Geldanamycin

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Cat.No. 1368 - Geldanamycin | C29H40N2O9 | CAS No. 30562-34-6
Description: Selective Hsp90 inhibitor
Chemical Name: 9,13-Dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-carbamate
Purity: ≥98% (HPLC)
Datasheet
Citations (3)
Literature

Biological Activity

Selectively inhibits heat shock protein 90 (Hsp90). Binds to the ATP site of Hsp90 (Kd = 1.2 μM) and inhibits its chaperone activity. Consequently inhibits activities of oncogenic kinases (e.g. src, Raf), p53 and steroid receptors. Demonstrates antiproliferative effect on breast cancer stem-like cells.

Technical Data

M. Wt 560.64
Formula C29H40N2O9
Storage Desiccate at -20°C
Purity ≥98% (HPLC)
CAS Number 30562-34-6
PubChem ID 13017912
InChI Key QTQAWLPCGQOSGP-PHLMVCJGSA-N
Smiles O=C1C(OC)=C(C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(C)/[C@H](OC(N)=O)[C@@H](OC)/C=C/C=C(C)/C2=O)C(C(N2)=C1)=O

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 5.61 10

Preparing Stock Solutions

The following data is based on the product molecular weight 560.64. 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 1.78 mL 8.92 mL 17.84 mL
5 mM 0.36 mL 1.78 mL 3.57 mL
10 mM 0.18 mL 0.89 mL 1.78 mL
50 mM 0.04 mL 0.18 mL 0.36 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.

Cardenas et al (1998) Signal-transduction cascades as targets for therapeutic intervention by natural products. Trends Biotechnol. 16 427 PMID: 9807840

Roe et al (1999) Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanomycin. J.Med.Chem. 42 260 PMID: 9925731

Whitesell et al (1994) Inhibition of heat shock protein HSP90-pp60v-src heteroprotein complex formation by benzoquinone ansamycins: essential role for stress proteins in oncogenic transformation. Proc.Natl.Acad.Sci.U.S.A. 91 8324 PMID: 8078881

Lee et al (2012) Inhibition of heat shock protein (Hsp) 27 potentiates the suppressive effect of Hsp90 inhibitors in targeting breast cancer stem-like cells. Biochimie. 94 1382 PMID: 22445681


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Keywords: Selective Hsp90 inhibitors inhibits Heat Shock Protein 90 antibiotics Hsp90

3 Citations for Geldanamycin

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

Barker et al (2006) Inhibition of Hsp90 acts synergistically with topoisomerase II poisons to increase the apoptotic killing of cells due to an increase in topoisomerase II mediated DNA damage. Neuroscience 34 1148 PMID: 16504968

Young et al (2015) A novel mechanism of autophagic cell death in dystrophic muscle regulated by P2RX7 receptor large-pore formation and HSP90. BMC Dev Biol 11 113 PMID: 25700737

Chung-Davidson et al (2015) Hsp90 and hepatobiliary transformation during sea lamprey metamorphosis. Nucleic Acids Res 15 47 PMID: 26627605


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Pathways for Geldanamycin

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