A Platinum Supramolecular Square as an Effective G-Quadruplex Binder and Telomerase Inhibitor

Kieltyka, Roxanne E.; Englebienne, Pablo; Fakhoury, Johans; Autexier, Chantal; Moitessier, Nicolas; Sleiman, Hanadi F.

doi:10.1021/ja8014023

Cited by 199 publications

(144 citation statements)

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“…Almost 20 years have passed since Fujita's group synthesised the first metalla-squares, [(en) 4 M 4 (4,4¢-bipyridine) 4 ] 8+ (en = ethylenediamine; M = Pd, Pt) (Chart 1). 1 Only recently the biological potential of such compounds has been studied, despite the tremendous success of cisplatin, 2 one of the most widely used anticancer metal-based drugs.…”

Section: Introductionmentioning

confidence: 99%

“…1 Only recently the biological potential of such compounds has been studied, despite the tremendous success of cisplatin, 2 one of the most widely used anticancer metal-based drugs. 3 These studies showed that the water soluble complex [(en) 4 Pt 4 (4,4¢-bipyridine) 4 ] 8+ possesses a good binding affinity for G-quadruplex DNA, 4 and a cytotoxicity comparable to cisplatin was observed against HL-60 tumour cells. 5 The application of multinuclear Pt compounds to overcome serious side effects and resistance mechanisms associated with cisplatin is not new.…”

Section: Introductionmentioning

confidence: 99%

“…15 We also synthesised rectangular tetranuclear arene ruthenium complexes incorporating 2,5-dioxydo-1,4-benzoquinonato (dhbq) or 2,5-dichloro-1,4-benzoquinonato (dcbq) and N«N linkers (N«N = 4,4¢-bipyridine, 1,2-bis(4-pyridyl)ethylene) which proved to be Chart 2 active against A2780 cancer cells. 16 The smaller metalla-rectangle [(p-cymene) 4 4 are soluble in polar organic solvents such as acetonitrile, acetone, methanol and also dimethylsulfoxide. It is worth noting that the precursor compounds 1 and 2 are only sparingly soluble in these solvents.…”

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

“…The cytotoxicities of the dinuclear and tetranuclear osmium complexes were established using ovarian A2780 cancer cell lines. The most active metalla-rectangle, [(p-cymene) 4 Os 4 (dhbq) 2 (4,4¢-bipyridine) 2 ] 4+ , shows an IC 50 value of 5.7 mM (comparable to cisplatin) against A2780 cancer cells and 7.5 mM against the cisplatin resistant A2780cisR cells. …”

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Anticancer activity of osmium metalla-rectangles

et al. 2010

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A series of cationic metalla-rectangles of the general formula [(p-cymene) 4 Os 4 (OO«OO) 2 (N«N) 2 ] 4+ have been obtained in methanol from the dinuclear arene osmium precursors [(p-cymene) 2 Os 2 (OO«OO) 2 Cl 2 ] (OO«OO = 2,5-dioxydo-1,4-benzoquinonato (dhbq), 2,5-dichloro-1,4-benzoquinonato (dcbq)) by reaction with bipyridine linkers (N«N = 4,4¢-bipyridine, 1,2-bis(4-pyridyl)ethylene) in the presence of AgCF 3 SO 3 . All complexes were isolated as triflate salts and characterised by NMR, IR and UV-visible spectroscopy. The cytotoxicities of the dinuclear and tetranuclear osmium complexes were established using ovarian A2780 cancer cell lines. The most active metalla-rectangle, [(p-cymene) 4 Os 4 (dhbq) 2 (4,4¢-bipyridine) 2 ] 4+ , shows an IC 50 value of 5.7 mM (comparable to cisplatin) against A2780 cancer cells and 7.5 mM against the cisplatin resistant A2780cisR cells.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Anticancer activity of osmium metalla-rectangles

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Bioinorganic supramolecular coordination complexes and their biomedical applications

Moreno‐Alcántar

Casini

2022

FEBS Letters

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The field of Bioinorganic Supramolecular Chemistry is an emerging research area including metal‐based supramolecules resulting from coordination‐driven self‐assembly (CDSA), whereby metal ions and organic ligands can be easily linked by metal–ligand bonds via Lewis' acid/base interactions. The focus of this ‘In a Nutshell’ review will be on the family of supramolecular coordination complexes, discrete entities formed by CDSA, which have recently captured widespread attention as a new class of versatile multifunctional materials with broad biological applications including molecular recognition, biosensing, therapy, imaging and drug delivery. Herein, we provide a summary of the state‐of‐the‐art use of these systems in biomedicine, with some selected representative examples, as well as our visions of the challenges and possible directions in the field.

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Interaction of Metal Complexes with G‐Quadruplexes

Jarjayes¹,

Lavergne²,

Thomas³

2020

Encyclopedia of Inorganic and Bioinorganic Chemistry

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There is growing evidence that guanine‐rich sequences are ubiquitous in the human genome. They provide DNA with the ability to fold under a topology known as G‐quadruplex (G4), which is distinct from the classical Watson–Crick double helix and characterized by a great polymorphism and dynamics. G4s are found in the promoter region of important oncogenes and in the telomeric region of chromosomes, where they play significant regulatory roles. The stabilization of G4 structures results in the downregulation of oncogenes such as c‐myc, but also inhibits telomerase, which is overexpressed in 85% of the cancer cells, hence contributing to their immortality. Therefore, G4s are now considered a promising target for designing new anticancer drugs. These important therapeutic perspectives have stimulated the development of G4 binders (organic and inorganic), which have grown exponentially during the past decade. The specific recognition of the G4, which is required for cellular applications, is based on the targeting of specific structural features: The upper guanine tetrad that exposes a large aromatic surface to the solvent, specific shape and folding of the loops and grooves. For this purpose, metal complexes proved to be a powerful platform. By combining the effects of the positively charged metal, which can be involved in electrostatic interactions with electronegative regions, and aromatic rings (chelating or not) designed to interact through π‐stacking, strong G4 binders were obtained. The typical versatility of the ligands and complexes synthesis allows for easy screening and, hence, convenient optimization, while offering the possibility to incorporate reactive or fluorescent fragments. Several families of complexes have emerged in the literature, with distinct metal ions and functionalities, which show tight and specific interactions with G4s, while G4s can be also used as scaffold for catalysis. All these aspects are reviewed and discussed in this article after a brief presentation of the main factors determining the G4 folding and the biological implications.

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A Platinum Supramolecular Square as an Effective G-Quadruplex Binder and Telomerase Inhibitor

Cited by 199 publications

References 26 publications

Anticancer activity of osmium metalla-rectangles

Anticancer activity of osmium metalla-rectangles

Bioinorganic supramolecular coordination complexes and their biomedical applications

Interaction of Metal Complexes with G‐Quadruplexes

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