Analysis of Diazofluorene DNA Binding and Damaging Activity: DNA Cleavage by a Synthetic Monomeric Diazofluorene1. Issue 35 (9th July 2014)

• Record Type: Journal Article
• Authors: Woo, Christina M.; Ranjan, Nihar; Arya, Dev P.; Herzon, Seth B.
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 35(2014)
• Page Start: 9325
• Page End: 9328
• Publication Date: 2014-07-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201404137
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The lomaiviticins and kinamycins are complex DNA damaging natural products that contain a diazofluorene functional group. Herein, we elucidate the influence of skeleton structure, ring and chain isomerization, D‐ring oxidation state, and naphthoquinone substitution on DNA binding and damaging activity. We show that the electrophilicity of the diazofluorene appears to be a significant determinant of DNA damaging activity. These studies identify the monomeric diazofluorene <bold>11</bold> as a potent DNA cleavage agent in tissue culture. The simpler structure of <bold>11</bold> relative to the natural products establishes it as a useful lead for translational studies.</p> </abstract>