Syntheses, structures, and anticancer activity of novel organometallic ruthenium–maltol complexes

Reddy, V.D.; Dayal, Divya; Szalda, David J.; Cosenza, Stephen C.; Reddy, M. V. Ramana

doi:10.1016/j.jorganchem.2011.12.011

Cited by 26 publications

(18 citation statements)

References 57 publications

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“…Maltol (3‐hydroxy‐2‐methyl‐4‐(1 H )‐pyrone) is a natural product that can be found in roasted malt, larch bark and pine needles and has shown synergistic effects in metal complexes . Several ruthenium‐maltol complexes, such as a triruthenium carbonyl complex containing two maltolato ligands, have shown activity against several types of human cancer cell lines, as reported by Reddy and co‐workers . Flavonoids are also natural products that have been used for thousands of years in Eastern medicine, known for their intrinsic biological activity, possessing antioxidant or antiproliferative properties…”

Section: Introductionmentioning

confidence: 85%

The First Anticancer Tris(pyrazolyl)borate Molybdenum(IV) Complexes: Tested in Vitro and in Vivo—A Comparison of O,O‐, S,O‐, and N,N‐Chelate Effects

Berasaluce

Cseh

Roller

et al. 2019

Chemistry A European J

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The synthesis, characterization and biological activity of molybdenum(IV) complexes containing Trofimenko's scorpionato ligand, hydrotris(3‐isopropylpyrazolyl)borate (TpiPr), in addition to varying biologically active as well as other conventional ligands is described. Ligands employed include (O,O‐) (S,O‐) (N,N‐) donors that have been successfully coordinated to the molybdenum center by means of oxygen‐atom transfer (OAT) reactions from the known MoVI starting material, TpiPrMoO2Cl. The synthesized complexes were characterized by standard analytical methods and where possible by X‐ray diffraction analysis. The aqueous stability of the compounds was studied by means of UV/Vis spectroscopy and the impact of the attached ligand scaffolds on the oxidation potentials (MoIV to MoV) was studied by cyclic voltammetry. Utilizing polyvinylpyrrolidone (PVP) as a solubilizing agent, adequate aqueous solubility for biological tests was obtained. Anticancer activity tests and preliminary mode of action studies have been performed in vitro and in vivo.

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Section: Introductionmentioning

confidence: 85%

The First Anticancer Tris(pyrazolyl)borate Molybdenum(IV) Complexes: Tested in Vitro and in Vivo—A Comparison of O,O‐, S,O‐, and N,N‐Chelate Effects

Berasaluce

Cseh

Roller

et al. 2019

Chemistry A European J

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“…To investigate cellular uptake and the cytotoxicity of Ru-BPPBIhx-SQ, two well-known human cancer cell lines were used, HT-29 colorectal and MCF-7 breast lines, frequently employed to screen drug compounds and, in particular used to test several Ru complexes (Oehninger et al, 2011;Reddy et al, 2012;Schatzschneider et al, 2008). (Neugebauer et al, 2008) (Puckett and Barton, 2007) (phen = 1,l0-phenanthroline; dppz = dipyrido[3,2-a:2 ,3 -c]phenazine).…”

Section: In Vitro Activity: Cellular Uptakementioning

confidence: 99%

Ruthenium polypyridyl squalene derivative: A novel self-assembling lipophilic probe for cellular imaging

Dosio¹,

Stella²,

Ferrero³

et al. 2013

International Journal of Pharmaceutics

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Transition metal complexes provide a promising avenue for designing new therapeutic and diagnostic agents. In particular, ruthenium(II) polypyridyl complexes are useful for studying cellular uptake, due to their easy synthesis and unique photophysical properties. Dyes are frequently combined with material substrates to modulate their properties, enhance stability, reduce toxicity, and improve delivery. A novel Ru polypyridyl complex linked to a derivative of the natural lipid squalene (Ru-BIPPBI-hx-SQ) is described. Using the solvent displacement method, Ru-BIPPBI-hx-SQ easily self-assembles into nanosized aggregates in aqueous solution, as characterized by dynamic light scattering. The nanoassemblies exhibit long-lived and intense luminescence.Preliminary biological assessment showed them to be non-toxic; they are efficiently and rapidly transported across the cell membrane without requiring its permeabilization. Ru-labeled nanoassemblies are likely to be significant cellular-imaging tools, probing cellular events at very low concentrations. Moreover co-nanoassembly, with drug-derivatives based on squalenoylation technology, including gemcitabine and paclitaxel, has given interesting preliminary results.

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“…[8][9][10][11][12] Maltolate complexes appear attractive to catalyze olefin polymerization reaction as well. In 2001, Sobota et al 13 synthesized and characterized titanium complexes of methylmaltol and verified their catalytic activity in ethylene and propylene polymerization.…”

Section: Introductionmentioning

confidence: 99%

“…7 Bis(maltolate) metal(IV) complexes are extensively used in medical studies to assess their therapeutic value as active agents against diabetes, as agents for controlling metal levels in the body and as contrast agents in imaging applications. [8][9][10][11][12] Maltolate complexes appear attractive to catalyze olefin polymerization reaction as well. In 2001, Sobota et al 13 synthesized and characterized titanium complexes of methylmaltol and verified their catalytic activity in ethylene and propylene polymerization.…”

Section: Introductionmentioning

confidence: 99%

A New Post-Metallocene-Ti Catalyst with Maltolate Bidentade Ligand: an Investigation in Heterogeneous Polymerization Reactions in Different Mesoporous Supports

Gheno¹,

Basso²,

Livotto³

et al. 2016

Journal of the Brazilian Chemical Society

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A new titanium catalyst easily synthesized from ethylmaltol bidentate chelator ligand was studied in homogeneous and heterogeneous ethylene polymerization. The dichlorobis(3-hydroxy-2-ethyl-4-pyrone)titanium(IV) complex was characterized by 1 H and 13 C NMR (nuclear magnetic resonance), UV-Vis and elemental analysis. Theoretical study by density functional theory (DFT) showed that the complex chlorines exhibit cis configuration, which is important for the activity in olefin polymerization. The complex was supported by two methods, direct impregnation or methylaluminoxane (MAO) pre-treatment, in five mesoporous supports: MCM-41 (micro and nano), SBA-15 and also the corresponding modified Al species. All the catalytic systems were active in ethylene polymerization and the catalytic activity was strongly influenced by the method of immobilization of the catalyst and the type of support. Keywords: catalysis, synthesis, mesoporous support, immobilization, polyethylene IntroductionPolyethylene (PE) has a broad application in different segments of the everyday life, from food packaging to resistant pieces for engineering. Due to the polymer industrial demands, continuous development of new technologies and synthetic methods for obtaining this material are necessary. Existing processes, involving polyethylene synthesis in industrial and/or research scale, use Ziegler-Natta, metallocene, and more recently, postmetallocene catalysts. Our research group has studied the synthesis of different post-metallocene catalysts and tested these complexes in ethylene polymerization. Organometallic complexes of Ti and Zr were obtained from bidentate chelator ligands as naphthoquinone, methylpyrone, ethylpyrone and 3-hydroxyflavone. [1][2][3][4][5] All the synthesized complexes were active in homogeneous ethylene polymerization at different reaction conditions. 3-Hydroxy-2-methyl-4-pyrone (methylpyrone or maltol) is a non-toxic compound of natural occurrence in many plants, 6 while 3-hydroxy-2-ethyl-4-pyrone (ethylmaltol) is a synthetic commercial product. These organic compounds are commonly used in food industries as flavor ingredients. Both hydroxypyrones are characterized by their synthetic versatility and they easily coordinate with transition metals of group IV to give L 2 MCl 2 complexes.7 Bis(maltolate) metal(IV) complexes are extensively used in medical studies to assess their therapeutic value as active agents against diabetes, as agents for controlling metal levels in the body and as contrast agents in imaging applications. [8][9][10][11][12] Maltolate complexes appear attractive to catalyze olefin polymerization reaction as well. In 2001, Sobota et al. 13 synthesized and characterized titanium complexes of methylmaltol and verified their catalytic activity in ethylene and propylene polymerization. Subsequently, our research group has synthesized several Ti and Zr complexes Gheno et al. 2083 Vol. 27, No. 11, 2016 analogous based in maltolate ligands. The synthesized complexes were shown to be active in the ethylene...

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Syntheses, structures, and anticancer activity of novel organometallic ruthenium–maltol complexes

Cited by 26 publications

References 57 publications

The First Anticancer Tris(pyrazolyl)borate Molybdenum(IV) Complexes: Tested in Vitro and in Vivo—A Comparison of O,O‐, S,O‐, and N,N‐Chelate Effects

The First Anticancer Tris(pyrazolyl)borate Molybdenum(IV) Complexes: Tested in Vitro and in Vivo—A Comparison of O,O‐, S,O‐, and N,N‐Chelate Effects

Ruthenium polypyridyl squalene derivative: A novel self-assembling lipophilic probe for cellular imaging

A New Post-Metallocene-Ti Catalyst with Maltolate Bidentade Ligand: an Investigation in Heterogeneous Polymerization Reactions in Different Mesoporous Supports

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