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Trp-Lys-Tyr-Met-Val-Met

FPR1, FPR2 and FPR3 receptor agonist CAS# 187986-17-0

Trp-Lys-Tyr-Met-Val-Met

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Chemical structure

Trp-Lys-Tyr-Met-Val-Met

3D structure

Chemical Properties of Trp-Lys-Tyr-Met-Val-Met

Cas No. 187986-17-0 SDF Download SDF
PubChem ID 71362579 Appearance Powder
Formula C41H60N8O8S2 M.Wt 857.1
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Leukocyte chemoattractant peptide
Solubility H2O
Peptide Solubility and Storage Guidelines:
1.  Calculate the length of the peptide.
2.  Calculate the overall charge of the entire peptide according to the following table:
3.  Recommended solution:
Sequence WKYMVM

(Modifications: Met-6 = D-Met & C-terminal amide)

Chemical Name (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-methylbutanoyl]amino]-4-methylsulfanylbutanoic acid
SMILES CC(C)C(C(=O)NC(CCSC)C(=O)O)NC(=O)C(CCSC)NC(=O)C(CC1=CC=C(C=C1)O)NC(=O)C(CCCCN)NC(=O)C(CC2=CNC3=CC=CC=C32)N
Standard InChIKey VQBTUIJFUPRJOH-LXOXETEGSA-N
Standard InChI InChI=1S/C41H60N8O8S2/c1-24(2)35(40(55)47-33(41(56)57)17-20-59-4)49-38(53)32(16-19-58-3)46-39(54)34(21-25-12-14-27(50)15-13-25)48-37(52)31(11-7-8-18-42)45-36(51)29(43)22-26-23-44-30-10-6-5-9-28(26)30/h5-6,9-10,12-15,23-24,29,31-35,44,50H,7-8,11,16-22,42-43H2,1-4H3,(H,45,51)(H,46,54)(H,47,55)(H,48,52)(H,49,53)(H,56,57)/t29-,31-,32-,33-,34-,35-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Trp-Lys-Tyr-Met-Val-Met

DescriptionSelective agonist for the formyl peptide receptors FPR1, FPR2 (EC50 = 75 pM) and FPR3 (EC50 = 3 nM), expressed on immune cells. Induces Ca2+ mobilization and superoxide production in, and chemotaxic migration of, monocytes and neutrophils. Also promotes monocyte survival through a PKC-, PI 3-kinase- and Akt-dependent pathway.

Trp-Lys-Tyr-Met-Val-Met Dilution Calculator

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References on Trp-Lys-Tyr-Met-Val-Met

Effect of a novel peptide, WKYMVm- and sirolimus-coated stent on re-endothelialization and anti-restenosis.[Pubmed:26438653]

J Mater Sci Mater Med. 2015 Oct;26(10):251.

The drug-eluting stent still has limitations such as thrombosis and inflammation. These limitations often occur in the absence of endothelialization. This study investigated the effects of WKYMVm- and sirolimus-coated stents on re-endothelialization and anti-restenosis. The WKYMVm peptide, specially synthesized for homing endothelial colony-forming cells, was coated onto a bare-metal stent with hyaluronic acid through a simple dip-coating method (designated HA-Pep). Thereafter, sirolimus was consecutively coated to onto the HA-Pep (designated Pep/SRL). The cellular response to stents by human umbilical-vein endothelial cells and vascular smooth-muscle cells was examined by XTT assay. Stents were implanted into rabbit iliac arteries, isolated 6 weeks post-implantation, and then subjected to histological analysis. The peptide was well attached to the surface of the stents and the sirolimus coating made the surface smooth. The release pattern for sirolimus was similar to that of commercial sirolimus-coated stents (57.2% within 7 days, with further release for up to 28 days). Endothelial-cell proliferation was enhanced in the HA-Pep group after 7 days of culture (38.2 +/- 7.62%, compared with controls). On the other hand, the proliferation of smooth-muscle cells was inhibited in the Pep/SRL group after 7 days of culture (40.7 +/- 6.71%, compared with controls). In an animal study, the restenosis rates for the Pep/SRL group (13.5 +/- 4.50%) and commercial drug-eluting stents (Xience Prime; 9.2 +/- 7.20%) were lower than those for bare-metal stents (25.2 +/- 4.52%) and HA-Pep stents (26.9 +/- 3.88%). CD31 staining was incomplete for the bare-metal and Xience Prime groups. On the other hand, CD31 staining showed a consecutive linear pattern in the HA-Pep and Pep/SRL groups, suggesting that WKYMVm promotes endothelialization. These results indicate that the WKYMVm coating could promote endothelial healing, and consecutive coatings of WKYMVm and sirolimus onto bare-metal stents have a potential role in re-endothelialization and neointimal suppression.

Injectable PLGA microspheres encapsulating WKYMVM peptide for neovascularization.[Pubmed:26216508]

Acta Biomater. 2015 Oct;25:76-85.

UNLABELLED: Formyl peptide receptor-2 (FPR-2) is expressed in various cell types, such as phagocytes, fibroblasts, and endothelial cells. FPR-2 has been reported to play a significant role in inflammation and angiogenic response, and synthetic WKYMVm peptide has been identified as a novel peptide agonist for the FPR-2. In this study, we demonstrate that WKYMVm peptides stimulate the angiogenic potential of outgrowth endothelial cells (OECs). Upon WKYMVm peptide exposure, migration and proliferation of OECs were stimulated. WKYMVm effectively stimulated angiogenesis in tube formation assay and aortic ring assay. Furthermore, we fabricated injectable poly (lactide-co-glycolide) (PLGA) microspheres encapsulating WKYMVm peptides, which showed sustained release of cargo molecule. When WKYMVm peptide encapsulated microspheres were injected into the hind limb ischemia model, a single injection of microspheres was as effective as multiple injections of WKYMVm peptide in restoring blood flow from ischemic injury and promoting capillary growth. These results demonstrate that sustained release of WKYMVm peptide from microspheres in the application to ischemic hind limb extended angiogenic stimulation. STATEMENT OF SIGNIFICANCE: Formyl peptide receptor (FPR) has been reported to play an important role in inflammation and angiogenic response. A synthetic WKYMVm peptide has been identified as a novel peptide activating the FPR-2 that is expressed in a various cell types, such as phagocytes, fibroblasts, and endothelial cells. In this manuscript we explored a unique property of high-affinity ligand for formyl peptide receptors-2 (FPR-2) (i.e., WKYMVm). WKYMVm-induced activation of FPR2 has been reported to be crucial in host defense and inflammation by activation of phagocytes, monocytes, and lymphocytes. In this study, highlight the efficacy of WKYMVm peptide's role in inducing neovascularization in vivo hind limb ischemia model when the peptide was released from injected PLGA microspheres in sustained manner. Our results demonstrate that sustained release of WKYMVm peptide from microspheres have extended angiogenic stimulation capacity.

Biomedical therapy using synthetic WKYMVm hexapeptide.[Pubmed:27077939]

Organogenesis. 2016 Apr 2;12(2):53-60.

WKYMVm hexapeptide has been identified as a strong FPR2 agonist through a library screening of synthetic peptides. The FPR2 has been reported to play a crucial role in inflammation and angiogenic responses via stimulation of chemotaxis, migration, cell proliferation, wound healing and vessel growth. Recently, the therapeutic effects of WKYMVm have been reported in various disease models. In cutaneous wound model in diabetic mice, WKYMVm facilitated wound healing processes by stimulating the formation of capillary and arteriole and re-epithelialization. In coronary artery stenosis model, WKYMVm coating on stent promoted re-endothelialization and lowered restenosis rate. In hindlimb ischemia mouse model, intramuscular injection of WKYMVm promoted homing of exogenously transplanted endothelial colony-forming cells and neovascularization, resulting in salvaging hindlimb. Furthermore, a single injection of WKYMVm encapsulated in poly (lactide-co-glycolide) microspheres was demonstrated to be as efficient as multiple injections of WKYMVm in restoring blood flow in hindlimb ischemia model. These observations may open up promising biomedical applications of WKYMVm for tissue repairs and regenerations.

Data on the NADPH-oxidase activity induced by WKYMVm and galectin-3 in bone marrow derived and exudated neutrophils isolated from four different mouse strains.[Pubmed:28018948]

Data Brief. 2016 Dec 13;10:349-353.

Neutrophils are the key players in inflammatory reactions and the release of superoxide through the NADPH-oxidase upon neutrophil activation contributes to bacterial clearance and surrounding tissue damage. Here we describe data on the mouse neutrophil NADPH-oxidase activation induced by the mouse formyl peptide receptor (Fpr) agonist WKYMVm and galectin-3. Neutrophils isolated from bone marrow, peritoneal exudated, and in vitro TNFalpha primed bone marrow neutrophils from four different laboratory strains (C57BL/6, DBA/1, BALB/c and NMRI) were used. Both Fpr agonist and galectin-3 activated neutrophils to release superoxide. No differences were observed in the amounts of superoxide released from neutrophils derived from four different strains.

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.[Pubmed:11285256]

J Biol Chem. 2001 Jun 15;276(24):21585-93.

Neutrophils express the G protein-coupled N-formyl peptide receptor (FPR) and its homologue FPRL1, whereas monocytes express FPR, FPRL1, and FPRL2, an orphan receptor sharing 83% amino acid identity with FPRL1. FPRL1 is a promiscuous receptor activated by serum amyloid A and by different synthetic peptides, including the hexapeptide Trp-Lys-Tyr-Met-Val-d-Met-NH(2) (WKYMVm). By measuring calcium flux in HL-60 cells transfected with FPR, FPRL1, or FPRL2, we show that WKYMVm activated all three receptors, whereas the l-conformer WKYMVM activated exclusively FPRL1 and FPRL2. The functionality of FPRL2 was further assessed by the ability of HL-60-FPRL2 cells to migrate toward nanomolar concentrations of hexapeptides. The half-maximal effective concentrations of WKYMVM for calcium mobilization in HL-60-FPRL1 and HL-60-FPRL2 cells were 2 and 80 nm, respectively. Those of WKYMVm were 75 pm and 3 nm. The tritiated peptide WK[3,5-(3)H(2)]YMVM bound to FPRL1 (K(D) approximately 160 nm), but not to FPR. The two conformers similarly inhibited binding of (125)I-labeled WKYMVm to FPRL2-expressing cells (IC(50) approximately 2.5-3 micrometer). Metabolic labeling with orthophosphoric acid revealed that FPRL1 was differentially phosphorylated upon addition of the l- or d-conformer, indicating that it induced different conformational changes. In contrast to FPRL1, FPRL2 was already phosphorylated in the absence of agonist and not evenly distributed in the plasma membrane of unstimulated cells. However, both receptors were internalized upon addition of either of the two conformers. Taken together, the results indicate that neutrophils are activated by WKYMVM through FPRL1 and that FPRL2 is a chemotactic receptor transducing signals in myeloid cells.

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.[Pubmed:10586077]

J Immunol. 1999 Dec 15;163(12):6777-84.

Trp-Lys-Tyr-Val-D-Met (WKYMVm) is a synthetic leukocyte-activating peptide postulated to use seven-transmembrane, G protein-coupled receptor(s). In the study to characterize the receptor(s) for WKYMVm, we found that this peptide induced marked chemotaxis and calcium flux in human phagocytes. The signaling induced by WKYMVm in phagocytes was attenuated by high concentrations of the bacterial chemotactic peptide fMLP, suggesting that WKYMVm might use receptor(s) for fMLP. This hypothesis was tested by using cells over expressing genes encoding two seven-transmembrane receptors, formyl peptide receptor (FPR) and formyl peptide receptor-like 1 (FPRL1), which are with high and low affinity for fMLP, respectively. Both FPR- and FPRL1-expressing cells mobilized calcium in response to picomolar concentrations of WKYMVm. While FPRL1-expressing cells migrated to picomolar concentrations of WKYMVm, nanomolar concentrations of the peptide were required to induce migration of FPR-expressing cells. In contrast, fMLP elicited both calcium flux and chemotaxis only in FPR-expressing cells with an efficacy comparable with WKYMVm. Thus, WKYMVm uses both FPR and FPRL1 to stimulate phagocytes with a markedly higher efficacy for FPRL1. Our study suggests that FPR and FPRL1 in phagocytes react to a broad spectrum of agonists and WKYMVm as a remarkably potent agonist provides a valuable tool for studying leukocyte signaling via these receptors.

Description

WKYMVM is a potent N-formyl peptide receptor (FPR1) and FPRL1/2 agonist, also activates several leukocyte effector functions such as chemotaxis, mobilization of complement receptor-3, and activation of the NADPH oxidase.

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