A sphingosine-1-phosphate receptor antagonist
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VPC 23019

Item No. 13240

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(R)-2-amino-3-((3-octylphenyl)amino)-3-oxopropyl dihydrogen phosphate
CAS Number
449173-19-7
Molecular Formula
C17H29N2O5P
Formula Weight
372.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 0.25 mg/ml
λmax
245 nm
SMILES
O=C([C@H](N)COP(O)(O)=O)NC1=CC(CCCCCCCC)=CC=C1
InChi Code
InChI=1S/C17H29N2O5P/c1-2-3-4-5-6-7-9-14-10-8-11-15(12-14)19-17(20)16(18)13-24-25(21,22)23/h8,10-12,16H,2-7,9,13,18H2,1H3,(H,19,20)(H2,21,22,23)/t16-/m1/s1
InChi Key
MRUSUGVVWGNKFE-MRXNPFEDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $44

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    1 mg

    $84

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    5 mg

    $283

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    10 mg

    $390

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    Product Description

    Sphingosine-1-phosphate (S1P; Item No. 62570) 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 VPC 23019 is an aryl amide-containing S1P analog that acts as a competitive antagonist at both S1P1 and S1P3 receptors (pKis = 7.86 and 5.93, respectively).4 It can inhibit S1P-induced migration of thyroid cancer cells, ovarian cancer cells, and neural stem cells.5

    WARNING This product is not for human or veterinary use.

    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. Davis, M.D., Clemens, J.J., Macdonald, T.L., et al. Sphingosine 1-phosphate analogs as receptor antagonists. The Journal of Biological Chemisty 280(11), 9833-9841 (2005).

    5. Takabe, K., Paugh, S.W., Milstien, S., et al. "Inside-out" signaling of sphingosine-1-phosphate: Therapeutic targets. Pharmacol. Rev. 60(2), 181-195 (2008).