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

W146 (trifluoroacetate salt)

Cayman Chemical Item Number 10009109

W146 (trifluoroacetate salt)

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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 W146 is a S1P1 receptor antagonist that exhibits a Ki value of 77 nM for the human receptor in a GTP-γS binding assay with equipotency at the murine S1P1 receptor (2a = W146; 2b = W140 in supplemental material).4 No agonist or antagonist activity was observed at 10 µM W146 at S1P2, S1P3, or S1P5 receptors. W146 is active in vivo causing skin capillary leakage in murine lung and skin as well as inhibition of S1P1 agonist-induced lymphocyte sequestration. The half-life of W146 in rat blood is 73 minutes.

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).

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).

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).

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Size Price Quantity 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
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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