88496-72-4Relevant academic research and scientific papers
Heteroleptic tris-chelate ruthenium(II) complexes of N,N-disubstituted-N′-acylthioureas: Synthesis, structural studies, cytotoxic activity and confocal microscopy studies
Barolli, Jo?o P.,Maia, Pedro I.S.,Colina-Vegas, Legna,Moreira, Jane,Plutin, Ana M.,Mocelo, Raúl,Deflon, Victor M.,Cominetti, Marcia R.,Camargo-Mathias, Maria I.,Batista, Alzir A.
, p. 33 - 41 (2017)
Ruthenium complexes have been assessed as anti-tumor agents against cancer cells. In this project, new heteroleptic ruthenium(II) complexes with general formulae [Ru(L)(bipy)(dppb)](PF6) (where L?=?N,N-disubstituted-N′-acylthiourea, bipy?=?2,2′-bipyridine and dppb?=?1,4-bis(diphenylphosphino)butane) were synthesized and characterized by elemental analysis, IR and NMR (1H and31P{1H}) spectroscopies, molar conductivity measurements and single crystal X-ray diffractometry. The IR and NMR data suggest the coordination of the ligands to the Ru(II) metal center through the thiocarbonyl and carbonyl groups. The structures of the new complexes were further studied by X-ray crystallography, which confirmed the coordination of the ligands with the metal through the sulfur and oxygen atoms, leading to the formation of distorted octahedral complexes. The N,N-disubstituted-N′-acylthioureas and their complexes were screened with respect to their in vitro cytotoxicity. All compounds exhibited considerable antiproliferative activity against MCF-7 (human breast tumor cells ATCC HTB-26), DU-145 (human prostate tumor cells ATCC HTB-26), and relatively low toxicity against fibroblast L929 cells (health cell line from mouse ATCC CCL-1). A preliminary study regarding the mechanism of action of these compounds by confocal microscopy shows alterations of the actin filaments leading to modifications in cytoskeletal supporting the cell death and that the cell nucleus is not main target of these complexes.
Polypyridyl ruthenium complexes: Novel DNA-intercalating agents against human breast tumor
Barolli, Jo?o P.,Corrêa, Rodrigo S.,Miranda, Fabio S.,Ribeiro, Juliana U.,Bloch, Carlos,Ellena, Javier,Moreno, Virtudes,Cominetti, Márcia R.,Batista, Alzir A.
, p. 1879 - 1889 (2017)
This paper describes a new series of four DNA-intercalating agents with promising anticancer activities, based on ruthenium(II) with the planar ligand dpqQX (dpqQX = dipyrido[3,2-a:2',3'-c] quinoxaline[2,3-b]quinoxaline). The complexes identified as trans-[RuCl2(dppb)(dpqQX)], cis-[RuCl2(dppb)(dpqQX)], ct-[RuCl(CO)(dppb)(dpqQX)]PF6and ct-[RuCl2(PPh3)2(dpqQX)] (dppb = 1,4-bis(diphenylphosphine)butane and PPh3 = triphenylphosphine) were characterized by 31P{1H} nuclear magnetic resonance (NMR) and infrared spectroscopies, cyclic voltammetry,molar conductance measurements, elemental analysis, mass spectrometry and X-ray diffraction analysis for complex ct-[RuCl2(PPh3)2(dpqQX)]. Their in vitro cytotoxic activities against MDAMB-213 and MCF-7 breast cancer cells were evaluated and compared with normal L-929 cells. Low drug concentration at which 50percent of the cells are viable relative to the control (IC50) values were obtained for all four complexes compared with a reference metallodrug, cisplatin. In addition, DNA affinity studies from titrations, as well as the images obtained by atomic force microscopy (AFM)involving pBR322 plasmid DNA, suggest interactions between the metal complexes and the DNA macromolecule, in which they act as intercalating agents. The intercalation of the complexes with DNA was confirmed by viscosity measurements.
Ruthenium (II)/allopurinol complex inhibits breast cancer progression via multiple targets
Travassos, Ingrid O.,Mello-Andrade, Francyelli,Caldeira, Raíssa P.,Pires, Wanessa C.,da Silva, Paula F. F.,Correa, Rodrigo S.,Teixeira, Tamara,Martins-Oliveira, Alisson,Batista, Alzir. A.,de Silveira-Lacerda, Elisangela P.
, p. 385 - 401 (2021)
Abstract: Metal complexes based on ruthenium have established excellent activity with less toxicity and great selectivity for tumor cells. This study aims to assess the anticancer potential of ruthenium(II)/allopurinol complexes called [RuCl2(allo)2(PPh3)2] (1) and [RuCl2(allo)2(dppb)] (2), where allo means allopurinol, PPh3 is triphenylphosphine and dppb, 1,4-bis(diphenylphosphino)butane. The complexes were synthesized and characterized by elemental analysis, IR, UV–Vis and NMR spectroscopies, cyclic voltammetry, molar conductance measurements, as well as the X-ray crystallographic analysis of complex 2. The antitumor effects of compounds were determined by cytotoxic activity and cellular and molecular responses to cell death mechanisms. Complex 2 showed good antitumor profile prospects because in addition to its cytotoxicity, it causes cell cycle arrest, induction of DNA damage, morphological and biochemical alterations in the cells. Moreover, complex 2 induces cell death by p53-mediated apoptosis, caspase activation, increased Beclin-1 levels and decreased ROS levels. Therefore, complex 2 can be considered a suitable compound in antitumor treatment due to its cytotoxic mechanism. Graphic abstract: [Figure not available: see fulltext.].
Formic Acid Dehydrogenation by a Cyclometalated κ3-CNN Ruthenium Complex
Beller, Matthias,Junge, Henrik,Léval, Alexander
supporting information, (2020/04/02)
Hydrogen utilization as a sustainable energy vector is of growing interest. We report herein a cyclometalated ruthenium complex [Ru(κ3-CNN)(dppb)Cl], originally described by Baratta, to be active in the selective dehydrogenation (DH) of formic
Ru(II)/clotrimazole/diphenylphosphine/bipyridine complexes: Interaction with DNA, BSA and biological potential against tumor cell lines and Mycobacterium tuberculosis
Colina-Vegas, Legna,Dutra, Jocely Lucena,Villarreal, Wilmer,de A. Neto, Jo?o Honorato,Cominetti, Marcia Regina,Pavan, Fernando,Navarro, Maribel,Batista, Alzir A.
, p. 135 - 145 (2016/11/12)
Three ruthenium complexes [RuCl(CTZ)(bipy)(P-P)]PF6 [P-P?=?1,2-bis(diphenylphosphino)ethane (dppe-1), 1,4-bis(diphenylphosphino)butane (dppb-2) and 1,1′-bis(diphenylphosphino)ferrocene (dppf-3), bipy?=?2,2′-bipiridine and clotrimazole (CTZ) 1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole] were synthesized. These complexes were characterized by a combination of elemental analysis, molar conductivity, infrared and UV–vis spectroscopy, 1H, 13C{1H} and 31P{1H} nuclear magnetic resonance techniques, cyclic voltammetry and mass spectroscopy. Bovine serum albumin binding constants, which were in the range of 1.30–36.00?×?104?M??1, and thermodynamic parameters suggest spontaneous interactions with this protein by electrostatic forces due to the positive charge of the complexes. DNA interactions studied by spectroscopic titration, viscosity measurements, gel electrophoresis, circular dichroism, ethidium bromide displacement and reactions with guanosine and guanosine monophosphate indicated the DNA binding affinity primarily through non-covalent interactions. All complexes 1–3 were tested against the human carcinoma cell lines MCF-7 (breast), A549 (lung) and DU-145 (prostate) presenting promising IC50 values, between 0.50 and 14.00?μM, in some cases lower than the IC50 for the reference drug (cisplatin). The antimicrobial activity assays of the complexes provided evidence that they are potential agents against mycobacterial infections, specifically against Mycobacterium tuberculosis H37Rv.
Net amine dealkylation at a diruthenium center: Dehydrogenation of a secondary amine and hydrolysis of a coordinated imine
Fogg, Deryn E.,James, Brian R.
, p. 2557 - 2561 (2008/10/08)
Reaction of excess benzylamine with Ru2Cl4(dppb)2 (1) or RuCl2(dppb)(PPh3) (2) under Ar or with Ru2Cl5-(dppb)2 (3) under H2 or in air generates RuCl2(dppb)(NH2CH2Ph)2 [dppb = 1,4-bis(diphenylphosphino)butane, Ph2P(CH2)4PPh2]. Use of 1 equiv of amine per [Ru(II)]2 gives dinuclear Ru2Cl4(dppb)2(NH2CH2Ph) (4a) as a mixture of isomers. The corresponding reactions with dibenzylamine yield only dinuclear products: either Ru2-Cl4(dppb)2[NH(CH2Ph) 2] (4b), for reactions under H2, or a mixture of this species and the dealkylation product 4a. The mechanism proposed for formation of the latter involves dehydrogenation of the secondary amine adduct to Ru2Cl4(dppb)2[PhCH2N=C(H)Ph], followed by hydrolysis of the coordinated imine. Direct reaction of PhCH2N=C(H)Ph with 3 under H2 permits isolation of solely 4b. The findings are of interest also in context of thermal degradation of tertiary amines and hydrogenation of imines catalyzed by Ru ditertiary phosphine complexes.
Reexamination of the reactions of Ph2P(CH2)nPPh2 (n = 1-4) with RuCl2(PPh3)3
Jung, Chu W.,Garrou, Philip E.,Huffman, Paul R.,Caulton, Kenneth G.
, p. 726 - 729 (2008/10/08)
A reinvestigation of the reaction of RuCl2(PPh3)3 with the chelating diphosphines Ph2P(CH2)nPPh2, n = 1-4, reveals chemistry very dependent on the length of the methylene chain. Only for n = 4 is the complex RuCl2(PPh3)(chelate) isolatable. 31P NMR studies reveal numerous halo-bridged species in solution for the various ligands. Neither dppe nor dppm forms coordinatively unsaturated RuCl2(PPh3)(chelate), which is explained as a function of the chelate bite angle.
