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W146 (trifluoroacetate salt)

Item № 10009109
CAS № 909725-62-8
Purity ≥95%
product image
                (CAS 909725-62-8)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     500 µg $63.00 0.00
     1 mg $120.00 0.00
     5 mg $504.00 0.00
     10 mg $882.00 0.00

Pricing updated 2019-07-17. Prices are subject to change without notice.

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.

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Technical Information
Formal Name
[3R-amino-4-[(3-hexylphenyl)amino]-4-oxobutyl]-phosphonic acid, mono(trifluoroacetate)
CAS Number
909725-62-8
Molecular Formula
C16H27N2O4P • CF3COOH
Formula Weight
456.4
Purity
≥95%
Formulation
A crystalline solid
λmax
205, 245 nm
SMILES
CCCCCCC1=CC=CC(NC([C@H](N)CCP(O)(O)=O)=O)=C1.FC(F)(C(O)=O)F
InChI Code
InChI=1S/C16H27N2O4P.C2HF3O2/c1-2-3-4-5-7-13-8-6-9-14(12-13)18-16(19)15(17)10-11-23(20,21)22;3-2(4,5)1(6)7/h6,8-9,12,15H,2-5,7,10-11,17H2,1H3,(H,18,19)(H2,20,21,22);(H,6,7)/t15-;/m1./s1
InChI Key
JDWCNCPWPLHFEX-XFULWGLBSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

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References & Product Citations
Product Description References

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(6), 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(1-3), 72-80 (2002).

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

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