Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(η6-toluene) complexes of picolinate derivatives.

Abstract:

:Five Ru(II)(η6-toluene) complexes formed with 2-picolinic acid and its various derivatives have been synthesized and characterized. X-ray structures of four complexes are also reported. Complex formation processes of [Ru(II)(η6-toluene)(H2O)3]2+ organometallic cation with the metal-free ligands were studied in aqueous solution in the presence of chloride ions by the combined use of 1H NMR spectroscopy, UV-visible spectrophotometry and pH-potentiometry. Solution stability, chloride ion affinity and lipophilicity of the complexes were characterized together with in vitro cytotoxic and antiproliferative activity in cancer cell lines being sensitive and resistant to classic chemotherapy and in normal cells as well. Formation of mono complexes such as [Ru(η6-toluene)(L)(Z)]+/0 (L: completely deprotonated ligand; Z = H2O/Cl-) with high stability and [Ru(η6-toluene)(L)(OH)] was found in solution. The pKa values (8.3-8.7) reflect the formation of low amount of mixed hydroxido species at pH 7.4 at 0.2 M KCl ionic strength. The complexes are fairly hydrophilic and show moderate chloride ion affinity and fast chloride-water exchange processes. The studied complexes exhibit no cytotoxic activity in human cancer cells (IC50 > 100 μM), only complexes formed with 2-picolinic acid (1) and its 3-methyl derivative (2) represented a moderate antiproliferative effect (IC50 = 84.8 (1), 79.2 μM (2)) on a multidrug resistant colon adenocarcinoma cell line revealing considerable multidrug resistant selectivity. Complexes 1 and 2 bind to human serum albumin covalently and relatively slowly with moderate strength at multiple binding sites without ligand cleavage.

journal_name

J Inorg Biochem

authors

Poljarević JM,Tamás Gál G,May NV,Spengler G,Dömötör O,Savić AR,Grgurić-Šipka S,Enyedy ÉA

doi

10.1016/j.jinorgbio.2017.12.017

subject

Has Abstract

pub_date

2018-04-01 00:00:00

pages

74-85

eissn

0162-0134

issn

1873-3344

pii

S0162-0134(17)30671-2

journal_volume

181

pub_type

杂志文章
  • Non-innocent bma ligand in a dissymetrically disubstituted diiron dithiolate related to the active site of the [FeFe] hydrogenases.

    abstract::The purpose of the present study was to evaluate the use of a non-innocent ligand as a surrogate of the anchored [4Fe4S] cubane in a synthetic mimic of the [FeFe] hydrogenase active site. Reaction of 2,3-bis(diphenylphosphino) maleic anhydride (bma) with [Fe(2)(CO)(6)(mu-pdt)] (propanedithiolate, pdt=S(CH(2))(3)S) in ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2010.05.011

    authors: Si Y,Charreteur K,Capon JF,Gloaguen F,Pétillon FY,Schollhammer P,Talarmin J

    更新日期:2010-10-01 00:00:00

  • Cu(II)-selective bispidine-dye conjugates.

    abstract::The substitution of tetradentate bispidine ligands with rhodamine and cyanine dye molecules, coupled to an amine donor, forming an amide as potential fifth donor, is described. Bispidines are known to lead to very stable Cu(II) complexes, and the coordination to Cu(II) was expected to efficiently quench the fluorescen...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2015.05.009

    authors: Brox D,Comba P,Herten DP,Kimmle E,Morgen M,Rühl CL,Rybina A,Stephan H,Storch G,Wadepohl H

    更新日期:2015-07-01 00:00:00

  • A family of insulinomimetic zinc(II) complexes of amino ligands with Zn(Nn) (n=3 and 4) coordination modes.

    abstract::Several metal ions and their complexes have been known to mimic the action of insulin in in vitro and in vivo systems. We prepared a family of Zn(II) complexes derived from amino ligands with Zn(Nn) (n=3 and 4) coordination modes, the insulinomimetic activity being estimated by an inhibitory effect of free fatty acid ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2005.04.011

    authors: Yoshikawa Y,Kondo M,Sakurai H,Kojima Y

    更新日期:2005-07-01 00:00:00

  • Cyclic tetranuclear half-sandwich ruthenium(II) complexes with 4,7-phenanthroline and hydroxo bridges: crystal structure, solution behaviour and binding to nucleosides.

    abstract::The reaction between [(eta(6)-p-cymene)Ru(H2O)3]X2 and 4,7-phenanthroline (phen) leads to the formation of the rectangular tetranuclear complexes [(eta(6)-p-cymene)4Ru4(mu-4,7-phen-N4,N7)(2)(mu-OH)4]X4 (X=NO3, 1a; SO3CF3, 1b) which have been structurally characterised by X-ray crystallography. 1H NMR spectroscopic stu...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2007.11.009

    authors: Galindo MA,Quirós M,Romero MA,Navarro JA

    更新日期:2008-05-01 00:00:00

  • Involvement of organic molybdenum compounds in the interaction between copper, molybdenum, and sulfur.

    abstract::The effect on Cu metabolism of two organic Mo compounds, cysteine-Mo (CM) and cysteine-Mo-S (CMS), and of an inorganic compound, tetrathiomolybdate (TTM), was investigated in sheep. Intravenous administration of CMS or TTM increased total plasma Cu concentrations and promoted the appearance of trichloroacetic acid (TC...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(86)80011-3

    authors: Allen JD,Gawthorne JM

    更新日期:1986-06-01 00:00:00

  • Recent advances in uranyl binding in proteins thanks to biomimetic peptides.

    abstract::Uranium is an element belonging to the actinide series. It is ubiquitous in rock, soil, and water. Uranium is found in the ecosystem due to mining and milling industrial activities and processing to nuclear fuel, but also to the extensive use of phosphate fertilizers. Understanding uranium binding in vivo is critical,...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.jinorgbio.2019.110936

    authors: Garai A,Delangle P

    更新日期:2020-02-01 00:00:00

  • Quercetin as a shuttle for labile iron.

    abstract::The antioxidant activity of flavonoids may involve their ability to complex body iron in non-redox-active forms. In this study, it was found that the catechol flavonoids rutin and quercetin are able to suppress redox-active labile plasma iron (LPI) in both buffered solution and in iron-overloaded sera. Both flavonoids...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2011.11.014

    authors: Baccan MM,Chiarelli-Neto O,Pereira RM,Espósito BP

    更新日期:2012-02-01 00:00:00

  • Trace metal uptake in liver cells. 1. Influence of albumin in the medium on the uptake of copper by hepatoma cells.

    abstract::Cultured rat hepatoma cells (HTC-cells) were used to study the transfer of copper from a well-defined medium to and across the cell membrane and particularly the role of albumin in this process. HTC-cells, maintained in a minimal salt-glucose medium, accumulated far more copper than when maintained in the same medium,...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(84)80016-1

    authors: van den Berg GJ,van den Hamer CJ

    更新日期:1984-10-01 00:00:00

  • Inhibition of protein tyrosine phosphatase 1B and alkaline phosphatase by bis(maltolato)oxovanadium (IV).

    abstract::Vanadate has been recognized as a specific and potent phosphatase inhibitor since its structure is similar to that of phosphate. In this study, we measured the inhibition of glutathione S-transferase-tagged protein tyrosine phosphatase 1B (GST-PTP1B) and alkaline phosphatase (ALP) by the insulin enhancing compounds, b...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2008.06.007

    authors: Li M,Ding W,Baruah B,Crans DC,Wang R

    更新日期:2008-10-01 00:00:00

  • Crystal packing and hydrogen bonding in platinum(II) nucleotide complexes: X-ray crystal structure of [Pt(MeSCH(2)CH(2)SMe)(5'-GMP-N7)(2)].6H(2)O.

    abstract::We have synthesised the complex [Pt(CH(3)SCH(2)CH(2)SCH(3))(5'-GMP-N7)(2)].6H(2)O (1), where 5'-GMP is 5'-guanosine monophosphate, and determined its X-ray crystal structure. Pt(II) adopts a square-planar geometry in which the bases are coordinated head-to-tail (HT) in the Delta configuration. The nucleotide conformat...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(01)00351-8

    authors: Djuran MI,Milinkovic SU,Habtemariam A,Parsons S,Sadler PJ

    更新日期:2002-02-01 00:00:00

  • Antiproliferative activity of Pt(IV)-bis(carboxylato) conjugates on malignant pleural mesothelioma cells.

    abstract::The bifunctional Pt(IV) conjugate cis,cis,trans-diamminedichloridobis(valproato)platinum(IV), based on the cisplatin square-plane with two axial valproato (2-propylpentanoate, VPA) ligands, has been re-synthesized with a modified procedure and its biological activity was compared with that of its isomer cis,cis,trans-...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2013.09.003

    authors: Alessio M,Zanellato I,Bonarrigo I,Gabano E,Ravera M,Osella D

    更新日期:2013-12-01 00:00:00

  • The copper-enzyme dopamine beta-monooxygenase: studies on the ability of several metals to inhibit the enzyme activity and to replace the copper.

    abstract::The ability of several metals to inhibit dopamine beta-monooxygenase was measured and compared with their ability to compete with the binding of 64Cu to the water-soluble form of the bovine adrenal enzyme at pH 6.0. In the presence of an optimal concentration of copper (0.5 microM in the present assay system), an inhi...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(84)80006-9

    authors: Skotland T,Flatmark T

    更新日期:1984-01-01 00:00:00

  • Haem-peptide-protein interactions: Part 5. The haem undecapeptide microperoxidase-11 (Fe3+MP-11)/human serum albumin (HSA) reaction in aqueous methanolic solution. A simple system demonstrating the effect of hydrophobicity on ligand release from a ligand-

    abstract::Previous studies of the interaction of the haem undecapeptide (MP-11) with lipidated human serum albumin in aqueous solution have been extended to a range of MeOH/H2O solution compositions. It is demonstrated that the kinetic mechanism for the interaction does not change from a simple second- and first-order reversibl...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(93)80009-x

    authors: Adams PA,Thumser AE

    更新日期:1993-04-01 00:00:00

  • Synthesis, characterization and DNA binding studies of a ruthenium(II) complex.

    abstract::[Ru(bzimpy)(2)]Cl(2), where bzimpy is 2,6-bis(benzimidazol-2-yl) pyridine was synthesized and characterized by ESI-MS, UV-Visible, (1)H NMR and fluorescence spectra. Absorption titration and thermal denaturation experiments indicate that the complex binds to DNA with moderate strength. Viscosity measurement shows that...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(02)00448-8

    authors: Vaidyanathan VG,Nair BU

    更新日期:2002-08-15 00:00:00

  • Design, synthesis, and evaluation of phosphorescent Ir(III) complexes with anticancer activity.

    abstract::A range of phosphorescent Ir(III) complexes containing four diverse P^P-chelating ligands of the type [Ir(ppy)2(L)][PF6], (ppy = 2‑phenylpyridine) where L is 1,2‑bis(diphenylphosphino)benzene (L1), 1,2‑bis(diphenylphosphino)ethane (L2), 1,2‑bis(diphenylphosphino)propane(L3) and 1,8‑bis(diphenylphosphino)naphthalene (L...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110703

    authors: Liu Z,Li J,Ge X,Zhang S,Xu Z,Gao W

    更新日期:2019-08-01 00:00:00

  • Comparative solution equilibrium studies of anticancer gallium(III) complexes of 8-hydroxyquinoline and hydroxy(thio)pyrone ligands.

    abstract::The stoichiometry and stability constants of the Ga(III) complexes of 8-hydroxyquinoline (HQ), 8-hydroxyquinoline-5-sulfonate (HQS), maltol, thiomaltol, allomaltol and thioallomaltol were determined by means of pH-potentiometry, UV-vis spectrophotometry, spectrofluorometry and (1)H NMR spectroscopy in aqueous solution...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2012.08.005

    authors: Enyedy ÉA,Dömötör O,Varga E,Kiss T,Trondl R,Hartinger CG,Keppler BK

    更新日期:2012-12-01 00:00:00

  • N-acetylaspartate complexes with calcium and lanthanide ions.

    abstract::N-acetylaspartate (NAA) is the one of the most prominent resonances observed in the solvent-suppressed NMR spectrum of the human brain. Although it is present in the brain at about 10 mM, its precise metabolic function is still unclear, We have examined the NAA as a potential chelator for divalent metal ions such as C...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(94)00132-t

    authors: Rubin Y,Connelly GP,Lenkinski RE

    更新日期:1995-10-01 00:00:00

  • The electrochemical profiles of Auranofin and Aubipyc, two representative medicinal gold compounds: A comparative study.

    abstract::A micro-electrochemical reaction cell was coupled to an electrospray mass spectrometer in order to track redox transformations for two representative medicinal gold compounds - i.e. [(2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosato-S)(triethylphosphine)gold(I)] and [Au(bipydmb-H)(OH)][PF6] (where bipydmb-H is deprot...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110714

    authors: Kupiec M,Ziółkowski R,Massai L,Messori L,Pawlak K

    更新日期:2019-09-01 00:00:00

  • Factors that influence siderophoremediated iron bioavailability: catalysis of interligand iron (III) transfer from ferrioxamine B to EDTA by hydroxamic acids.

    abstract::Deferriferrioxamine B (H3DFB) is a linear trihydroxamic acid siderophore with molecular formula NH2(CH2)5[N(OH)C(O)(CH2)2C(O)NH(CH2)5]2N(OH)C(O)CH3 that forms a kinetically and thermodynamically stable complex with iron(III), ferrioxamine B. Under the conditions of our study (pH = 4.30, 25 degrees C), ferrioxamine B, ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(83)85010-7

    authors: Monzyk B,Crumbliss AL

    更新日期:1983-08-01 00:00:00

  • BioMOF@cellulose fabric composites for bioactive molecule delivery.

    abstract::This work describes in situ synthesis and application of the zinc glutamate Bio Metal-Organic Framework (BioMOF) supported on cellulose fabrics as a dual material for nitric oxide (NO) and 5-fluorouracil (5FU) controlled delivery for wound and/or skin cancer therapy. In situ synthesis of BioMOF on the cotton fabric wa...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110818

    authors: Noorian SA,Hemmatinejad N,Navarro JAR

    更新日期:2019-12-01 00:00:00

  • Stability constants of copper(II) mixed complexes with some 4-quinolone antibiotics and (N-N) donors.

    abstract::Studies of complexation equilibria of the antibiotic anions nalidixate and cinoxacinate with [Cu(phen)]2+ and [Cu(bipy)]2+ are reported. These studies indicate that the stability of this type of complex is strongly related to the metal environment. A correlation between the stability constants, determined here, with t...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(96)00041-4

    authors: Mendoza-Díaz G,Perez-Alonso R,Moreno-Esparza R

    更新日期:1996-11-15 00:00:00

  • Tetra-chloro-(bis-(3,5-dimethylpyrazolyl)methane)gold(III) chloride: An HIV-1 reverse transcriptase and protease inhibitor.

    abstract::The title compound ([3,5-Me(2)bpzaH(2)][AuCl(4)]Cl, 1) (Me(2)bpza=bis(3,5-dimethylpyrazolyl)acetic acid), was prepared by reacting H[AuCl(4)] with 3,5-Me(2)bpza; and spectroscopically and structurally characterized. In the solid state structure of 1, the pyrazolyl ligand is doubly protonated to form two strong charge ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2008.10.001

    authors: Fonteh PN,Keter FK,Meyer D,Guzei IA,Darkwa J

    更新日期:2009-02-01 00:00:00

  • Reduction of DL-selenocystine and isolation of L-seleoncysteine.

    abstract::Cystine, selenocytsine, and several analogs were reduced by dithiothreitol (DTT), beta-mercaptoethanol (ME) and sodium borohydride (NaBH4). DTT was the most effective; DTT to cystine ratios from 10 to 80 were equally effective. With selenocysteine, however, absorption was considerably reduced at all ratios. Selenocyst...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(00)80275-5

    authors: Burnell JN,Karle JA,Shrift A

    更新日期:1980-07-01 00:00:00

  • Copper transporter 1 in human colorectal cancer cell lines: Effects of endogenous and modified expression on oxaliplatin cytotoxicity.

    abstract::Oxaliplatin-based chemotherapy is the mainstay for the treatment of advanced colorectal cancer. Copper transporter proteins have been implicated in the transport of platinum-based anticancer drugs, but their expression in human colorectal cancer cell lines and roles in controlling their sensitivity to oxaliplatin are ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2017.04.022

    authors: Cui H,Zhang AJ,McKeage MJ,Nott LM,Geraghty D,Guven N,Liu JJ

    更新日期:2017-12-01 00:00:00

  • Axially-modified paddlewheel diruthenium(II,III)-ibuprofenato metallodrugs and the influence of the structural modification on U87MG and A172 human glioma cell proliferation, apoptosis, mitosis and migration.

    abstract::The metallodrug chloridotetrakis(ibuprofenato)diruthenium(II,III) ([Ru2(Ibp)4Cl] or RuIbpCl (1), Ibp=carboxylate anion derived from the non-steroidal anti-inflammatory drug ibuprofen) has shown promising results in vitro and in vivo, which point to its potential as an inhibitor of glioma tumour growth in vivo. In orde...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2016.10.003

    authors: Hanif-Ur-Rehman,Freitas TE,Gomes RN,Colquhoun A,de Oliveira Silva D

    更新日期:2016-12-01 00:00:00

  • Cognitive dysfunction associated with aluminum hydroxide-induced macrophagic myofasciitis: A reappraisal of neuropsychological profile.

    abstract::Patients with macrophagic myofasciitis (MMF) present with diffuse arthromyalgias, chronic fatigue, and cognitive disorder. Representative features of MMF-associated cognitive dysfunction include attentional dysfunction, dysexecutive syndrome, visual memory deficit and left ear extinction. Our study aims to reevaluate ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2017.09.019

    authors: Aoun Sebaiti M,Kauv P,Charles-Nelson A,Van Der Gucht A,Blanc-Durand P,Itti E,Gherardi RK,Bachoud-Levi AC,Authier FJ

    更新日期:2018-04-01 00:00:00

  • X-ray absorption studies of the copper-beta domain of rat liver metallothionein.

    abstract::Rat liver metallothionein contains two domains, each of which enfolds a separate metal-thiolate cluster. The binding stoichiometry of these clusters depends on the particular metal ion bound. In the aminoterminal beta domain the cluster can accommodate either three Cd(II) ions or six Cu(I) ions. The Cd ions are known ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(86)80062-9

    authors: George GN,Winge D,Stout CD,Cramer SP

    更新日期:1986-07-01 00:00:00

  • Oxovanadium(IV) complexes of carbohydrates: a brief overview.

    abstract::In this brief review the most recent studies and the most relevant aspects of the complexes generated by interaction of carbohydrates and related molecules with the oxovanadium(IV) cation, VO(2+), are presented and discussed. The survey includes complexes of mono-, di- and polysaccharides, and of other molecules relat...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.jinorgbio.2008.10.008

    authors: Baran EJ

    更新日期:2009-04-01 00:00:00

  • Interaction of iron(II)-heme and artemisinin with a peptide mimic of Plasmodium falciparum HRP-II.

    abstract::The interaction of heme or heme-artemisinin adducts (heme-art) with different peptides mimicking repeat sequences of the Histidine-Rich-Protein-II of Plasmodium falciparum (PfHRP-II) was investigated. The pseudo-first order rate constants of the coordination of heme or heme-art onto a histidine rich peptide, used as a...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2007.04.016

    authors: Accardo A,Laurent SA,Mazarguil H,Meyer M,Robert A,Meunier B

    更新日期:2007-11-01 00:00:00

  • Effect of Zinc (II) on the interactions of bovine serum albumin with flavonols bearing different number of hydroxyl substituent on B-ring.

    abstract::The impact of Zn(2+) ion on interactions of flavonols galangin (Gal), kaempferol (Kae), quercetin (Que) and myricetin (Myr) with bovine serum albumin (BSA) in aqueous solution were studied by fluorescence quenching technique. The results exhibited that Zn(2+) ion affected significantly the interactions and the effect ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2009.10.014

    authors: Cao S,Jiang X,Chen J

    更新日期:2010-02-01 00:00:00