850185 | 08:0 PI(4,5)P2

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

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08:0 PI(4,5)P2

08:0 PI(4,5)P2

1,2-dioctanoyl-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.
The dioctanoyl derivative of PI(4,5)P2 is more water soluble than its long chain counterparts.
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C25H58N3O19P3
Percent Composition
C 37.64%, H 7.33%, N 5.27%, O 38.11%, P 11.65%
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
852043-37-9
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
797.658
Exact Mass
797.288
Synonyms
PIP2[4',5'](8:0/8:0)
110665

Koizumi A, Narita S, Nakanishi H, Ishikawa M, Eguchi S, Kimura H, Takasuga S, Huang M, Inoue T, Sasaki J, Yoshioka T, Habuchi T, Sasaki T. Increased fatty acyl saturation of phosphatidylinositol phosphates in prostate cancer progression. Sci Rep. 2019 Sep 13;9(1):13257. doi: 10.1038/s41598-019-49744-3.

 PubMed ID: 31520002

Vivas O, Tiscione SA, Dixon RE, Ory DS, Dickson EJ. Niemann-Pick Type C Disease Reveals a Link between Lysosomal Cholesterol and PtdIns(4,5)P2 That Regulates Neuronal Excitability. Cell Rep. 2019 May 28;27(9):2636-2648.e4. doi: 10.1016/j.celrep.2019.04.099.

 PubMed ID: 31141688

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]

 PubMed ID: 26992353

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]

PubMed ID: 24429282

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]

 PubMed ID: 23229899

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]

PubMed ID: 22977244

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]

 PubMed ID: 22950482

Hansen, S.B., X. Tao, and R. Mackinnon. (2011). Structural basis of PIP(2) activation of the classical inward rectifier K(+) channel Kir2.2. Nature[PubMed]

 PubMed ID: 21874019

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. [PubMed]

 PubMed ID: 22722250