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Tetradecyl Phosphonate

Catalog No.GC17617

pan-antagonist of lysophosphatidic acid 1 (LPA1), LPA2, and LPA3 receptors

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Tetradecyl Phosphonate Chemical Structure

Cas No.: 4671-75-4

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Sample solution is provided at 25 µL, 10mM.

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Background

Tetradecyl phosphonate is a pan-antagonist of lysophosphatidic acid 1 (LPA1), LPA2, and LPA3 receptors. The IC50 value for inhibition of LPA-induced calcium mobilization was 10 μM, 5.5 μM, and 3.1 μM, respectively. At a concentration of 10 μM, tetradecyl phosphonate activates a peroxisome proliferator-activated receptor γ reporter construct 4-fold when compared with the controls and partially inhibits autotaxin with an IC50 value of approximately 3 μM [1].

Lysophosphatidic acid (LPA), also known as autotaxin (ATX), is a lipid signalling molecule formed by the hydrolysis of lysophosphatidyl choline by lysophospholipase D [2]. LPA signals through four different G protein-coupled receptors, named as LPA1/EDG-2, LPA2/EDG-4, LPA3/EDG-7, and LPA4/GPR23 [3]. It has been reported that LPA was involved in activating peroxisome proliferator-activated receptor γ (PPARγ) [4].

References:
[1].  Durgam G G, Virag T, Walker M D, et al. Synthesis, structure activity relationships, and biological evaluation of fatty alcohol phosphates as lysophosphatidic acid receptor ligands, activators of PPARγ, and inhibitors of autotaxin[J]. Journal of medicinal chemistry, 2005, 48(15): 4919-4930.
[2].  Tokumura A, Majima E, Kariya Y, et al. Identification of human plasma lysophospholipase D, a lysophosphatidic acid-producing enzyme, as autotaxin, a multifunctional phosphodiesterase[J]. Journal of Biological Chemistry, 2002, 277(42): 39436-39442.
[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]. Journal of Biological Chemistry, 2003, 278(28): 25600-25606.
[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[J]. Proceedings of the National Academy of Sciences, 2003, 100(1): 131-136.

Chemical Properties

Cas No. 4671-75-4 SDF
Chemical Name tetradecylphosphonic acid
Canonical SMILES CCCCCCCCCCCCCCP(=O)(O)O
Formula C14H31O3P M.Wt 278.4
Solubility ≥ 27.8mg/mL in ETOH Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 3.592 mL 17.9598 mL 35.9195 mL
5 mM 0.7184 mL 3.592 mL 7.1839 mL
10 mM 0.3592 mL 1.796 mL 3.592 mL
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