U6756

U-73122 hydrate

Name: U-73122 hydrate
Brand: SIGMA

≥97.5% (HPLC), phospholipase C inhibitor, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₄₀N₂O₃ · xH₂O

CAS Number:

112648-68-7

Molecular Weight:

464.64 (anhydrous basis)

UNSPSC Code:

41106300

PubChem Substance ID:

24278065

NACRES:

NA.77

MDL number:

MFCD12910450

Product Name

U-73122 hydrate, powder

SMILES string

O.COc1ccc2C3CC[C@]4(C)[C@H](CCC4C3CCc2c1)NCCCCCCN5C(=O)C=CC5=O

InChI key

WCOYJDRCHHGMRK-BDEPKWELSA-N

InChI

1S/C29H40N2O3.H2O/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;/h8,10,13-14,19,23-26,30H,3-7,9,11-12,15-18H2,1-2H3;1H2/t23-,24-,25+,26+,29+;/m1./s1

assay

≥97.5% (HPLC)

form

powder

color

off-white

solubility

ethanol: ~0.7 mg/mL
DMSO: ~0.9 mg/mL
chloroform: ~10 mg/mL
DMSO: ≤2.6 mg/mL (Achieved with heating.)
ethanol: ≤5 mg/mL (Achieved with heating.)
H₂O: insoluble

storage temp.

room temp

Quality Level

100

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

U-73122 hydrate 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-73122 has also been used to study local calcium responses in human umbilical vein endothelial cells (HUVECs).

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.

Features and Benefits

This compound is featured on the Phospholipase C page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

U-73122 hydrate is soluble in ethanol (approx. 0.7 mg/ml or ≤ 5 mg/ml with heating), chloroform (approx. 10 mg/ml) and DMSO (approx. 0.9 mg/ml or ≤ 2.6 mg/ml with heating). U-73122 hydrate is insoluble in water.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000455133

0000445003

0000153720

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17β-Estradiol Inhibits PCSK9-Mediated LDLR Degradation Through GPER/PLC Activation in HepG2 Cells.

Wei Fu et al.

Frontiers in endocrinology, 10, 930-930 (2020-02-23)

Plasma levels of PCSK9 are significantly higher in postmenopausal women. Pharmacologically increased estrogen levels have been shown to lower PCSK9 and LDL-C levels in animals and humans. The action of estrogen suggests that it has the ability to prevent PCSK9-mediated

Superpriming of synaptic vesicles after their recruitment to the readily releasable pool.

Jae Sung Lee et al.

Proceedings of the National Academy of Sciences of the United States of America, 110(37), 15079-15084 (2013-08-28)

Recruitment of release-competent vesicles during sustained synaptic activity is one of the major factors governing short-term plasticity. During bursts of synaptic activity, vesicles are recruited to a fast-releasing pool from a reluctant vesicle pool through an actin-dependent mechanism. We now

Calcium signaling in live cells on elastic gels under mechanical vibration at subcellular levels.

Wagner Shin Nishitani et al.

PloS one, 6(10), e26181-e26181 (2011-11-05)

A new device was designed to generate a localized mechanical vibration of flexible gels where human umbilical vein endothelial cells (HUVECs) were cultured to mechanically stimulate these cells at subcellular locations. A Fluorescence Resonance Energy Transfer (FRET)-based calcium biosensor (an

U73122 inhibits Ca2+ oscillations in response to cholecystokinin and carbachol but not to JMV-180 in rat pancreatic acinar cells.

D I Yule et al.

The Journal of biological chemistry, 267(20), 13830-13835 (1992-07-15)

Stimulation of rat pancreatic acinar cells with low concentrations of phosphatidylinositol (PI)-linked secretagogues induces [Ca2+]i oscillations, without measurable changes in the formation of inositol 1,4,5-trisphosphate. Therefore, we tested U73122 a new phospholipase C inhibitor to determine if PI turnover is

Selective inhibition of receptor-coupled phospholipase C-dependent processes in human platelets and polymorphonuclear neutrophils.

J E Bleasdale et al.

The Journal of pharmacology and experimental therapeutics, 255(2), 756-768 (1990-11-01)

Aggregation of human platelets induced by a variety of agonists was inhibited by 1-[6-[[17 beta-3-methoxyestra-1,3,5(10)-trien-17-yl] amino]hexyl]-1H-pyrrole-2,5-dionel (U-73122) (IC50 values 1-5 microM), but not by the close analog 1-[6-[[17 beta-3-methoxyestra- 1,3,5(10)-trien-17-yl]amino]hexyl]-2,5-pyrrolidine-dione (U-73343) in which pyrrolidinedione was substituted for pyrroledione. Inhibition by

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