ChemicalBook Product Catalog Biochemical Engineering Inhibitors Metabolism Phospholipase (e.g. PLA) inhibitors U-73122

U-73122

Product NameU-73122
CAS112648-68-7
MFC29H40N2O3
MW464.64
EINECS
MOL File112648-68-7.mol

Chemical Properties

Boiling point	617.1±55.0 °C(Predicted)
Density	1.16±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	ethanol: 0.7 mg/mL
form	solid
pka	10.69±0.40(Predicted)
color	off-white
Water Solubility	Soluble in DMSO, ethanol, or DMF at approx. 0.5mg/ml. May require heating or overnight mixing. Insoluble in water
Stability	Stable for 1 year from date of purchase as supplied. Use caution when storing DMSO solutions. Typically solutions in DMSO can be stored at -20°C for approximately 2 months. However, any solutions that turn pink should be discarded.
InChIKey	LUFAORPFSVMJIW-PFQOISFUNA-N
SMILES	[C@@]12([H])CCC3C=C(OC)C=CC=3[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])NCCCCCCN1C(=O)C=CC1=O \|&1:0,12,16,18,21,r\|

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

U-73122 is an inhibitor of PLC-dependent processes, however, the mechanism of action remains unclear. The IC₅₀ values for inhibition of platelet aggregation induced by collagen or thrombin are 0.6 and 5 μM, respectively. It also exhibits inhibitory activity against HIV-1 integrase with an IC₅₀ value of 7 μM.

Uses

It is used as a phospholipase C, phospholipase A2, and 5-LO inhibitor. It is also determined that in SK-N-SH neuroblastoma cells, U-73122 inhibits agonist-induced down-regulation of muscarinic receptors. In addition, it is a useful tool to investigate receptor-mediated PI turnover in signal transduction. U-73122 is a potent inhibitor of human neutrophil adhesion to biological surfaces (IC50 = 50 nM) as well as adhesion-dependent granule exocytosis and oxidative burst. U-73343 (sc-201422) is useful as a negative control for investigations of U-73122 phospholipase C antagonism and its cellular consequences.

Definition

ChEBI: An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.

Biological Activity

Phospholipase C inhibitor. Inhibits agonist-induced platelet aggregation with IC 50 values of 1-5 μ M. Potently inhibits human polymorphonuclear neutrophil adhesion on biological surfaces (IC 50 < 50 nM) and exhibits antinociceptive activity in vivo .

Biochem/physiol Actions

Inhibits the hydrolysis of PPI to IP3, which leads to a decrease in cytosolic free calcium. Inhibits the coupling of G protein-phospholipase C activation, while remaining unaffected by production of cAMP.

storage

Store at RT

References

[1] J E BLEASDALE. Selective inhibition of receptor-coupled phospholipase C-dependent processes in human platelets and polymorphonuclear neutrophils.[J]. Journal of Pharmacology and Experimental Therapeutics, 1990, 255 2: 756-768.
[2] ALEXANDER V ZHOLOS. Phospholipase C, but not InsP3 or DAG, -dependent activation of the muscarinic receptor-operated cation current in guinea-pig ileal smooth muscle cells[J]. British Journal of Pharmacology, 2009, 141 1: 23-36. DOI:10.1038/sj.bjp.0705584
[3] YOUNGSOO JUN William W Rutilio A Fratti. Diacylglycerol and its formation by phospholipase C regulate Rab- and SNARE-dependent yeast vacuole fusion.[J]. The Journal of Biological Chemistry, 2004: 53186-53195. DOI:10.1074/jbc.m411363200
[4] INÉS FERNÁNDEZ-ULIBARRI. Diacylglycerol is required for the formation of COPI vesicles in the Golgi-to-ER transport pathway.[J]. Molecular Biology of the Cell, 2007, 18 9: 3250-3263. DOI:10.1091/mbc.e07-04-0334

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