Molecular Playground/Taxol
One of the CBI Molecules being studied in the University of Massachusetts Amherst Chemistry-Biology Interface Program at UMass Amherst and on display at the Molecular Playground.
Paclitaxel, also called Taxol (Bristol-Myers Squibb), is a plant derived anti-cancer agent that was first isolated from the bark of Pacific yew tree, Taxus brevifolia, in 1971. It is a complex diterpenoid with a bulky, fused ring system as well as a number of hydrophobic substituents. It is currently being used in the treatment of ovarian, breast and lung cancers, and additional therapies are being developed for treatment of Alzheimer's and post-heart surgery patients. Taxol causes cell death by promoting the assembly of microtubules, preventing cell mitosis.
Originally, paclitaxel was produced through the extraction of the drug from the bark of Taxus trees. This process was unsustainable because nearly 40,000 trees were required to meet the demands for the drug each year. A semi-synthetic route was developed and utilized for paclitaxel production which utilized Taxol precursors which can be extracted from the needles of Taxus trees. This process was more sustainable because the Taxus needles could be harvested depending on their seasonal availability. Currently, paclitaxel is being produced through plant cell culture. This was the first plant cell culture production route approved by the FDA for the production of a pharmaceutical.
Docetaxel (Taxotere, sanofi-aventis) is a semi-synthetic analog of Taxol that was discovered during the search for a more easily produced taxane anti-cancer agent. There are two differences between the chemical structure of paclitaxel and docetaxel. The hydroxyl group modification on docetaxel leads to an increase in the lipid solubility of the drug. It is currently used in the treatment of breast, stomach and prostate cancer.
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Molecular Playground Banner: "Paclitaxel (Taxol),a plant-derived natural product to treat cancer"
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