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U6881

Sigma-Aldrich

U-73343

Synonym(s):

1-[6-[((17β)-3-Methoxyestra-1,3,5[10]-trien-17-yl)amino]hexyl]-2,5-pyrrolidinedione

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About This Item

Empirical Formula (Hill Notation):
C29H42N2O3
CAS Number:
142878-12-4
Molecular Weight:
466.66
MDL number:
MFCD00211221
UNSPSC Code:
41106300
PubChem Substance ID:
24900662
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

200

form

powder

color

white

solubility

DMSO: soluble

SMILES string

[H][C@]12CC[C@]3(C)[C@H](CC[C@@]3([H])[C@]1([H])CCc4cc(OC)ccc24)NCCCCCCN5C(=O)CCC5=O

InChI

1S/C29H42N2O3/c1-29-16-15-23-22-10-8-21(34-2)19-20(22)7-9-24(23)25(29)11-12-26(29)30-17-5-3-4-6-18-31-27(32)13-14-28(31)33/h8,10,19,23-26,30H,3-7,9,11-18H2,1-2H3/t23-,24-,25+,26+,29+/m1/s1

InChI key

CJHWFIUASFBCKN-ZRJUGLEFSA-N

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General description

U-73343 is used to assess the involvement of G protein-coupled 1-phosphatidylinositol-phosphodiesterase or phospholipase C in receptor-mediated cell activation. It functions downstream of phospholipase C to block receptor-mediated phospholipase D activation.

Application

U-73343 has been used for studying the role of phospholipase C (PLC) signaling in modulating epithelial Na+ channel (ENaC) function in gerbil Reissner′s membranes (RMs). U-73343 has also been used as a negative control for PLC inhibition in mechanically stimulated (MS) and its neighboring (NB) cells.
U-73343 has been used in measuring the fluorescence of intracellular Ca2+.

Biochem/physiol Actions

Inactive analog of U73122; used as a negative control.

Preparation Note

U-73343 is soluble in chloroform at 10 mg/ml and yields a clear, colorless to faint yellow solution. It is also soluble in ethanol (0.93 mg/ml) and DMSO (2.3 mg/ml), but is insoluble in water.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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R J Smith et al.
The Journal of pharmacology and experimental therapeutics, 253(2), 688-697 (1990-05-01)
1-[6-[[17 beta-3-Methoxyestra-1,3,5(10)-trien-17-yl]amino]hexyl]- 1H-pyrrole-2,5-dione (U-73122), an inhibitor of phospholipase C (PLC)-dependent processes in human platelets, was found to be a potent inhibitor of human polymorphonuclear neutrophil (PMN) activation by structurally unrelated receptor-specific agonists. U-73122 caused a time- and concentration-dependent (0.1-1 microM)
Shou-Yuan Zhuang et al.
Neuropharmacology, 48(8), 1086-1096 (2005-05-25)
Exogenously administered cannabinoids are neuroprotective in several different cellular and animal models. In the current study, two cannabinoid CB1 receptor ligands (WIN 55,212-2, CP 55,940) markedly reduced hippocampal cell death, in a time-dependent manner, in cultured neurons subjected to high
Ayako Kataoka et al.
Journal of neurochemistry, 108(1), 115-125 (2008-11-19)
Microglia are implicated as a source of diverse proinflammatory factors in the CNS. Extracellular nucleotides are well known to be potent activators of glial cells and trigger the release of cytokines from microglia through purinergic receptors. However, little is known
U73122 and U73343 inhibit receptor-mediated phospholipase D activation downstream of phospholipase C in CHO cells
Bosch RR, et al.
European Journal of Pharmacology, 346(2-3), 345-351 (1998)
Jue-Long Wang et al.
Toxicology letters, 160(1), 76-83 (2005-07-20)
The effect of the environmental toxicant nonylphenol on cytosolic free Ca2+ concentration ([Ca2+]i) and proliferation has not been explored in human osteoblast-like cells. This study examined whether nonylphenol alters Ca2+ levels and causes cell death in MG63 human osteosarcoma cells.
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