All Photos(2)

857130C

Avanti

18:1 Lyso PA

1-oleoyl-2-hydroxy-sn-glycero-3-phosphate (sodium salt), chloroform

Synonym(s):
oleoyl lysophosphatidic acid; 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate (sodium salt); PA(18:1(9Z)/0:0); 18:1 LPA; o-LPA; 110681
Empirical Formula (Hill Notation):
C21H40O7PNa
CAS Number:
Molecular Weight:
458.50
NACRES:
NA.25

assay

>99% (LPA; may contain up to 10% of the 2-LPA isomer, TLC)

packaging

pkg of 1 × 2.5 mL (857130C-25mg)
pkg of 2 × 4 mL (857130C-200mg)

manufacturer/tradename

Avanti Polar Lipids 857130C

concentration

10 mg/mL (857130C-25mg)
25 mg/mL (857130C-200mg)

shipped in

dry ice

storage temp.

−20°C

General description

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.
Lysophosphatidic acid (1- or 2-acyl-lysophosphatidic acid/LPA), a bioactive phospholipid is seen at a low level in plasma (~100 nM). It is usually formed during the synthesis of phospholipid of cell membranes. It is produced by various cells like, activated platelets, epithelial cells, leukocytes, neuronal cells and tumor cells.

Application

18:1 Lyso PA is suitable:
  • for liposome preparations
  • to study its apoptotic effect in HeLa cells
  • to determine the extraction recovery of LPA at neutral pH and acidic pH by chromatography
  • to use as a LPA agonist supplement in oocytes maturation medium to study its effects during in vitro maturation of bovine cumulus–oocyte complexes

Biochem/physiol Actions

Lysophosphatidic acid (1- or 2-acyl-lysophosphatidic acid/LPA) modulates cell motility, proliferation, invasion, survival and production of growth factors via G protein-coupled receptor (GPCR). 1-oleoyl-lysophosphatidic acid (LPA) has the ability to stimulate tyrosine phosphorylation of numerous substrates in Swiss 3T3 cells. It also helps to release calcium from the platelet subcellular fraction.

Packaging

5 mL Clear Glass Sealed Ampule (857130C-25mg)
5 mL Clear Glass Sealed Ampule (857130C-200mg)

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

does not flash

Flash Point(C)

does not flash

Certificate of Analysis

Certificate of Origin

Lysophosphatidic acid stimulates tyrosine phosphorylation of focal adhesion kinase, paxillin, and p130. Signaling pathways and cross-talk with platelet-derived growth factor.
SeufferleinT and Rozengurt E
Test, 269(12), 9345- 9351 (1994)
Lysophosphatidic acids. Influence on platelet aggregation and intracellular calcium flux.
Gerrard JM, et al.
The American Journal of Pathology, 96(2), 423-423 (1979)
The effect of lysophosphatidic acid during in vitro maturation of bovine cumulus- oocyte complexes: cumulus expansion, glucose metabolism and expression of genes involved in the ovulatory cascade, oocyte and blastocyst competence
Boruszewska D, et al.
Reproductive Biology and Endocrinology, 13(1), 44-44 (2015)
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.
Lysophosphatidic acid triggers apoptosis in HeLa cells through the upregulation of tumor necrosis factor receptor superfamily member 21
Dong Y, et al.
Mediators of Inflammation, 2017 (2017)

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