N-Formyl-Met-Leu-Phe (Synonyms: Chemotactic Peptide, fMLF, fMLP, NSC 350593) |
| Katalog-Nr.GC16673 |
N-Formyl-Met-Leu-Phe (fMLP; N-Formyl-MLF) ist ein chemotaktisches Peptid und ein spezifischer Ligand des N-Formyl-Peptid-Rezeptors (FPR).
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 59880-97-6
Sample solution is provided at 25 µL, 10mM.
N-Formyl-Met-Leu-Phe (fMLP) is an endogenous chemotactic peptide and an agonist of formyl peptide receptor 1 (FPR1) with a Ki value of 38 nM[1]. N-Formyl-Met-Leu-Phe activates various functions of neutrophils and monocytes by binding to G protein-coupled receptors, causing cell polarization, the production of reactive oxygen species, and the release of arachidonic acid metabolites. production and release of lysosomal enzymes[2]. N-Formyl-Met-Leu-Phe is a bacterial-derived peptide that synergizes with lipopolysaccharide to induce inflammatory responses through multiple signaling pathways[3].
In vitro, N-Formyl-Met-Leu-Phe (1μM) stimulated human osteoblasts for 1 hour, significantly increased the activities of intracellular PLC and PLD, increased the expression levels of Runx2 and COX2, and promoted the differentiation of cells into osteoblasts[4]. N-Formyl-Met-Leu-Phe (100nM) treated U937 cells, which enhanced intracellular Ca2+ signal transduction and hyperpolarized the cells[5]. N-Formyl-Met-Leu-Phe (10μM/ml) treated human neutrophils and stimulated the production of superoxide anions [6].
In vivo, N-Formyl-Met-Leu-Phe (1μM) treated newly fertilized zebrafish embryos and promoted bone development; N-Formyl-Met-Leu-Phe (50μM) treated rabbits with skull defects and promoted bone reconstruction[4]. N-Formyl-Met-Leu-Phe (1μM) treatment of mice increased leukocyte infiltration in the air sacs and aggravated air sac inflammation [7].
References:
[1]Mills J S, Miettinen H M, Cummings D, et al. Characterization of the binding site on the formyl peptide receptor using three receptor mutants and analogs of Met-Leu-Phe and Met-Met-Trp-Leu-Leu[J]. Journal of Biological Chemistry, 2000, 275(50): 39012-39017.
[2]Panaro M A, Mitolo V. Cellular responses to FMLP challenging: a mini-review[J]. Immunopharmacology and immunotoxicology, 1999, 21(3): 397-419.
[3]Chen L Y, Pan W W, Chen M, et al. Synergistic induction of inflammation by bacterial products lipopolysaccharide and fMLP: an important microbial pathogenic mechanism[J]. The Journal of Immunology, 2009, 182(4): 2518-2524.
[4]Shin M K, Jang Y H, Yoo H J, 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]. Journal of Biological Chemistry, 2011, 286(19): 17133-17143.
[5]Penna A, Stutzin A. KCa3. 1-dependent hyperpolarization enhances intracellular Ca2+ signaling induced by fMLF in differentiated U937 cells[J]. PLoS One, 2015, 10(9): e0139243.
[6]Chniguir A, Pintard C, Liu D, et al. Eugenol prevents fMLF-induced superoxide anion production in human neutrophils by inhibiting ERK1/2 signaling pathway and p47phox phosphorylation[J]. Scientific reports, 2019, 9(1): 18540.
[7]Cui Y, Hou X, Chen J, et al. Sesamin inhibits bacterial formylpeptide-induced inflammatory responses in a murine air-pouch model and in THP-1 human monocytes[J]. The Journal of nutrition, 2010, 140(2): 377-381.
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Cell experiment [1]: |
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Cell lines |
human MSCs |
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Preparation method |
MSCs were cultured in growth media or differentiated into osteoblasts for 12 days, labeled with [3H]myoinositol, pretreated with or without CysH (1μM) for 30 min, and treated with or without 1μm N-Formyl-Met-Leu-Phe for 1 h. PLC and PLD activity was then measured. |
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Reaction Conditions |
1μM; 1 h |
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Applications |
In differentiated cells, both basal and N-Formyl-Met-Leu-Phe stimulated PLC or PLD activity showed a significant increase, compared with undifferentiated cells. |
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Animal experiment [2]: |
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Animal models |
C57BL/6 mice |
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Preparation method |
1mL endotoxin-free normal saline containing 1μL DMSO or 1μL 1 mmol/L N-Formyl-Met-Leu-Phe was injected into the air pouch. Four hours after the injection, mice were killed by CO2 asphyxiation. The air pouches were washed with PBS containing 5mmol/L EDTA and 20kU/L heparin, and leukocytes recovered from the air pouches were counted by Wright's staining. |
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Dosage form |
1μM; injected into the air pouch |
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Applications |
In an air-pouch inflammation model, injection of N-Formyl-Met-Leu-Phe increased leukocyte infiltration more than in mice injected with vehicle. |
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References: [1]Shin M K, Jang Y H, Yoo H J, 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]. Journal of Biological Chemistry, 2011, 286(19): 17133-17143. [2]Cui Y, Hou X, Chen J, et al. Sesamin inhibits bacterial formylpeptide-induced inflammatory responses in a murine air-pouch model and in THP-1 human monocytes[J]. The Journal of nutrition, 2010, 140(2): 377-381. |
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| Cas No. | 59880-97-6 | SDF | |
| Überlieferungen | Chemotactic Peptide, fMLF, fMLP, NSC 350593 | ||
| Chemical Name | (S)-2-((S)-2-((S)-2-formamido-4-(methylthio)butanamido)-4-methylpentanamido)-3-phenylpropanoic acid | ||
| Canonical SMILES | O=C([C@H](CC(C)C)NC([C@H](CCSC)NC=O)=O)N[C@H](C(O)=O)CC1=CC=CC=C1 | ||
| Formula | C21H31N3O5S | M.Wt | 437.55 |
| Löslichkeit | DMF: 25 mg/mL,DMSO: 30 mg/mL,Ethanol: 0.5 mg/mL,PBS (pH 7.2): 0.1 mg/mL | Storage | Desiccate at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.2855 mL | 11.4273 mL | 22.8545 mL |
| 5 mM | 0.4571 mL | 2.2855 mL | 4.5709 mL |
| 10 mM | 0.2285 mL | 1.1427 mL | 2.2855 mL |
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
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Quality Control & SDS
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- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 7 reference(s) in Google Scholar.)
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