| Epothilone |  Epothilone A (R = H) and B (R = Me) | | Chemical formula | C26H39NO6S (Epothilone A)
C27H41NO6S (Epothilone B) A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ...
| | Molecular mass | 493.66 g/mol (Epothilone A)
507.68 g/mol (Epothilone B) The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ...
| | CAS number | 152044-53-6 (Epothilone A)
152044-54-7 (Epothilone B) CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ...
| | 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. The taxanes are a widely used class of chemotherapy drugs. ...
Metabolites are the intermediates and products of metabolism. ...
Sorangium cellulosum is a soil-dwelling Gram-negative bacteria of the group myxobacteria. ...
History The structure of epothilone A was determined in 1996 using x-ray crystallography.[2] 1996 (MCMXCVI) was a leap year starting on Monday of the Gregorian calendar, and was designated the International Year for the Eradication of Poverty. ...
X-ray crystallography or single-crystal X-ray diffraction is an analytical technique which uses the diffraction pattern produced by bombarding a single crystal with X-rays to solve the crystal structure. ...
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. Microtubules are one of the components of the cytoskeleton. ...
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. The Food and Drug Administration (FDA) is an agency of the United States Department of Health and Human Services and is responsible for regulating food (humans and animal), dietary supplements, drugs (human and animal), cosmetics, medical devices (human and animal) and radiation emitting devices (including non-medical devices), biologics, and...
In medicine, a clinical trial (synonyms: clinical studies, research protocols, medical research) is the application of the scientific method to human health. ...
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]. A total synthesis is the complete chemical synthesis of complex organic molecules from simple, commercially available (petrochemical) precursors. ...
Kyriacos Costa Nicolaou is an American chemist. ...
References - ^ 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
- ^ Hofle, G.; Bedorf, N.; Steinmertz, H.; Schomburg, D.; Gerth, K.; Reichenach, H. Angew. Chem. 1996, 35, 1567.
- ^ 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)
- ^ Luduvico, I.; Hyaric, M. L.; Almeida, M. V.; Da Silva, A. D. Mini-Reviews in Organic Chemistry 2006, 3, 49-75. (Review)
- ^ Balog, D. M.; Meng, D.; Kamanecka, T.; Bertinato, P.; Su, D.-S.; Sorensen, E. J.; Danishefsky, S. J. Angew. Chem. 1996, 108, 2976.
- ^ 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.
- ^ Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1997, 36, 166.
- ^ Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. Int. Ed. Engl. 1997, 36, 523.
- ^ Mulzer, J.; Mantoulidis, A.; Öhler, E. J. Org. Chem. 2000, 65, 7456-7467. (DOI:10.1021/jo0007480)
- ^ Bode, J. W.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 3611-3612. (DOI:10.1021/ja0155635)
Angewandte Chemie or Angewandte Chemie International Edition is the chemistry journal of the Gesellschaft Deutscher Chemiker (Society of German Chemists). ...
Angewandte Chemie or Angewandte Chemie International Edition is the chemistry journal of the Gesellschaft Deutscher Chemiker (Society of German Chemists). ...
Angewandte Chemie or Angewandte Chemie International Edition is the chemistry journal of the Gesellschaft Deutscher Chemiker (Society of German Chemists). ...
Kyriacos Costa Nicolaou is an American chemist. ...
Angewandte Chemie or Angewandte Chemie International Edition is the chemistry journal of the Gesellschaft Deutscher Chemiker (Society of German Chemists). ...
Angewandte Chemie or Angewandte Chemie International Edition is the chemistry journal of the Gesellschaft Deutscher Chemiker (Society of German Chemists). ...
The Journal of Organic Chemistry (abbreviated as ) is a scientific journal for original contributions of fundamental research in organic and bioorganic chemistry. ...
A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...
The Journal of the American Chemical Society (usually abbreviated as , or JACS), is a peer-reviewed scientific journal, published since 1879 by the American Chemical Society. ...
A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...
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