Redox-dependent cytotoxicity of ferrocene derivatives and ROS-activated prodrugs based on ferrocenyliminoboronates

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Authors

VĚŽNÍK Jakub KONHEFR Martin FOHLEROVÁ Zdenka LACINA Karel

Year of publication 2021
Type Article in Periodical
Magazine / Source Journal of Inorganic Biochemistry
MU Faculty or unit

Central European Institute of Technology

Citation
Web https://www.sciencedirect.com/science/article/pii/S0162013421002087?via%3Dihub
Doi http://dx.doi.org/10.1016/j.jinorgbio.2021.111561
Keywords Aminoferrocene; Redox-dependent cytotoxicity; ROS-activated prodrugs; Ferrocenyliminoboronates; MG-63; Electrochemical characterization
Description Four ferrocene derivatives - ferrocenecarboxylic acid, ferrocenium salt, ferroceneboronic acid, and amino-ferrocene - were characterized electrochemically, and their cytotoxicity was probed using cancer cells (line MG -63). We related the observed cytotoxicity with the determined redox potentials of these four ferrocenes - ami-noferrocene with its lowest redox potential exhibited the highest cytotoxicity. Thus, we synthesized four de-rivatives consisting of aminoferrocene and phenylboronic acid residue with the intent to employ them as ROS-activated prodrugs (ROS - reactive oxygen species). We characterized them and studied their time-dependent stability in aqueous environments. Then, we performed electrochemical measurements at oxidative conditions to confirm ROS-responsivity of the synthesized molecules. Finally, the cytotoxicity of the synthesized molecules was tested using cancer MG-63 cells and noncancerous NIH-3T3 cells. The experiments revealed sought behaviour, especially for para-regioisomers of synthesized ferrocenyliminoboronates.
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