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L9908

Sigma-Aldrich

LY-294,002 hydrochloride

solid, ≥98% (HPLC)

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Synonym(s):
2-(4-Morpholinyl)-8-phenyl-1(4H)-benzopyran-4-one hydrochloride
Empirical Formula (Hill Notation):
C19H17NO3 · HCl
CAS Number:
Molecular Weight:
343.80
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

microbial (Staphylococcus roseus)

Quality Level

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

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L1170440202SML0693
vibrant-m

L9908

LY-294,002 hydrochloride

vibrant-m

L1170

LY-487379 hydrochloride

vibrant-m

440202

LY 294002

vibrant-m

SML0693

LY-333531 hydrochloride

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

solubility

DMSO: >5 mg/mL, H2O: insoluble

solubility

DMSO: >20 mg/mL

solubility

DMSO: 20 mg/mL, ethanol: soluble

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

color

white to off-white

color

off-white

color

off-white

color

orange-red

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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)
miR-126 suppresses epithelial-to-mesenchymal transition and metastasis by targeting PI3K/AKT/Snail signaling of lung cancer cells
Jia Z, et al.
Oncology Letters, 15(5), 7369-7375 (2018)
Endothelial cell activation on 3D-matrices derived from PDGF-BB-stimulated fibroblasts is mediated by Snail1
Herrera A, et al.
Oncogenesis, 7(9), 76-76 (2018)
The Phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002 modulates cytokine expression in macrophages via p50 nuclear factor kappa B inhibition, in a PI3K-independent mechanism
Avni D, et al.
Biochemical Pharmacology, 83(1), 106-114 (2012)

Articles

We presents an article on Autophagy in Cancer Promotes Therapeutic Resistance

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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