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L7260 Sigma-Aldrich

Oleoyl-L-α-lysophosphatidic acid sodium salt

≥98%, solid

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

  • CAS Number 22556-62-3

  • Empirical Formula (Hill Notation) C21H41O7P · xNa+

  • Molecular Weight 436.52 (free acid basis)

  •  MDL number MFCD00133427

  •  PubChem Substance ID 24896456

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Research, Cell Biology,
Quality Level   200
assay   ≥98%
form   solid
color   white
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

Description

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

Packaging

1, 5, 25 mg in glass bottle

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.

Caution

Hygroscopic, photosensitive

Preparation Note

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

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Discover Bioactive Small Molecules for Lipid Signaling Research

Within mammalian cells, a multitude of lipid compounds are found with a variety of cellular functions, including structural components of cell membranes and as second messengers in cell signaling pat...
Keywords: Absorption, Atomic absorption spectroscopy, Cancer, Cardiovascular, Cell signaling, Diabetes, Digestions, Diseases, Growth factors, Hormones, Inflammation, Lipid Metabolism, Lipid signaling, Metabolism

Peer-Reviewed Papers
15

References

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