850165 | 18:0-20:4 PI(4,5)P2

1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-myo-inositol-4',5'-bisphosphate) (ammonium salt)


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18:0-20:4 PI(4,5)P2

18:0-20:4 PI(4,5)P2

1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-myo-inositol-4',5'-bisphosphate) (ammonium salt)

Although PI(4,5)P2 is a minor component of cell membranes, it plays a critical role as a substrate for a number of important signaling proteins. PI(4,5)P2 is an intermediate in the IP3/DAG pathway where it is hydrolyzed by phospholipase C to liberate the second messengers, inositol 1,4,5-triphosphate (IP3) and diacylglycerol (DAG). PI(4,5)P2 is also a substrate for PI 3-kinase where it is phosphorylated to PI(3,4,5)P3, an activator of downstream signaling components such as the protein kinase AKT.
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C47H94N3O19P3
Percent Composition
C 51.40%, H 8.63%, N 3.83%, O 27.68%, P 8.46%
Purity
>99%
Stability
3 Months
Storage Temperature
-20°C
CAS Number
799268-59-0
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
1098.179
Exact Mass
1097.569
Synonyms
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-[phosphoinositol-4,5-bisphosphate] (ammonium salt)PIP2[4',5'](18:0/20:4(5Z,8Z,11Z,14Z))
Mercredi, P.Y., N. Bucca, B. Loeliger, C.R. Gaines, M. Mehta, P. Bhargava, P.R. Tedbury, L. Charlier, N. Floquet, D. Muriaux, C. Favard, C.R. Sanders, E.O. Freed, J. Marchant, and M.F. Summers. (2016). Structural and Molecular Determinants of Membrane Binding by the HIV-1 Matrix Protein. J Mol Biol [PubMed] Liang, T., L. Xie, C. Chao, Y. Kang, X. Lin, T. Qin, H. Xie, Z.P. Feng, and H.Y. Gaisano. (2014). Phosphatidylinositol 4,5-biphosphate (PIP2) Modulates Interaction of Syntaxin-1Awith Sulfonylurea Receptor 1 to Regulate Pancreatic Beta-Cell ATP-Sensitive Potassium Channels. J Biol Chem [PubMed] PtdIns4P synthesis by PI4KIIIalpha at the plasma membrane and its impact on plasma membrane identity. Nakatsu, F., J.M. Baskin, J. Chung, L.B. Tanner, G. Shui, S.Y. Lee, M. Pirruccello, M. Hao, N.T. Ingolia, M.R. Wenk, and P. De Camilli. (2012). J Cell Biol 199:1003-16.[PubMed] Wang, K., Z. Yang, U. Nair, K. Mao, X. Liu, and D.J. Klionsky. (2012). Phosphatatidylinositol 4-kinases are required for autophagic membrane trafficking. J Biol Chem [PubMed] Khelashvili, G., A. Galli, and H. Weinstein. (2012). Phosphatidylinositol 4,5-Biphosphate (PIP(2)) Lipids Regulate the Phosphorylation of Syntaxin N-Terminus by Modulating Both Its Position and Local Structure. Biochemistry 51:7685-98. [PubMed] Hammond, G.R., M.J. Fischer, K.E. Anderson, J. Holdich, A. Koteci, T. Balla, and R.F. Irvine. (2012). PI4P and PI(4,5)P2 are essential but independent lipid determinants of membrane identity. Science 337:727-30. The quantitatively minor phospholipid phosphatidylinositol (4,5)-bisphosphate [PI(4,5)P(2)] fulfills many cellular functions in the plasma membrane (PM), whereas its synthetic precursor, phosphatidylinositol 4-phosphate (PI4P), has no assigned PM roles apart from PI(4,5)P(2) synthesis. We used a combination of pharmacological and chemical genetic approaches to probe the function of PM PI4P, most of which was not required for the synthesis or functions of PI(4,5)P(2). However, depletion of both lipids was required to prevent PM targeting of proteins that interact with acidic lipids or activation of the transient receptor potential vanilloid 1 cation channel. Therefore, PI4P contributes to the pool of polyanionic lipids that define plasma membrane identity and to some functions previously attributed specifically to PI(4,5)P(2), which may be fulfilled by a more general polyanionic lipid requirement.[PubMed]