Lysosome-targeting amplifiers of reactive oxygen species as anticancer prodrugs
Cancer cells produce elevated levels of reactive oxygen species, which has been used to design cancer specific prodrugs. Their activation relies on at least a bimolecular process, in which a prodrug reacts with ROS. However, at low micromolar concentrations of the prodrugs and ROS, the activation is...
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| Main Authors: | , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
November 9, 2017
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| In: |
Angewandte Chemie. International edition
Year: 2017, Volume: 56, Issue: 49, Pages: 15545-15549 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201706585 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/anie.201706585 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201706585 
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| Author Notes: | Steffen Daum, M.S. Viktor Reshetnikov, Miroslav Sisa, Tetyana Dumych, Maxim D. Lootsik, Rostyslav Bilyy, Evgenia Bila, Christina Janko, Christoph Alexiou, Martin Herrmann, Leopold Sellner, and Andriy Mokhir |
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| 520 | |a Cancer cells produce elevated levels of reactive oxygen species, which has been used to design cancer specific prodrugs. Their activation relies on at least a bimolecular process, in which a prodrug reacts with ROS. However, at low micromolar concentrations of the prodrugs and ROS, the activation is usually inefficient. Herein, we propose and validate a potentially general approach for solving this intrinsic problem of ROS-dependent prodrugs. In particular, known prodrug 4-(N-ferrocenyl-N-benzylaminocarbonyloxymethyl)phenylboronic acid pinacol ester was converted into its lysosome-specific analogue. Since lysosomes contain a higher concentration of active ROS than the cytoplasm, activation of the prodrug was facilitated with respect to the parent compound. Moreover, it was found to exhibit high anticancer activity in a variety of cancer cell lines (IC50=3.5-7.2 μm) and in vivo (40 mg kg−1, NK/Ly murine model) but remained weakly toxic towards non-malignant cells (IC50=15-30 μm). | ||
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