SMB00960

Etoposide quinone

research grade

• 동의어(들): Etoposide 3′,4′-quinone, Etoposide o-quinone
• 실험식(Hill 표기법): C₂₈H₂₈O₁₃
• CAS Number: 105016-65-7
• Molecular Weight: 572.51
• UNSPSC 코드: 12352201
• NACRES: NA.79

속성

• 생물학적 소스: synthetic
• Quality Level: 100
• 분석: ≥93% (H-NMR)
• 양식: solid
• 기술: HPLC: suitable
• 색상: dark red
• mp: 200—210 °C
• 저장 온도: −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

설명

일반 설명

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.

애플리케이션

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

생화학적/생리학적 작용

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

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안전성 정보

• 픽토그램: GHS08,GHS07
• 신호어: Danger
• 유해 및 위험 성명서: H302,H350,H361d
• 예방조치 성명서: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Repr. 2
• Storage Class Code: 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