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About This Item
Empirical Formula (Hill Notation):
C21H40O7PNa
CAS Number:
Molecular Weight:
458.50
MDL number:
UNSPSC Code:
51191904
NACRES:
NA.25
description
1-oleoyl-2-hydroxy-sn-glycero-3-phosphate (sodium salt)
assay
>99% (LPA; may contain up to 10% of the 2-LPA isomer, TLC)
form
powder
packaging
pkg of 1 × 1 g (857130P-1g), pkg of 2 × 100 mg (857130P-200mg), pkg of 1 × 25 mg (857130P-25mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
lipid type
cardiolipins
phospholipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
O[C@](COP([O-])(O)=O)([H])COC(CCCCCCC/C=C\CCCCCCCC)=O.[Na+]
InChI
1S/C21H41O7P.Na/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);/q;+1/p-1/b10-9-;/t20-;/m1./s1
InChI key
XGRLSUFHELJJAB-JGSYTFBMSA-M
General description
Lysophosphatidic acid (LPA) belongs to a class of phospholipids, which has a glycerol backbone attached through a phosphate group, an aliphatic chain and a hydroxyl group. The phosphate group is linked to the sn-3 position and the aliphatic chain is linked to either sn-1 or sn-2 position. The hydroxyl group is connected to the remaining sn-1 or sn-2 position.
Application
18:1 Lyso PA or 1-oleoyl-2-hydroxy-sn-glycero-3-phosphate has been used: to study its effects on intracellular calcium concentration [Ca2+]i transient in pheochromocytoma cell 12 (PC12) cells and primary astrocytes. It has also been used to study its effects on blood glucose level and physical endurance in fasted mice.
Biochem/physiol Actions
Biological responses to LPA: Cell Proliferation, Inhibition of differentiation (neuroblastoma cells, myoblasts), Platelet aggregation, Smooth muscle contraction, Neurotransmitter release, Stress fibre formation/cell rounding/neurite retraction, Cell-surface-fibronectin binding, Tumor cell invasion, Chemotaxis (dictyostelium amoebae), Cl--mediated membrane depolarization (fibroblasts), Inhibition of connexin 43 based cell-cell communication, Increased tight junction permeability (brain endothelial cells). Note: The bioactivity of LPA appears to require long (i.e., C16 to C18) acyl carbon chains of the type usually found associated with membrane lipids although optimum requirements for a single type of acyl carbon chain are not universal. The bioactivity decreases with shorter chain length. In serum, oleoyl and palmitoyl fatty acid containing LPA are the predominant species.
Packaging
5 mL Clear Glass Sealed Ampule (857130P-200mg)
5 mL Clear Glass Sealed Ampule (857130P-25mg)
60 mL Amber Wide Mouth Screw Cap Glass Bottle (857130P-1g)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
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Storage Class
11 - Combustible Solids
wgk
WGK 3
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Ethan Sagher et al.
Cancer cell international, 14, 75-75 (2014-10-18)
The small molecule NSC676914A was previously identified as an NF-κB inhibitor in TPA-stimulated HEK293 cells (Mol Can Ther 8:571-581, 2009). We hypothesized that this effect would also be seen in ovarian cancer cells, and serve as its mechanism of cytotoxicity.
Byung-Hwan Lee et al.
Neuroscience letters, 612, 256-260 (2015-12-27)
Ginseng has a long history of use as a tonic for restoration of vigor. One example of ginseng-derived tonic effect is that it can improve physical stamina under conditions of stress. However, the active ingredient and the underlying molecular mechanism
Susumu Antoku et al.
Developmental cell, 51(5), 602-616 (2019-12-04)
Mutations in the lamin A/C gene (LMNA) cause cardiomyopathy and also disrupt nuclear positioning in fibroblasts. LMNA mutations causing cardiomyopathy elevate ERK1/2 activity in the heart, and inhibition of the ERK1/2 kinase activity ameliorates pathology, but the downstream effectors remain
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 857130P-1G | 04061835231959 |
| 857130P-200MG | 04061835231966 |
| 857130P-25MG | 04061835231973 |