Reaction of N-Ferrocenylcarbamates with Nitric Oxide: An Application for Detection of Inflammatory Sites In Vivo
Selin R, Özkan HG, Bila G, Bilyy R, Mokhir A (2025)
Publication Language: English
Publication Type: Journal article
Publication year: 2025
Journal
Book Volume: 20
Article Number: e202500356
Journal Issue: 19
Abstract
Electron-deficient aminoferrocenes (edAFs) exhibit anticancer activity both in vitro and in vivo. However, their mechanism of action remains unclear. Studies using fluorogenic edAF derivatives suggest that the ferrocenyl moiety undergoes oxidation or decomposition within cells, resulting in the formation of unknown products. Interestingly, this process is not significantly facilitated by H2O2, indicating that this intracellular oxidant does not alter edAFs in the cellular environment. To identify alternative endogenous oxidants, NO is investigated as a potential candidate. Under aerobic conditions, NO is found to efficiently induce the oxidation and decomposition of edAFs. This transformation is mediated by an electrophilic nitrosation reaction, followed by nitroso-oxime tautomerism and subsequent degradation of the ferrocenyl moiety with the release of ligand-derived oxime 7 and iron ions. These findings suggest that NO may play a key role in the intracellular modification of edAFs, potentially contributing to their anticancer activity or their metabolism or both. Building on this mechanism, an effective probe is developed for detecting NO in living cells and identifying sites of inflammation in vivo. These probes are based on a modular design that enables facile substitution of the fluorescent dye, allowing straightforward customization for diverse applications both in cellulo and in vivo.
Authors with CRIS profile
Roman Selin
Lehrstuhl für Organische Chemie II
Hülya Özkan
Lehrstuhl für Organische Chemie II
Andriy Mokhir
Professur für Organische Chemie
Involved external institutions
Ukraine (UA)How to cite
APA:
Selin, R., Özkan, H.G., Bila, G., Bilyy, R., & Mokhir, A. (2025). Reaction of N-Ferrocenylcarbamates with Nitric Oxide: An Application for Detection of Inflammatory Sites In Vivo. ChemMedChem, 20(19). https://doi.org/10.1002/cmdc.202500356
MLA:
Selin, Roman, et al. "Reaction of N-Ferrocenylcarbamates with Nitric Oxide: An Application for Detection of Inflammatory Sites In Vivo." ChemMedChem 20.19 (2025).
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