Competition with glutathione explains the impact of lysosomal pH on the pro-oxidant and anticancer activity of the copper-phenanthroline complex Article Swipe
Enrico Falcone
,
Vincenzo Vigna
,
Hemma Schueffl
,
Francesco Stellato
,
Bertrand Vileno
,
Merwan Bouraguba
,
Gloria Mazzone
,
Olivier Proux
,
Silvia Morante
,
Petra Heffeter
,
Emilia Sicilia
,
Peter Faller
·
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.26434/chemrxiv-2024-zhswk
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.26434/chemrxiv-2024-zhswk
Several Cu-ligands, including 1,10-phenanthroline (Phen), have been investigated for anticancer purposes based on their capacity to bind excess Cu in cancer tissues and form redox active complexes able to catalyse the formation of reactive oxygen species (ROS), ultimately leading to oxidative stress and cell death. However, the stability and pro-oxidant activity of Cu-based drugs such as Cu-Phen2 is affected in most cell compartments (e.g. cytosol and nucleus) by the presence of compounds such as glutathione (GSH) and metallothioneins, which can reduce and dissociate Cu(II) from the ligand forming poorly redox-active Cu(I)-thiolate clusters. Here, cell culture studies suggested that lysosomal acidification may play a pivotal role in the anticancer activity of Cu-Phen2. In addition, ROS generation catalysed by Cu-Phen2 in the presence of GSH was shown to be remarkably accelerated at the acidic pH typical of lysosomes. The catalytic mechanism was thoroughly investigated by means of density functional theory (DFT) calculations, which disclose key reaction intermediate species, including a ternary Phen-Cu-GSH complex formed upon dissociation of one Phen ligand. Spectroscopic measurements (including low-temperature luminescence, UV-vis absorption and X-ray absorption spectroscopy) corroborated the formation of such a reactive intermediate ternary complex. Furthermore, they revealed that the faster ROS generation observed at lower pH is due to a pH-dependent competition between Phen and GSH for Cu, which results in a higher stability of Cu-Phen2 against dissociation and de-activation by GSH at lower pH. Overall, this study points to lysosomal targeting as an innovative and effective strategy to improve the stability and cytotoxic activity of Cu-based drugs.
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Metadata
- Type
- preprint
- Language
- en
- Landing Page
- https://doi.org/10.26434/chemrxiv-2024-zhswk
- OA Status
- gold
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4400126130
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4400126130Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.26434/chemrxiv-2024-zhswkDigital Object Identifier
- Title
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Competition with glutathione explains the impact of lysosomal pH on the pro-oxidant and anticancer activity of the copper-phenanthroline complexWork title
- Type
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preprintOpenAlex work type
- Language
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enPrimary language
- Publication year
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2024Year of publication
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2024-06-28Full publication date if available
- Authors
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Enrico Falcone, Vincenzo Vigna, Hemma Schueffl, Francesco Stellato, Bertrand Vileno, Merwan Bouraguba, Gloria Mazzone, Olivier Proux, Silvia Morante, Petra Heffeter, Emilia Sicilia, Peter FallerList of authors in order
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https://doi.org/10.26434/chemrxiv-2024-zhswkPublisher landing page
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YesWhether a free full text is available
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goldOpen access status per OpenAlex
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https://doi.org/10.26434/chemrxiv-2024-zhswkDirect OA link when available
- Concepts
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Chemistry, Glutathione, Ternary complex, Phenanthroline, Redox, Reactive oxygen species, Dissociation (chemistry), Cytosol, Reactive intermediate, Ligand (biochemistry), Oxidative stress, Photochemistry, Stereochemistry, Catalysis, Inorganic chemistry, Biochemistry, Receptor, Organic chemistry, EnzymeTop concepts (fields/topics) attached by OpenAlex
- Cited by
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0Total citation count in OpenAlex
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10Other works algorithmically related by OpenAlex
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