Synthesis, characterization, X-ray structure and preliminary in vitro antitumor activity of the nitrosyl complex fac-[RuCl3(NO)(dppf)], dppf=1,1′-bis(diphenylphosphine)ferrocene

Poelhsitz, Gustavo Von; Bogado, André L.; Araujo, Márcio P. de; Selistre-de-Araújo, Heloísa Sobreiro; Ellena, Javier; Castellano, Eduardo E.; Batista, Alzir A.

doi:10.1016/j.poly.2007.03.009

Cited by 51 publications

(34 citation statements)

References 49 publications

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“…Among several transition metals, ruthenium has been highlighted in several publications with a diversity of applications in the biological area [2][3][4][5][6][7]. In this sense, ruthenium-based compounds, including phosphines containing ruthenium complexes, constitute active anticancer [4,[8][9][10][11][12][13], antiprotozoals [14,15], and antiviral [16] agents.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium (II) complexes containing 2-mercaptothiazolinates as ligands and evaluation of their antimicrobial activity

Appelt

Fagundes

Facchin

et al. 2015

Inorganica Chimica Acta

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Section: Introductionmentioning

confidence: 99%

Ruthenium (II) complexes containing 2-mercaptothiazolinates as ligands and evaluation of their antimicrobial activity

Appelt

Fagundes

Facchin

et al. 2015

Inorganica Chimica Acta

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“…39 Although the slow NO release may narrow some biological applications, such as improving the population spike of neurons, 39 it can act as a prodrug for vasodilation with slow blood pressure decrease, as observed in hypertensive male Wistar rats. 19 On replacing cyclam with four amine ligands the resulting ruthenium tetraamine nitrosyl complexes, 3 ), 4-picoline (4-pic), 4-chloropyridine (4-Clpy), imidazole (imC or imN), 4-acetylpyridine (4-acpy) and L-histidine (L-hist)) and k −NO can be tuned by a judicious choice of the trans ligand L. [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] In previous theoretical studies we have addressed this issue. 54,55 Unlike Thus, N-(or C-) functionalization could be a suitable approach to control the reactivity of coordinated NO.…”

Section: Introductionmentioning

confidence: 99%

The nature of Ru–NO bonds in ruthenium tetraazamacrocycle nitrosyl complexes—a computational study

et al. 2012

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2012The nature of Ru-NO bonds in ruthenium tetraazamacrocycle nitrosyl complexes-a computational study DALTON TRANSACTIONS, CAMBRIDGE, v. 41, n. 24, Ruthenium complexes including nitrosyl or nitrite complexes are particularly interesting because they can not only scavenge but also release nitric oxide in a controlled manner, regulating the NO-level in vivo.The judicious choice of ligands attached to the [RuNO] core has been shown to be a suitable strategy to modulate NO reactivity in these complexes. In order to understand the influence of different equatorial ligands on the electronic structure of the Ru-NO chemical bonding, and thus on the reactivity of the coordinated NO, we propose an investigation of the nature of the Ru-NO chemical bond by means of energy decomposition analysis (EDA), considering tetraamine and tetraazamacrocycles as equatorial ligands, prior to and after the reduction of the {RuNO} 6 moiety by one electron. This investigation provides a deep insight into the Ru-NO bonding situation, which is fundamental in designing new ruthenium nitrosyl complexes with potential biological applications.

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“…27 One of the earliest works of biological activity with biphosphine ligand coordinated to ruthenium complexes was performed with fac-[RuCl 3 (NO)(dppf)] (dppf =1,1′-bis-(diphenylphosphino)ferrocene), which yielded a highly potent compound with IC 50 = 10 ± 3 μmol L −1 in MDA-MB-231 cell line, a value that is lower than those observed for the RuCl 3 NO· 2H 2 O precursor, free dppf ligand and cisplatin. 20 The cytotoxic activity of mer-[RuCl 3 (dppb)H 2 O] (dppb =1,4 bis-(diphenylphospine)butane) against MCF-7, TK-10, and UACC-62 human tumors was of the same order of magnitude as that of the clinical drugs etoposide and colchicines. 21 Therefore, coordination to biphosphine ligands to ruthenium complexes with oxidation state +2 or +3 improved the cytotoxic activity.…”

Section: Introductionmentioning

confidence: 95%

Correlation of [RuCl₃(dppb)(VPy)] Cytotoxicity with its Effects on the Cell Membranes: An Investigation Using Langmuir Monolayers as Membrane Models

et al. 2014

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One of the major challenges in drug design is to identify compounds with potential toxicity toward target cells, preferably with molecular-level understanding of their mode of action. In this study, the antitumor property of a ruthenium complex, mer-[RuCl 3 (dppb)(VPy)] (dppb =1,4-bis(diphenylphosphine)butane and VPy = 4-vinylpyridine) (RuVPy), was analyzed. Results showed that this compound led to a mortality rate of 50% of HEp-2 cell with 120 ± 10 μmol L −1 , indicating its high toxicity. Then, to prove if its mode of action is associated with its interaction with cell membranes, Langmuir monolayers were used as a membrane model. RuVPy had a strong effect on the surface pressure isotherms, especially on the elastic properties of both the zwitterionic dipalmitoylphosphatidylcholine (DPPC) and the negatively charged dipalmitoylphosphatidylglycerol (DPPG) phospholipids. These data were confirmed by polarization-modulated infrared reflection−absorption spectroscopy (PM-IRRAS). In addition, interactions between the positive group from RuVPy and the phosphate group from the phospholipids were corroborated by density functional theory (DFT) calculations, allowing the determination of the Ru complex orientation at the air−water interface. Although possible contributions from receptors or other cell components cannot be discarded, the results reported here represent evidence for significant effects on the cell membranes which are probably associated with the high toxicity of RuVPy.

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Synthesis, characterization, X-ray structure and preliminary in vitro antitumor activity of the nitrosyl complex fac-[RuCl3(NO)(dppf)], dppf=1,1′-bis(diphenylphosphine)ferrocene

Cited by 51 publications

References 49 publications

Ruthenium (II) complexes containing 2-mercaptothiazolinates as ligands and evaluation of their antimicrobial activity

Ruthenium (II) complexes containing 2-mercaptothiazolinates as ligands and evaluation of their antimicrobial activity

The nature of Ru–NO bonds in ruthenium tetraazamacrocycle nitrosyl complexes—a computational study

Correlation of [RuCl₃(dppb)(VPy)] Cytotoxicity with its Effects on the Cell Membranes: An Investigation Using Langmuir Monolayers as Membrane Models

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Synthesis, characterization, X-ray structure and preliminary in vitro antitumor activity of the nitrosyl complex fac-[RuCl3(NO)(dppf)], dppf=1,1′-bis(diphenylphosphine)ferrocene

Cited by 51 publications

References 49 publications

Ruthenium (II) complexes containing 2-mercaptothiazolinates as ligands and evaluation of their antimicrobial activity

Ruthenium (II) complexes containing 2-mercaptothiazolinates as ligands and evaluation of their antimicrobial activity

The nature of Ru–NO bonds in ruthenium tetraazamacrocycle nitrosyl complexes—a computational study

Correlation of [RuCl3(dppb)(VPy)] Cytotoxicity with its Effects on the Cell Membranes: An Investigation Using Langmuir Monolayers as Membrane Models

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Correlation of [RuCl₃(dppb)(VPy)] Cytotoxicity with its Effects on the Cell Membranes: An Investigation Using Langmuir Monolayers as Membrane Models