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L9908

Sigma-Aldrich

LY-294,002 hydrochloride

solid, ≥98% (HPLC)

Synonym(s):

2-(4-Morpholinyl)-8-phenyl-1(4H)-benzopyran-4-one hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C19H17NO3 · HCl
CAS Number:
934389-88-5
Molecular Weight:
343.80
MDL number:
MFCD00270881
UNSPSC Code:
12352207
PubChem Substance ID:
24278828
NACRES:
NA.77

biological source

microbial (Staphylococcus roseus)

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >5 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

O=C1C=C(Oc2c1cccc2-c3ccccc3)N4CCOCC4

InChI

1S/C19H17NO3/c21-17-13-18(20-9-11-22-12-10-20)23-19-15(7-4-8-16(17)19)14-5-2-1-3-6-14/h1-8,13H,9-12H2

InChI key

CZQHHVNHHHRRDU-UHFFFAOYSA-N

General description

LY-294,002 hydrochloride is a derivative of the flavonoid, quercetin and elicits higher inhibition on the enzyme phosphoinositide 3-kinase (PI3K). LY-294,002 inhibits nuclear factor kappa B signaling in macrophages. It elevates expression of autophagosomal protein LC3 and promotes apoptosis in gastric and nasopharyngeal cancer cells. LY-294,002 modulates action potential repolarization and improves myocyte contractility.

Application

LY-294,002 hydrochloride has been used in the inhibition of:
  • phosphoinositide 3-kinase (PI3K) in human lung cancer cell line
  • autophagy in mesenchymal stem cells (MSCs).
  • serine/threonine-specific protein kinase (AKT) signaling in fibroblasts and cardiac cells.

Biochem/physiol Actions

Specific cell permeable phosphatidylinositol 3-kinase inhibitor.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide and Kinase Phosphatase Biology research. Discover more featured Cyclic Nucleotide and Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the G Proteins (Heterotrimeric) and Phosphoinositide Kinases pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

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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Carboxyl-Terminal Modulator Protein Ameliorates Pathological Cardiac Hypertrophy by Suppressing the Protein Kinase B Signaling Pathway
Liu X, et al.
Journal of the American Heart Association, 7(13), e008654-e008654 (2018)
Structural determinants of phosphoinositide 3-kinase inhibition by wortmannin, LY294002, quercetin, myricetin, and staurosporine
Walker EH, et al.
Molecular Cell, 6(4), 909-919 (2000)
Regulation of PKCbeta levels and autophagy by PML is essential for high-glucose-dependent mesenchymal stem cell adipogenesis
Morganti C, et al.
International Journal of Obesity, 1-1 (2018)
C J Vlahos et al.
Journal of immunology (Baltimore, Md. : 1950), 154(5), 2413-2422 (1995-03-01)
Neutrophils contain a multicomponent NADPH oxidase system that is involved in the production of microbicidal oxidants. Stimulation of human neutrophils with the peptide FMLP activates this respiratory burst enzyme to produce superoxide and also has been shown to result in
G J Brunn et al.
The EMBO journal, 15(19), 5256-5267 (1996-10-01)
The immunosuppressant, rapamycin, inhibits cell growth by interfering with the function of a novel kinase, termed mammalian target of rapamycin (mTOR). The putative catalytic domain of mTOR is similar to those of mammalian and yeast phosphatidylinositol (PI) 3-kinases. This study
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