Products

18:1 Lyso PA | 857130

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

857130P

Powder

25 mg
$160.00
200 mg
$345.00
500 mg
$605.00
1 g
$1095.00

857130C

Chloroform

25 mg
$145.00
200 mg
$330.00
500 mg
$590.00
1 g
$1080.00

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  • Solubility & Storage
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.
Molecular Formula
C21H40O7PNa
Percent Composition
C 55.01%, H 8.79%, Na 5.01%, O 24.43%, P 6.76%
Purity
>99% LPA; may contain up to 10% of the 2-LPA isomer
Stability
6 Months
Storage
-20°C
CAS Number
325465-93-8
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
458.502
Exact Mass
458.241
CMC
0.346 - 1.3mM
Synonyms
oleoyl lysophosphatidic acid
1-(9Z-octadecenoyl)-sn-glycero-3-phosphate (sodium salt)
PA(18:1(9Z)/0:0)
18:1 LPA
o-LPA
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Notes
GIF Graphics File. 
GIF Graphics File. 
MDL Molfile. 
CDX File. 
Williams, J.R., Khandoga, A.L., Goyal, P., Fells, J.I., Perygin, D.H., Siess, W., Parrill, A..L, Tigyi, G., Fujiwara, Y. (2009) Unique ligand selectivity of the GPR92/LPA5 lysophosphatidate receptor indicates role in human platelet activation. J Biol Chem. 284:17304-19. [PubMed]

Organic Solvents: Product is soluble in chloroform at all concentrations. Saturated analogs are more difficult to solubilize in organic solvents. Solubility of saturated analogs in chloroform is enhanced by adding small amounts of alcohol and water (to obtain a concentration of 10mg/ml saturated LPA in chloroform add 1.2% methanol and 0.6% water relative to chloroform volume)
 
Biologically Compatible Solvents: Solubility in biologically compatible solvents such as dimethylsulfoxide (DMSO) or ethanol is limited. Product is completely soluble in ethanol:water (1:1, v/v), although heating and sonication may be necessary to disperse. Product is only partially soluble at higher ethanol content. Solubility in water (buffer) is limited to concentrations below the CMC of the molecule. In order to obtain maximum interaction with biological systems at concentrations above the CMC it is necessary to reduce the particle size of the micelle by sonication or absorption of the LPA to fatty acid serum albumin (BSA). LPA's bound to fatty acid free albumin will appear as clear solutions. Solution has been achieved in phosphate buffered saline (PBS), pH 7.2, at up to 0.3 mM (0.14 mg per ml) in the presence of 0.1% (w/v) bovine serum albumin (essentially fatty acid free).

Note: Absorption of dilute stock solutions to plastic and glass can be a serious source of variation. Approximately 75% of a 5uM stock solution was found to stick tightly to the wall of an Eppendorf vial within 30 minutes.
 
Storage: LPA should be stable in organic or aqueous solution at neutral conditions. Freezer storage (-20°C) is recommended for organic solutions (including ethanol:water, 1:1), while aqueous preparations (stable for 24-48 hours) should be stored refrigerated (4°C). Partial acyl migration from the gamma (1) position to the beta (2) position may be possible under certain non-neutral conditions, such as those stimulating the formation of an equilibrium mixture of 1,2 and 1,3-diglycerides in acidic or basic solution. Oxidation of the fatty acid double bond may occur if submitted to oxidizing conditions. Maintaining the product under an inert atmosphere (nitrogen or argon) may be appropriate for some applications.