IUPAC/Chemical Name
2-((hydroxy((R)-2-((5-oxopentanoyl)oxy)-3-(palmitoyloxy)propoxy)phosphoryl)oxy)-N,N,N-trimethylethan-1-aminium
InChi Key
RKIDALSACBQVTN-HHHXNRCGSA-N
InChi Code
InChI=1S/C29H56NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20-28(32)36-25-27(39-29(33)21-18-19-23-31)26-38-40(34,35)37-24-22-30(2,3)4/h23,27H,5-22,24-26H2,1-4H3/t27-/m1/s1
SMILES Code
CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCC[N](C)(C)C)OC(=O)CCCC=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
>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
2934.99.9001
More Info
Side Chain Carbon Sum: 21:0
Biological target:
POV-PC is an oxLDL species that confers CD36 scavenger receptor binding affinity more potently than any hydroperoxy PC species.
In vitro activity:
POVPC induced EMT, resulting in increase of migration and invasion of human hepatocellular carcinoma cells (HepG2) and human breast cancer cells (MCF7). POVPC induced autophagic flux through AMPK-mTOR pathway. Pharmacological inhibition or siRNA knockdown of autophagy decreased migration and invasion of POVPC-treated HepG2 and MCF7 cells. POVPC and PGPC levels were greatly increased at stage II of patient-derived intrahepatic cholangiocarcinoma tissues.
Reference: Cells. 2021 Mar 4;10(3):558. https://pubmed.ncbi.nlm.nih.gov/33806593/
In vivo activity:
Also, AngII interacted with metabolite/precursor of PAF (lyso-PAF), and an oxidized phospholipid, 1-palmitoyl-2-(5'-oxo-valeroyl)-sn-glycero-3-phosphocholine (POVPC), which bears a marked structural resemblance to PAF. Furthermore, POVPC dose-dependently inhibited AngII-mediated attenuation of PAF-induced paw oedema. These results suggest that Ang peptides can attenuate PAF-induced inflammatory activity through binding to PAF and lyso-PAF in rats. Therefore, Ang peptides may be closely involved in the regulation of many inflammatory diseases caused by PAF.
Reference: Peptides. 2015 Nov;73:60-6. https://pubmed.ncbi.nlm.nih.gov/26348270/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
15.0 |
25.22 |
|
| dmso |
10.0 |
16.81 |
|
| Ethanol |
30.0 |
50.44 |
|
| PBS (pH 7.2) |
10.0 |
16.81 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
594.75
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 |
Formulation protocol:
1. Seok JK, Hong EH, Yang G, Lee HE, Kim SE, Liu KH, Kang HC, Cho YY, Lee HS, Lee JY. Oxidized Phospholipids in Tumor Microenvironment Stimulate Tumor Metastasis via Regulation of Autophagy. Cells. 2021 Mar 4;10(3):558. doi: 10.3390/cells10030558. PMID: 33806593; PMCID: PMC8001732.
2. Li Y, Zhang YX, Ning DS, Chen J, Li SX, Mo ZW, Peng YM, He SH, Chen YT, Zheng CJ, Gao JJ, Yuan HX, Ou JS, Ou ZJ. Simvastatin inhibits POVPC-mediated induction of endothelial-to-mesenchymal cell transition. J Lipid Res. 2021;62:100066. doi: 10.1016/j.jlr.2021.100066. Epub 2021 Mar 10. PMID: 33711324; PMCID: PMC8063863.
3. Yeon SH, Yang G, Lee HE, Lee JY. Oxidized phosphatidylcholine induces the activation of NLRP3 inflammasome in macrophages. J Leukoc Biol. 2017 Jan;101(1):205-215. doi: 10.1189/jlb.3VMA1215-579RR. Epub 2016 Jun 2. PMID: 27256568.
4. Sato A, Yokoyama I, Ebina K. Angiotensin peptides attenuate platelet-activating factor-induced inflammatory activity in rats. Peptides. 2015 Nov;73:60-6. doi: 10.1016/j.peptides.2015.09.002. Epub 2015 Sep 5. PMID: 26348270.
In vitro protocol:
1. Seok JK, Hong EH, Yang G, Lee HE, Kim SE, Liu KH, Kang HC, Cho YY, Lee HS, Lee JY. Oxidized Phospholipids in Tumor Microenvironment Stimulate Tumor Metastasis via Regulation of Autophagy. Cells. 2021 Mar 4;10(3):558. doi: 10.3390/cells10030558. PMID: 33806593; PMCID: PMC8001732.
2. Li Y, Zhang YX, Ning DS, Chen J, Li SX, Mo ZW, Peng YM, He SH, Chen YT, Zheng CJ, Gao JJ, Yuan HX, Ou JS, Ou ZJ. Simvastatin inhibits POVPC-mediated induction of endothelial-to-mesenchymal cell transition. J Lipid Res. 2021;62:100066. doi: 10.1016/j.jlr.2021.100066. Epub 2021 Mar 10. PMID: 33711324; PMCID: PMC8063863.
In vivo protocol:
1. Yeon SH, Yang G, Lee HE, Lee JY. Oxidized phosphatidylcholine induces the activation of NLRP3 inflammasome in macrophages. J Leukoc Biol. 2017 Jan;101(1):205-215. doi: 10.1189/jlb.3VMA1215-579RR. Epub 2016 Jun 2. PMID: 27256568.
2. Sato A, Yokoyama I, Ebina K. Angiotensin peptides attenuate platelet-activating factor-induced inflammatory activity in rats. Peptides. 2015 Nov;73:60-6. doi: 10.1016/j.peptides.2015.09.002. Epub 2015 Sep 5. PMID: 26348270.
1. Podrez, E.A., Febbraio, M., Sheibani, N., et al. Macrophage scavenger receptor CD36 is the major receptor for LDL modified by monocyte-generated reactive nitrogen species. J. Clin. Invest. 105(8), 1095-1108 (2000).
2. Podrez, E.A., Poliakov, E., Shen, Z., et al. A novel family of atherogenic oxidized phospholipids promotes macrophage foam cell formation via the scavenger receptor CD36 and is enriched in atherosclerotic lesions. J. Biol. Chem. 277 (41), 38517-38523 (2002).
3. Podrez, E.A., Poliakov, E., Shen, Z., et al. Identification of a novel family of oxidized phospholipids that serve as ligands for the macrophage scavenger receptor CD36. The Journal of Biological Chemisty 277(41), 38503-38516 (2002).
4. Leitinger, N., Tyner, T.R., Oslund, L., et al. Structurally similar oxidized phospholipids differentially regulate endothelial binding of monocytes and neutrophils. Proceedings of the National Academy of Sciences of the United States of America 96(21), 12010-12015 (1999).
5: Karki P, Li Y, Zhang CO, Ke Y, Promnares K, Birukova AA, Eggerman TL, Bocharov AV, Birukov KG. Amphipathic Helical Peptide L37pA Protects against Lung Vascular Endothelial Dysfunction Caused by Truncated Oxidized Phospholipids via Antagonism with CD36 Receptor. Am J Respir Cell Mol Biol. 2024 Jan;70(1):11-25. doi: 10.1165/rcmb.2023-0127OC. PMID: 37725486; PMCID: PMC10768836.
6: Karki P, Zhang CO, Promnares K, Li Y, Ke Y, Birukova AA, Birukov KG. Truncated oxidized phospholipids exacerbate endothelial dysfunction and lung injury caused by bacterial pathogens. Cell Signal. 2023 Sep;109:110804. doi: 10.1016/j.cellsig.2023.110804. Epub 2023 Jul 10. PMID: 37437826; PMCID: PMC10544726.
