WKYMVm TFA
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MedKoo CAT#: 464511

CAS#: unknown

Description: WKYMVm is a synthetic peptide agonist of formyl peptide receptor 1 (FPR1) and FPR2, which was previously known as formyl peptide receptor-like 1 (FPRL1). It induces calcium mobilization in ETFR rat basophilic leukemia cells transfected with FPR1 or FPR2 when used at a concentration of 0.1 nM. WKYMVm stimulates chemotaxis of monocytes, dendritic cells, and natural killer (NK) cells, as well as induces superoxide production in monocytes and neutrophils, in vitro. In vivo, WKYMVm (8 mg/kg) reverses mucosal destruction, decreases in body weight, and colonic shortening in a mouse model of colitis induced by dextran sulfate (sodium salt) (DSS). Topical application of WKYMVm stimulates angiogenesis and accelerates re-epithelialization and granulation tissue formation in a rat model of diabetic cutaneous wounds.

Chemical Structure

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WKYMVm TFA
CAS# unknown
Instruction

Theoretical Analysis

MedKoo Cat#: 464511
Name: WKYMVm TFA
CAS#: unknown
Chemical Formula: C43H62F3N9O9S2
Exact Mass: 0.00
Molecular Weight: 970.138
Elemental Analysis: C, 53.24; H, 6.44; F, 5.87; N, 12.99; O, 14.84; S, 6.61

Price and Availability

Size Price Availability Quantity
50mg USD -2 2 Weeks
100mg USD -2 2 Weeks
200mg USD -2 2 Weeks
500mg USD -2 2 Weeks
2g USD -2 2 Weeks
1mg USD 250 2 Weeks
5mg USD 570 2 Weeks
10mg USD 930 2 Weeks
25mg USD 1400 2 Weeks
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Synonym: WKYMVm TFA; WKYMVm-TFA; Trp-Lys-Tyr-Met-Val-D-Met;

IUPAC/Chemical Name: (S)-6-amino-2-((S)-2-amino-3-(1H-indol-3-yl)propanamido)-N-((5R,8S,11S,14S)-5-carbamoyl-15-(4-hydroxyphenyl)-8-isopropyl-11-(2-(methylthio)ethyl)-7,10,13-trioxo-2-thia-6,9,12-triazapentadecan-14-yl)hexanamide 2,2,2-trifluoroacetate

InChi Key: MYVYQWVNXDVTBW-HQORXVKSSA-N

InChi Code: InChI=1S/C41H61N9O7S2.C2HF3O2/c1-24(2)35(41(57)46-31(36(44)52)16-19-58-3)50-39(55)33(17-20-59-4)48-40(56)34(21-25-12-14-27(51)15-13-25)49-38(54)32(11-7-8-18-42)47-37(53)29(43)22-26-23-45-30-10-6-5-9-28(26)30;3-2(4,5)1(6)7/h5-6,9-10,12-15,23-24,29,31-35,45,51H,7-8,11,16-22,42-43H2,1-4H3,(H2,44,52)(H,46,57)(H,47,53)(H,48,56)(H,49,54)(H,50,55);(H,6,7)/t29-,31+,32-,33-,34-,35-;/m0./s1

SMILES Code: OC1=CC=C(C[C@H](NC([C@@H](NC([C@H](CC2=CNC3=CC=CC=C23)N)=O)CCCCN)=O)C(N[C@H](C(N[C@H](C(N[C@H](CCSC)C(N)=O)=O)C(C)C)=O)CCSC)=O)C=C1.OC(C(F)(F)F)=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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 30.00
DMSO 30.0 30.00
Ethanol 30.0 30.00
Ethanol:PBS (pH 7.2) (1:4) 0.2 0.20

Preparing Stock Solutions

The following data is based on the product molecular weight 970.14 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Jun JH, Park SY, Park S, Park HJ, Kim JY, Park GT, Bae SH, Kim JH, Kim GJ. Formyl Peptide Receptor 2 Alleviates Hepatic Fibrosis in Liver Cirrhosis by Vascular Remodeling. Int J Mol Sci. 2021 Feb 20;22(4):2107. doi: 10.3390/ijms22042107. PMID: 33672682; PMCID: PMC7924385.

2: Zhao W, Hu J, He Q. The effect of the WKYMVm peptide on promoting mBMSC secretion of exosomes to induce M2 macrophage polarization through the FPR2 pathway. J Orthop Surg Res. 2021 Mar 3;16(1):171. doi: 10.1186/s13018-021-02321-9. PMID: 33658070; PMCID: PMC7927268.

3: Ammendola R, Parisi M, Esposito G, Cattaneo F. Pro-Resolving FPR2 Agonists Regulate NADPH Oxidase-Dependent Phosphorylation of HSP27, OSR1, and MARCKS and Activation of the Respective Upstream Kinases. Antioxidants (Basel). 2021 Jan 19;10(1):134. doi: 10.3390/antiox10010134. PMID: 33477989; PMCID: PMC7835750.

4: Khajah MA, El-Hashim AZ, Orabi KY, Hawai S, Sary HG. Onion bulb extract can both reverse and prevent colitis in mice via inhibition of pro-inflammatory signaling molecules and neutrophil activity. PLoS One. 2020 Oct 23;15(10):e0233938. doi: 10.1371/journal.pone.0233938. PMID: 33095803; PMCID: PMC7584208.

5: Lee H, Lee J, Park Y, Kim JH, Eickelberg O, Yang SR. WKYMVm ameliorates acute lung injury via neutrophil antimicrobial peptide derived STAT1/IRF1 pathway. Biochem Biophys Res Commun. 2020 Dec 10;533(3):313-318. doi: 10.1016/j.bbrc.2020.09.036. Epub 2020 Sep 18. PMID: 32958247.

6: Zhang S, Gong H, Ge Y, Ye RD. Biased allosteric modulation of formyl peptide receptor 2 leads to distinct receptor conformational states for pro- and anti- inflammatory signaling. Pharmacol Res. 2020 Nov;161:105117. doi: 10.1016/j.phrs.2020.105117. Epub 2020 Aug 5. PMID: 32768626.

7: Hao L, Marshall AJ, Liu L. Bam32/DAPP1-Dependent Neutrophil Reactive Oxygen Species in WKYMVm-Induced Microvascular Hyperpermeability. Front Immunol. 2020 May 27;11:1028. doi: 10.3389/fimmu.2020.01028. PMID: 32536926; PMCID: PMC7267069.

8: Wang H, Peng X, Ge Y, Zhang S, Wang Z, Fan Y, Huang W, Qiu M, Ye RD. A Ganoderma-Derived Compound Exerts Inhibitory Effect Through Formyl Peptide Receptor 2. Front Pharmacol. 2020 Mar 24;11:337. doi: 10.3389/fphar.2020.00337. PMID: 32265709; PMCID: PMC7105723.

9: Ge Y, Zhang S, Wang J, Xia F, Wan JB, Lu J, Ye RD. Dual modulation of formyl peptide receptor 2 by aspirin-triggered lipoxin contributes to its anti- inflammatory activity. FASEB J. 2020 May;34(5):6920-6933. doi: 10.1096/fj.201903206R. Epub 2020 Apr 2. PMID: 32239559.

10: Chen T, Xiong M, Zong X, Ge Y, Zhang H, Wang M, Won Han G, Yi C, Ma L, Ye RD, Xu Y, Zhao Q, Wu B. Structural basis of ligand binding modes at the human formyl peptide receptor 2. Nat Commun. 2020 Mar 5;11(1):1208. doi: 10.1038/s41467-020-15009-1. PMID: 32139677; PMCID: PMC7058083.

11: Bae IH, Jeong MH, Park DS, Lim KS, Shim JW, Kim MK, Park JK. Mechanical and physio-biological properties of peptide-coated stent for re-endothelialization. Biomater Res. 2020 Jan 23;24:4. doi: 10.1186/s40824-020-0182-x. PMID: 31998531; PMCID: PMC6979279.

12: Li L, Liu W, Zhao Y, Ma P, Zha S, Chen P, Lu H, Jiang X, Wan S, Luo J, Dai Q, Hu J, Utomo YKS, Han X, Yang Z, Yang L, He Q. Dual-Peptide-Functionalized Nanofibrous Scaffolds Recruit Host Endothelial Progenitor Cells for Vasculogenesis to Repair Calvarial Defects. ACS Appl Mater Interfaces. 2020 Jan 22;12(3):3474-3493. doi: 10.1021/acsami.9b21434. Epub 2020 Jan 10. PMID: 31874023.

13: Hu J, Li X, Chen Y, Han X, Li L, Yang Z, Duan L, Lu H, He Q. The protective effect of WKYMVm peptide on inflammatory osteolysis through regulating NF-κB and CD9/gp130/STAT3 signalling pathway. J Cell Mol Med. 2020 Jan;24(2):1893-1905. doi: 10.1111/jcmm.14885. Epub 2019 Dec 14. PMID: 31837208; PMCID: PMC6991638.

14: Cattaneo F, Russo R, Castaldo M, Chambery A, Zollo C, Esposito G, Pedone PV, Ammendola R. Phosphoproteomic analysis sheds light on intracellular signaling cascades triggered by Formyl-Peptide Receptor 2. Sci Rep. 2019 Nov 29;9(1):17894. doi: 10.1038/s41598-019-54502-6. PMID: 31784636; PMCID: PMC6884478.

15: Park GT, Kwon YW, Lee TW, Kwon SG, Ko HC, Kim MB, Kim JH. Formyl Peptide Receptor 2 Activation Ameliorates Dermal Fibrosis and Inflammation in Bleomycin- Induced Scleroderma. Front Immunol. 2019 Sep 3;10:2095. doi: 10.3389/fimmu.2019.02095. PMID: 31552041; PMCID: PMC6733889.

16: Hao L, Lei X, Zhou H, Marshall AJ, Liu L. Critical role for PI3Kγ-dependent neutrophil reactive oxygen species in WKYMVm-induced microvascular hyperpermeability. J Leukoc Biol. 2019 Nov;106(5):1117-1127. doi: 10.1002/JLB.3A0518-184RR. Epub 2019 Jun 19. PMID: 31216371.

17: Lind S, Sundqvist M, Holmdahl R, Dahlgren C, Forsman H, Olofsson P. Functional and signaling characterization of the neutrophil FPR2 selective agonist Act-389949. Biochem Pharmacol. 2019 Aug;166:163-173. doi: 10.1016/j.bcp.2019.04.030. Epub 2019 May 11. PMID: 31085160.

18: Kim YE, Park WS, Ahn SY, Sung DK, Sung SI, Kim JH, Chang YS. WKYMVm hexapeptide, a strong formyl peptide receptor 2 agonist, attenuates hyperoxia- induced lung injuries in newborn mice. Sci Rep. 2019 May 2;9(1):6815. doi: 10.1038/s41598-019-43321-4. PMID: 31048743; PMCID: PMC6497690.

19: Vellaisamy K, Li G, Wang W, Leung CH, Ma DL. A long-lived peptide-conjugated iridium(iii) complex as a luminescent probe and inhibitor of the cell migration mediator, formyl peptide receptor 2. Chem Sci. 2018 Oct 1;9(43):8171-8177. doi: 10.1039/c8sc02733a. PMID: 30568767; PMCID: PMC6256120.

20: Graves N, Venu VP, Yipp BG, Petri B, Hirota S, Gilleard J, McKay DM, Lopes F. A Trypsin-Sensitive Proteoglycan from the Tapeworm Hymenolepis diminuta Inhibits Murine Neutrophil Chemotaxis in vitro by Suppressing p38 MAP Kinase Activation. J Innate Immun. 2019;11(2):136-149. doi: 10.1159/000492303. Epub 2018 Sep 11. PMID: 30205385; PMCID: PMC6738252.