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| Product Name | Geldanamycin- FITC |
| Description |
Hsp90 fluorescent probe |
| Purity | >97% (TLC), NMR conforms |
| CAS No. | 30562-34-6 |
| Molecular Formula | C55H63N5O13S |
| Molecular Weight | 1034.2 |
| Field of Use | Not for use in humans. Not for use in diagnostics or therapeutics. For in vitro research use only. |
Properties
| Storage Temperature | -20ºC |
| Shipping Temperature | Shipped Ambient |
| Solubility | May be dissolved in DMSO (>10 mg/ml) |
| Source | Synthetic |
| Appearance | Purple Solid |
| SMILES | C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)/C)OC)OC(=O)N)C)C)O)OC |
| InChI | InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35) |
| InChIKey | QTQAWLPCGQOSGP-KSRBKZBZSA-N |
| Safety Phrases |
Classification: Harmful. May be harmful if inhaled, swallowed or absorbed through skin. Safety Phrases: S22 - Do not breathe dust S24/25 - Avoid contact with skin and eyes S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection Risk Phrases: R68- Possible risk of irreversible effects |
| Cite This Product | Geldanamycin- FITC (StressMarq Biosciences Inc., Victoria BC CANADA, Catalog # SIH-113) |
Biological Description
| Alternative Names | (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 |
| Research Areas | Cancer, Heat Shock |
| PubChem ID | Geldanamycin: 5288382 |
| Scientific Background | Geldanamycin is a benzoquinoid ansamycin produced by Streptomyces hygroscopicus. It binds specifically to heat shock protein HSP90 and downregulates target proteins including tyrosine kinases, steroid receptors, transcription factors and cell cycle regulatory kinases (1,2). It induces the inactivation, destabilization and eventual degradation of HIF-1α (3). It is also an inhibitor of pp60src tyrosine kinase and of c-myc gene expression in murine lymphoblastoma cells. It inhibits the transforming activity of abl, erbB, fps, src, and yes (4). Geldanamycin is capable of destabilizing several oncogene and proto-oncogene products; it is a potent inhibitor of the nuclear hormone receptor family (5). It protects against α-synuclein toxicity to dopaminergic neurons in Drosophila, and destabilizes mutant p53 protein from a number of breast, leukemic, and prostate cell lines (6). Inhibits basal and hypoxia-induced expression of c-Jun (IC50=75nM) and abolishes hypoxia-induced increase in c-Jun N-terminal kinase (JNK) activity. Inhibits telomerase activity through inhibition of HSP90, a chaperone required for the assembly and activation of telomerase in human cells (6). It is ~10-fold more potent than herbimycin A. Specifically, the geldanamycin fluorescent probe may be used for detection of cell surface Hsp90, may be used in fluorescence polarization assays, and characterizations of geldanamycin drug-target interactions. |
| References |
1. Whitesell L., et al. (1994) Proc. Natl. Acad. Sci. USA 91:8324. 2. Neckers L. (2002) Trends Mol. Med. 8: S55. 3. Mabjeesh N.J., et al. (2002) Cancer Res. 62: 2478. 4. Chavany C., et al. 1996) Amer. Society Biochem Mol Bio. 9: 4974-4977. 5. Villa R., et al. (2003) Carcinogenesis. 24(5): 851-9. 6. Yamaki H., Iguchi-Ariga S.M., and Ariga H. (1989) J Antibiot (Tokyo). 42(4): 604-10. |
Product Images
Chemical structure of Geldanamycin- FITC (SIH-113), a Hsp90 Fluorescent Probe. Molecular Formula: C55H63N5O13S. Molecular Weight: 1034.2 g/mol.
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Based on validation through cited publications.