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850155P

Avanti

18:1 PI(4,5)P2

Avanti Polar Lipids

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Synonym(s):
1,2-di-(9Z-octadecenoyl)-sn-glycero-3-[phosphoinositol-4,5-bisphosphate] (ammonium salt); PIP2[4′,5′](18:1(9Z)/18:1(9Z))
Empirical Formula (Hill Notation):
C45H94N3O19P3
CAS Number:
Molecular Weight:
1074.16
NACRES:
NA.25

description

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

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 100 μg (with stopper and crimp cap (850155P-100ug))
pkg of 1 × 500 μg (with stopper and crimp cap (850155P-500ug))

manufacturer/tradename

Avanti Polar Lipids

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@@](COP([O-])(O[C@H]1[C@H](O)[C@@H](OP(O)([O-])=O)[C@H](OP([O-])(O)=O)[C@@H](O)[C@H]1O)=O)(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O.[NH4+].[NH4+].[NH4+]

General description

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.
Phosphatidylinositol is a structural phospholipid. Phosphatidylinositol phosphate (PIP) is located in the plasma membrane.

Application

18:1 PI(4,5)P2 is suitable to use as a supplement in native macrophage membranes to generate phospholipid enriched membrane liposome.s It has also been used:
  • in the preparation of anionic phospholipid liposomes
  • as a component in supported membrane tube (SMrT) templates
  • in liposome preparation

Biochem/physiol Actions

Phosphatidylinositol bisphosphate (PIP2) can effectively stimulate the ATPase.

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (850155P-100ug)
2 mL Amber Serum Vial with Stopper and Crimp Cap (850155P-500ug)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


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Phosphatidylinositol Turnover and Receptors
Ramazzotti G, et al.
Archives of Biochemistry and Biophysics (2016)
Dissociation of Rac1 (GDP)-RhoGDI complexes by the cooperative action of anionic liposomes containing phosphatidylinositol 3, 4, 5-trisphosphate, Rac guanine nucleotide exchange factor, and GTP
Ugolev Y, et al.
The Journal of Biological Chemistry, 283(32), 22257-22271 (2008)
Tripartite Chimeras Comprising Functional Domains Derived from the Cytosolic NADPH Oxidase Components p47phox, p67phox, and Rac1 Elicit Activator-independent Superoxide Production by Phagocyte Membranes AN ESSENTIAL ROLE FOR ANIONIC MEMBRANE PHOSPHOLIPIDS
Berdichevsky Y, et al.
The Journal of biological chemistry, 282(30), 22122- 22139 (2007)
Use of the supported membrane tube assay system for real time analysis of membrane fission reactions
Dar S, et al.
Nature Protocols, 12(2), 390-390 (2017)
Phosphatidylinositol phosphate, phosphatidylinositol bisphosphate, and the phosphoinositol sphingolipids are found in the plasma membrane and stimulate the plasma membrane H+-ATPase of Saccharomyces cerevisiae
Patton JL and Lester RL
Archives of Biochemistry and Biophysics, 292(1), 70-76 (1992)

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