期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 25, 页码 8421-8425出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902456
关键词
antitumor agents; bioinorganic chemistry; ferrocifen; non-covalent interactions; quinones
资金
- PGG foundation
- PSL University
- Feroscan
- European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme [648558]
Ferrociphenols, especially those possessing a heterocycle at the terminus of an aliphatic chain, display strong anticancer activity through a novel redox mechanism that generates active metabolites such as quinone methides (QMs). X-ray crystallography and UV/Vis spectroscopy reveal that the specific lone pair (lp)-pi interaction between a carbonyl group of the imide and the quinone motif of the QM plays an important role in the exceptional cytotoxic behaviour of their imido-ferrociphenol precursors. This intramolecular lp-pi interaction markedly enhanced the stability of the QMs and lowered the pK(a) values of the corresponding phenol/phenolate couples. As the first example of such a non-covalent interaction that stabilizes QMs remotely, it not only expands the scope of the lp-pi interaction in supramolecular chemistry, but also represents a new mode of stabilization of a QM. This unprecedented application of lp-pi interactions in imido-ferrociphenol anticancer drug candidates may also have great potential in drug discovery and organocatalyst design.
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