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187986-17-0,MFCD04974480
Catalog No.:AA002GIZ

187986-17-0 | D-Methioninamide, L-tryptophyl-L-lysyl-L-tyrosyl-L-methionyl-L-valyl-

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1mg
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5mg
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10mg
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25mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002GIZ
Chemical Name:
D-Methioninamide, L-tryptophyl-L-lysyl-L-tyrosyl-L-methionyl-L-valyl-
CAS Number:
187986-17-0
Molecular Formula:
C41H61N9O7S2
Molecular Weight:
856.1091
MDL Number:
MFCD04974480
SMILES:
CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N)CCSC)C(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)N)CCCCN
Properties
Computed Properties
 
Complexity:
1360  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Heavy Atom Count:
59  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
10  
Rotatable Bond Count:
26  
XLogP3:
1.5  

Literature

Title: Functional characterization of three mouse formyl peptide receptors.

Journal: Molecular pharmacology 20130201

Title: Airway activation of formyl peptide receptors inhibits Th1 and Th17 cell responses via inhibition of mediator release from immune and inflammatory cells and maturation of dendritic cells.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20120215

Title: A WKYMVm-containing combination elicits potent anti-tumor activity in heterotopic cancer animal model.

Journal: PloS one 20120101

Title: Stimulation of human formyl peptide receptors by calpain inhibitors: homology modeling of receptors and ligand docking simulation.

Journal: Archives of biochemistry and biophysics 20111215

Title: NADPH-oxidase-dependent reactive oxygen species mediate EGFR transactivation by FPRL1 in WKYMVm-stimulated human lung cancer cells.

Journal: Free radical biology & medicine 20110915

Title: Role(s) of formyl-peptide receptors expressed in nasal epithelial cells.

Journal: Journal of biological regulators and homeostatic agents 20110101

Title: Kinetic and thermodynamic analyses of adhesion of a peptide, Trp-Lys-Tyr-Met-Val-D-Met (WKYMVm), and human formyl peptide receptor (hFPR).

Journal: Biotechnology letters 20100601

Title: PKC-delta controls the fMLF-induced overproduction of superoxide by neutrophils.

Journal: Free radical biology & medicine 20100115

Title: Functional expression of formyl peptide receptor family in human NK cells.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20091101

Title: Lipoxin A(4) metabolites/analogues from two commercial sources have no effects on TNF-alpha-mediated priming or activation through the neutrophil formyl peptide receptors.

Journal: Scandinavian journal of immunology 20091001

Title: 6-methyl-2,4-disubstituted pyridazin-3(2H)-ones: a novel class of small-molecule agonists for formyl peptide receptors.

Journal: Journal of medicinal chemistry 20090827

Title: Oxygen radical production in leukocytes and disease severity in multiple sclerosis.

Journal: Journal of neuroimmunology 20090818

Title: JAM-A promotes neutrophil chemotaxis by controlling integrin internalization and recycling.

Journal: Journal of cell science 20090115

Title: Cyclosporin H, Boc-MLF and Boc-FLFLF are antagonists that preferentially inhibit activity triggered through the formyl peptide receptor.

Journal: Inflammation 20071201

Title: Oxygen radical production and severity of the Guillain--Barré syndrome.

Journal: Journal of neuroimmunology 20071201

Title: Formyl peptide receptor like 1 differentially requires mitogen-activated protein kinases for the induction of glial fibrillary acidic protein and interleukin-1alpha in human U87 astrocytoma cells.

Journal: Cellular signalling 20071001

Title: Pharmacological characterization of a novel nonpeptide antagonist for formyl peptide receptor-like 1.

Journal: Molecular pharmacology 20071001

Title: The non-steroidal anti-inflammatory drug piroxicam blocks ligand binding to the formyl peptide receptor but not the formyl peptide receptor like 1.

Journal: Biochemical pharmacology 20071001

Title: Discovery of Trp-Nle-Tyr-Met as a novel agonist for human formyl peptide receptor-like 1.

Journal: Biochemical pharmacology 20070715

Title: Protein kinase C-alpha and -delta are required for NADPH oxidase activation in WKYMVm-stimulated IMR90 human fibroblasts.

Journal: Archives of biochemistry and biophysics 20070315

Title: Differential production of leukotriene B4 or prostaglandin E2 by WKYMVm or serum amyloid A via formyl peptide receptor-like 1.

Journal: Biochemical pharmacology 20060928

Title: The peptide Trp-Lys-Tyr-Met-Val-D-Met activates neutrophils through the formyl peptide receptor only when signaling through the formylpeptide receptor like 1 is blocked. A receptor switch with implications for signal transduction studies with inhibitors and receptor antagonists.

Journal: Biochemical pharmacology 20060514

Title: Changes in activation states of murine polymorphonuclear leukocytes (PMN) during inflammation: a comparison of bone marrow and peritoneal exudate PMN.

Journal: Clinical and vaccine immunology : CVI 20060501

Title: Granulocyte function is stimulated by a novel hexapeptide, WKYMVm, in chemotherapy-treated cancer patients.

Journal: Experimental hematology 20060401

Title: The synthetic peptide Trp-Lys-Tyr-Met-Val-D-Met as a novel adjuvant for DNA vaccine.

Journal: Vaccine 20050907

Title: The immunostimulatory peptide WKYMVm-NH activates bone marrow mouse neutrophils via multiple signal transduction pathways.

Journal: Scandinavian journal of immunology 20050801

Title: The synthetic peptide Trp-Lys-Tyr-Met-Val-D-Met inhibits human monocyte-derived dendritic cell maturation via formyl peptide receptor and formyl peptide receptor-like 2.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20050715

Title: The synthetic chemoattractant peptide WKYMVm induces superoxide production by human eosinophils via the phosphoinositide 3-kinase-mediated activation of ERK1/2.

Journal: International archives of allergy and immunology 20050101

Title: Lysophosphatidic acid is a mediator of Trp-Lys-Tyr-Met-Val-d-Met-induced calcium influx.

Journal: Biochemical and biophysical research communications 20041105

Title: A novel nonpeptide ligand for formyl peptide receptor-like 1.

Journal: Molecular pharmacology 20041101

Title: Activation of formyl peptide receptor-like 1 by WKYMVm induces serine phosphorylation of STAT3, which inhibits its tyrosine phosphorylation and nuclear translocation induced by hydrogen peroxide.

Journal: Life sciences 20040917

Title: Agonist-induced trafficking of the low-affinity formyl peptide receptor FPRL1.

Journal: Cellular and molecular life sciences : CMLS 20040701

Title: The mechanism for activation of the neutrophil NADPH-oxidase by the peptides formyl-Met-Leu-Phe and Trp-Lys-Tyr-Met-Val-Met differs from that for interleukin-8.

Journal: Immunology 20040601

Title: Trp-Lys-Tyr-Met-Val-Met stimulates phagocytosis via phospho-lipase D-dependent signaling in mouse dendritic cells.

Journal: Experimental & molecular medicine 20040430

Title: Low-affinity receptor-mediated induction of superoxide by N-formyl-methionyl-leucyl-phenylalanine and WKYMVm in IMR90 human fibroblasts.

Journal: Free radical biology & medicine 20040115

Title: Differential activation of formyl peptide receptor-like 1 by peptide ligands.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20031215

Title: Membrane lipid microdomains differentially regulate intracellular signaling events in human neutrophils.

Journal: International immunopharmacology 20031201

Title: Differential activation of formyl peptide receptor signaling by peptide ligands.

Journal: Molecular pharmacology 20031001

Title: Differential signaling of formyl peptide receptor-like 1 by Trp-Lys-Tyr-Met-Val-Met-CONH2 or lipoxin A4 in human neutrophils.

Journal: Molecular pharmacology 20030901

Title: Histamine inhibits neutrophil NADPH oxidase activity triggered by the lipoxin A4 receptor-specific peptide agonist Trp-Lys-Tyr-Met-Val-Met.

Journal: Scandinavian journal of immunology 20030901

Title: NADPH-oxidase activation in murine neutrophils via formyl peptide receptors.

Journal: Experimental cell research 20030115

Title: Phagocyte activation by Trp-Lys-Tyr-Met-Val-Met, acting through FPRL1/LXA4R, is not affected by lipoxin A4.

Journal: Scandinavian journal of immunology 20021101

Title: The chemoattractant Trp-Lys-Tyr-Met-Val-D-Met activates eosinophils through the formyl peptide receptor and one of its homologues, formyl peptide receptor-like 1.

Journal: Journal of leukocyte biology 20021001

Title: Human dendritic cells express functional formyl peptide receptor-like-2 (FPRL2) throughout maturation.

Journal: Journal of leukocyte biology 20020901

Title: The synthetic chemoattractant peptide, Trp-Lys-Tyr-Met-Val-D-Met, enhances monocyte survival via PKC-dependent Akt activation.

Journal: Journal of leukocyte biology 20020201

Title: Beta amyloid peptide (Abeta42) is internalized via the G-protein-coupled receptor FPRL1 and forms fibrillar aggregates in macrophages.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20011101

Title: The synthetic peptide Trp-Lys-Tyr-Met-Val-Met-NH2 specifically activates neutrophils through FPRL1/lipoxin A4 receptors and is an agonist for the orphan monocyte-expressed chemoattractant receptor FPRL2.

Journal: The Journal of biological chemistry 20010615

Title: The synthetic peptide WKYMVm attenuates the function of the chemokine receptors CCR5 and CXCR4 through activation of formyl peptide receptor-like 1.

Journal: Blood 20010515

Title: The synthetic peptide Trp-Lys-Tyr-Met-Val-D-Met is a potent chemotactic agonist for mouse formyl peptide receptor.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20001015

Title: The synthetic chemoattractant Trp-Lys-Tyr-Met-Val-DMet activates neutrophils preferentially through the lipoxin A(4) receptor.

Journal: Blood 20000301

Title: Utilization of two seven-transmembrane, G protein-coupled receptors, formyl peptide receptor-like 1 and formyl peptide receptor, by the synthetic hexapeptide WKYMVm for human phagocyte activation.

Journal: Journal of immunology (Baltimore, Md. : 1950) 19991215

Title: Trp-Lys-Tyr-Met-Val-D-Met is a chemoattractant for human phagocytic cells.

Journal: Journal of leukocyte biology 19991201

Title: Trp-Lys-Tyr-Met-Val-D-Met stimulates superoxide generation and killing of Staphylococcus aureus via phospholipase D activation in human monocytes.

Journal: Journal of leukocyte biology 19990201

Title: Trp-Lys-Tyr-Met-Val-Met activates mitogen-activated protein kinase via a PI-3 kinase-mediated pathway independent of PKC.

Journal: Life sciences 19990101

Title: Christophe T, et al. The synthetic peptide Trp-Lys-Tyr-Met-Val-Met-NH2 specifically activates neutrophils through FPRL1/lipoxin A4 receptors and is an agonist for the orphan monocyte-expressed chemoattractant receptor FPRL2. J Biol Chem. 2001 Jun 15;276(24):21585-93.

Title: Christophe T, et al. Phagocyte activation by Trp-Lys-Tyr-Met-Val-Met, acting through FPRL1/LXA4R, is not affected by lipoxin A4. Scand J Immunol. 2002 Nov;56(5):470-6.

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Tags:187986-17-0 Molecular Formula|187986-17-0 MDL|187986-17-0 SMILES|187986-17-0 D-Methioninamide, L-tryptophyl-L-lysyl-L-tyrosyl-L-methionyl-L-valyl-