A family of hydroxypyrone ligands designed and synthesized as iron chelators.

Abstract:

:The use of chelating agents for iron and aluminum in different clinical applications has found increasing attention in the last thirty years. Desferal, deferiprone and deferasirox, chelating agents nowadays in use, are based on hydroxamic groups, hydroxyl-substituted pyridinones or aromatic ring systems. With the aim of designing new chelators, we synthesized a series of kojic acid derivatives composed by two kojic units joined by linkers variously substituted. The huge advantages of these molecules are that they are easy and cheap to produce. Preliminary works on complex formation equilibria of the first group of ligands with iron and aluminium highlighted extremely good pMe values and gave evidence of the ability to scavenge iron from inside cells. On these bases a second set of bis-kojic ligands, whose linkers between the kojic chelating moieties are differentiated both in terms of type and size, has been designed, synthesized and characterized. The structural characterization of these new ligands is presented, and the protonation and iron(III) complex formation equilibria studied by potentiometry, UV-Visible spectrophotometry, electrospray ionization mass (ESI-MS) and (1)H NMR spectroscopy will be described and discussed.

journal_name

J Inorg Biochem

authors

Toso L,Crisponi G,Nurchi VM,Crespo-Alonso M,Lachowicz JI,Santos MA,Marques SM,Niclós-Gutiérrez J,González-Pérez JM,Domínguez-Martín A,Choquesillo-Lazarte D,Szewczuk Z

doi

10.1016/j.jinorgbio.2013.06.009

subject

Has Abstract

pub_date

2013-10-01 00:00:00

pages

220-31

eissn

0162-0134

issn

1873-3344

pii

S0162-0134(13)00150-5

journal_volume

127

pub_type

杂志文章
  • Characterization of the second conserved domain in the heme uptake protein HtaA from Corynebacterium diphtheriae.

    abstract::HtaA is a heme-binding protein that is part of the heme uptake system in Corynebacterium diphtheriae. HtaA contains two conserved regions (CR1 and CR2). It has been previously reported that both domains can bind heme; the CR2 domain binds hemoglobin more strongly than the CR1 domain. In this study, we report the bioph...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2016.11.027

    authors: Uluisik RC,Akbas N,Lukat-Rodgers GS,Adrian SA,Allen CE,Schmitt MP,Rodgers KR,Dixon DW

    更新日期:2017-02-01 00:00:00

  • Synthesis, characterization and DNA binding studies of a zinc complex with 2,6-bis(benzimidazol-2-yl) pyridine.

    abstract::A zinc(II) complex having planar tridentate ligand, bzimpy, where bzimpy is 2,6-bis(benzimidazol-2-yl) pyridine was synthesized and characterized by UV, NMR, infrared spectroscopy and fluorescence spectra. The zinc complex acts as dibasic acids, in which N-H protons on benzimidazole moieties are responsible for a depr...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2004.12.018

    authors: Wang J,Shuai L,Xiao X,Zeng Y,Li Z,Matsumura-Inoue T

    更新日期:2005-03-01 00:00:00

  • Improved syntheses of β-octabromo-meso-triarylcorrole derivatives.

    abstract::In spite of significant applications as starting materials for a variety of metallocorrole derivatives, free-base β-octabromo-meso-triarylcorroles continue to be viewed as inaccessible. The reasons range from the need for tedious column-chromatographic purification to limitations of the reductive demetallation protoco...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2015.07.017

    authors: Capar J,Berg S,Thomas KE,Beavers CM,Gagnon KJ,Ghosh A

    更新日期:2015-12-01 00:00:00

  • Copper chelating anti-inflammatory agents; N1-(2-aminoethyl)-N2-(pyridin-2-ylmethyl)-ethane-1,2-diamine and N-(2-(2-aminoethylamino)ethyl)picolinamide: an in vitro and in vivo study.

    abstract::An in vitro and in vivo study of some copper chelating anti-inflammatory agents for alleviation of inflammation associated with rheumatoid arthritis (RA) has been conducted. Two copper chelating agents, N(1)-(2-aminoethyl)-N(2)-(pyridin-2-ylmethyl)ethane-1,2-diamine ([555-N]) and N-(2-(2-aminoethylamino)ethyl)picolina...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2006.09.006

    authors: Zvimba JN,Jackson GE

    更新日期:2007-01-01 00:00:00

  • Synergistic antibacterial effect of Bi2S3 nanospheres combined with ineffective antibiotic gentamicin against methicillin-resistant Staphylococcus aureus.

    abstract::In this paper, Bi2S3 nanospheres with size of 212nm were prepared by a simple hydrothermal process. The selectively enhanced antibacterial effects of Bi2S3 nanospheres with three classes of ineffective antibiotics, β-lactam (cefuroxime, CXM; cefotaxime, CTX and piperacillin, PIP), quinolone (ciprofloxacin, CIP) and am...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2016.12.005

    authors: Ma L,Wu J,Wang S,Yang H,Liang D,Lu Z

    更新日期:2017-03-01 00:00:00

  • Insights into the recognition and electron transfer steps in nitric oxide reductase from Marinobacter hydrocarbonoclasticus.

    abstract::Marinobacter hydrocarbonoclasticus nitric oxide reductase, cNOR, is an integral membrane protein composed of two subunits with different roles, NorC (electron transfer) and NorB (catalytic) that receives electrons from the soluble cytochrome c552 and reduces nitric oxide to nitrous oxide in the denitrification pathway...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2017.09.001

    authors: Ramos S,Almeida RM,Cordas CM,Moura JJG,Pauleta SR,Moura I

    更新日期:2017-12-01 00:00:00

  • Unprecedented formation of palladium(II)-pyrazole based thiourea from chromone thiosemicarbazone and [PdCl2(PPh3)2]: Interaction with biomolecules and apoptosis through mitochondrial signaling pathway.

    abstract::Two novel pyrazole based thiourea palladium(II) complexes, [PdCl(PPh3)(C9H8NO2S-pz)] (1) and [PdCl(PPh3)(C14H10NO2S-pz)] (2) [pz = pyrazole (C3H2N2)] have been obtained unexpectedly from chromone thiosemicarbazones (L1 and L2) and [PdCl2(PPh3)2]. The compounds have been fully characterized by physicochemical studies. ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110988

    authors: Haribabu J,Balachandran C,Tamizh MM,Arun Y,Bhuvanesh NSP,Aoki S,Karvembu R

    更新日期:2020-04-01 00:00:00

  • Synthesis, crystal structure, characterization of zinc(II), cadmium(II) complexes with 3-thiophene aldehyde thiosemicarbazone (3TTSCH). Biological activities of 3TTSCH and its complexes.

    abstract::The reaction of zinc(II) chloride, cadmium(II) chloride and bromide with 3-thiophene aldehyde thiosemicarbazone leads to the formation of a series of new complexes. They have been characterized by spectroscopic studies: infrared, (1)H NMR, and electronic spectra. The crystal structures of the compound [ZnCl(2)(3TTSCH)...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2009.11.012

    authors: Alomar K,Landreau A,Kempf M,Khan MA,Allain M,Bouet G

    更新日期:2010-04-01 00:00:00

  • Inhibition of Na+/K+- and Ca2+-ATPase activities by phosphotetradecavanadate.

    abstract::Polyoxometalates (POMs) are promising inorganic inhibitors for P-type ATPases. The experimental models used to study the effects of POMs on these ATPases are usually in vitro models using vesicles from several membrane sources. Very recently, some polyoxotungstates, such as the Dawson anion [P2W18O62]6-, were shown to...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110700

    authors: Fraqueza G,Fuentes J,Krivosudský L,Dutta S,Mal SS,Roller A,Giester G,Rompel A,Aureliano M

    更新日期:2019-08-01 00:00:00

  • Antitumor platinum(IV) derivatives of oxaliplatin with axial valproato ligands.

    abstract::We report new anticancer prodrugs, platinum(IV) derivatives of oxaliplatin conjugated with valproic acid (VPA), a well-known drug having histone deacetylase inhibitory activity. Like most platinum(IV) derivatives, the cytotoxicity of the conjugates was lower in cell culture than that of oxaliplatin, but greater than t...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2014.07.004

    authors: Novohradsky V,Zerzankova L,Stepankova J,Vrana O,Raveendran R,Gibson D,Kasparkova J,Brabec V

    更新日期:2014-11-01 00:00:00

  • Heat shock protein 90α increases superoxide generation from neuronal nitric oxide synthases.

    abstract::Neuronal nitric oxide synthase (nNOS) generates superoxide, particularly at sub-optimal l-arginine (l-Arg) substrate concentrations. Heat shock protein 90 (Hsp90) was reported to inhibit superoxide generation from nNOS protein. However, commercially available Hsp90 product from bovine brain tissues with unspecified Hs...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2020.111298

    authors: Zheng H,Weaver JM,Feng C

    更新日期:2021-01-01 00:00:00

  • Kinetics of chromium(V) formation and reduction in fronds of the duckweed Spirodela polyrhiza--a low frequency EPR study.

    abstract::The uptake of chromate by the duckweed Spirodela polyrhiza was investigated with atomic absorption spectroscopy and the reduction of Cr(VI) to Cr(V) was measured using low frequency EPR spectroscopy. The biphasic kinetics of the uptake was fitted to parameters of a proposed kinetic model. Another model was developed t...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(00)00018-0

    authors: Appenroth KJ,Bischoff M,Gabryś H,Stoeckel J,Swartz HM,Walczak T,Winnefeld K

    更新日期:2000-02-01 00:00:00

  • Delaying of insulin signal transduction in skeletal muscle cells by selenium compounds.

    abstract::Supranutritional selenium (Se) intake and high serum Se levels have been associated epidemiologically with increased risk for type 2 diabetes, suggesting adverse effects of dietary Se compounds and/or antioxidant selenoenzymes on the sensitivity of target tissues for insulin. Here, we compared the capability of inorga...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2011.03.010

    authors: Pinto A,Speckmann B,Heisler M,Sies H,Steinbrenner H

    更新日期:2011-06-01 00:00:00

  • Copper(II) and zinc(II) complexes of the peptides Ac-HisValHis-NH2 and Ac-HisValGlyAsp-NH2 related to the active site of the enzyme CuZnSOD.

    abstract::Copper(II) and zinc(II) complexes of the peptides Ac-HisValHis-NH2 and Ac-HisValGlyAsp-NH2 related to the active site of the enzyme CuZnSOD were studied by potentiometric and spectroscopic (UV-Vis, CD and EPR) techniques. The results reveal that both ligands have effective metal binding sites, but the tripeptide is a ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2003.09.012

    authors: Bóka B,Myari A,Sóvágó I,Hadjiliadis N

    更新日期:2004-01-01 00:00:00

  • The two modes of binding of Ru(phen)(2)dppz(2+) to DNA: thermodynamic evidence and kinetic studies.

    abstract::The binding of Ru(phen)(2)dppz(2+) (dppz=dipyrido[3,2-a:2',3'-c]phenazine) to DNA was investigated at pH 7.0 and 25 degrees C using stopped-flow and spectrophotometric methods. Equilibrium measurements show that two modes of binding, whose characteristics depend on the polymer to dye ratio (C(P)/C(D)), are operative. ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2006.11.009

    authors: Biver T,Cavazza C,Secco F,Venturini M

    更新日期:2007-03-01 00:00:00

  • Active site structure of SoxB-type cytochrome bo3 oxidase from thermophilic Bacillus.

    abstract::Two-subunit SoxB-type cytochrome c oxidase in Bacillus stearothermophilus was over-produced, purified, and examined for its active site structures by electron paramagnetic resonance (EPR) and resonance Raman (RR) spectroscopies. This is cytochrome bo3 oxidase containing heme B at the low-spin heme site and heme O at t...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(00)00145-8

    authors: Uchida T,Tsubaki M,Kurokawa T,Hori H,Sakamoto J,Kitagawa T,Sone N

    更新日期:2000-11-01 00:00:00

  • Light-stable bis(norharmane)silver(I) compounds: synthesis, characterization and antiproliferative effects in cancer cells.

    abstract::Four different-anion Ag(I) compounds with the ligand norharmane (9H-Pyrido[3,4-b]indole; Hnor) and having the general formula [Ag(Hnor)2](anion) (anion=ClO4(-), NO3(-) and BF4(-)) [Ag(Hnor)2(MeCN)](PF6) are reported, and studied in detail regarding their coordination mode and in vitro antiproliferative effects. X-ray ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2014.06.019

    authors: Ahmad Khan R,Al-Farhan K,de Almeida A,Alsalme A,Casini A,Ghazzali M,Reedijk J

    更新日期:2014-11-01 00:00:00

  • Proton-linked subunit heterogeneity in ferrous nitrosylated human adult hemoglobin: an EPR study.

    abstract::The effect of pH on the X-band electron paramagnetic resonance (EPR) spectrum of ferrous nitrosylated human adult tetrameric hemoglobin (HbNO) as well as of ferrous nitrosylated monomeric alpha- and beta-chains has been investigated, at -163 degrees C. At pH 7.3, the X-band EPR spectrum of tetrameric HbNO and ferrous ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2005.01.009

    authors: Ascenzi P,Bocedi A,Fasano M,Gioia M,Marini S,Coletta M

    更新日期:2005-05-01 00:00:00

  • New copper(I) and heteronuclear copper(I)-ruthenium(II) complexes: Synthesis, structural characterization and cytotoxicity.

    abstract::A new family of copper(I) complexes of general formula [Cu(dppe)(NN)]+ have been synthesized and fully characterized, with dppe=1.2-bis(diphenylphosphino)ethane and NN representing several bidentate heteroaromatic ligands: 2,2'-bipy=2.2'-bipyridine (1), Me2bpy=4.4'-dimethyl-2,2'-bipyridine (2), dpytz=3-(2-pyridyl)-5,6...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2017.01.007

    authors: Lopes J,Alves D,Morais TS,Costa PJ,Piedade MF,Marques F,Villa de Brito MJ,Helena Garcia M

    更新日期:2017-04-01 00:00:00

  • Comparison of wild type neuronal nitric oxide synthase and its Tyr588Phe mutant towards various L-arginine analogues.

    abstract::Crystal structures of nitric oxide synthases (NOS) isoforms have shown the presence of a strongly conserved heme active-site residue, Tyr588 (numbering for rat neuronal NOS, nNOS). Preliminary biochemical studies have highlighted its importance in the binding and oxidation to NO of natural substrates L-Arg and N(omega...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2010.06.001

    authors: Giroud C,Moreau M,Sagami I,Shimizu T,Frapart Y,Mansuy D,Boucher JL

    更新日期:2010-10-01 00:00:00

  • The enhanced rate of transcription of methyl mercury-exposed DNA by RNA polymerase is not sufficient to explain the stimulatory effect of methyl mercury on RNA synthesis in isolated nuclei.

    abstract::Previous work demonstrated two stimulatory effects of methyl mercury on nucleic acid synthesis: (1) in isolated nuclei, methyl mercury stimulates RNA synthesis which is catalyzed by RNA polymerase II [Frenkel and Randles, J. Biol. Chem. 257, 6275-6279 (1982)]. (2) Brief exposure of purified DNA to methyl mercury incre...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(87)80054-5

    authors: Frenkel GD,Ducote J

    更新日期:1987-10-01 00:00:00

  • Small-volume potentiometric titrations: EPR investigations of Fe-S cluster N2 in mitochondrial complex I.

    abstract::EPR-based potentiometric titrations are a well-established method for determining the reduction potentials of cofactors in large and complex proteins with at least one EPR-active state. However, such titrations require large amounts of protein. Here, we report a new method that requires an order of magnitude less prot...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2016.04.025

    authors: Wright JJ,Salvadori E,Bridges HR,Hirst J,Roessler MM

    更新日期:2016-09-01 00:00:00

  • Iron uptake by ferritin: NMR relaxometry studies at low iron loads.

    abstract::Twenty ferritin samples were prepared at pH 6.5 with average loadings of 0-89 Fe atoms per molecule. Nuclear magnetic relaxation times T1 and T2 were measured at 3 degrees C, 23 degrees C, and at 37 degrees C and at field strength from 0.025 to 1.5 T. The field dependence, temperature dependence, and approximate equal...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(98)10047-8

    authors: Vymazal J,Brooks RA,Bulte JW,Gordon D,Aisen P

    更新日期:1998-09-01 00:00:00

  • Resonance Raman spectroscopy of Compound II and its decay in Mycobacterium tuberculosis catalase-peroxidase KatG and its isoniazid resistant mutant S315T.

    abstract::The reaction of Mycobacterium tuberculosis KatG and the mutant KatG(S315T) with two different organic peroxides is studied using resonance Raman spectroscopy. For the first time, an intermediate is observed in a catalase-peroxidase with vibrations that are characteristic of Compound II. The observation of this interme...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2005.03.016

    authors: Kapetanaki SM,Chouchane S,Yu S,Magliozzo RS,Schelvis JP

    更新日期:2005-06-01 00:00:00

  • Synthesis, properties, and antitumor effects of a new mixed phosphine gold(I) compound in human colon cancer cells.

    abstract::The antineoplastic potential of a new stable mixed phosphine gold(I) complex containing tris(tert-butyl)phosphine (tBu3P) and bis(diphenylphosphino)ethene (dppet), namely [Au(tBu3P)(dppet)Cl], has been investigated in the human colon cancer HCT-116 cell line. The (31)P NMR solution study, confirms the structural featu...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2013.03.014

    authors: Lupidi G,Avenali L,Bramucci M,Quassinti L,Pettinari R,Khalife HK,Gali-Muhtasib H,Marchetti F,Pettinari C

    更新日期:2013-07-01 00:00:00

  • Activation of hydrogen peroxide by copper (II) complexes with some histidine-containing peptides and their SOD-like activities.

    abstract::The reactivities of copper(II) complexes with histidine-containing oligopeptides towards active oxygen species such as hydrogen peroxide (H2O2) and superoxide ion (O2-) were investigated by electron spin resonance (ESR)-spin trapping and thiobarbituric acid (TBA) methods. At physiological pH values, Cu(II) complexes w...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(94)85034-8

    authors: Ueda J,Ozawa T,Miyazaki M,Fujiwara Y

    更新日期:1994-08-01 00:00:00

  • Quantum mechanical investigation of aqueous desferrioxamine B metal complexes: trends in structure, binding, and infrared spectroscopy.

    abstract::A systematic density functional theory study supported by extended X-ray absorption fine structure (EXAFS) and infrared spectroscopic data was conducted to elucidate how structure and vibrational spectra of aqueous desferrioxamine B (DFOB) metal complexes vary with the metal ion identity. Structural parameters derived...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2013.08.008

    authors: Kruft BI,Harrington JM,Duckworth OW,Jarzęcki AA

    更新日期:2013-12-01 00:00:00

  • New dimanganese(III) complexes of pentadentate (N2O3) Schiff base ligands with the [Mn2(mu-OAc)(mu-OR)2]3+ core: synthesis, characterization and mechanistic studies of H2O2 disproportionation.

    abstract::Two new diMn(III) complexes [Mn(2)(III)L(1)(mu-AcO)(mu-MeO)(methanol)(2)]Br (1) and [Mn(2)(III)L(2)(mu-AcO)(mu-MeO)(methanol)(ClO(4))] (2) (L(1)H(3)=1,5-bis(2-hydroxybenzophenylideneamino)pentan-3-ol; L(2)H(3)=1,5-bis(2-hydroxynaphtylideneamino)pentan-3-ol) were synthesized and structurally characterized. Structural s...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2006.05.016

    authors: Biava H,Palopoli C,Shova S,De Gaudio M,Daier V,González-Sierra M,Tuchagues JP,Signorella S

    更新日期:2006-10-01 00:00:00

  • Behavior of the potential antitumor V(IV)O complexes formed by flavonoid ligands. 1. Coordination modes and geometry in solution and at the physiological pH.

    abstract::The coordination modes and geometry assumed in solution by the potent antitumor oxidovanadium(IV) complexes formed by different flavonoids were studied by spectroscopic (Electron Paramagnetic Resonance, EPR) and computational (Density Functional Theory, DFT) methods. A series of bidentate flavonoid ligands (L) with in...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2014.07.007

    authors: Sanna D,Ugone V,Lubinu G,Micera G,Garribba E

    更新日期:2014-11-01 00:00:00

  • Biochemical characterization of phospholipases C from Coffea arabica in response to aluminium stress.

    abstract::Signal transduction in plants determines their successful adaptation to diverse stress factors. Our group employed suspension cells to study the phosphoinositide pathway, which is triggered by aluminium stress. We investigated about members of the PI-specific phospholipase C (PLC) family and evaluated their transcript...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110951

    authors: González-Mendoza VM,Sánchez-Sandoval ME,Munnik T,Hernández-Sotomayor SMT

    更新日期:2020-03-01 00:00:00