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Vincristine Michael Doe CHEM 23202

Vincristine Michael Doe CHEM 23202. Overview. I. Physical Properties II. Synthesis III. Characterization IV. History and Uses V. How it works. General Information 2. CAS Number: 57-22-7 Molecular Formula: C 46 H 56 N 4 O 10 Molecular Weight: 824.97 Melting Point: 218-220 °C

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Vincristine Michael Doe CHEM 23202

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  1. VincristineMichael DoeCHEM 23202

  2. Overview • I. Physical Properties • II. Synthesis • III. Characterization • IV. History and Uses • V. How it works

  3. General Information2 • CAS Number: 57-22-7 • Molecular Formula: C46H56N4O10 • Molecular Weight: 824.97 • Melting Point: 218-220°C • Clear liquid (taken by injection)

  4. Synthesis from a Natural Source • Vincristine has two natural sources: Catharanthus roseus (Vinca rosea), the Madagascar periwinkle, and Tabernaemontana pachysiphon • This yield from the Madagascar periwinkle is less than 1μg/g (.0003%)6

  5. Synthesis from vinblastine H2CrO4 Ethyl Acetate 2 hours, -83- -25°C 80-90% yield5 • This is the easiest and most common method of • synthesis, as well as one can give high yields

  6. Synthetic Production • Discovered in 2004 • First route to make synthetic vincristine6

  7. Spectroscopy • Mass Spectrum4: M+1=825 • UV Spectrum1: 220, 255, 296 nm • IR Spectrum6: 3445, 2924, 2852, 1740, 1681, 1597, 1498, 1458, 1369, 1230, 1033, 747 cm-1

  8. History and Uses • Discovered in 1953 by Robert L. Noble, and cleared by the FDA in 1963 as Oncovin, marketed by Eli Lilly and Co. • Used to treat acute leukemias and all lymphomas • Side effects include nervous system damage and constipation • Work is being done to develop more effective derivatives with fewer side effects8

  9. How it works • Stops division of cells • Enters cell during mitosis and blocks formation of microtubules of the mitotic spindle during metaphase3,7

  10. Bibliography • (1) Anonymous Vincristine. In The Merck index: an encyclopedia of chemicals, drugs, and biologicals; O'Neil, M. J., Ed.; Merck: Whitehouse Station, NJ, 2006; pp 1717-1718. • (2) Anonymous Chemfinder.com Database and Internet Searching. http://chemfinder.cambridgesoft.com (accessed Jan. 22, 2007). • (3) Anonymous Overview: The Mitotic Spindle. http://www.sinauer.com/pdf/nsp-cellcycle-6-0.pdf (accessed Apr. 15, 2007). • (4) Choi, Y. H.; Kim, J.; Yoo, K. Supercritical Fluid Extraction and Liquid Chromatography-Electrospray Mass Analysis of Vinblastine from Catharanthus roseus. Chem. Pharm. Bull. 2002, 50, 1294--1296. • (5) Huhtikangas, A.; Laakso, I.; Seppaenen-Laakso, T.; Verma, A. Patent Application Country: Application: FI; Patent Country: FI Patent 107924, 2001. • (6) Kuboyama, T.; Yokoshima, S.; Tokuyama, H.; Fukuyama, T. Stereocontrolled total synthesis of (+)-vincristine. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 11966-11970. • (7) Lurie, P. M.; Manaster, J.; Stryckmans, P. A.; Vamecq, G. Mode of Action of Chemotherapy in vivo on Human Acute Leukemia--II. Vincristine. Europ. J. Cancer 1973, 9, 613--620. • (8) Szabo, L.; Bolcskei, H.; Eszter, B.; Mak, M.; Szantay, C. Synthesis of vinca alkaloids and related compounds, Part XCV: Nitration study of vinblastine-type bisindole alkaloids. Arch. Pharm. Pharm. Med. Chem. 2001, 334, 339--405.

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