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L7260

Sigma-Aldrich

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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24 EA
CN¥3,997.99

CN¥3,997.99

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24 EA
CN¥3,997.99

About This Item

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

CN¥3,997.99

Please contact Customer Service for Availability
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Quality Level

200

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

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This Item
CLS431845CLS431847CLS431846
Corning® centrifuge bottle with silicon O-ring screw cap, capacity 500 mL, polypropylene

CLS431844

Corning® centrifuge bottle

Corning® centrifuge bottle with standard screw cap, capacity 500 mL, polypropylene

CLS431845

Corning® centrifuge bottle

Corning® centrifuge bottle with standard screw cap, capacity 500 mL, polycarbonate

CLS431847

Corning® centrifuge bottle

Corning® centrifuge bottle with silicon O-ring screw cap, capacity 500 mL, polycarbonate

CLS431846

Corning® centrifuge bottle

material

flat bottom tube, round bottle, wide-mouth bottle, polypropylene , translucent bottle

material

flat bottom tube, polypropylene , round bottle, translucent bottle, wide-mouth bottle

material

clear bottle, flat bottom tube, polycarbonate , round bottle, wide-mouth bottle

material

clear bottle, flat bottom tube, polycarbonate , round bottle, wide-mouth bottle

manufacturer/tradename

Corning 431844

manufacturer/tradename

Corning 431845

manufacturer/tradename

Corning 431847

manufacturer/tradename

Corning 431846

packaging

pkg of 24 ea

packaging

pkg of 24 ea

packaging

pkg of 24 ea

packaging

pkg of 24 ea

capacity

500 mL

capacity

500 mL

capacity

500 mL

capacity

500 mL

feature

autoclavable

feature

autoclavable, cap

feature

autoclavable, cap

feature

autoclavable, cap

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.[1] Oleoyl-L-α-lysophosphatidic acid activates the receptor LPA4.[2] In keratinocytes, oleoyl-L-α-lysophosphatidic acid promotes growth to some extent.[3]

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[4]
  • in RH7777 cells for cyclic adenosine monophosphate (cAMP) accumulation assay and calcium mobilisation assay[5]
  • in vitro luciferase assay and live-cell imaging[6]

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000366504
0000366505
0000348481
0000329014
0000329015

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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
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
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.
Identification of compounds acting as negative allosteric modulators of the LPA 1 receptor
Ellery J, et al.
European Journal of Pharmacology (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)
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