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Antineoplastic Agents. 548. Synthesis of lodo- and Diiodocombstatin Phosphate Prodrugs

  1. Author:
    Pettit, G. R.
    Rosenberg, H. J.
    Dixon, R.
    Knight, J. C.
    Hamel, E.
    Chapuis, J. C.
    Pettit, R. K.
    Hogan, F.
    Sumner, B.
    Ain, K. B.
    Trickey-Platt, B.

  2. Author Address

    [Pettit, George R.; Rosenberg, Heidi J.; Dixon, Rachel; Knight, John C.; Chapuis, Jean-Charles; Pettit, Robin K.; Hogan, Fiona; Sumner, Brandy; Trickey-Platt, Brindi] Arizona State Univ, Canc Res Inst, Tempe, AZ 85287 USA. [Pettit, George R.; Rosenberg, Heidi J.; Dixon, Rachel; Knight, John C.; Chapuis, Jean-Charles; Pettit, Robin K.; Hogan, Fiona; Sumner, Brandy; Trickey-Platt, Brindi] Arizona State Univ, Dept Chem & Biochem, Tempe, AZ 85287 USA. [Hamel, Ernest] NCI, Toxicol & Pharmacol Branch, Dev Therapeut Program, Div Canc Treatment & Diag,NIH, Frederick, MD 21702 USA. [Ain, Kenneth B.] Univ Kentucky, Med Ctr, Dept Internal Med, Div Endocrinol & Mol Med, Lexington, KY 40536 USA.;Pettit, GR (reprint author), Arizona State Univ, Canc Res Inst, Tempe, AZ 85287 USA;bpettit@asu.edu
    1. Year: 2012
    2. Date: Mar
  2. Journal: Journal of Natural Products
    1. 75
    2. 3
    3. Pages: 385-393
  4. Type of Article: Article
  5. ISSN: 0163-3864
  1. Abstract:

    Toward the objective of designing a structurally modified analogue of the combretastatin A-4 phosphate prodrug (1b) with the potential for increased specificity toward thyroid carcinoma, synthesis of a series of iodocombstatin phosphate (11a-h) and diiodocombstatin phosphate prodrugs (12a-h) has been accomplished. The diiodo series was obtained via 8a and 9c from condensation of 4 and 6, and the iodo sequence involved a parallel pathway. Both series of iodocombstatins were found to display significant to powerful inhibition of the growth of a panel of human cancer cell lines and of the murine P388 lymphocytic leukemia cell line. Of the diiodo series, 12a was also found to markedly inhibit growth of pediatric neuroblastoma, and monoiodocombstatin 9a strongly inhibited HUVEC growth. Overall, the strongest activity was found against the breast, CNS, leukemia, lung, and prostate cancer cell lines and the least activity against the pancreas and colon lines. Parallel biological investigations of tubulin interaction, antiangiogenesis, and antimicrobial effects were also conducted.

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External Sources

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  2. DOI: 10.1021/np200797x
  3. View record in Web of Science®
  4. WOS: 000301810700009

Library Notes

  1. Fiscal Year: FY2011-2012
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