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E-Combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory beta-E-nitrostyrenes

  1. Author:
    Pettit, R. K.
    Pettit, G. R.
    Hamel, E.
    Hogan, F.
    Moser, B. R.
    Wolf, S.
    Pon, S.
    Chapuis, J. C.
    Schmidt, J. M.

  2. Author Address

    Pettit, Robin K.; Pettit, George R.; Hogan, Fiona, Wolf, Sonja, Pon, Sandy, Chapuis, Jean-Charles, Schmidt, Jean M.] Arizona State Univ, Canc Res Inst, Tempe, AZ 85287 USA. [Pettit, Robin K.; Pettit, George R.; Hogan, Fiona, Wolf, Sonja, Pon, Sandy, Chapuis, Jean-Charles, Schmidt, Jean M.] 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. [Moser, Bryan R.] ARS, USDA, Natl Ctr Agr Utilizat Res, Peoria, IL 61604 USA.
    1. Year: 2009
  2. Journal: Bioorganic & Medicinal Chemistry
    1. 17
    2. 18
    3. Pages: 6606-6612
  4. Type of Article: Article
  1. Abstract:

    As part of a broad-based SAR investigation of E-resveratrol (strong sirtuin activator and antineoplastic) and the anticancer vascular-targeting combretastatin-type stilbenes, a series of twenty-three beta-E-nitrostyrenes was synthesized in order to evaluate potential antineoplastic, antitubulin, and antimicrobial activities. The beta-E-nitrostyrenes evaluated ranged from monosubstituted phenols to trimethoxy and 3-methoxy- 4,5-methylenedioxy derivatives. Two of the beta-nitrostyrenes were synthesized as water-soluble sodium phosphate derivatives (4t, 4v). All except four (4r, 4s, 4t, 4u) of the series significantly inhibited a minipanel of human cancer cell lines. All but eight led to an IC50 of < 10 mu M for inhibition of tubulin polymerization, and all except three (4l, 4t, 4v) displayed antimicrobial activity. (C) 2009 Published by Elsevier Ltd.

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  2. DOI: 10.1016/j.bmc.2009.07.076
  3. PMID: 19709889

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