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Merck

L7260

Oleoyl-L-α-lysophosphatidic acid sodium salt

≥98%, solid

Synonym(s):

1-Oleoyl-sn-glycerol 3-phosphate sodium salt, 3-sn-Lysophosphatidic acid, 1-oleoyl sodium salt, LPA sodium salt

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About This Item

Empirical Formula (Hill Notation):
C21H41O7P · xNa+
CAS Number:
22556-62-3
Molecular Weight:
436.52 (free acid basis)
NACRES:
NA.77
PubChem Substance ID:
24896456
UNSPSC Code:
12352211
MDL number:
MFCD00133427

Key Documents

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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+;;

SMILES string

O[C@](COP([O-])(O)=O)([H])COC(CCCCCCC/C=C\CCCCCCCC)=O.[Na+]

InChI key

CHJOEWDRTPWOCY-TTWKNDKESA-N

assay

≥98%

form

solid

color

white

lipid type

phosphoglycerides

storage temp.

−20°C

Quality Level

200

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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.

Disclaimer

Hygroscopic, photosensitive

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.

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.

Preparation Note

Prepared by the action of phospholipase A on L-α-phosphatidic acid, dioleoyl.

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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Certificates of Analysis (COA)

Lot/Batch Number
SLCG1241
SLCD6593
SLCD4408
SLBT7200
SLBP0958V

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Biological roles of lysophosphatidic acid signaling through its production by autotaxin
Okudaira S, et al.
Biochimie, 92(6), 698-706 (2010)
A LATS biosensor screen identifies VEGFR as a regulator of the Hippo pathway in angiogenesis
Azad T, et al.
Nature Communications, 9(1), 1061-1061 (2018)
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)
F N van Leeuwen et al.
Biochemical Society transactions, 31(Pt 6), 1209-1212 (2003-12-04)
LPA (lysophosphatidic acid), the simplest of al glycerophospholipids, is a potent inducer of cell proliferation, migration and survival. It does so by activating its cognate G-protein-coupled receptors, four of which have been identified. LPA receptors couple to at least three
Phosphatidic acid has a potential to promote hair growth in vitro and in vivo, and activates mitogen-activated protein kinase/extracellular signal-regulated kinase kinase in hair epithelial cells
Takahashi T, et al.
The Journal of Investigative Dermatology, 121(3), 448-456 (2003)
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