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SML0183

Sigma-Aldrich

EM20-25

≥98% (HPLC)

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C15H9ClN4O6
Numero CAS:
141266-44-6
Peso molecolare:
376.71
Numero MDL:
MFCD00624842
Codice UNSPSC:
12352200
ID PubChem:
329825212
NACRES:
NA.77

Saggio

≥98% (HPLC)

Stato

powder

Colore

light yellow to yellow

Solubilità

DMSO: ≥5 mg/mL at ~60 °C

Temperatura di conservazione

2-8°C

Stringa SMILE

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)
GGEVZGGAQHNWQN-UHFFFAOYSA-N

Applicazioni

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.

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
101M4607V

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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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