SMB00960

Etoposide quinone

research grade

• Sinónimos: Etoposide 3′,4′-quinone, Etoposide o-quinone
• Fórmula empírica (notación de Hill): C₂₈H₂₈O₁₃
• Número de CAS: 105016-65-7
• Peso molecular: 572.51
• Código UNSPSC: 12352201
• NACRES: NA.79

Propiedades

• origen biológico: synthetic
• Nivel de calidad: 100
• Ensayo: ≥93% (H-NMR)
• Formulario: solid
• técnicas: HPLC: suitable
• color: dark red
• mp: 200—210 °C
• temp. de almacenamiento: −20°C
• cadena SMILES: Canonical SMILES: CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=O)C(=O)C(=C7)OC)O)OIsomeric SMILES: CC1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=O)C(=O)C(=C7)OC)O)O
• InChI: 1S/C28H28O13/c1-10-35-8-19-26(39-10)23(31)24(32)28(40-19)41-25-13-6-17-16(37-9-38-17)5-12(13)20(21-14(25)7-36-27(21)33)11-3-15(29)22(30)18(4-11)34-2/h3-6,10,14,19-21,23-26,28,31-32H,7-9H2,1-2H3/t10?,14?,19-,20?,21?,23-,24-,25?,26-,28+/m1/s1

Descripción

Descripción general

Etoposide quinone, a major metabolite of the anticancer drug etoposide, is believed to play a role in the development of secondary acute myeloid leukemias (t-AMLs) in some etoposide patients. It acts as a covalent poison of human topoisomerase IIβ, inducing approximately four times more topoisomerase IIβ-mediated DNA cleavage than its parent drug, etoposide. This metabolite is also a potent irreversible inhibitor of TCPTP protein tyrosine phosphatase, with an IC50 of 7 μM. Its inhibition of TCPTP leads to an increase in STAT1 tyrosine phosphorylation, contributing to the leukemogenic effects associated with etoposide. Understanding the unique properties and mechanisms of etoposide quinone is essential for unraveling its potential impact on cancer research, specifically its association with the development of t-AMLs.

Aplicación

Etoposide quinone can be used in biochemical, metabolomics and cancer research

Acciones bioquímicas o fisiológicas

Etoposide undergoes a metabolic transformation by CYP3A4, resulting in the formation of etoposide catechol, which can be subsequently oxidized to produce etoposide quinone.

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Información de seguridad

• Pictogramas: GHS08,GHS07
• Palabra de señalización: Danger
• Frases de peligro: H302,H350,H361d
• Consejos de prudencia: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Clasificaciones de peligro: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• Código de clase de almacenamiento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable