Geldanamycin

SKU
G-1047
  • CAS:30562-34-6
  • Formula:C29H40N2O9
  • MW:560.6 Da
  • Appearance:Yellow crystalline powder
  • Purity:>99% by HPLC

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Product Name Qty
Geldanamycin, Streptomyces hygroscopicus
500 ug
$45.45
Geldanamycin
1 mg
$61.68
Geldanamycin
5 mg
$113.62
Geldanamycin
10 mg
$216.42

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
Preparation
N/A
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.
Merck Index
N/A
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
Citations 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
Assigned Assay Grant No: 1 R03 MH086456-01
P489Geldanamycin-induced IkBa cleavage potentiates autophagy in angiotensin II -mediated hypertrophy
MDM2 binding induces a conformational change in p53 that is opposed by heat-shock protein 90 and precedes p53 proteasomal degradation
PS 16-17 GELDANAMYCIN-INDUCED IκBα CLEAVAGE POTENTIATES AUTOPHAGY IN ANGIOTENSIN II-MEDIATED HYPERTROPHY
The basal flux of Akt in the mitochondria is mediated by heat shock protein 90
Proteome-wide changes induced by the Hsp90 inhibitor, geldanamycin in anaplastic large cell lymphoma cells
Heat shock protein 90 facilitates formation of the HBV capsid via interacting with the HBV core protein dimers
Geldanamycin, a HSP90 inhibitor, attenuates the hypoxia-induced vascular endothelial growth factor expression in retinal pigment epithelium cells in vitro
Proteasomes and antigen presentation: evidence that a KEKE motif does not promote presentation of the class I epitope SIINFEKL
Simian Virus 40 depends on ER protein folding and quality control factors for entry into host cells
Epidermal growth factor receptors with tyrosine kinase domain mutations exhibit reduced Cbl association, poor ubiquitylation, and down-regulation but are efficiently internalized
Hsp90 orchestrates temperature-dependent Candida albicans morphogenesis via Ras1-PKA signaling
Candida albicans white and opaque cells undergo distinct programs of filamentous growth
PKC signaling regulates drug resistance of the fungal pathogen Candida albicans via circuitry comprised of Mkc1, calcineurin, and Hsp90
Hsp90 governs echinocandin resistance in the pathogenic yeast Candida albicans via calcineurin
Design, synthesis, and biological evaluation of hydroquinone derivatives of 17-amino-17-demethoxygeldanamycin as potent, water-soluble inhibitors of Hsp90
Pim-1 kinase stability is regulated by heat shock proteins and the ubiquitin-proteasome pathway
Unc45 activates Hsp90-dependent folding of the myosin motor domain
Developmentally induced changes of the proteome in the protozoan parasite Leishmania donovani
Regulated proteolysis of Candida albicans Ras1 is involved in morphogenesis and quorum sensing regulation
Attenuation of cadmium-induced necrotic cell death by necrostatin-1: potential necrostatin-1 acting sites
Cdc28 provides a molecular link between Hsp90, morphogenesis, and cell cycle progression in Candida albicans
Hydrogen sulfide protects SH-SY5Y cells against 6-hydroxydopamine-induced endoplasmic reticulum stress
Role of the heat shock protein 90 in immune response stimulation by bacterial DNA and synthetic oligonucleotides
Hydrogen sulfide protects neurons against hypoxic injury via stimulation of ATP-sensitive potassium channel/protein kinase C/extracellular signal-regulated kinase/heat shock protein 90 pathway
Reactive oxygen species promote heat shock protein 90-mediated HBV capsid assembly
Molecular mechanisms of cold-induced CYP1A activation in rat liver microsomes
Geldanamycin selectively targets the nascent form of ERBB3 for degradation
A time-resolved fluorescence resonance energy transfer-based HTS assay and a surface plasmon resonance-based binding assay for heat shock protein 90 inhibitors
Anti-cancer Mechanisms of the Natural Plant Derived Compound, Withaferin A in HER-2/neu Breast Cancer
Uncovering New Roles for Hsp90 in Candida albicans Morphogenesis
Stress and release: chemical modulation of secondary metabolite production in Aspergillus sp.
Role of Hsp105 in CFTR biogenesis
In vivo effects of genistein, herbimycin a and geldanamycin on rat hepatic cytochrome P4501A
Interaction between nucleophosmin and HBV core protein increases HBV capsid assembly
Geldanamycin promotes premature mitotic entry and micronucleation in irradiated p53/p21 deficient colon carcinoma cells
Translocation and Function of Akt in the Mitochondria
Antagonistic control of disease resistance protein stability in the plant immune system
Hypoxia-mediated up-regulation of Pim-1 contributes to solid tumor formation
A BC-box domain-related mechanism for VHL protein degradation
Pharmacologically enhanced expression of GPNMB increases the sensitivity of melanoma cells to the CR011-vcMMAE antibody-drug conjugate
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