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

Robin Pettit, George Pettit, Ernest Hamel, Fiona Hogan, Bryan R. Moser, Sonja Wolf, Sandy Pon, Jean Chapuis, Jean M. Schmidt

Research output: Contribution to journalArticle

28 Scopus citations

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 β-E-nitrostyrenes was synthesized in order to evaluate potential antineoplastic, antitubulin, and antimicrobial activities. The β-E-nitrostyrenes evaluated ranged from monosubstituted phenols to trimethoxy and 3-methoxy-4,5-methylenedioxy derivatives. Two of the β-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 μM for inhibition of tubulin polymerization, and all except three (4l, 4t, 4v) displayed antimicrobial activity.

Original languageEnglish (US)
Pages (from-to)6606-6612
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number18
DOIs
StatePublished - Sep 15 2009

Keywords

  • Anticancer agent
  • Combretastatin
  • Resveratrol
  • β-E-Nitrostyrene

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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