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Chemical compound
(+)-Discodermolide is a polyketide natural product found to stabilize microtubules. (+)-discodermolide was isolated by Gunasekera and his co-workers at the Harbor Branch Oceanographic Institute from the deep-sea sponge Discodermia dissoluta in 1990.[1] (+)-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,[2][3] potent induction of an accelerated senescence phenotype,[4] and synergistic antiproliferative activity in combination with paclitaxel.[5] 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.[6]
^Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. J. Org. Chem.1990, 55, 4912-4915. (doi:10.1021/jo00303a029)
^Longley, R. E.; Caddigan, D.; Harmody, D.; Gunasekera, M.; Gunasekera, S. P. Transplantation 1991, 52, 650-655.
^Longley, R. E.; Caddigan, D.; Harmody, D.; Gunasekera, M.; Gunasekera, S. P. Transplantation 1991, 52, 656-661.
^Klein, L.; Freeze, B. S.; Smith, A. B., III; Horwitz, S. B. Cell Cycle 2005, 4, 501–507.
^Longley, R. E.; Gunasekera, S. P.; Faherty, D.; McLane, J.; Dumont, F. Ann. N.Y. Acad. Sci. 1993, 696, 94–107.
^Mickel, S. J. et al. Org. Process Res. Dev. 2004, 8
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