Geldanamycin
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Geldanamycin is a 1,4-benzoquinone ansamycin antitumor antibiotic that inhibits the function of Hsp90 (Heat Shock Protein 90) by binding to the unusual ADP/ATP-binding pocket of the protein.[1] HSP90 client proteins play important roles in the regulation of the cell cycle, cell growth, cell survival, apoptosis, angiogenesis and oncogenesis.[2]
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IUPAC name
(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy- | |
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C29H40N2O9 | |
Molar mass | 560.64 g/mol |
Appearance | Gold-yellow fine crystalline powder |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Geldanamycin induces the degradation of proteins that are mutated or overexpressed in tumor cells such as v-Src, Bcr-Abl, p53, and ERBB2. This effect is mediated via HSP90. Despite its potent antitumor potential, geldanamycin presents several major drawbacks as a drug candidate such as hepatotoxicity, further, Jilani et al.. reported that geldanamycin induces the apoptosis of erythrocytes under physiological concentrations.[4] These side effects have led to the development of geldanamycin analogues, in particular analogues containing a derivatisation at the 17 position: