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857235P

Avanti

(2S)-OMPT

1-oleoyl-2-methyl-sn-glycero-3-phosphothionate (ammonium salt), powder

Synonyme(s) :

(2S)-1-(9Z-octadecenoyl)-2-O-methyl-glycero-3-phosphothionate (ammonium salt)

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About This Item

Formule empirique (notation de Hill):
C22H46NO6PS
Numéro CAS:
645408-61-3
Poids moléculaire :
483.64
Code UNSPSC :
51191904

Essai

>99% (TLC)

Forme

powder

Conditionnement

package of 1 × 1 mg ((857235P-1mg))
package of 1 × 500 μg ((857235P-500ug))

Fabricant/nom de marque

Avanti Polar Lipids 857235P

Type de lipide

phospholipids
cardiolipins

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

[H][C@](COP([O-])(O)=S)(OC)COC(CCCCCCC/C=C\CCCCCCCC)=O.[NH4+]

Catégories apparentées

Description générale

OMPT is a selective agonist of the LPA3 receptor. It exhibits EC50 values of 68 nM and >6.8 μM for calcium mobilization in LPA3 and LPA2-expressing Sf9 cells, respectively. The (2S)-OMPT enantiomer is 5- to 20-fold more active than (2R)-OMPT in calcium release assays in both LPA3-transfected Sf9 and rat hepatoma Rh7777 cells.

Application

(2S)-OMPT may be used:
  • to study its effects on lysophosphatidic acid receptor-3 (LPAR3) receptor
  • to pre-incubate hepatocytes and also characterize the role of LPAR3 on insulin-cascade
  • as an analog of LPA to study its effects on tube stability of 10T cells

Conditionnement

2 mL Amber Serum Vial with Stopper and Crimp Cap (857235P-1mg)
2 mL Amber Serum Vial with Stopper and Crimp Cap (857235P-500ug)

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

49.5 °F - closed cup

Point d'éclair (°C)

9.7 °C - closed cup

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Lian Qian et al.
Journal of medicinal chemistry, 46(26), 5575-5578 (2003-12-12)
The metabolically stabilized LPA analogue, 1-oleoyl-2-O-methyl-rac-glycerophosphothioate (OMPT), is a potent agonist for the LPA(3) G-protein-coupled receptor. A new enantiospecific synthesis of both (2R)-OMPT and (2S)-OMPT is described. Calcium release assays in both LPA(3)-transfected insect Sf9 and rat hepatoma Rh7777 cells
Identification of a phosphothionate analogue of lysophosphatidic acid (LPA) as a selective agonist of the LPA3 receptor.
Hasegawa Y, et al.
The Journal of Biological Chemistry, 278, 11962-11969 (2003)
Yutaka Hasegawa et al.
The Journal of biological chemistry, 278(14), 11962-11969 (2003-01-30)
Lysophosphatidic acid (LPA) is a bioactive lysophospholipid mediator that acts through G protein-coupled receptors. Most cell lines in culture express one or more LPA receptors, making it difficult to assign a response to specific LPA receptors. Dissection of the signaling
Pericytes prevent regression of endothelial cell tubes by accelerating metabolism of lysophosphatidic acid
Motiejunaite R, et al.
Microvascular Research, 93(2), 62-71 (2014)
Enantioselective responses to a phosphorothioate analogue of lysophosphatidic acid with LPA3 receptor-selective agonist activity.
Qian L, et al.
Journal of Medicinal Chemistry, 46, 5575-5578 (2003)
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