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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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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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
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
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
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
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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