Discodermolide
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IUPAC name
[(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-Trihydroxy-19-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-5,7,9,11,13,15-hexamethylnonadeca-1,3,11,16-tetraen-6-yl] carbamate
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| C33H55NO8 | |
| Molar mass | 593.79 g/mol |
| Melting point | 112 to 113 °C (234 to 235 °F; 385 to 386 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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(+)-Discodermolide is a polyketide natural product found to stabilize microtubule. (+)-discodermolide was isolated by Gunasekera and his co-workers at the Harbor Branch Oceanographic Institute from the deep-sea sponge Discodermia dissoluta in 1990. (+)-Discodermolide was found to be a potent inhibitor of tumor cell growth in several MDR cancer cell lines. (+)-discodermolide also shows some unique characters, including a linear backbone structure, immunosuppressive properties both in vitro and in vivo, potent induction of an accelerated senescence phenotype, and synergistic antiproliferative activity in combination with paclitaxel. Discodermolide was recognized as one of the most potent natural promoters of tubulin assembly. A large number of efforts toward the total synthesis of (+)-discodermolide were directed by its interesting biological activities and extreme scarcity of natural sources (0.002% w/w from frozen marine sponge). The compound supply necessary for complete clinical trials cannot be met by harvesting, isolation, and purification. As of 2005, attempts at synthesis or semi-synthesis by fermentation have proven unsuccessful. As a result, all discodermolide used in preclinical studies and clinical trials has come from large-scale total synthesis.
Discodermolide was first isolated in 1990 from the Caribbean marine sponge Discodermia dissoluta by chemist Dr. Sarath Gunasekera and biologist Dr. Ross Longley, scientists at the Harbor Branch Oceanographic Institution. The sponge contained 0.002% of discodermolide (7 mg/434 g of sponge). Since the compound is light-sensitive, the sponge must be harvested at a minimum depth of 33 meters. Discodermolide was initially found to have immunosuppressive and antifungal activities.
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