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SMB00960

Sigma-Aldrich

Etoposide quinone

Sinonimo/i:

Etoposide 3′,4′-quinone, Etoposide o-quinone

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About This Item

Formula empirica (notazione di Hill):
C28H28O13
Numero CAS:
Peso molecolare:
572.51
Codice UNSPSC:
12352201
NACRES:
NA.79

Origine biologica

synthetic

Livello qualitativo

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 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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Pittogrammi

Health hazardExclamation mark

Avvertenze

Danger

Indicazioni di pericolo

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


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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

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