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About This Item
Empirical Formula (Hill Notation):
C21H41O7P · xNa+
CAS Number:
Molecular Weight:
436.52 (free acid basis)
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
assay
≥98%
form
solid
color
white
lipid type
phosphoglycerides
storage temp.
−20°C
SMILES string
O[C@](COP([O-])(O)=O)([H])COC(CCCCCCC/C=C\CCCCCCCC)=O.[Na+]
InChI
1S/C21H41O7P.Na.H/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26;;/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26);;/b10-9+;;
InChI key
CHJOEWDRTPWOCY-TTWKNDKESA-N
Related Categories
General description
Lysophosphatidic acid (LPA) is an essential metabolite for membrane biosynthesis. LPA interacts with the G protein-coupled receptors (GPCRs), called the LPA receptor and mediates signaling. Oleoyl-L-α-lysophosphatidic acid activates the receptor LPA4. In keratinocytes, oleoyl-L-α-lysophosphatidic acid promotes growth to some extent.
Application
Oleoyl-L-α-lysophosphatidic acid sodium salt has been used:
- for the activation of Ras homolog gene family, member A (RhoA) and expression of claudin-1 in human breast cancer epithelial cell line
- in RH7777 cells for cyclic adenosine monophosphate (cAMP) accumulation assay and calcium mobilisation assay
- in vitro luciferase assay and live-cell imaging
Biochem/physiol Actions
Endogenous agonist for LPA1 and LPA2 receptors. LPA does not induce angiogenesis, but has effects on endothelial cell physiology that are similar to those of sphingosine 1-phosphate. Induces cell migration of cancer and non-cancer cells.
Features and Benefits
This compound is featured on the Lysophospholipid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Preparation Note
Prepared by the action of phospholipase A on L-α-phosphatidic acid, dioleoyl.
Disclaimer
Hygroscopic, photosensitive
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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TRPM7 controls mesenchymal features of breast cancer cells by tensional regulation of SOX4
Kuipers AJ, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1864(7), 2409-2419 (2018)
Tracee Scalise Panetti
Biochimica et biophysica acta, 1582(1-3), 190-196 (2002-06-19)
This review discusses multiple effects of sphingosine 1-phosphate (S1P) and lysophosphatidic acid (LPA) on endothelial cells and proposes that S1P and LPA are important regulators of the vascular system. Two physiologic sources of S1P and LPA are platelets and lipoproteins.
A Gohla et al.
The Journal of biological chemistry, 273(8), 4653-4659 (1998-03-21)
Lysophosphatidic acid (LPA) utilizes a G-protein-coupled receptor to activate the small GTP-binding protein Rho and to induce rapid remodeling of the actin cytoskeleton. We studied the signal transduction from LPA receptors to Rho activation. Analysis of the G-protein-coupling pattern of
Identification of compounds acting as negative allosteric modulators of the LPA 1 receptor
Ellery J, et al.
European Journal of Pharmacology (2018)
T Nishizaki et al.
Brain research. Molecular brain research, 50(1-2), 121-126 (1997-12-24)
The effect of lysophosphatidic acid (lysoPA) on acetylcholine (ACh)-evoked currents was examined using normal and mutant Torpedo nicotinic ACh receptors expressed in Xenopus oocytes. LysoPA enhanced ACh-evoked currents in a washing time- and dose-dependent manner at concentrations of 0.1-3 microM
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