Coordination‐Driven Self‐Assembly of Arene–Ruthenium Compounds

Mishra, Anurag; Kang, Se Chan; Chi, Ki‐Whan

doi:10.1002/ejic.201300729

Cited by 88 publications

(30 citation statements)

References 100 publications

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“…174,175 The lipophilicities and water solubilities of the new multinuclear ruthenium complexes with large positive charges are distinct from the mononuclear arene ruthenium complexes. l Multinuclear ruthenium compounds mainly contain dinuclear, trinuclear, tetranuclear, hexanuclear, octanuclear, or supermolecular derivatives.…”

Section: Arene Ruthenium(ii) Complexesmentioning

confidence: 99%

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

et al. 2017

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Cancer is rapidly becoming the top killer in the world. Most of the FDA approved anticancer drugs are organic molecules, while metallodrugs are very scarce. The advent of first metal based therapeutic agent, cisplatin, launched a new era in the application of transition metal complexes for therapeutic design. Due to their unique and versatile biochemical properties, ruthenium-based compounds have emerged as promising anti-cancer agents that serve as alternatives to cisplatin and its derivertives. The ruthenium(III) complexes have successfully been used in clinical research and their mechanisms of anticancer action have been reported in large volumes over the past few decades. Ruthenium(II) complexes have also attracted significant attention as anticancer candidates; however, only few of them have been reported comprehensively. In this review, we discuss the development of ruthenium(II) complexes as anticancer candidates and biocatalysts, including arene ruthenium complexes, polypyridyl ruthenium complexes, and ruthenium nanomaterial complexes. This review focuses on the likely mechanisms of action of ruthenium(II)-based anticancer drugs and the relationship between their chemical structures and biological properties. This review also highlights the catalytic activity and the photoinduced activation of ruthenium(II) complexes, their targeted delivery, and their activity in nanomaterial systems.

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Section: Arene Ruthenium(ii) Complexesmentioning

confidence: 99%

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

et al. 2017

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“…Since the pioneering example reported by Fujita [1], a plethora of ever more sophisticated metalla-rings and -cages constructed by coordination-driven self-assembly have been reported [2][3][4][5][6][7]. This methodology takes advantage of the labile character of the coordination bonds to produce high yields and single step thermodynamically stable architectures, with complex structures that would be challenging to reach through traditional organic chemistry.…”

Section: Introductionmentioning

confidence: 99%

A M2L2 Redox-Active Metalla-Macrocycle Based on Electron-Rich 9-(1,3-Dithiol-2-ylidene)Fluorene

et al. 2018

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A redox-active M 2 L 2 metalla-macrocycle is depicted, of which construction has been achieved through coordination driven self-assembly from an electron-rich 9-(1,3-dithiol-2-ylidene)fluorene bis-pyridyl ligand and a cis-blocked square planar palladium complex (Pd(dppf)OTf 2 , dppf = 1,1 -Bis(diphenylphosphino)ferrocene). The resulting metalla-macrocycle has been fully characterized in solution, as well as in the solid state (X-ray crystal structure). Its electronic properties show that both constitutive ligands can be oxidized independently through a one-electron process.

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“…[1][2][3][4][5][6] Thus, a growing number of Ru(II)-based, self-assembled large two-dimensional and three-dimensional architectures have been developed which have shown promising results in human cancer cell lines as antitumor agents. [7][8][9][10][11][12][13][14] Therrien and others exploited the self-assembly approach to design finite, nano-sized molecular architectures by combining organometallic halfsandwich acceptor clips and pyridyl-based donors. [15][16][17][18] Nanostructures based on halfsandwich arene-ruthenium complexes are promising candidates for cancer treatments, as they possess advantageous features such as low toxicity and a balance of hydrophilicity and hydrophobicity, a key issue for their transport in biological media.…”

Section: Introductionmentioning

confidence: 99%

“…Studies on similar complexes suggest that phenanthrene-derived donors and arene-Ru-based acceptors will work together in a synergistic manner as complementary building blocks; the phenanthrene unit will interact with DNA, whereas the ruthenium center will bind to proteins. 6 Anthracene, 17 naphthelenediimide, 11 carbazole, 8 and many other dipyridyl donors have been used in the self-assembly of various molecular architectures 9 that have shown promising anticancer activities; however, Ru-based architectures generated with phenanthrene derivatives have not been explored.…”

Section: Introductionmentioning

confidence: 99%

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Anticancer activities of self-assembled molecular bowls containing a phenanthrene-based donor and Ru(II) acceptors

Kim¹,

Song

Singh

et al. 2015

IJN

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Nano-sized multinuclear ruthenium complexes have rapidly emerged as promising therapeutic candidates with unique anticancer activities. Here, we describe the coordination-driven self-assembly and anticancer activities of a set of three organometallic tetranuclear Ru(II) molecular bowls. [2+2] Coordination-driven self-assembly of 3, 6-bis(pyridin-3- ylethynyl) phenanthrene (bpep) ( 1 ) and one of the three dinuclear arene ruthenium clips, [(η 6 - p -iPrC 6 H 4 Me) 2 Ru 2 -(OO\OO)][OTf] 2 (OO\OO =2, 5-dioxido-1, 4-benzoquinonato, OTf = triflate) ( 2 ), 5, 8-dioxido-1, 4-naphthoquinonato ( 3 ), or 6, 11-dioxido-5, 12-naphthacenediona ( 4 ), resulted in three molecular bowls 5 – 7 of general formula [{(η 6 - p -iPrC 6 H 4 Me) 2 Ru 2 -(OO\OO)} 2 (bpep) 2 ][OTf] 4 . All molecular bowls were obtained as triflate salts in very good yields (>90%) and were fully characterized using multinuclear nuclear magnetic resonance (NMR), electrospray ionization–mass spectrometry (ESI-MS), and elemental analysis. The structure of the representative molecular bowl 5 was confirmed by single-crystal X-ray diffraction analysis. The anticancer activities of molecular bowls 5 – 7 were determined by 3-[4, 5-dimethylthiazol-2-yl]-2, 5-diphenyltetrazolium bromide, autophagy, and Western blot analysis. Bowl 6 showed the strongest cytotoxicity in AGS human gastric carcinoma cells and was more cytotoxic than doxorubicin. In addition, autophagic activity and the ratio of apoptotic cell death increased in AGS cells by treatment with bowl 6 . Bowl 6 also induced autophagosome formation via upregulation of p62 and promotion of the conversion of LC3-I to LC3-II. Moreover, bowl 6 promoted apoptotic cell death through downregulation of Akt/mTOR activation, followed by increased caspase-3 activity. These results suggest that bowl 6 induces gastric cancer cell death via modulation of autophagy and apoptosis. Bowl 6 is a potent anticancer agent and a potential treatment for human gastric cancer that merits further study.

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Coordination‐Driven Self‐Assembly of Arene–Ruthenium Compounds

Cited by 88 publications

References 100 publications

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

A M2L2 Redox-Active Metalla-Macrocycle Based on Electron-Rich 9-(1,3-Dithiol-2-ylidene)Fluorene

Anticancer activities of self-assembled molecular bowls containing a phenanthrene-based donor and Ru(II) acceptors

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