PtdIns-(4,5)-P2 (1,2-dipalmitoyl) (ammonium salt)

PtdIns-(4,5)-P₂ (1,2-dipalmitoyl) (ammonium salt)

Cayman Chemical Item Number 64924

Phosphatidylinositol-4,5-diphosphate C-16; DPPI-4,5-P₂

Description

The phosphatidylinositol 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-(4,5)-P₂ incorporated into membrane lipids can bind to important proteins such as Group IV cPLA₂ and PLCδ1, enhancing their adherence to the membrane and increasing the rate of substrate hydrolysis.³ PtdIns-(4,5)-P₂ can be further phosphorylated to give triphosphates such as PtdIns-(3,4,5)-P₃. It can also be cleaved by PI-specific PLC to give inositol triphosphates. The diacyl glycerol and IP₃ generated by this PLC-cleavage are also part of a complex biochemical and signal transduction cascade which has not been entirely elucidated. For some additional reading, please see references ², ⁴, and ⁵.

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 Mosior, M., Six, D.A., and Dennis, E.A. Group IV cytosolic phospholiase A₂ binds with high affinity and specificity to phosphatidylinositol 4,5-bisphosphate resulting in dramatic increases in activity. J Biol Chem 273 2184-2191 (1998).

4 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).

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

Synonyms

Phosphatidylinositol-4,5-diphosphate C-16
DPPI-4,5-P2

Formal Name

1-(1,2R-dihexadecanoylphosphatidyl)inositol-4,5-bisphosphate, triammonium salt

Molecular Formula

C₄₁H₇₈O₁₉P₃ · 3NH₄

Formula Weight

1022.1

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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CCCCCCCCCCCCCCCC(OCC(COP(O[C@@H]1[C@H](O)[C@H](O)[C@@H](OP([O-])(O)=O)[C@H](OP([O-])(O)=O)[C@H]1O)([O-])=O)OC(CCCCCCCCCCCCCCC)=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).

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).

Mosior, M., Six, D.A., and Dennis, E.A. Group IV cytosolic phospholiase A₂ binds with high affinity and specificity to phosphatidylinositol 4,5-bisphosphate resulting in dramatic increases in activity. J Biol Chem 273 2184-2191 (1998).

Oates, J.C., Christensen, E.F., Reilly, C.M., et al. Prospective measure of serum 3-nitrotyrosine levels in systemic lupus erythematosus: Correlation with disease activity. Proc Assoc Am Physicians 111 611-621 (1999).

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

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500 µg 
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PtdIns-(4,5)-P₂ (1,2-dipalmitoyl) (ammonium salt)