An anticancer inositol phosphate
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D-myo-Inositol-1,3,4,5,6-pentaphosphate (sodium salt)

Item No. 10007784

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
D-myo-inositol-1,3,4,5,6-penta(hydrogen phosphate), pentasodium salt
Synonyms
  • Ins(1,3,4,5,6)P5
  • 1,3,4,5,6-IP5
Molecular Formula
C6H12O21P5 • 5Na
Formula Weight
690.0
Purity
≥98%
Formulation (Request formulation change)
A lyophilized powder
SMILES
O[C@@H]1[C@H](OP([O-])(O)=O)[C@@H](OP([O-])(O)=O)[C@H](OP([O-])(O)=O)[C@@H](OP([O-])(O)=O)[C@@H]1OP([O-])(O)=O.[Na+].[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C6H17O21P5.5Na/c7-1-2(23-28(8,9)10)4(25-30(14,15)16)6(27-32(20,21)22)5(26-31(17,18)19)3(1)24-29(11,12)13;;;;;/h1-7H,(H2,8,9,10)(H2,11,12,13)(H2,14,15,16)(H2,17,18,19)(H2,20,21,22);;;;;/q;5*+1/p-5/t1-,2?,3?,4?,5?,6?;;;;;
InChi Key
QSNOOIWNTRYOFK-HKUWTPFQSA-I
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µg

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    Product Description

    The phosphatidylinositol 3-kinase (PI3K)/Akt signal transduction pathway plays critical roles in cell growth and proliferation making it an attractive target for anticancer agents.1 Inositol-1,3,4,5,6-pentaphosphate (Ins(1,3,4,5,6)P5) is one of the many inositol phosphate isomers that act as small, soluble second messengers in the transmission of cellular signals.2,3,4 It can be interconverted with Ins(3,4,5,6)P4 by a 1-kinase/1-phosphatase cycle, as well as with Ins(1,4,5,6)P4 in a 3-kinase/3-phosphatase cycle.4 Ins(1,3,4,5,6)P5 inhibits the phosphorylation and kinase activity of Akt/PKB, inducing apoptosis in ovarian, lung, and breast cancer cells.5 It exhibits antiangiogenic activity in vitro, blocking capillary tube formation of HUVEC, as well as antitumor effects against cancer xenografts in nude mice.6 Ins(1,3,4,5,6)P5 binds to the PH domain of Grp1 with a Kd value of 590 nM.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vivanco, I., and Sawyers, C.L. The phosphatidylinositol 3-kinase-AKT pathway in human cancer. Nat. Rev. Cancer 2(7), 489-501 (2002).

    2. Majerus, P.W. Inositol phosphate biochemistry. Annu. Rev. Biochem. 61, 225-250 (1992).

    3. Berridge, M.J. Inositol trisphosphate and calcium signalling. Nature 361(6410), 315-325 (1993).

    4. Shears, S.B. The versatility of inositol phosphates as cellular signals. Biochim. Biophys. Acta 1436(1-2), 49-67 (1998).

    5. Piccolo, E., Vignati, S., Maffucci, T., et al. Inositol pentakisphosphate promotes apoptosis through the PI 3-K/Akt pathway. Oncogene 23(9), 1754-1765 (2004).

    6. Maffucci, T., Piccolo, E., Cumashi, A., et al. Inhibition of the phosphatidylinositol 3-kinase/Akt pathway by inositol pentakisphosphate results in antiangiogenic and antitumor effects. Cancer Res. 65(18), 8339-8349 (2005).

    7. Kavran, J.M., Klein, D.E., Lee, A., et al. Specificity and promiscuity in phosphoinositide binding by pleckstrin homology domains. The Journal of Biological Chemisty 273(46), 30497-30508 (1998).