An S1P1 receptor antagonist
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Enantiomer(s)
10009110W140 (trifluoroacetate salt)
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W146 (trifluoroacetate salt)

Item No. 10009109

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
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
Solubility(Learn about Variance in Solubility)
Methanol: 0.1 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $86

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    1 mg

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    5 mg

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    10 mg

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    Product Description

    W146 is a sphingosine-1-phosphate receptor 1 (S1P1) antagonist (Ki = 77 nM).1 It is selective for S1P1 over S1P2, S1P3, and S1P5 receptors (Kis = >10 µM for all). W146 prevents ligand-induced receptor internalization in CHO cells and inhibits the phosphorylation of ERK1 and Akt when used at a concentration of 10 µM. W146 (5 mg/kg) increases AMD3100-induced Kit+/Sca-1+/Lin− hematopoietic stem progenitor cell (KSL-HSPC) entrance into mouse blood circulation from the bone marrow when administered in combination with the chemokine (C-X-C motif) receptor 4 (CXCR4) antagonist and stem cell-mobilizer AMD3100.2 Intranasal or intradermal administration of W146 (10 µg) also disrupts the endothelial barrier and induces the infiltration of polymorphonuclear (PMN) neutrophils into the lungs and skin in an ovalbumin-induced mouse model of immune cell-mediated vascular injury.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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. Nat. Chem. Biol. 2(8), 434-441 (2006).

    2. Liu, J., Zhao, J., Lee, J.-F., et al. 3-Amino-4-(3-hexylphenylamino)-4-oxobutyl phosphonic acid (W146), a selective antagonist of sphingosine-1-phospahte receptor subtype 1, enhances AMD3100-stimulated mobilization of hematopoietic stem progenitor cells in animals. J. Biochem. Pharmacol. Res. 1(4), 197-203 (2013).

    3. Burg, N., Swendeman, S., Worgall, S., et al. Sphingosine 1-phosphate receptor 1 signaling maintains endothelial cell barrier function and protects against immune complex-induced vascular injury. Arthritis Rheumatol. 70(11), 1879-1889 (2018).

    Product Citations

    Wang, M., Wu, H., Wang, R., et al. Inhibition of sphingosine 1-phosphate (S1P) receptor ½/3 ameliorates biological dysfunction in rheumatoid arthritis fibroblast-like synoviocyte MH7A cells through Gαi/Gαs rebalancing. Clin. Exp. Pharmacol. Physiol. 48(8), 1080-1089 (2021).

    Beach, J.A., Aspuria, P.J., Cheon, D.J., et al. Sphingosine kinase 1 is required for TGF-β mediated fibroblast-to-myofibroblast differentiation in ovarian cancer. Oncotarget 7(4), 4167-4182 (2016).