Geldanamycin | CAS 30562-34-6 | Binds HSP90 | Anti-Tumor Activity

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Geldanamycin

G-1047
  • CAS: 30562-34-6
  • Formula: C29H40N2O9
  • MW: 560.6 Da
  • Appearance: Yellow crystalline powder
  • Purity: 98.4%

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Geldanamycin is a benzoquinone ansamycin antibiotic which binds to Hsp90 (Heat Shock Protein 90) and alters it function. HSP90 client proteins play important roles in the regulation of the cell cycle, cell growth, cell survival, apoptosis, and oncogenesis.Cdc28 provides a molecular link between Hsp90, morphogenesis, and cell cycle progression inCandida albicans.Epidermal Growth Factor Receptors with Tyrosine Kinase Domain Mutations Exhibit Reduced Cbl Association, Poor Ubiquitylation, and Down-regulation but Are Efficiently Internalized.Inhibition of HSP90 in Trypanosoma cruzi Induces a Stress Response but No Stage Differentiation, Role of the Heat Shock Protein 90 in Immune Response Stimulation by Bacterial DNA and Synthetic Oligonucleotides.

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SynonymsGeldanomycin
Product #G-1047
CAS #30562-34-6
Chemical Name[(4~{Z},6~{Z},8~{S},9~{S},10~{Z},12~{S},13~{R},14~{S},16~{R})-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
FormulaC29H40N2O9
MW560.6 Da
AppearanceYellow crystalline powder
Purity98.4%
SolubilityDMSO: Clear yellow solution at 10 mg/ml, CH2Cl2: Clear yellow solution at 5 mg/mL
Melting Point260°C
Storage Temp-20°C
Therapeutic AreaOncological Disorders
UseGeldanamycin Analogue in Treating Patients With Colon Cancer

Additional Information

MDL NumberMFCD00274570
ChemACXX1035747-8
InChIQTQAWLPCGQOSGP-BMBHCMFXSA-N
SMILESC[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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RTECSLX8920000
HandlingStore in a tightly sealed vial. PROTECT FROM LIGHT!

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msds 1G-1047, Geldanamycin, SDS, diamond format.pdf
Certificate of Analysis 1G-1047, J1171.pdf
Certificate of Analysis 2G-1047, H1223F.pdf
Certificate of Analysis 3G-1047, H1223E.pdf
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CitationsXie, Li, et al. "Hydrogen Sulfide Protects SH-SY5Y Cells against 6-Hydroxydopamine-Induced Endoplasmic Reticulum Stress." American Journal of Physiology-Cell Physiology, vol. 303, no. 1, 1 July 2012, doi:10.1152/ajpcell.00281.2011.
Senn, Heather, et al. "Cdc28 Provides a Molecular Link between Hsp90, Morphogenesis, and Cell Cycle Progression in Candida Albicans." Molecular Biology of the Cell, vol. 23, no. 2, 16 Nov. 2012, pp. 268-283., doi:10.1091/mbc.e11-08-0729.
Troeger, Anja, et al. "A Unique Carboxyl-Terminal Insert Domain in the Hematopoietic-Specific, GTPase-Deficient Rho GTPase RhoH Regulates Post-Translational Processing." Journal of Biological Chemistry, vol. 288, no. 51, 4 Nov. 2013, pp. 36451-36462., doi:10.1074/jbc.m113.505727.
Bigenzahn, Johannes W., et al. "An Inducible Retroviral Expression System for Tandem Affinity Purification Mass-Spectrometry-Based Proteomics Identifies Mixed Lineage Kinase Domain-like Protein (MLKL) as an Heat Shock Protein 90 (HSP90) Client." Molecular & Cellular Proteomics, vol. 15, no. 3, 29 Dec. 2015, pp. 1139-1150., doi:10.1074/mcp.m115.055350.
Al-Alwan, L. A., et al. "CXCL1 Inhibits Airway Smooth Muscle Cell Migration through the Decoy Receptor Duffy Antigen Receptor for Chemokines." The Journal of Immunology, vol. 193, no. 3, 1 Aug. 2014, pp. 1416-1426., doi:10.4049/jimmunol.1302860.
Leach, Michelle D., et al. "Hsp90 Orchestrates Transcriptional Regulation by Hsf1 and Cell Wall Remodelling by MAPK Signalling during Thermal Adaptation in a Pathogenic Yeast." PLoS Pathogens, vol. 8, no. 12, 27 Dec. 2012, doi:10.1371/journal.ppat.1003069.
Si, Haoyu, et al. "Candida Albicans White and Opaque Cells Undergo Distinct Programs of Filamentous Growth." PLoS Pathogens, vol. 9, no. 3, 7 Mar. 2013, doi:10.1371/journal.ppat.1003210.
Perepechaeva, Maria L., and Alevtina Y. Grishanova. "In Vivo Effects of Genistein, Herbimycin a and Geldanamycin on Rat Hepatic Cytochrome P4501A." Journal of Biophysical Chemistry, vol. 03, no. 04, Nov. 2012, pp. 334-340., doi:10.4236/jbpc.2012.34041.
Kim, Yoon Sik, et al. "Reactive Oxygen Species Promote Heat Shock Protein 90-Mediated HBV Capsid Assembly." Biochemical and Biophysical Research Communications, vol. 457, no. 3, 13 Feb. 2015, pp. 328-333., doi:10.1016/j.bbrc.2014.12.110.
Singh-Babak, Sheena D., et al. "Global Analysis of the Evolution and Mechanism of Echinocandin Resistance in Candida Glabrata." PLoS Pathogens, vol. 8, no. 5, 17 May 2012, doi:10.1371/journal.ppat.1002718.\n
Vincent. Thiohydantoin Derivatives and Uses Thereof. 17 Apr. 2018.
Barksdale, Keri A., and Gautam N. Bijur. "The Basal Flux of Akt in the Mitochondria Is Mediated by Heat Shock Protein 90." Journal of Neurochemistry, vol. 108, no. 5, 9 Feb. 2009, pp. 1289-1299., doi:10.1111/j.1471-4159.2009.05878.x.
Mount, Harley O'Connor, et al. "Global analysis of genetic circuitry and adaptive mechanisms enabling resistance to the azole antifungal drugs." PLoS genetics 14.4 (2018): e1007319.

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