Cayman Chemical | Tetradecyl Phosphonate | Description (CAS 4671-75-4)

10007565 Tetradecyl Phosphonate

(CAS 4671-75-4)

• See more Receptor Biochemistry; Lipids; Nuclear Receptors; Phospholipase; Phospholipids; Cancer; Cell Biology; Signal Transduction; Vascular Disease

Chemical structure definitions are available for many Cayman products. See Chemical Structure Database for details.

Lysophosphatidic acid (LPA) is a lipid signalling molecule formed by the hydrolysis of lysophosphatidyl choline by lysophospholipase D, also known as autotaxin (ATX).¹ LPA signals through four different G protein-coupled receptors, LPA₁/EDG-2, LPA₂/EDG-4, LPA₃/EDG-7, and LPA₄/GPR23.^2,3 Activation of peroxisome proliferator-activated receptor γ (PPARγ) by LPA has also been reported.⁴ Tetradecyl phosphonate is a pan-antagonist of LPA₁, LPA₂, and LPA₃ receptors with IC₅₀ values for inhibition of LPA-induced calcium mobilization of 10 µM, 5.5 µM, and 3.1 µM, respectively.⁵ At a concentration of 10 µM, tetradecyl phosphonate activates a PPARγ reporter construct 4-fold compared to controls and partially inhibits ATX with an IC₅₀ of approximately 3 µM.⁵

1 Tokumura, A., Majima, E., Kariya, Y., et al. Identification of human lysophospholipase D, a lysophosphatidic acid-producing enzyme, as autotaxin, a multifunctional phosphodiesterase. J Biol Chem 277(42) 39436-39442 (2002 Oct 18).

2 Chun, J., Goetzl, E.J., Hla, T., et al. International union of pharmacology. XXXIV. Lysophospholipid receptor nomenclature. Pharmacol Rev 54 265-269 (2002).

3 Noguchi, K., Ishii, S., Shimizu, T. Identification of p2y9/GPR23 as a novel G protein-coupled receptor for lysophosphatidic acid, structurally distant from the Edg family. J Biol Chem 278(28) 25600-25606 (2003).

4 McIntyre, T.M., Pontsler, A.V., Silva, A.R., et al. Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARγ agonist. Proc Natl Acad Sci USA 100(1) 131-136 (2003).

5 Durgam, G.G., Virag, T., Walker, M.D., et al. Synthesis, structure-activity relationships, and biological evaluation of fatty alcohol phosphates as lysophosphatidic acid receptors ligands, activators of PPARγ, and inhibitors of autotaxin. J Med Chem 48 4919-4930 (2005).

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Pricing updated 2010-03-13.
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