsa stain after cytocentrifuge. For TNF-α protein release, BAL fluid is collected and secreted TNF-α is measured by ELISA as described above[2].
References

[1]. Shin MK, et al. N-formyl-methionyl-leucyl-phenylalanine (fMLP) promotes osteoblast differentiation via the N-formyl peptide receptor 1-mediated signaling pathway in human mesenchymal stem cells from bone marrow. J Biol Chem. 2011 May 13;286(19):17133-43.

[2]. Chen LY, et al. Synergistic induction of inflammation by bacterial products lipopolysaccharide and fMLP: an important microbial pathogenic mechanism. J Immunol. 2009 Feb 15;182(4):2518-24.

[3]. Hetland G, et al. Chemotaxins C5a and fMLP induce release of calprotectin (leucocyte L1 protein) from polymorphonuclear cells in vitro. Mol Pathol. 1998 Jun;51(3):143-8.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 783.5±60.0 °C at 760 mmHg
Melting Point 271-274 °C(lit.)
Molecular Formula C21H31N3O5S
Molecular Weight 437.553
Flash Point 427.6±32.9 °C
Exact Mass 437.198456
PSA 149.90000
LogP 3.13
Vapour Pressure 0.0±2.9 mmHg at 25°C
Index of Refraction 1.551
Storage condition 2-8°C
Water Solubility DMF: 50 mg/mL, clear, colorless

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases S26-S36-S22
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS SJ6050000
HS Code 2922299090

 Synthetic Route

 Customs

HS Code 2922299090
Summary 2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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 Synonyms

N-Formyl-Met-Leu-Phe
formyl-Met-Leu-Phe
N-formyl-methionyl-leucyl-phenylalanine
L-Phenylalanine, N-(N-(N-formyl-L-methionyl)-L-leucyl)-
Chemotactic peptide
formyl-MLF
MFCD00012901
N-Formyl-L-methionyl-L-leucyl-L-phenylalanine
N-Formylmethionine leucyl-phenylalanine
EINECS 200-462-5
L-Phenylalanine, N-formyl-L-methionyl-L-leucyl-
N-formyl-L-methyonyl-L-leucyl-L-phenylalanine
NformylLmethionylLleucylLphenylalaninol
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