ArticleAngewandte Chemie (International ed. in English)2014
Analysis of diazofluorene DNA binding and damaging activity: DNA cleavage by a synthetic monomeric diazofluorene.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Role of a FAD-dependent monooxygenase in diazo group functionalization of kinamycin inMicrobiology (Reading, England) · 2025Article
- O-methyltransferase-like enzyme catalyzed diazo installation in polyketide biosynthesis.Nature communications · 2023Article
- Synthesis and Biological Evaluation of (2Journal of the American Chemical Society · 2021Article
- Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.Chemical reviews · 2017Review
- Diazo Compounds: Versatile Tools for Chemical Biology.ACS chemical biology · 2016Review
- Linker dependent intercalation of bisbenzimidazole-aminosugars in an RNA duplex; selectivity in RNA vs. DNA binding.Bioorganic & medicinal chemistry letters · 2016Article
- Structural basis for DNA cleavage by the potent antiproliferative agent (-)-lomaiviticin A.Proceedings of the National Academy of Sciences of the United States of America · 2016Article
- Identification of Alp1U and Lom6 as epoxy hydrolases and implications for kinamycin and lomaiviticin biosynthesis.Nature communications · 2015Article
- Mechanism of action studies of lomaiviticin A and the monomeric lomaiviticin aglycon. Selective and potent activity toward DNA double-strand break repair-deficient cell lines.Journal of the American Chemical Society · 2015Article
Corrections and comments
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Authors and funding
4 authors.
Funding
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.
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