Synthesis, Molecular Structure and Cytotoxicity of Molecular Materials Based on Water Soluble Half-Sandwich Rh(III) and Ir(III) Tetranuclear Metalla-Cycles

Gupta, Gajendra; Murray, Benjamin; Dyson, Paul J.; Therrien, Bruno

doi:10.3390/ma6115352

Cited by 29 publications

(4 citation statements)

References 43 publications

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“…The new dipyridine‐functionalized BODIPY ligand L was synthesized by the procedure described in the Supporting Information. The starting materials 1 and 2 were prepared according to reported methods . The diiodo‐BODIPY derivative was synthesized by following previously reported method .…”

Section: Methodsmentioning

confidence: 99%

Self‐Assembled BODIPY‐Based Iridium Metallarectangles: Cytotoxicity and Propensity to Bind Biomolecules

et al. 2018

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A new 4‐ethynylpyridine 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY)‐based ligand L, which was synthesized by means of the Sonogashira coupling method, was used to obtain two new [2+2] iridium‐based metallarectangles, 3 and 4. Ligand L and metallarectangles 3 and 4 were fully characterized through various analytical techniques. The structure of rectangle 4 was further confirmed by single‐crystal X‐ray diffraction analysis, which showed the formation of an expected [2+2] supramolecule, in which the iridium metal centers were bridged with ligand L to form the desired metallarectangle 4. In the context of the growing biological interest in metallarectangles, rectangle 4 was found to be highly active against two types of cancer cells, with IC50 values almost threefold superior to those of cisplatin. Both 3 and 4 showed dose‐dependent abilities to bind bovine serum albumin and salmon sperm DNA; this indicated their tendency to interact with such biomolecules as a potential mode of action.

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Section: Methodsmentioning

confidence: 99%

Self‐Assembled BODIPY‐Based Iridium Metallarectangles: Cytotoxicity and Propensity to Bind Biomolecules

et al. 2018

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“…However, at this stage, the parameters dictating the biological activity of these metalla-rectangles remain unclear. It has been suggested that the size and the nature of the connectors are important factors, as well as the charge and lipophilicity of the assembly [66]; however, replacing the arene ruthenium units by other half-sandwich complexes showed almost no impact on the activity [67,68]. Clearly, these studies suggest that the best combination of arenes, metals, and connectors has yet to be found.…”

Section: Water-soluble Arene Ruthenium Complexesmentioning

confidence: 96%

The Biological Side of Water-Soluble Arene Ruthenium Assemblies

Therrien

Furrer

2014

Advances in Chemistry

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This review article covers the synthetic strategies, structural aspects, and host-guest properties of ruthenium metalla-assemblies, with a special focus on their use as drug delivery vectors. The two-dimensional metalla-rectangles show interesting host-guest possibilities but seem less appropriate for being used as drug carriers. On the other hand, metalla-prisms allow encapsulation and possible targeted release of bioactive molecules and consequently show some potential as drug delivery vectors. The reactivity of these metalla-prisms can be fine-tuned to allow a fine control of the guest’s release. The larger metalla-cubes can be used to stabilize the formation of G-quadruplex DNA and can be used to encapsulate and release photoactive molecules such as porphins. These metalla-assemblies demonstrate great prospective in photodynamic therapy.

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“…It has been proposed that this is due to the increased nuclearity and presence of the extended π‐conjugated system [10a] . Furthermore, many Ir(III) SCCs have been synthesized, with many displaying good to excellent biological properties, along with increased selectivity toward cancer cells over non‐malignant cells [6h–j,11] …”

Section: Introductionmentioning

confidence: 99%

Quinolyl‐Based PGM Metallarectangles: Antiproliferative Activity, DNA and BSA Protein Interactions, and a Molecular Docking Perspective

et al. 2023

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The increased success of small metal-containing molecules as pharmaceutical agents has prompted investigations into the pharmacological activity of a different class of metal-based compounds; supramolecular coordination complexes (SCCs). Such complexes have been extensively investigated for their anticancer activity, with many displaying activities comparable or superior to available clinical chemotherapeutic drugs. Here, we evaluated a series of quinoline-containing binuclear complexes and metallarectangles for their in vitro anticancer activity in the hormone receptor positive MCF-7 and triple negative MDA-MB-231 breast cancer cell lines. The preliminary cytotoxic screen, in the MCF-7 cell line, revealed that the ligand (7-chloro-4-(pyridin-4-yl)quinoline, L) and metallarectangle [{Ir(μ-Cl)(Cp*)} 4 (μ-L) 2 ](OTf) 4 display superior activity to cisplatin, while [{Ru(p-cymene)} 4 (μ-η 2 -η 2 -C 2 O 4 ) 2 (μ-L) 2 ](OTf) 4 was more potent than cisplatin in the triple-negative MDA-MD-231 cell line. Upon evaluation in a multidose screen, ligand L and metallarectangle [{Ir(μ-Cl)(Cp*)} 4 (μ-L) 2 ](OTf) 4 displayed antiproliferative activity almost two-fold greater than cisplatin in the MCF-7 cell line, while [{Ru(p-cymene)} 4 (μ-η 2 -η 2 -C 2 O 4 ) 2 (μ-L) 2 ](OTf) 4 was over two-times more active than cisplatin in the MDA-MB-231 cell line. Additionally, using the non-tumorigenic MCF-12 A breast epithelial cell line, the compounds demonstrate increased selectivity toward breast cancer cells over non-tumorigenic cells. Furthermore, investigations into the interactions of ligand L and selected complexes with calf thymus DNA (CT-DNA) and bovine serum albumin (BSA) indicate favourable binding.

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Synthesis, Molecular Structure and Cytotoxicity of Molecular Materials Based on Water Soluble Half-Sandwich Rh(III) and Ir(III) Tetranuclear Metalla-Cycles

Cited by 29 publications

References 43 publications

Self‐Assembled BODIPY‐Based Iridium Metallarectangles: Cytotoxicity and Propensity to Bind Biomolecules

Self‐Assembled BODIPY‐Based Iridium Metallarectangles: Cytotoxicity and Propensity to Bind Biomolecules

The Biological Side of Water-Soluble Arene Ruthenium Assemblies

Quinolyl‐Based PGM Metallarectangles: Antiproliferative Activity, DNA and BSA Protein Interactions, and a Molecular Docking Perspective

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