SMB00960

Etoposide quinone

• Synonim(y): Etoposide 3′,4′-quinone, Etoposide o-quinone
• Wzór empiryczny (zapis Hilla): C₂₈H₂₈O₁₃
• Numer CAS: 105016-65-7
• Masa cząsteczkowa: 572.51
• Kod UNSPSC: 12352201
• NACRES: NA.79

Właściwości

• pochodzenie biologiczne: synthetic
• Poziom jakości: 100
• klasa czystości: research grade
• Próba: ≥93% (H-NMR)
• Postać: solid
• metody: HPLC: suitable
• kolor: dark red
• mp: 200—210 °C
• temp. przechowywania: −20°C
• ciąg SMILES: 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
• Klucz InChI: SBLYXIKLMHGUJZ-LBMXFXLMSA-N

Opis

Opis ogólny

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.

Zastosowanie

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

Działania biochem./fizjol.

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

Inne uwagi

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS08,GHS07
• Hasło ostrzegawcze: Danger
• Zwroty wskazujące rodzaj zagrożenia: H302,H350,H361d
• Zwroty wskazujące środki ostrożności: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Klasyfikacja zagrożeń: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• Kod klasy składowania: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Klasa zagrożenia wodnego (WGK): WGK 3
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable