SMB00960

Etoposide quinone

• Sinonimo/i: Etoposide 3′,4′-quinone, Etoposide o-quinone
• Formula empirica (notazione di Hill): C₂₈H₂₈O₁₃
• Numero CAS: 105016-65-7
• Peso molecolare: 572.51
• Codice UNSPSC: 12352201
• NACRES: NA.79

Proprietà

• Origine biologica: synthetic
• Livello qualitativo: 100
• Grado: research grade
• Saggio: ≥93% (H-NMR)
• Stato: solid
• tecniche: HPLC: suitable
• Colore: dark red
• Punto di fusione: 200—210 °C
• Temperatura di conservazione: −20°C
• Stringa SMILE: 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; SBLYXIKLMHGUJZ-LBMXFXLMSA-N

Descrizione

Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

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

Altre note

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Informazioni sulla sicurezza

• Pittogrammi: GHS08,GHS07
• Avvertenze: Danger
• Indicazioni di pericolo: H302,H350,H361d
• Consigli di prudenza: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Classi di pericolo: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• Codice della classe di stoccaggio: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable