SMB00960

Sigma-Aldrich

Etoposide quinone

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

Quality Level

biological source

synthetic

grade

research grade

assay

≥93% (H-NMR)

form

solid

application(s)

HPLC: suitable

color

dark red

storage temp.

−20°C

Related Categories

General description

Etoposide-quinone is a major metabolite of anticancer drug etoposide, which may contribute to the development of secondary acute myeloid leukemias in some etoposide patients. Etoposide-quinone is a covalent poison of human topoisomerase IIb, which induces four times more topoisomerase IIb mediated DNA cleavage than etoposide. Etoposide-quinone is a potent (IC50 = 7 μM) irreversible inhibitor of TCPTP protein tyrosine phosphatase that increases STAT1 tyrosine phosphorylation and contributes to etoposide dependent leukemogenesis.

Application

Application: Metabolomics

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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...
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...
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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