Epothilone

From Wikipedia, the free encyclopedia

You have new messages (last change).
Epothilone
Epothilone A (R = H) and B (R = Me)

Epothilone A (R = H) and B (R = Me)
Chemical formula C26H39NO6S (Epothilone A)

C27H41NO6S (Epothilone B)
Molecular mass 493.66 g/mol (Epothilone A)

507.68 g/mol (Epothilone B)
CAS number 152044-53-6 (Epothilone A)

152044-54-7 (Epothilone B)
Disclaimer and references

The epothilones are a new class of cytotoxic molecules, including epothilone A, epothilone B, and epothilone D, identified as potential chemotherapy drugs.[1] Their mechanism of action is similar to that of the taxanes, but their chemical structure is simpler and they are more soluble in water. Early studies in cancer cell lines and in human cancer patients indicate superior efficacy to the taxanes. Epothilones were originally identified as metabolites produced by the myxobacterium Sorangium cellulosum.

Contents

[edit] History

The structure of epothilone A was determined in 1996 using x-ray crystallography.[2]

[edit] Mechanism of action

The principal mechanism of the epothilone class is inhibition of microtubule function.[3] Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing.

[edit] Clinical trials

Several epothilone analogs are currently undergoing clinical development for treatment of various cancers, although none is currently approved by international regulatory authorities such as the United States Food and Drug Administration. Epothilones can only be administered to humans in the context of a clinical trial.

[edit] Organic synthesis

Due to the high potency and clinical need for cancer treatments, epothilones have been the target of many total syntheses.[4] The first group to publish the total synthesis of epothilones was S. J. Danishefsky et al. in 1996.[5][6] Other syntheses of epothilones have been published by Nicolaou[7], Schinzer[8], Mulzer[9], and Carreira[10].

[edit] References

  1. ↑  Vincent T. DeVita, Jr., MD; Samuel Hellman, MD; and Steven A. Rosenberg, MD, PhD (2004) Cancer: Principles And Practice Of Oncology (7th Edition) Lippincott Williams & Wilkins ISBN 0-7817-4450-4
  2. ↑  Hofle, G.; Bedorf, N.; Steinmertz, H.; Schomburg, D.; Gerth, K.; Reichenach, H. Angew. Chem. 1996, 35, 1567.
  3. ↑  Epothilones: Mechanism of Action and Biologic Activity, Susan Goodin, Michael P. Kane, Eric H. Rubin, Journal of Clinical Oncology, Vol 22, No 10 (May 15), 2004: pp. 2015-2025. (Article)
  4. ↑  Luduvico, I.; Hyaric, M. L.; Almeida, M. V.; Da Silva, A. D. Mini-Reviews in Organic Chemistry 2006, 3, 49-75. (Review)
  5. ↑  Balog, D. M.; Meng, D.; Kamanecka, T.; Bertinato, P.; Su, D.-S.; Sorensen, E. J.; Danishefsky, S. J. Angew. Chem. 1996, 108, 2976.
  6. ↑  Su, D.-S.; Meng, D.; Bertinato, P.; Balog, D. M.; Sorensen, E. J.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem. Int. Ed. Engl. 1997, 36, 757.
  7. ↑  Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1997, 36, 166.
  8. ↑  Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. Int. Ed. Engl. 1997, 36, 523.
  9. ↑  Mulzer, J.; Mantoulidis, A.; Öhler, E. J. Org. Chem. 2000, 65, 7456-7467. (DOI:10.1021/jo0007480)
  10. ↑  Bode, J. W.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 3611-3612. (DOI:10.1021/ja0155635)

[edit] See also


 This medical treatment article is a stub. You can help Wikipedia by expanding it.
Retrieved from "http://en.wikipedia.org../../../e/p/o/Epothilone.html"
In other languages