MedKoo Cat#: 597529 | Name: F-Chemotactic peptide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

F-Chemotactic peptide is a potent chemoattractant for human neutrophils.

Chemical Structure

F-Chemotactic peptide
F-Chemotactic peptide
CAS#71901-21-8

Theoretical Analysis

MedKoo Cat#: 597529

Name: F-Chemotactic peptide

CAS#: 71901-21-8

Chemical Formula: C43H65N7O9

Exact Mass: 823.4844

Molecular Weight: 824.03

Elemental Analysis: C, 62.68; H, 7.95; N, 11.90; O, 17.47

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Synonym
F-Chemotactic peptide; FNLPNTL; FNLELFNLRYK; F-Peptide; Cho-nle-leu-phe-nle-tyr-lys; N-Formyl hexapeptide;
IUPAC/Chemical Name
((S)-2-((S)-2-((S)-2-((S)-2-formamidohexanamido)-4-methylpentanamido)-3-phenylpropanamido)hexanoyl)-L-tyrosyl-L-lysine
InChi Key
XZMLMTGOWVWIRV-DUGSHLAESA-N
InChi Code
InChI=1S/C43H65N7O9/c1-5-7-16-32(45-27-51)38(53)48-35(24-28(3)4)40(55)50-36(25-29-14-10-9-11-15-29)41(56)46-33(17-8-6-2)39(54)49-37(26-30-19-21-31(52)22-20-30)42(57)47-34(43(58)59)18-12-13-23-44/h9-11,14-15,19-22,27-28,32-37,52H,5-8,12-13,16-18,23-26,44H2,1-4H3,(H,45,51)(H,46,56)(H,47,57)(H,48,53)(H,49,54)(H,50,55)(H,58,59)/t32-,33-,34-,35-,36-,37-/m0/s1
SMILES Code
NCCCC[C@@H](C(O)=O)NC([C@H](CC1=CC=C(O)C=C1)NC([C@H](CCCC)NC([C@H](CC2=CC=CC=C2)NC([C@H](CC(C)C)NC([C@H](CCCC)NC=O)=O)=O)=O)=O)=O
Appearance
Solid powder
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 824.03 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.

Recalculate based on batch purity %
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: Wass JA, Varani J, Piontek GE, Ward PA, Orr FW. Responses of normal and malignant cells to collagen, collagen-derived peptides and the C5-related tumor cell chemotactic peptide. Cell Differ. 1981 Dec;10(6):329-32. PubMed PMID: 7317948. 2: Niggli V. Microtubule-disruption-induced and chemotactic-peptide-induced migration of human neutrophils: implications for differential sets of signalling pathways. J Cell Sci. 2003 Mar 1;116(Pt 5):813-22. PubMed PMID: 12571279. 3: Jiang MS, Corley EG, Wagner HN Jr, Tsan MF. Localization of abscess with an iodinated synthetic chemotactic peptide. Nuklearmedizin. 1982 Jun;21(3):110-3. PubMed PMID: 7150425. 4: Malech HL, Gardner JP, Heiman DF, Rosenzweig SA. Asparagine-linked oligosaccharides on formyl peptide chemotactic receptors of human phagocytic cells. J Biol Chem. 1985 Feb 25;260(4):2509-14. PubMed PMID: 3919002. 5: Sklar LA, Oades ZG, Jesaitis AJ, Painter RG, Cochrane CG. Fluoresceinated chemotactic peptide and high-affinity antifluorescein antibody as a probe of the temporal characteristics of neutrophil stimulation. Proc Natl Acad Sci U S A. 1981 Dec;78(12):7540-4. PubMed PMID: 7038681; PubMed Central PMCID: PMC349304. 6: Braun MC, Wang JM, Lahey E, Rabin RL, Kelsall BL. Activation of the formyl peptide receptor by the HIV-derived peptide T-20 suppresses interleukin-12 p70 production by human monocytes. Blood. 2001 Jun 1;97(11):3531-6. PubMed PMID: 11369647. 7: Niedel J, Davis J, Cuatrecasas P. Covalent affinity labeling of the formyl peptide chemotactic receptor. J Biol Chem. 1980 Aug 10;255(15):7063-6. PubMed PMID: 7391068. 8: Gardner JP, Melnick DA, Malech HL. Characterization of the formyl peptide chemotactic receptor appearing at the phagocytic cell surface after exposure to phorbol myristate acetate. J Immunol. 1986 Feb 15;136(4):1400-5. PubMed PMID: 3511145. 9: Schmitt M, Kanayama N, Henschen A, Hollrieder A, Hafter R, Gulba D, Jänicke F, Graeff H. Elastase released from human granulocytes stimulated with N-formyl-chemotactic peptide prevents activation of tumor cell prourokinase (pro-uPA). FEBS Lett. 1989 Sep 11;255(1):83-8. PubMed PMID: 2529137. 10: Hauert AB, Martinelli S, Marone C, Niggli V. Differentiated HL-60 cells are a valid model system for the analysis of human neutrophil migration and chemotaxis. Int J Biochem Cell Biol. 2002 Jul;34(7):838-54. PubMed PMID: 11950599. 11: Bonser RW, Siegel MI, McConnell RT, Cuatrecasas P. Chemotactic peptide stimulated endogenous arachidonic acid metabolism in HL-60 granulocytes. Biochem Biophys Res Commun. 1981 Oct 30;102(4):1269-75. PubMed PMID: 6797423. 12: Stenfeldt AL, Karlsson J, Wennerås C, Bylund J, Fu H, Dahlgren C. The non-steroidal anti-inflammatory drug piroxicam blocks ligand binding to the formyl peptide receptor but not the formyl peptide receptor like 1. Biochem Pharmacol. 2007 Oct 1;74(7):1050-6. Epub 2007 Jul 7. PubMed PMID: 17692291. 13: Glinski W, Anhalt T, Mansbridge JN. Reduced expression of surface receptors for synthetic N-formylated chemotactic oligopeptides by stimulated peripheral blood neutrophils in psoriasis. J Invest Dermatol. 1987 Nov;89(5):523-8. PubMed PMID: 3668297. 14: Ryder MI. Nicotine effects on neutrophil F-actin formation and calcium release: implications for tobacco use and pulmonary diseases. Exp Lung Res. 1994 Jul-Aug;20(4):283-96. PubMed PMID: 7988493. 15: Niedel J, Kahane I, Lachman L, Cuatrecasas P. A subpopulation of cultured human promyelocytic leukemia cells (HL-60) displays the formyl peptide chemotactic receptor. Proc Natl Acad Sci U S A. 1980 Feb;77(2):1000-4. PubMed PMID: 6928654; PubMed Central PMCID: PMC348411. 16: Lane TA, Lamkin GE. Myeloperoxidase-mediated modulation of chemotactic peptide binding to human neutrophils. Blood. 1983 Jun;61(6):1203-7. PubMed PMID: 6301583. 17: Stark B, Kahane I. Cord blood polymorphonuclear leukocyte chemotaxis. Differential response to formyl peptide and endotoxin-activated serum. Isr J Med Sci. 1983 Jan;19(1):34-9. PubMed PMID: 6339439. 18: Remes JJ, Petäjä-Repo UE, Tuukkanen KJ, Rajaniemi HJ. Significance of the extracellular domain and the carbohydrates of the human neutrophil N-formyl peptide chemotactic receptor for the signal transduction by the receptor. Exp Cell Res. 1993 Nov;209(1):26-32. PubMed PMID: 8224002. 19: Zigmond SH, Levitsky HI, Kreel BJ. Cell polarity: an examination of its behavioral expression and its consequences for polymorphonuclear leukocyte chemotaxis. J Cell Biol. 1981 Jun;89(3):585-92. PubMed PMID: 7251666; PubMed Central PMCID: PMC2111809. 20: Vaidyanathan G, Zalutsky MR. Fluorine-18 labeled chemotactic peptides: a potential approach for the PET imaging of bacterial infection. Nucl Med Biol. 1995 Aug;22(6):759-64. PubMed PMID: 8535336.