biological source
synthetic
Quality Segment
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
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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signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 1B - Repr. 2
存储类别
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