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

Cayman Chemical Item Number 10008390

PIP3C-16; DHPI-3,4,5-P3; Phosphatidylinositol-3,4,5-triphosphate C-6 (CAS 799268-62-5)

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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, 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).

  • PIP3C-16
  • DHPI-3,4,5-P3
  • Phosphatidylinositol-3,4,5-triphosphate C-6
Formal Name 1-​(1,​2R-​dihexanoylphosphatidyl)inositol-​3,​4,​5-​triphosphate,​ tetraammonium salt
CAS Number 799268-62-5
Molecular Formula C21H54N4O22P4 · 4NH4
Formula Weight 838.6
Formulation A lyophilized powder
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
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Size Price Quantity Subtotal
100 µg $40.00 $0.00
500 µg $180.00 $0.00
1 mg $320.00 $0.00
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Cart Total $0.00

Pricing updated 2015-08-01. Prices are subject to change without notice.

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