Geldanamycin An inhibitor of HSP 90 and nuclear hormone receptor family

Geldanamycin (CAS 30562-34-6)

Geldanamycin | CAS 30562-34-6 is rated 5.0 out of 5 by 1.
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Synonym: 2-azabicyclo[16.3.1]docasa-4, 6, 10, 18, 21-pentaene-3, 20, 22-trione, 9, 13-dihydroxy-8, 14, 19-trimethoxy-4, 10, 12, 16-tetramethyl-9-carbamate
Application: An inhibitor of HSP 90 and nuclear hormone receptor family
CAS Number: 30562-34-6
Purity: >95%
Molecular Weight: 560.64
Molecular Formula: C29H40N2O9
* Refer to Certificate of Analysis for lot specific data (including water content).
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Geldanamycin, a benzoquinone ansamycin, has been found to revert tyrosine kinase-induced oncogenic transformation. In the same study it was reported that Geldanamycin was able to bind elements of Hsp90 (heat shock protein 90) clients, such as HIF-1α (Hypoxia-inducible factor-1-α), and inhibit them. Geldanamycin binds in a specific and stable manner and as a result inhibits new protein maturation. Geldanamycin binds with high affinity into the ATP binding pocket of Hsp90. These heat shock proteins might positively impact cell proliferation by being a chaperone required for the assembly and activation of telomerase in cells. By binding them, Geldanamycin is thought to reduce new protein maturation and their downstream transcriptional activity. Geldanamycin has also displayed a capacity to bind to the endoplasmic reticulum homologue of the heat-shock protein, GP-96 and thus interferes with the cellular stress response. In addition, Geldanamycin has been reported as a potent inhibitor of the nuclear hormone receptor family. Other research has demonstrated Geldanamycin to be a protective agent against α-synuclein toxicity to dopaminergic neurons in Drosophila. Geldanamycin is an inhibitor of c-Src.


References

1. Whitesell, L., 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. Proceedings of the National Academy of Sciences of the United States of America. 91(18): 8324-8. PMID: 8078881
2. Mabjeesh, Nicola J., et al., 2002. Geldanamycin induces degradation of hypoxia-inducible factor 1alpha protein via the proteosome pathway in prostate cancer cells. Cancer research. 62(9): 2478-82. PMID: 11980636
3. Koga, Fumitaka., et al., 2007. Low dose geldanamycin inhibits hepatocyte growth factor and hypoxia-stimulated invasion of cancer cells. Cell cycle (Georgetown, Tex.). 6(11): 1393-402. PMID: 17525527
4. Li, Yan-Ping., et al., 2010. Synthesis and biological evaluation of heat-shock protein 90 inhibitors: geldanamycin derivatives with broad antiviral activities. Antiviral chemistry & chemotherapy. 20(6): 259-68. PMID: 20710066

Physical State :
Solid
Solubility :
Soluble in DMSO (10 mg/ml), chloroform (Slightly soluble), methanol (Slightly soluble), and dichloromethane (10 mg/ml). Insoluble in water.
Storage :
Store at -20° C
Melting Point :
255° C
Boiling Point :
~783.9° C at 760 mmHg (Predicted)
Density :
~1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.56
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
2
RTECS :
LX8920000
PubChem CID :
5288382
MDL Number :
MFCD00274570
SMILES :
C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)/C)OC)OC(=O)N)\C)C)O)OC

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Certificate of Analysis

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Geldanamycin  Product Citations

See how others have used Geldanamycin. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 28360195  Giráldez, S. et al. 2017. FASEB J. 31: 2925-2936.

PMID: # 26791531  Wang, HH. et al. 2016. Histochemistry and cell biology. 145: 647-57.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from Anneken et al Anneken et al. (PubMed ID 26271031) used Geldanamycin to prevent estradiol-induced increase by inhibiting heat-shock protein-90 (Hsp90).
Date published: 2015-05-11
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