A stable pan-antagonist at LPA receptors
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Tetradecyl Phosphonate

Item No. 10007565

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
tetradecylphosphonic acid
CAS Number
4671-75-4
Molecular Formula
C14H31O3P
Formula Weight
278.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 2 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2)(1:3): .25 mg/ml
SMILES
CCCCCCCCCCCCCCP(=O)(O)O
InChi Code
InChI=1S/C14H31O3P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18(15,16)17/h2-14H2,1H3,(H2,15,16,17)
InChi Key
BVQJQTMSTANITJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $22

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    500 mg

    $49

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    1 g

    $81

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    Product 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 lysophosphatidic acid 1 (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 peroxisome proliferator-activated receptor γ reporter construct 4-fold compared to controls and partially inhibits autotaxin with an IC50 of approximately 3 µM.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tokumura, A., Majima, E., Kariya, Y., et al. Identification of human lysophospholipase D, a lysophosphatidic acid-producing enzyme, as autotaxin, a multifunctional phosphodiesterase. The Journal of Biological Chemisty 277(42), 39436-39442 (2002).

    2. Chun, J., Goetzl, E.J., Hla, T., et al. International union of pharmacology. XXXIV. Lysophospholipid receptor nomenclature. Pharmacol. Rev. 54(2), 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. The Journal of Biological Chemisty 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).