Fluorescent schweinfurthin B and F analogs with anti-proliferative activity

Joseph J. Topczewski, Craig H. Kuder, Jeffrey D. Neighbors, Raymond J. Hohl, David F. Wiemer

Research output: Contribution to journalArticlepeer-review

11 Scopus citations


The natural tetracyclic schweinfurthins are potent and selective inhibitors of cell growth in the National Cancer Institute's 60 cell-line screen. At this time, the mechanism or cellular target that underlies this activity has not yet been identified, and efforts to illuminate the schweinfurthins' mode of action would benefit from development of potent fluorescent analogs that could be readily visualized within cells. This report describes the synthesis of fluorescent analogs of schweinfurthins B and F, and demonstrates that these compounds retain the potent and differentially toxic activities against select human cancer cells that are characteristic of the natural schweinfurthins. In addition, the synthesis of control compounds that maintain parallel fluorescent properties, but lack the potent activity of the natural schweinfurthin is described. Use of fluorescence microscopy shows differences between the localization of the active and relatively inactive schweinfurthin analogs. The active compounds localize in peripheral puncta which may identify the site(s) of activity.

Original languageEnglish (US)
Pages (from-to)6734-6741
Number of pages8
JournalBioorganic and Medicinal Chemistry
Issue number18
StatePublished - Sep 15 2010
Externally publishedYes

Bibliographical note

Funding Information:
We thank the University of Iowa for a Shriner Fellowship (JJT). Financial support from the Roy J. Carver Charitable Trust and the National Cancer Institute ( R41CA126020 via Terpenoid Therapeutics, Inc.) is gratefully acknowledged. The content is solely the responsibility of the authors, and does not necessarily represent the official views of the National Cancer Institute or the National Institutes of Health.


  • Anti-proliferative
  • Bioassay
  • Fluorescent probes
  • Natural products
  • Schweinfurthin
  • Stilbene
  • Synthesis


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