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SML0183

Sigma-Aldrich

EM20-25

≥98% (HPLC)

Sinónimos:

5-(6-Chloro-2,4-dioxo-1,3,4,10-tetrahydro-2H-9-oxa-1,3-diaza-anthracen-10-yl)-pyrimidine-2,4,6-trione

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About This Item

Fórmula empírica (notación de Hill):
C15H9ClN4O6
Número de CAS:
141266-44-6
Peso molecular:
376.71
MDL number:
MFCD00624842
UNSPSC Code:
12352200
PubChem Substance ID:
329825212
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

light yellow to yellow

solubility

DMSO: ≥5 mg/mL at ~60 °C

storage temp.

2-8°C

SMILES string

Clc1ccc2OC3=C(C(C4C(=O)NC(=O)NC4=O)c2c1)C(=O)NC(=O)N3

InChI

1S/C15H9ClN4O6/c16-4-1-2-6-5(3-4)7(8-10(21)17-14(24)18-11(8)22)9-12(23)19-15(25)20-13(9)26-6/h1-3,7-8H,(H2,19,20,23,25)(H2,17,18,21,22,24)

InChI key

GGEVZGGAQHNWQN-UHFFFAOYSA-N

Application

EM20-25 was screened among other anti-cancer drugs to evaluate the effect on mitochondrial membrane potential in human prostate cancer cells and healthy mouse liver tissue.

Biochem/physiol Actions

EM20-25 disrupts the BCL-2/BAX interactions and activates caspase-9 in cells overexpressing BCL-2. It sensitizes the BCL-2 expressing leukemic cells to the effects of chemotherapy involving staurosporine and chlorambucil.
EM20-25 is an analog of HA14-1 that antagonizes the effects of the anti-apoptotic protein BCL-2, and causes opening of the mitochondrial permeability transition pore. Unlike HA14-1, EM20-25 does not effect mitochondrial respiration.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Nelly Buron et al.
PloS one, 5(3), e9924-e9924 (2010-04-03)
Current limitations of chemotherapy include toxicity on healthy tissues and multidrug resistance of malignant cells. A number of recent anti-cancer strategies aim at targeting the mitochondrial apoptotic machinery to induce tumor cell death. In this study, we set up protocols
Aayushi Singh et al.
Biomolecular concepts, 12(1), 94-109 (2021-07-26)
We previously reported that M. tb on its own as well as together with HIV inhibits macrophage apoptosis by upregulating the expression of Bcl2 and Inhibitor of Apoptosis (IAP). In addition, recent reports from our lab showed that stimulation of
Eva Milanesi et al.
The Journal of biological chemistry, 281(15), 10066-10072 (2006-02-17)
We have investigated the mitochondrial effects of BH3I-2', Chelerythrine, and HA14-1, small organic molecules that share the ability to bind the BH3 domain of BCL-2. All compounds displayed a biphasic effect on mitochondrial respiration with uncoupling at low concentrations and
Dennis Ma et al.
Scientific reports, 7, 42957-42957 (2017-02-22)
Enhanced mitochondrial stability and decreased dependence on oxidative phosphorylation confer an acquired resistance to apoptosis in cancer cells, but may present opportunities for therapeutic intervention. The compound pancratistatin (PST) has been shown to selectively induce apoptosis in cancer cells. However

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