Synonym
Chemotactic peptide; N-Formyl-Met-Leu-Phe, FMLP; fMLF.
IUPAC/Chemical Name
N-Formylmethionyl-leucylphenylalanine
InChi Key
PRQROPMIIGLWRP-BZSNNMDCSA-N
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
SMILES Code
O=C(O)[C@H](CC1=CC=CC=C1)NC([C@H](CC(C)C)NC([C@H](CCSC)NC=O)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
437.56
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Hu Y, Cheng N, Wu H, Kang S, Ye RD, Cai J. Design, synthesis and characterization of fMLF-mimicking AApeptides. Chembiochem. 2014 Nov 3;15(16):2420-6. doi: 10.1002/cbic.201402396. Epub 2014 Sep 15. PubMed PMID: 25224835; PubMed Central PMCID: PMC4259043.
2: He HQ, Liao D, Wang ZG, Wang ZL, Zhou HC, Wang MW, Ye RD. Functional characterization of three mouse formyl peptide receptors. Mol Pharmacol. 2013 Feb;83(2):389-98. doi: 10.1124/mol.112.081315. Epub 2012 Nov 15. PubMed PMID: 23160941; PubMed Central PMCID: PMC4170117.
3: Zhang XG, Hui YN, Huang XF, Du HJ, Zhou J, Ma JX. Activation of formyl peptide receptor-1 enhances restitution of human retinal pigment epithelial cell monolayer under electric fields. Invest Ophthalmol Vis Sci. 2011 May 16;52(6):3160-5. doi: 10.1167/iovs.10-5156. PubMed PMID: 21228377.
4: Sogawa Y, Ohyama T, Maeda H, Hirahara K. Inhibition of neutrophil migration in mice by mouse formyl peptide receptors 1 and 2 dual agonist: indication of cross-desensitization in vivo. Immunology. 2011 Mar;132(3):441-50. doi: 10.1111/j.1365-2567.2010.03367.x. Epub 2010 Oct 29. PubMed PMID: 21039475; PubMed Central PMCID: PMC3044910.
5: Movitz C, Brive L, Hellstrand K, Rabiet MJ, Dahlgren C. The annexin I sequence gln(9)-ala(10)-trp(11)-phe(12) is a core structure for interaction with the formyl peptide receptor 1. J Biol Chem. 2010 May 7;285(19):14338-45. doi: 10.1074/jbc.M109.080465. Epub 2010 Mar 10. PubMed PMID: 20220135; PubMed Central PMCID: PMC2863206.
6: Southgate EL, He RL, Gao JL, Murphy PM, Nanamori M, Ye RD. Identification of formyl peptides from Listeria monocytogenes and Staphylococcus aureus as potent chemoattractants for mouse neutrophils. J Immunol. 2008 Jul 15;181(2):1429-37. PubMed PMID: 18606697; PubMed Central PMCID: PMC2705627.
7: Zhou C, Zhang S, Nanamori M, Zhang Y, Liu Q, Li N, Sun M, Tian J, Ye PP, Cheng N, Ye RD, Wang MW. Pharmacological characterization of a novel nonpeptide antagonist for formyl peptide receptor-like 1. Mol Pharmacol. 2007 Oct;72(4):976-83. Epub 2007 Jul 25. Erratum in: Mol Pharmacol. 2007 Nov;72(5):1391. PubMed PMID: 17652444.
