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Sigma-Aldrich

Etoposide quinone

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Synonym(s):
Etoposide 3′,4′-quinone, Etoposide o-quinone
Empirical Formula (Hill Notation):
C28H28O13
CAS Number:
105016-65-7
Molecular Weight:
572.51

biological source

synthetic

Quality Level

100

grade

research grade

Assay

≥93% (H-NMR)

form

solid

technique(s)

HPLC: suitable

color

dark red

storage temp.

−20°C

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

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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Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Statements

H302 - H350 - H361d

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Repr. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Elizabeth G Gibson et al.
Chemical research in toxicology, 29(9), 1541-1548 (2016-08-18)
Topoisomerase II is an essential nuclear enzyme involved in regulating DNA topology to facilitate replication and cell division. Disruption of topoisomerase II function by chemotherapeutic agents is in use as an effective strategy to fight cancer. Etoposide is an anticancer
Nicholas A Smith et al.
Biochemistry, 53(19), 3229-3236 (2014-04-29)
Etoposide is a topoisomerase II poison that is utilized to treat a broad spectrum of human cancers. Despite its wide clinical use, 2-3% of patients treated with etoposide eventually develop treatment-related acute myeloid leukemias (t-AMLs) characterized by rearrangements of the
Qing Nian et al.
Molecular pharmacology, 96(2), 297-306 (2019-06-22)
Etoposide is a widely prescribed anticancer drug that is, however, associated with an increased risk of secondary leukemia. Although the molecular basis underlying the development of these leukemias remains poorly understood, increasing evidence implicates the interaction of etoposide metabolites [i.e.

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