Arene Ruthenium Metalla-Assemblies with Anthracene Moieties for PDT Applications

Gaschard, Marie; Nehzat, Farzaneh; Cheminel, Thomas; Therrien, Bruno

doi:10.3390/inorganics6030097

Cited by 18 publications

(13 citation statements)

References 78 publications

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“…For example, several ruthenium-arene metalla-assemblies coupled to photosensitizers, including porphyrins, were prepared and tested as PDT agents 97. Recently, Therrien and coworkers have synthesized an anthracene-based metalla-rectangle with the idea to improve the cell uptake of the photosensitizer (anthracene) 98. In the presence of oxygen and light activation, anthracene forms an endoperoxide intermediate.…”

Section: Sccs As Anticancer Agentsmentioning

confidence: 99%

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Recent Developments of Supramolecular Metal-based Structures for Applications in Cancer Therapy and Imaging

Pöthig¹,

Casini²

2019

Theranostics

160

110

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The biomedical application of discrete supramolecular metal-based structures, including supramolecular coordination complexes (SCCs), is still an emergent field of study. However, pioneering studies over the last 10 years demonstrated the potential of these supramolecular compounds as novel anticancer drugs, endowed with different mechanisms of action compared to classical small-molecules, often related to their peculiar molecular recognition properties. In addition, the robustness and modular composition of supramolecular metal-based structures allows for an incorporation of different functionalities in the same system to enable imaging in cells via different modalities, but also active tumor targeting and stimuli-responsiveness. Although most of the studies reported so far exploit these systems for therapy, supramolecular metal-based structures may also constitute ideal scaffolds to develop multimodal theranostic agents. Of note, the host-guest chemistry of 3D self-assembled supramolecular structures - within the metallacages family - can also be exploited to design novel drug delivery systems for anticancer chemotherapeutics. In this review, we aim at summarizing the pivotal concepts in this fascinating research area, starting with the main design principles and illustrating representative examples while providing a critical discussion of the state-of-the-art. A section is also included on supramolecular organometallic complexes (SOCs) whereby the (organic) linker is forming the organometallic bond to the metal node, whose biological applications are still to be explored. Certainly, the myriad of possible supramolecular metal-based structures and their almost limitless modularity and tunability suggests that the biomedical applications of such complex chemical entities will continue along this already promising path.

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Section: Sccs As Anticancer Agentsmentioning

confidence: 99%

“…The endoperoxide formation is reversible, and oxygen can be released in a different environment. Unfortunately, upon formation of the metalla-assembly, the propensity of the anthracene moiety to react with oxygen to form endoperoxide derivatives was lost 98.…”

Section: Sccs As Anticancer Agentsmentioning

confidence: 99%

Recent Developments of Supramolecular Metal-based Structures for Applications in Cancer Therapy and Imaging

Pöthig¹,

Casini²

2019

Theranostics

160

110

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“…Granzhan et al), structurally close to the compounds previously studied by D. Chenoweth and coworkers; 25,26 and a newly reported organometallic cage Rec-(AN)-DONQ (562). 34 Classical DNA intercalators are also identified, notably two porphyrins, TMPyP4 (545) 35 and TEGPy (546), 36 and two cationic pyrene derivatives, AZ03 (414) and AZ04 (415), 37 owing to their innate ability to interact with negatively charged nucleic acids.…”

Section: Selection Of Chemical Libraries For Twj-screen Evaluationsmentioning

confidence: 99%

Identification of Three-Way DNA Junction Ligands through Screening of Chemical Libraries and Validation by Complementary in Vitro Assays

et al. 2019

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The human genome is replete with repetitive DNA sequences that can fold into thermodynamically stable secondary structures such as hairpins and quadruplexes. Cellular enzymes exist to cope with these structures whose stable accumulation would result in DNA damage through interference with DNA transactions such as transcription and replication. Therefore, chemical stabilization of secondary DNA structures offers an attractive way to foster DNA transaction-associated damages to trigger cell death in proliferating cancer cells. While much emphasis has been recently given to DNA quadruplexes, we focused here on three-way DNA junctions (TWJ) and report on a strategy to identify TWJ-targeting agents through a combination of in vitro techniques (TWJ-Screen, PAGE, FRET-melting, ESI-MS, dialysis equilibrium and SRB assays). We designed a complete workflow and screened 1200 compounds to identify promising TWJ-ligands selected on stringent criteria in terms of TWJ folding ability, affinity and selectivity.

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“…The endoperoxide formation is reversible, and oxygen can be released in a different environment. Therefore, knowing that arene ruthenium metalla-assemblies can be internalized to cells and can be coupled to photosensitizers, we have recently synthesized an anthracene-based metalla-rectangle (Figure 8) (Gaschard et al, 2018). Despite an unsuccessful endoperoxide formation on the metalla-rectangle, the ultimate goal of this project was to transport oxygen and a photosensitizer to cells for an optimization of PDT treatments in hypoxic cancers.…”

Section: Oxygen Interactionsmentioning

confidence: 99%

“…Anthracene-based tetranuclear arene ruthenium metalla-assemblies for o 2 interactions (Gaschard et al, 2018). …”

Section: Oxygen Interactionsmentioning

confidence: 99%

The Role of the Second Coordination Sphere in the Biological Activity of Arene Ruthenium Metalla-Assemblies

Therrien

2018

Front. Chem.

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For nearly 15 years, the biological and biomedical applications of arene ruthenium metalla-assemblies have flourished. Today, the synthetic strategies to generate arene ruthenium assemblies are well-established, and these compounds offer tremendous possibilities in terms of structural diversities and chemical properties. However, the second coordination sphere is often poorly considered, if not ignored, when designing such arene ruthenium metalla-assemblies. These weak interactions (hydrogen bonding, hydrophobic, ionic, electrostatic, van der Waals, π-π stacking) that take place in the solid state or in solution are generally key interactions for the foreseen applications. Therefore, in this review, we want to emphasize this important property of arene ruthenium metalla-assemblies by showing examples dealing with second coordination sphere interactions and how this can be better integrated in the design of these versatile supramolecular metal-based entities.

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Arene Ruthenium Metalla-Assemblies with Anthracene Moieties for PDT Applications

Cited by 18 publications

References 78 publications

Recent Developments of Supramolecular Metal-based Structures for Applications in Cancer Therapy and Imaging

Recent Developments of Supramolecular Metal-based Structures for Applications in Cancer Therapy and Imaging

Identification of Three-Way DNA Junction Ligands through Screening of Chemical Libraries and Validation by Complementary in Vitro Assays

The Role of the Second Coordination Sphere in the Biological Activity of Arene Ruthenium Metalla-Assemblies

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