SMB00960

Etoposide quinone

• Synonym(s): Etoposide 3′,4′-quinone, Etoposide o-quinone
• Empirical Formula (Hill Notation): C₂₈H₂₈O₁₃
• CAS Number: 105016-65-7
• Molecular Weight: 572.51
• UNSPSC Code: 12352201
• NACRES: NA.79

Properties

• biological source: synthetic
• Quality Level: 100
• grade: research grade
• assay: ≥93% (H-NMR)
• form: solid
• technique(s): HPLC: suitable
• color: dark red
• mp: 200—210 °C
• storage temp.: −20°C
• SMILES string: 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
• InChI key: SBLYXIKLMHGUJZ-LBMXFXLMSA-N

Description

General description

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.

Application

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

Biochem/physiol Actions

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

Other Notes

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Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H350,H361d
• pcodes: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable