Wednesday, October 30, 2013
Paclitaxel (Taxol) Chirality
Paclitaxel (Taxol) is a chemotherapy drug used to treat many solid tumors including breast, ovarian, lung, esophageal, etc. cancers. It must be administered intravenously, as there is no pill form yet developed. As with many chemotherapy drugs, Taxol is cell-cycle specific, meaning it attacks the mechanism for cell division. Cancer is classified by uncontrolled cell division because cancerous cells are unable to halt mitosis like normal cells. The taxol attacks the microtubules necessary for mitosis, altering their structure. This prevents the cells from replicating, thus helping to alter the spread and growth of the tumor. The problem is that the drug cannot tell the difference between the tumor cells and normal, healthy cells. This is why chemotherapy is so draining and takes such an effect on the body. Side effects include, nausea, vomiting, mouth sores, hair loss, etc. I chose Taxol as my chiral molecule for several reasons. One, it has many chiral centers (11) so it fit the criteria, but mainly because my girlfriend's father just ended chemo treatment of Taxol so I was very interested in researching more information about it. He had oral-pharyngeal cancer but after 5 months of Taxol treatment the tumor is completely gone as of now. He did not lose any hair interestingly but he has had a major problem with mouth sores. After 2 months off of the Taxol, he is still not able to eat hard food due to this side effect. However, the Taxol did its job and got rid of the cancer. The structure of Taxol is below, drawn in ChemDraw.