Gambogic acid

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Cat.No. 3590 - Gambogic acid | C38H44O8 | CAS No. 2752-65-0
Description: Apoptosis inducer. Activates caspases and inhibits Bcl-2 family proteins
Chemical Name: (2Z)-2-Methyl-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-hydroxy-3,3,11-trimethyl-13-(3-methyl-2-butenyl)-11-(4-methyl-3-pentenyl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-butenoic acid
Datasheet
Citations (2)
Literature
Pathways

Biological Activity

Apoptosis inducer in several tumor cell lines including T47D cells. Activates caspases (EC50 values are 0.78 - 1.64 μM) and competitively inhibits antiapoptotic Bcl-2 family proteins (IC50 values are 1.47, 1.21, 2.02, 0.66, 1.06 and 0.79 μM for Bcl-XL, Bcl-2, Bcl-W, Bcl-B, Bfl-1 and Mcl-1 respectively). Reverses gefitinib-resistance in mice bearing tumors with EGFR-T790M mutation. Also blocks Kir2.1 channels (EC50 ≤ 100 nM).

Technical Data

M. Wt 628.75
Formula C38H44O8
Storage Store at -20°C
CAS Number 2752-65-0
PubChem ID 15559465
InChI Key GEZHEQNLKAOMCA-MYCCNKBCSA-N
Smiles C/C(C)=C/CC[C@@](C=C2)(C)OC1=C2C(O)=C(C(C([C@]45O3)=C[C@H](C[C@@H]56)C([C@](OC(C)6C)4C/C=C(C(O)=O)/C)=O)=O)C3=C1C/C=C(C)/C

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 47.16 75
ethanol 62.87 100

Preparing Stock Solutions

The following data is based on the product molecular weight 628.75. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.59 mL 7.95 mL 15.9 mL
5 mM 0.32 mL 1.59 mL 3.18 mL
10 mM 0.16 mL 0.8 mL 1.59 mL
50 mM 0.03 mL 0.16 mL 0.32 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Zhang et al (2004) Discovery, characterization and SAR of gambogic acid as a potent apoptosis inducer by a HTS assay. Bioorg.Med.Chem. 12 309 PMID: 14723951

Zhai et al (2008) Gambogic acid is an antagonist of antiapoptotic Bcl-2 family proteins. Mol.Cancer Ther. 7 1639 PMID: 18566235

Qi et al (2008) Anti-invasive effect of gambogic acid in MDA-MB-231 human breast carcinoma cells. Biochem.Cell Biol. 86 386 PMID: 18923540

Zaks-Makhina et al (2009) Specific and slow inhibition of the Kir2.1 K+ channel by Gambogic acid. J.Biol.Chem. 284 15432 PMID: 19366693

Wang et al (2015) Combined therapy with EGFR TKI and gambogic acid for overcoming resistance in EGFR-T790M mutant lung cancer. Oncol.Lett. 10 2063 PMID: 26622796


If you know of a relevant reference for Gambogic acid, please let us know.

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2 Citations for Gambogic acid

Citations are publications that use Tocris products. Selected citations for Gambogic acid include:

Tan et al (2015) Brown Adipose Tissue Thermogenic Capacity Is Regulated by Elovl6. Proc Natl Acad Sci U S A 13 2039 PMID: 26628376

Kühn et al (2013) Label-free cytotoxicity screening assay by digital holographic microscopy. Assay Drug Dev Technol 11 101 PMID: 23062077


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Reviews

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Programmed Cell Death

Programmed Cell Death Poster

There are two currently recognized forms of programmed cell death: apoptosis and necroptosis. This poster summarizes the signaling pathways involved in apoptosis, necroptosis and cell survival following death receptor activation, and highlights the influence of the molecular switch, cFLIP, on cell fate.

Pathways for Gambogic acid

Apoptosis

Apoptosis Signaling Pathway

Apoptosis is a physiological process for cell death that is critical during aging and development. It may also be referred to as cell 'suicide'. Apoptosis can be triggered by events both inside and outside of the cell.

Protocols

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