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- Title
Analysis of Diazofluorene DNA Binding and Damaging Activity: DNA Cleavage by a Synthetic Monomeric Diazofluorene.
- Authors
Woo, Christina M.; Ranjan, Nihar; Arya, Dev P.; Herzon, Seth B.
- Abstract
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 11 as a potent DNA cleavage agent in tissue culture. The simpler structure of 11 relative to the natural products establishes it as a useful lead for translational studies.
- Subjects
DNA damage; DRUG-DNA interactions; ISOMERIZATION; NAPHTHOQUINONE; DNA-binding proteins
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 35, p9325
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201404137