Synthesis and biological activity of a fluorescent schweinfurthin analogue

Craig H Kuder; Jeffrey D Neighbors; Raymond J Hohl; David F Wiemer

doi:10.1016/j.bmc.2009.04.071

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Synthesis and biological activity of a fluorescent schweinfurthin analogue

Journal article

Peer reviewed

Synthesis and biological activity of a fluorescent schweinfurthin analogue

Craig H Kuder, Jeffrey D Neighbors, Raymond J Hohl and David F Wiemer

Bioorganic & medicinal chemistry, Vol.17(13), pp.4718-4723

2009

DOI: 10.1016/j.bmc.2009.04.071

PMCID: PMC6685536

PMID: 19464190

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https://www.ncbi.nlm.nih.gov/pmc/articles/6685536View

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Abstract

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.

Schweinfurthin

Fluorescent

60-Cell assay

Cytotoxic

Stilbene

Details

Title: Subtitle: Synthesis and biological activity of a fluorescent schweinfurthin analogue
Creators: Craig H Kuder - Department of Pharmacology, University of Iowa, Iowa City, IA 52242-1294, USA
Jeffrey D Neighbors - Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA
Raymond J Hohl - Department of Pharmacology, University of Iowa, Iowa City, IA 52242-1294, USA
David F Wiemer - Department of Pharmacology, University of Iowa, Iowa City, IA 52242-1294, USA
Resource Type: Journal article
Publication Details: Bioorganic & medicinal chemistry, Vol.17(13), pp.4718-4723
DOI: 10.1016/j.bmc.2009.04.071
PMID: 19464190
PMCID: PMC6685536
NLM abbreviation: Bioorg Med Chem
ISSN: 0968-0896
eISSN: 1464-3391
Publisher: Elsevier Ltd
Language: English
Date published: 2009
Academic Unit: Neuroscience and Pharmacology; Chemistry; Internal Medicine
Record Identifier: 9983985948302771

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