Synthesis and biological activity of a fluorescent schweinfurthin analogue

Synthesis of a fluorescent schweinfurthin analogue has been accomplished, and its biological activity and sub-cellular localization have been studied. Most of the natural schweinfurthins are potent and selective inhibitors of cell growth as measured by the National Cancer Institute’s 60-cell line sc...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2009-07, Vol.17 (13), p.4718-4723
Main Authors: Kuder, Craig H., Neighbors, Jeffrey D., Hohl, Raymond J., Wiemer, David F.
Format: Article
Language:English
Subjects:
60-Cell assay
Adenocarcinoma - drug therapy
Antineoplastic agents
Antineoplastic Agents, Phytogenic - analysis
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
Biological and medical sciences
Cell Line, Tumor
Cell Proliferation - drug effects
Cytotoxic
Euphorbiaceae - chemistry
Fluorescent
Fluorescent Dyes - analysis
Fluorescent Dyes - chemistry
General aspects
Humans
Lung Neoplasms - drug therapy
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
Schweinfurthin
Stilbene
Structure-Activity Relationship
Xanthenes - analysis
Xanthenes - chemical synthesis
Xanthenes - chemistry
Xanthenes - pharmacology
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Summary:Synthesis of a fluorescent schweinfurthin analogue has been accomplished, and its biological activity and sub-cellular localization have been studied. Most of the natural schweinfurthins are potent and selective inhibitors of cell growth as measured by the National Cancer Institute’s 60-cell line screen. Due to the limited supply of these natural products, we have initiated a program aimed at their synthesis. To date, this effort has led to the preparation of three natural schweinfurthins and more than 40 analogues, and assays on these compounds have afforded some understanding of structure–activity relationships in this family. Further development of schweinfurthins as chemotherapeutic agents would benefit from characterization of their mechanism(s) of action. This perspective led to development of a fluorescent schweinfurthin analogue that retains the differential activity of the natural products, and yet has properties that facilitate its visualization within cells.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2009.04.071