| Identification | Back Directory | [Name]
Gambogenic acid | [CAS]
173932-75-7 | [Synonyms]
Gambogenic acid
(2Z)-4-[(1R,3aS,5S,12aS)-9-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]-3a,4,5,7-tetrahydro-8,10-dihydroxy-3,3-dimethyl-11-(3-methyl-2-buten-1-yl)-7,13-dioxo-1,5-methano-1H,3H-furo[3,4-d]xanthen-1-yl]-2-methyl-2-butenoic acid
2-Butenoic acid, 4-[(1R,3aS,5S,12aS)-9-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-3a,4,5,7-tetrahydro-8,10-dihydroxy-3,3-dimethyl-11-(3-methyl-2-buten-1-yl)-7,13-dioxo-1,5-methano-1H,3H-furo[3,4-d]xanthen-1-yl]-2-methyl-, (2Z)- | [Molecular Formula]
C38H46O8 | [MOL File]
173932-75-7.mol | [Molecular Weight]
630.77 |
| Chemical Properties | Back Directory | [Melting point ]
108 °C | [Boiling point ]
818.6±65.0 °C(Predicted) | [density ]
1.27±0.1 g/cm3(Predicted) | [storage temp. ]
4°C, protect from light | [solubility ]
DMSO : 250 mg/mL (396.34 mM; Need ultrasonic) | [form ]
Powder | [pka]
4.58±0.36(Predicted) | [color ]
Light yellow to yellow |
| Hazard Information | Back Directory | [Chemical Properties]
Brown-red crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Garcinia. | [Uses]
Gambogenic acid is an active ingredient that can be isolated from gamboge. Gambogenic acid acts as an effective inhibitor of EZH2, specifically and covalently binds to Cys668 within the EZH2-SET domain, and induces EZH2 ubiquitination. Gambogenic acid can be used for the research of cancer[1][2]. | [in vivo]
Gambogenic acid (4-12 mg/kg, i.v., every 2 days, 14 days) inhibits tumor growth in SCLC mouse xenograft model[2].
| Animal Model: | SCLC mouse xenograft model[1] | | Dosage: | 4-12 mg/kg | | Administration: | i.v., every 2 days, 14 days | | Result: | Increased the expression of pro-apoptotic proteins (cleaved caspase-3, -8 and -9, Bax, cleaved PARP and p53 proteins).
Decreased the anti-apoptotic proteins (Bcl-2).
|
| [IC 50]
EZH2 | [storage]
4°C, protect from light | [References]
[1] Wang X, et al. A covalently bound inhibitor triggers EZH2 degradation through CHIP-mediated ubiquitination. EMBO J. 2017 May 2;36(9):1243-1260. DOI:10.15252/embj.201694058
[2] Huang T, et al. Gambogenic acid inhibits the proliferation of small?cell lung cancer cells by arresting the cell cycle and inducing apoptosis. Oncol Rep. 2019 Mar;41(3):1700-1706. DOI:10.3892/or.2018.6950 |
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