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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: 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))

  • CAS Number 799268-59-0

  • Empirical Formula (Hill Notation) C47H94N3O19P3

  • Molecular Weight 1098.18

  •  NACRES NA.25

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Properties

Related Categories Avanti PI, PIP & LPI, Avanti Phospholipids, Avanti Polar Lipids Products, Biochemicals and Reagents, Lipids More...
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))
mfr. no.   Avanti Polar Lipids, 850165P
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+]

Description

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)

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Storage & Handling of Lipids - Avanti® Polar Lipids

The following statements pertain specifically to Avanti’s lipid products for research and should not necessarily be applied to cGMP lipids intended for pharmaceutical or diagnostic applications.
Keywords: Diagnostic, Oxidations, Pharmaceutical, Solvents

Protocols

Determination of Phospholipid Oxidation by UV/VIS Spectroscopy - Avanti® Polar Lipids

The percent oxidation of a phospholipid can be determined by using Beer’s Law to calculate the peroxidized phospholipid’s concentration from its absorbance at 234 nm.
Keywords: Extinction coefficient, Oxidations

General Lipid/BSA Solubilization Protocol For Cell Delivery

Water Solutions: Solubilizing some lipids is difficult using organic solvents. Typically, lipids are suspended in methanol to aliquot, the methanol is then dried and the residue dispersed using fatty...
Keywords: Evaporation, Solvents

Peer-Reviewed Papers
15

References

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