SMB00960

Etoposide quinone

• Synonyme(s) : Etoposide 3′,4′-quinone, Etoposide o-quinone
• Formule empirique (notation de Hill): C₂₈H₂₈O₁₃
• Numéro CAS: 105016-65-7
• Poids moléculaire : 572.51
• Code UNSPSC : 12352201
• Nomenclature NACRES : NA.79

Propriétés

• Source biologique: synthetic
• Niveau de qualité: 100
• Qualité: research grade
• Essai: ≥93% (H-NMR)
• Forme: solid
• Technique(s): HPLC: suitable
• Couleur: dark red
• Pf: 200—210 °C
• Température de stockage: −20°C
• Chaîne 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
• Clé InChI: SBLYXIKLMHGUJZ-LBMXFXLMSA-N

Description

Description générale

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

Actions biochimiques/physiologiques

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

Autres remarques

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Informations sur la sécurité

• Pictogrammes: GHS08,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H302,H350,H361d
• Conseils de prudence: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Classification des risques: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable