Combretastatin dinitrogen-substituted stilbene analogues as tubulin-binding and vascular-disrupting agents

Rogelio Siles, J. Freeland Ackley, Mallinath B. Hadimani, John J. Hall, Benon E. Mugabe, Rajsekhar Guddneppanavar, Keith A. Monk, Jean Chapuis, George Pettit, David J. Chaplin, Klaus Edvardsen, Mary Lynn Trawick, Charles M. Garner, Kevin G. Pinney

Research output: Contribution to journalArticlepeer-review

39 Scopus citations


Several stilbenoid compounds having structural similarity to the combretastatin group of natural products and characterized by the incorporation of two nitrogen-bearing groups (amine, nitro, serinamide) have been prepared by chemical synthesis and evaluated in terms of biochemical and biological activity. The 2′,3′-diamino B-ring analogue 17 demonstrated remarkable cytotoxicity against selected human cancer cell lines in vitro (average GI50 = 13.9 nM) and also showed good activity in regard to inhibition of tubulin assembly (IC50 = 2.8 μM). In addition, a single dose (10 mg/kg) of compound 17 caused a 40% tumor-selective blood flow shutdown in tumor-bearing SCID mice at 24 h, thus suggesting the potential value of this compound and its corresponding salt formulations as new vascular-disrupting agents.

Original languageEnglish (US)
Pages (from-to)313-320
Number of pages8
JournalJournal of Natural Products
Issue number3
StatePublished - Mar 2008

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry


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