W140 (trifluoroacetate salt)

Cayman Chemical Item Number 10009110

W140 (trifluoroacetate salt)

Description

Sphingosine-1-phosphate (S1P) is a bioactive lipid that exhibits a broad spectrum of biological activities including cell proliferation, survival, migration, cytoskeletal organization, and morphogenesis.^1,2,3 It exerts its activity by binding to five distinct G protein-coupled receptors, S1P₁/EDG-1, S1P₂/EDG-5, S1P₃/EDG-3, S1P₄/EDG-6, and S1P₅/EDG-8.^1,2 W140 is an inactive enantiomer of W146, a selective S1P₁ antagonist (K_i = 77 nM), that binds to the S1P₁ receptor with a K_i of 4.6 µM (2a = W146; 2b = W140 in supplemental material).⁴ It exhibits no biological activity in vivo and can therefore serve as an effective control compound for experiments involving W146.

1 Takuwa, Y., Takuwa, N., and Sugimoto, N. The Edg family G protein-coupled receptors for lysophospholipids: Their signaling properties and biological activities. J Biochem 131 767-771 (2002).

2 Ishii, I., Fukushima, N., Ye, X., et al. Lysophospholipid receptors: Signaling and biology. Annu Rev Biochem 73 321-354 (2004).

3 Kluk, M.J., and Hla, T. Signaling of sphingosine-1-phosphate via the S1P/EDG-family of G-protein-coupled receptors. Biochim Biophys Acta 1582 72-80 (2002).

4 Sanna, M.G., Wang, S., Gonzalez-Cabrera, P.J., et al. Enhancement of capillary leakage and restoration of lymphocyte egress by a chiral S1P₁ antagonist in vivo. Nat Chem Biol 2(8) 434-441 (2006).

Formal Name

3-amino-4-(3-hexylphenylamino)-4-oxobutyl phosphonic acid

Molecular Formula

C₁₆H₂₇N₂O₄P • C₂HF₃O₂

Formula Weight

456.4

Formulation

A crystalline solid

Purity

≥95%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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CCCCCCc1cccc(c1)NC(=O)[C@@H](N)CCP(=O)(O)O

Background Reading

Ishii, I., Fukushima, N., Ye, X., et al. Lysophospholipid receptors: Signaling and biology. Annu Rev Biochem 73 321-354 (2004).

Sanna, M.G., Wang, S., Gonzalez-Cabrera, P.J., et al. Enhancement of capillary leakage and restoration of lymphocyte egress by a chiral S1P₁ antagonist in vivo. Nat Chem Biol 2(8) 434-441 (2006).

Kluk, M.J., and Hla, T. Signaling of sphingosine-1-phosphate via the S1P/EDG-family of G-protein-coupled receptors. Biochim Biophys Acta 1582 72-80 (2002).

Takuwa, Y., Takuwa, N., and Sugimoto, N. The Edg family G protein-coupled receptors for lysophospholipids: Their signaling properties and biological activities. J Biochem 131 767-771 (2002).

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Subtotal

500 µg 
$63.00

$0.00

1 mg 
$120.00

$0.00

5 mg 
$504.00

$0.00

10 mg 
$882.00

$0.00

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W140 (trifluoroacetate salt)