化学
蒽醌类
蒽醌
反应性(心理学)
醌
环加成
组合化学
生物活性
作者
Giovanni Ribaudo,Alberto Ongaro,Maira Zorzan,Raffaele Pezzani,Marco Redaelli,Giuseppe Zagotto,Maurizio Memo,Alessandra Gianoncelli
标识
DOI:10.1002/ardp.201900030
摘要
The design of a multitarget and multifunctional small molecule containing two functional groups reacting through different mechanisms represents an attractive goal for the medicinal chemist. The preparation of two bifunctional oxiranylmethyloxy anthraquinones, previously investigated as anticancer agents, is described here. These compounds combine a planar, DNA-intercalating and pro-oxidant anthraquinone scaffold and the alkylating epoxide functions which can covalently react with the nucleic acid. Their multilevel molecular reactivity was studied through a combination of analytical techniques: The DNA-binding properties were investigated using a mass spectrometry-based binding assay and by nuclear magnetic resonance, highlighting the formation of a covalent adduct with a nucleobase. Moreover, the contribution of the pro-oxidant redox cycling was evaluated.
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