SMB00960

Etoposide quinone

• 同義詞: Etoposide 3′,4′-quinone, Etoposide o-quinone
• 經驗公式（希爾表示法）: C₂₈H₂₈O₁₃
• CAS號碼: 105016-65-7
• 分子量：: 572.51
• 分類程式碼代碼: 12352201
• NACRES: NA.79

屬性

• 生物源: synthetic
• 品質等級: 100
• 等級: research grade
• 化驗: ≥93% (H-NMR)
• 形狀: solid
• 技術: HPLC: suitable
• 顏色: dark red
• mp: 200—210 °C
• 儲存溫度: −20°C
• SMILES 字串: 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 密鑰: SBLYXIKLMHGUJZ-LBMXFXLMSA-N

描述

一般說明

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.

應用

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.

其他說明

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安全資訊

• 象形圖: GHS08,GHS07
• 訊號詞: Danger
• 危險聲明: H302,H350,H361d
• 防範說明: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• 危險分類: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• 儲存類別代碼: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• 水污染物質分類（WGK）: WGK 3
• 閃點（°F）: Not applicable
• 閃點（°C）: Not applicable