Allison, M, Wilson, D, Pask, CM orcid.org/0000-0002-2241-5069 et al. (2 more authors) (2020) β‐Diketonate versus β‐Ketoiminate: The Importance of a Ferrocenyl Moiety in Improving the Anticancer Potency. ChemBioChem, 21 (14). pp. 1988-1996. ISSN 1439-4227
Abstract
Herein we present a library of fully characterized β‐diketonate and β‐ketoiminate compounds that are functionalized with a ferrocenyl moiety. Their cytotoxic potential has been determined by screening against human breast adenocarcinomas (MCF‐7 and MDA‐MB‐231), human colorectal carcinoma p53 wild type (HCT116 p53 +/+ ) and normal human prostate (PNT2) cell lines. The ferrocenyl β‐diketonate compounds are more than 18 times more cytotoxic than the ferrocenyl β‐ketoiminate analogues. Against MCF‐7, compounds functionalized at the meta position are up to nine times more cytotoxic than when functionalized at the para position. The ferrocenyl β‐diketonate compounds have increased selectivity towards MCF‐7 and MDA‐MB‐231, with several complexes having selectivity index (SI) values that are more than nine times (MCF‐7) and more than six times (MDA‐MB‐231) that of carboplatin. The stability of these compounds in dimethyl sulfoxide (DMSO) and dimethylformamide (DMF) has been assessed by NMR spectroscopy and mass spectrometry studies, and the compounds show no oxidation of the iron center from FeII to FeIII. Cytotoxicity screening was performed in both DMSO and DMF, with no significant differences observedin their potency.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/. |
Keywords: | bioinorganic chemistry; cancer; ferrocenyl compounds; β-diketonate ligands; β-ketoiminate ligands |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Inorganic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 06 Jul 2020 13:32 |
Last Modified: | 25 Jun 2023 22:20 |
Status: | Published |
Publisher: | Wiley |
Identification Number: | 10.1002/cbic.202000028 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:162851 |