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SMB00960

Sigma-Aldrich

Etoposide quinone

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别名:
Etoposide 3′,4′-quinone, Etoposide o-quinone
经验公式（希尔记法）:
C28H28O13
CAS号:
105016-65-7
分子量:
572.51

生物来源

synthetic

质量水平

100

等级

research grade

检测方案

≥93% (H-NMR)

形式

solid

technique(s)

HPLC: suitable

颜色

dark red

储存温度

−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

一般描述

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.

应用

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

生化/生理作用

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

其他说明

For additional information on our range of Biochemicals, please complete this form.
To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

象形图

Exclamation markHealth hazard
GHS07,GHS08

警示用语：

Danger

危险分类

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

储存分类代码

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

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°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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