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U6756

Sigma-Aldrich

U-73122 hydrate

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)
MDL number:
MFCD12910450
UNSPSC Code:
41106300
PubChem Substance ID:
24278065
NACRES:
NA.77

assay

≥97.5% (HPLC)

Quality Level

100

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

SMILES string

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

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

InChI key

WCOYJDRCHHGMRK-BDEPKWELSA-N

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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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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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
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
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
R C Smallridge et al.
Endocrinology, 131(4), 1883-1888 (1992-10-01)
TRH increases cytosolic-free calcium ([Ca2+]i) by activating phospholipase C(PL-C), which induces phosphoinositol hydrolysis, leading to Ca2+ mobilization from inositol trisphosphate (IP3) sensitive stores, and by increasing Ca2+ influx. Increases in [Ca2+]i stimulate PRL secretion. We investigated the effects of U-73122
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
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