D-myo-Inositol-1,3,4,5,6-pentaphosphate (sodium salt)

D-myo-Inositol-1,3,4,5,6-pentaphosphate (sodium salt)

Cayman Chemical Item Number 10007784

1,3,4,5,6-IP₅ (sodium salt); Ins(1,3,4,5,6)P₅ (sodium salt)

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 K_d value of 590 nM.⁷

1 Vivanco, I., and Sawyers, C.L. The phosphatidylinositol 3-kinase-AKT pathway in human cancer. Nat Rev Cancer 2 489-501 (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 361 315-325 (1993).

4 Shears, S.B. The versatility of inositol phosphates as cellular signals. Biochim Biophys Acta 1436 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 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. J Biol Chem 273(46) 30497-30508 (1998).

Synonyms

1,3,4,5,6-IP5 (sodium salt)
Ins(1,3,4,5,6)P5 (sodium salt)

Formal Name

D-myo-inositol-1,3,4,5,6-penta(hydrogen phosphate), pentasodium salt

Molecular Formula

C₆H₁₂O₂₁P₅ · 5Na

Formula Weight

690.0

Formulation

A lyophilized powder

Purity

≥98%

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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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+]

Background Reading

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

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

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

Kavran, J.M., Klein, D.E., Lee, A., et al. Specificity and promiscuity in phosphoinositide binding by pleckstrin homology domains. J Biol Chem 273(46) 30497-30508 (1998).

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).

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

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

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100 µg 
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500 µg 
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1 mg 
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5 mg 
$1,715.00

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D-myo-Inositol-1,3,4,5,6-pentaphosphate (sodium salt)