PtdIns-(3,4,5)-P3 (1,2-dihexanoyl) (ammonium salt)

PtdIns-(3,4,5)-P₃ (1,2-dihexanoyl) (ammonium salt)

Cayman Chemical Item Number 10008390

Phosphatidylinositol-3,4,5-triphosphate C-6 (ammonium salt); DHPI-3,4,5-P₃ (ammonium salt); PIP3C-16 (ammonium 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.¹² PtdIns-(3,4,5)-P₃, also known as PIP₃, is resistant to cleavage by PI-specific phospholipase C (PLC).³ Thus, it is likely to function in signal transduction as a modulator in its own right, rather than as a source of inositol tetraphosphates. PIP₃ can serve as an anchor for the binding of signal transduction proteins bearing pleckstrin homology (PH) domains.⁴⁵ Protein binding to PIP₃ is important for cytoskeletal rearrangement and membrane trafficking.⁶ PtdIns-(3,4,5)-P₃ (1,2-dihexanoyl) is a synthetic analog of natural PIP₃ with C₆:0 fatty acids at the sn-1 and sn-2 positions. The compound features the same inositol and diacylglycerol (DAG) stereochemistry as that of the natural compound. The short fatty acid chains of this analog give it different physical properties from naturally-occurring PIP₃, including higher solubility in aqueous media.

1 Guan, X., and Wenk, M.R. Biochemistry of inositol lipids. Front Biosci 13 3239-3251 (2008).

2 Kashiwada, M., Lu, P., and Rothman, P.B. PIP₃ pathway in regulatory T cells and autoimmunity. Immunol Res 39 194-224 (2007).

3 Serunian, L.A., Haber, M.T., Fukui, T., et al. Polyphosphoinositides produced by phosphatidylinositol 3-kinase are poor substrates for phospholipases C from rat liver and bovine brain. J Biol Chem 264(30) 17809-17815 (1989).

4 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).

5 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).

6 Hamaguchi, N., Ihara, S., Ohdaira, T., et al. Pleckstrin-2 selectively interacts with phosphatidylinositol 3-kinase lipid products and regulates actin organization and cell spreading. Biochem Biophys Res Commun 361 270-275 (2007).

Synonyms

Phosphatidylinositol-3,4,5-triphosphate C-6 (ammonium salt)
DHPI-3,4,5-P3 (ammonium salt)
PIP3C-16 (ammonium salt)

Formal Name

1-(1,2R-dihexanoylphosphatidyl)inositol-3,4,5-triphosphate, tetraammonium salt

Molecular Formula

C₂₁H₅₄N₄O₂₂P₄ · 4NH₄

Formula Weight

838.6

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](O)[C@H]1OP([O-])(OC[C@H](OC(CCCCC)=O)COC(CCCCC)=O)=O

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100 µg 
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500 µg 
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1 mg 
$304.00

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5 mg 
$1,330.00

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PtdIns-(3,4,5)-P₃ (1,2-dihexanoyl) (ammonium salt)