SDS
CofA
Description
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 in Candida 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.
More Information
Alternate Name/Synonyms
Geldanomycin
SKU
G-1047
CAS #
30562-34-6
Chemical Name
[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-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
Chemical Formula
C29H40N2O9
Molecular Weight
560.6 Da
Appearance
Yellow crystalline powder
Purity
>99% by HPLC
Solubility
DMSO: Clear yellow solution at 10 mg/ml, CH2Cl2: Clear yellow solution at 5 mg/mL
Melting Point
260°C
Storage Temp
-20°C
THERAPEUTIC AREA
Oncological Disorders
USE
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.
MDL NUMBER
MFCD00274570
CHEMACX
X1035747-8
INCHI
QTQAWLPCGQOSGP-BMBHCMFXSA-N
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
RTECS
LX8920000
Handling
Ensure adequate ventilation, especially in confined areas. Use personal protective equipment as required. Use with local exhaust ventilation. Do not breathe dust/fume/gas/mist/vapors/spray. Handle in accordance with good industrial hygiene and safety practice. Corrosive hazard. Wear protective gloves/clothing and eye/face protection
Certificate of Analysis 1
Certificate of Analysis 2
Certificate of Analysis 3
| GHS PICTOGRAMS |  |
|---|---|
| Handling | Ensure adequate ventilation, especially in confined areas. Use personal protective equipment as required. Use with local exhaust ventilation. Do not breathe dust/fume/gas/mist/vapors/spray. Handle in accordance with good industrial hygiene and safety practice. Corrosive hazard. Wear protective gloves/clothing and eye/face protection |
