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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Tetradecyl Phosphonate

Cayman Chemical Item Number 10007565

(CAS 4671-75-4)

Tetradecyl Phosphonate (CAS 4671-75-4)

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Description

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., and 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).

Formal Name tetradecylphosphonic acid
CAS Number 4671-75-4
Molecular Formula C14H31O3P
Formula Weight 278.4
Formulation A crystalline solid
Purity >98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCCCCCCCCCCP(=O)​(O)​O

Background Reading

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).

Noguchi, K., Ishii, S., and 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).

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).

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).

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

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Tetradecyl Phosphonate is available in the following screening library:

Size Price Quantity Subtotal
100 mg $12.00 $0.00
500 mg $54.00 $0.00
1 g $96.00 $0.00
5 g $420.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-11. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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