Atypical Lone Pair-π Interaction with Quinone Methides in a Series of Imido-Ferrociphenol Anticancer Drug Candidates.
antitumor agents
bioinorganic chemistry
ferrocifen
non-covalent interactions
quinones
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
17 06 2019
17 06 2019
Historique:
received:
25
02
2019
revised:
29
03
2019
pubmed:
13
4
2019
medline:
15
9
2020
entrez:
13
4
2019
Statut:
ppublish
Résumé
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)-π 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-π interaction markedly enhanced the stability of the QMs and lowered the pK
Identifiants
pubmed: 30977944
doi: 10.1002/anie.201902456
doi:
Substances chimiques
Antineoplastic Agents
0
Ferrous Compounds
0
Imides
0
Indolequinones
0
ferrociphenol
0
quinone methide
138230-21-4
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
8421-8425Subventions
Organisme : H2020 European Research Council
ID : 648558
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.