PtdIns-(3,4,5)-P3 (1-stearoyl, 2-arachidonoyl) (sodium salt)

PtdIns-(3,4,5)-P₃ (1-stearoyl, 2-arachidonoyl) (sodium salt)

Cayman Chemical Item Number 64930

Phosphatidylinositol-3,4,5-triphosphate C-18 (sodium salt)

Description

The phosphatidylinositol (PtdIns) phosphates represent a small percentage of total membrane phospholipids. However, they play a critical role in the generation and transmission of cellular signals.^1,2 PtdIns-(3,4,5)-P₃ can serve as an anchor for the binding of signal transduction proteins bearing pleckstrin homology (PH) domains. Centuarin α and Akts are examples of PtdIns-(3,4,5)-P₃-binding proteins.^3,4 Protein-binding to PtdIns-(3,4,5)-P₃ is important for cytoskeletal rearrangements and membrane trafficking. PtdIns-(3,4,5)-P₃ is resistant to cleavage by PI-specific PLC. Thus, it is likely to function in signal transduction as a modulator in its own right, rather than as a source of inositol tetraphosphates. For further reading on inositol phospholipids, see also references ⁵ and ⁶.

1 Lapetina, E.G., Billah, M.M., and Cuatrecasas, P. The phosphatidylinositol cycle and the regulation of arachidonic acid production. Nature 292 367-369 (1981).

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

3 Tanaka, K., Imajoh-Ohmi, S., Sawada, T., et al. A target of phosphatidylinositol 3,4,5-trisphosphate with a zinc finger motif similar to that of the ADP-ribosylation-factor GTPase-activating protein and two pleckstrin homology domains. Eur J Biochem 245 512-519 (1997).

4 Yang, X., Rudolf, M., Carew, M.A., et al. Inositol 1,3,4-trisphosphate acts in vivo as a specific regulator of cellular signaling by inositol 3,4,5,6-tetrakisphosphate. J Biol Chem 274 18973-18980 (1999).

5 Pike, L.J., and Casey, L. Localization and turnover of phosphatidylinositol 4,5-bisphosphate in caveolin-enriched membrane domains. J Biol Chem 271 26453-26456 (1996).

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

Synonyms

Phosphatidylinositol-3,4,5-triphosphate C-18 (sodium salt)

Formal Name

1-(1-octadecanoyl-2R-(5Z,8Z,11Z,14Z)-eicosatetraenoylphosphatidyl)inositol-3,4,5-trisphosphate, tetrasodium salt

Molecular Formula

C₄₇H₈₂O₂₂P₄ · 4Na

Formula Weight

1215.0

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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CCCCCCCCCCCCCCCCCC(OCC(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COP([O-])(O[C@@H]1[C@H](O)[C@H](OP([O-])(O)=O)[C@@H](OP([O-])(O)=O)[C@H](OP([O-])(O)=O)[C@H]1O)=O)=O

Background Reading

Lapetina, E.G., Billah, M.M., and Cuatrecasas, P. The phosphatidylinositol cycle and the regulation of arachidonic acid production. Nature 292 367-369 (1981).

Tanaka, K., Imajoh-Ohmi, S., Sawada, T., et al. A target of phosphatidylinositol 3,4,5-trisphosphate with a zinc finger motif similar to that of the ADP-ribosylation-factor GTPase-activating protein and two pleckstrin homology domains. Eur J Biochem 245 512-519 (1997).

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

Yang, X., Rudolf, M., Carew, M.A., et al. Inositol 1,3,4-trisphosphate acts in vivo as a specific regulator of cellular signaling by inositol 3,4,5,6-tetrakisphosphate. J Biol Chem 274 18973-18980 (1999).

Pike, L.J., and Casey, L. Localization and turnover of phosphatidylinositol 4,5-bisphosphate in caveolin-enriched membrane domains. J Biol Chem 271 26453-26456 (1996).

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

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PtdIns-(3,4,5)-P₃ (1-stearoyl, 2-arachidonoyl) (sodium salt)