Saturday, October 26, 2013

Chiral Molecule: Taxol


Taxol, an organic molecule with 11 chiral centers, is a chemotherapy drug that has been successful in treating cancers characterized by solid tumors including breast, ovarian, lung, and prostate. It is categorized as a plant alkaloid, a chemotherapy drug synthesized from plants. Plant alkaloids include a variety of antimicrotubule agents like Taxol. Antimicrotubule agents prohibit the activity of the microtubules which are required for cell division. The mechanism of prohibition of the microtubules is not yet fully understood. The chirality of this molecule speaks to its specificity in pathway interruption of the microtubules. Taxol only confers the desired effects in a specific arrangement: 7-S chiral centers and 4-R chiral centers. Taxanes are produced by the bark of the Pacific Yew tree. Stripping bark from the Pacific yew trees kills them, but it has been discovered that taxol can be made from a compound gathered from the needles of the common English yew tree. See the pictures below for the structure and stereochemistry of this natural product.

 

Consulted Pages:

http://chemocare.com/chemotherapy/drug-info/Taxol.aspx#.Umw9WJjD8ic

http://www.ncbi.nlm.nih.gov/pubmed/24155271

http://www.docbrown.info/page07/isomerism2a.htm

5 comments:

  1. I have heard about this compound before in both a chemistry sense and a medical sense. It is just very interesting to me that something as common as tree bark can have just an impact on our lives. It is also interesting that if something has a certain arrangement it may or may not have the desired effects we are looking for. I guess it just goes to show that sometimes we don't have to look far beyond nature to find answers for some of our hardest problems.

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  2. Tyler, I found this blog post to be very informative. I am astonished in the way such a small part of this earth could solve such a giant problem in the human race. I've never heard of Taxol before, but now I am definitely interested in researching it more. I would also love to find out what other microtubule agents are and if they also are used in cancer treatments.

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  3. Very cool info on this drug - I think this is the most chiral centers I've seen so far on anything that has been posted. It's pretty amazing how important stereochemistry is to the effectiveness of most drugs - only certain enantiomers work and others create a completely different effect.

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  4. I also did Taxol before I saw your post. I didn't realize before doing this assignment that it was found from plants but I found that very interesting. As I mentioned in my post, I chose it because my girlfriend's father just underwent chemo treatment using Taxol and his pharyngeal tumor is completely gone after the treatment. So it was very effective, though he is still struggling with the side effects of mouth sores.

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  5. Very interesting read, I am however not surprised that this could be found on tree bark. That is also how the discovery of Ibuprofen came to be. I think it would be very interesting to see if the 'raw'/'natural' form from the tree bark would be more beneficial in fighting cancer than the manipulated forms that are man made, especially for someone like myself who is a believer in homeopathic medicine.

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