A peptide agonist of FPRs
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N-Formyl-Met-Leu-Phe

Item No. 21495

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-formyl-L-methionyl-L-leucyl-L-phenylalanine
CAS Number
59880-97-6
Synonyms
  • Chemotactic Peptide
  • fMLF
  • fMLP
  • NSC 350593
Molecular Formula
C21H31N3O5S
Formula Weight
437.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 30 mg/mlEthanol: 0.5 mg/mlPBS (pH 7.2): 0.1 mg/ml
SMILES
O=C(O)[C@@H](N([H])C([C@@H](N(C([C@@H](N(C=O)[H])CCSC)=O)[H])CC(C)C)=O)CC1=CC=CC=C1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

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    Cayman Chemical
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    Product Description

    N-Formyl-Met-Leu-Phe (fMLF) is a synthetic peptide that acts as an agonist at formyl peptide receptors (FPRs; Ki = 0.8 pM), which are mainly localized on polymorphonuclear and mononuclear phagocytes.1 Activation of FPRs by fMLF leads to cellular activation, which is characterized by cellular polarization, chemotaxis, and release of proteolytic enzymes.2 fMLF induces contractions in isolated guinea pig jejunum (EC50 = 11 nM), proximal colon (EC50 = 3.5 nM), and distal colon (EC50 = 2.2 nM).3 In vitro, fMLF induces neurotransmitter release from enteric motor neurons.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Panaro, M.A., Acquafreddo, A., Sisto, M., et al. Biological role of the N-formyl peptide receptors. Immunopharmacol. Immunotoxicol. 28(1), 103-127 (2006).

    2. Wang, W., Li, T., Wang, X., et al. FAM19A4 is a novel cytokine ligand of formyl peptide receptor 1 (FPR1) and is able to promote the migration and phagocytosis of macrophages. Cell. Mol. Immunol. 12(5), 615-624 (2015).

    3. Colucci, M., Mastriota, M., Maione, F., et al. Guinea pig ileum motility stimulation elicited by N-formyl-Met-Leu-Phe (fMLF) involves neurotransmitters and prostanoids. Peptides 32(2), 266-271 (2011).