SMB00960

Etoposide quinone

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

Propriedades

• fonte biológica: synthetic
• Nível de qualidade: 100
• grau: research grade
• Ensaio: ≥93% (H-NMR)
• forma: solid
• técnica(s): HPLC: suitable
• cor: dark red
• pf: 200—210 °C
• temperatura de armazenamento: −20°C
• cadeia de caracteres 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
• chave InChI: SBLYXIKLMHGUJZ-LBMXFXLMSA-N

Descrição

Descrição geral

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.

Aplicação

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

Ações bioquímicas/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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Informações de segurança

• Pictogramas: GHS08,GHS07
• Palavra indicadora: Danger
• Frases de perigo: H302,H350,H361d
• Declarações de precaução: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Classificações de perigo: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• Código de classe de armazenamento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable