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850165P

Avanti

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

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

Synonym(s):

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))

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About This Item

Empirical Formula (Hill Notation):
C47H94N3O19P3
CAS Number:
799268-59-0
Molecular Weight:
1098.18
UNSPSC Code:
51191904
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 100 μg (with stopper and crimp cap (850165P-100ug))
pkg of 1 × 500 μg (with stopper and crimp cap (850165P-500ug))

manufacturer/tradename

Avanti Research™ - A Croda Brand 850165P

lipid type

cardiolipins
phospholipids

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(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=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 4,5-bisphosphate (PIP2) is a negatively charged phospholipid, abundant in the plasma membrane.

Application

18:0-20:4 PI(4,5)P2 or 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1′-myo-inositol-4′,5′-bisphosphate) (ammonium salt) has been used:
  • in cryo-electron microscopy (cryo-EM) grid preparation
  • in host 1-O-1-(Z)-octadecenyl-2-arachidonoyl-sn-glycero-3-phosphocholine (plasmenyl-SAPC) small unilamellar vesicles (SUVs) in the presence of H2O2 to activate cyt c plasmalogenase activity
  • to study whether acyl chain types affect phosphatidylinositol 4,5-bisphosphate (PIP2) cluster formation

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (850165P-100ug)
2 mL Amber Serum Vial with Stopper and Crimp Cap (850165P-500ug)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Peter Y Mercredi et al.
Journal of molecular biology, 428(8), 1637-1655 (2016-03-20)
Assembly of HIV-1 particles is initiated by the trafficking of viral Gag polyproteins from the cytoplasm to the plasma membrane, where they co-localize and bud to form immature particles. Membrane targeting is mediated by the N-terminally myristoylated matrix (MA) domain
Tao Liang et al.
The Journal of biological chemistry, 289(9), 6028-6040 (2014-01-17)
In β-cells, syntaxin (Syn)-1A interacts with SUR1 to inhibit ATP-sensitive potassium channels (KATP channels). PIP2 binds the Kir6.2 subunit to open KATP channels. PIP2 also modifies Syn-1A clustering in plasma membrane (PM) that may alter Syn-1A actions on PM proteins
Christopher M Jenkins et al.
The Journal of biological chemistry, 293(22), 8693-8709 (2018-03-14)
Plasmalogens are phospholipids critical for cell function and signaling that contain a vinyl ether linkage at the sn-1 position and are highly enriched in arachidonic acid (AA) at the sn-2 position. However, the enzyme(s) responsible for the cleavage of the
Qinrui Wang et al.
Structure (London, England : 1993), 28(2), 169-184 (2019-12-07)
Polycystin-2 (PC2) is a transient receptor potential (TRP) channel present in ciliary membranes of the kidney. PC2 shares a transmembrane fold with other TRP channels, in addition to an extracellular domain found in TRPP and TRPML channels. Using molecular dynamics
George Khelashvili et al.
Biochemistry, 51(39), 7685-7698 (2012-09-07)
Syntaxin (STX) is a N-ethylmaleimide-sensitive factor attachment protein receptor (SNARE) protein that binds to the plasma membrane and regulates ion channels and neurotransmitter transporters. Experiments have established the involvement of the N-terminal segment of STX in direct protein-protein interactions and
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