Novel C,N-chelate platinum(II) antitumor complexes bearing a lipophilic ethisterone pendant.

Abstract:

:The novel steroidal carrier ligand 17-α-[4'-ethynyl-dimethylbenzylamine]-17-β-testosterone (ET-dmba 1) and the steroid--C,N-chelate platinum(II) derivatives [Pt(ET-dmba)Cl(L)] (L = DMSO (2) and PTA (3; PTA =1,3,5-triaza-7-phosphaadamantane)) have been prepared. Values of IC(50) were calculated for the new platinum complexes 2 and 3 against a panel of human tumor cell lines representative of ovarian (A2780 and A2780cisR) and breast cancers (T47D). At 48h incubation time complexes 2 and 3 show very low resistance factors (RF of <2) against an A2780 cell line which has acquired resistant to cisplatin and were more active than cisplatin (about 4-fold for 3) in T47D (AR+, AR=androgen receptor). Compound 1 retains a moderate degree of relative binding affinity (RBA=0.94%) for androgen receptors. The cytotoxicity of the non steroidal platinum analogues [Pt(dmba)Cl(L)] (dmba=dimethylbenzylamine; L=DMSO (4) and PTA (5)) has also been studied for comparison purposes. Theoretical calculations at the BP86/def2-TZVP level of theory on complex 3 have been undertaken.

journal_name

J Inorg Biochem

authors

Ruiz J,Rodríguez V,Cutillas N,Espinosa A,Hannon MJ

doi

10.1016/j.jinorgbio.2010.12.005

subject

Has Abstract

pub_date

2011-04-01 00:00:00

pages

525-31

issue

4

eissn

0162-0134

issn

1873-3344

pii

S0162-0134(10)00286-2

journal_volume

105

pub_type

杂志文章
  • Metal-ion discrimination by phage T7.

    abstract::The discovery of new metal-selective complexing agents may be facilitated by applying an in vitro selection strategy. Such a strategy was recently devised to identify and enrich populations of bacteriophage that rely on Mg(II)-, Zn(II)-, or Au(III)-selective stabilization for survival in the presence of denaturing ure...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(96)85609-1

    authors: Whang T,Daly B,Yin J

    更新日期:1996-07-01 00:00:00

  • Terpyridine-platinum(II) complexes are effective inhibitors of mammalian topoisomerases and human thioredoxin reductase 1.

    abstract::Terpyridine-platinum(II) (TP-Pt(II)) complexes are known to possess DNA-intercalating activity and have been regarded as potential antitumor agents. However, their cytotoxic mechanism remains unclear. To investigate the possible mechanism, a series of TP-Pt(II) compounds were prepared and their biological activities a...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2009.05.006

    authors: Lo YC,Ko TP,Su WC,Su TL,Wang AH

    更新日期:2009-07-01 00:00:00

  • EPR of Cu+2 binding to apo-yeast enolase.

    abstract::We have studied the electron paramagnetic resonance (epr) spectra of complexes of apo-yeast enolase with 65Cu+2 in the presence and absence of substrate and magnesium ion. An unusual epr spectrum with large g parallel, large g and A rhombicity and very narrow line-widths (10 G) is seen for the first two 65Cu+2 bound i...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(00)80255-x

    authors: Dickinson LC,Rose SL,Westhead EW

    更新日期:1980-12-01 00:00:00

  • Polyoxometalates: Study of inhibitory kinetics and mechanism against α-glucosidase.

    abstract::Alpha-glucosidase is considered to be an important target for the treatment of noninsulin-dependent diabetes. In this work, the inhibitory effects of polyoxometalates (POMs) affected by three different factors (heteroatom, transition metal substitution element and vanadium substitution number) on α-glucosidase were st...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110784

    authors: Chi G,Wang L,Chen B,Li J,Hu J,Liu S,Zhao M,Ding X,Li Y

    更新日期:2019-10-01 00:00:00

  • Novel 3-hydroxy-4-pyridinonato oxidovanadium(IV) complexes to investigate structure/activity relationships.

    abstract::A previous evaluation of the insulin-like activity of three 3-hydroxy-4-pyridinonato oxidovanadium(IV) complexes raised questions about structure/activity relationships, namely the influence of the hydrophilic/lipophilic balance of the complex and the capacity of the ligand to stabilize the +4 oxidation state of vanad...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2008.12.019

    authors: Rangel M,Amorim MJ,Nunes A,Leite A,Pereira E,de Castro B,Sousa C,Yoshikawa Y,Sakurai H

    更新日期:2009-04-01 00:00:00

  • Bacterial metal-resistance proteins and their use in biosensors for the detection of bioavailable heavy metals.

    abstract::We have expressed and purified metal-resistance and metal regulatory proteins from the bacterial determinants of resistance to heavy metals and utilised these in the development of biosensors for heavy metals. Both the metallothionein from the cyanobacterium Synechococcus PCC 7942 and the MerR regulatory protein from ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(99)00234-2

    authors: Bontidean I,Lloyd JR,Hobman JL,Wilson JR,Csöregi E,Mattiasson B,Brown NL

    更新日期:2000-04-01 00:00:00

  • Synthesis, characterization and cytotoxic activities of the [RuCl2(NO)(dppp)(L)]PF6 complexes.

    abstract::The synthesis and characterization of ruthenium compounds of the type [RuCl(2)(NO)(dppp)(L)]PF(6) [dppp=1,3-bis(diphenylphosphino)propane; L=pyridine, 4-methylpyridine, 4-phenylpyridine and dimethyl sulfoxide] are described. The complexes were characterized by elemental analysis, UV/Vis and infrared spectroscopy, cycl...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2009.12.015

    authors: Golfeto CC,Von Poelhsitz G,Selistre-de-Araújo HS,de Araujo MP,Ellena J,Castellano EE,Lopes LG,Moreira IS,Batista AA

    更新日期:2010-05-01 00:00:00

  • Structural and biological aspects of copper (II) complexes with 2-methyl-3-amino-(3H)-quinazolin-4-one.

    abstract::A series of new copper (II) complexes with 2-methyl-3-amino(3H)-quinazolin-4-one (MAQ) and various anions (Cl-, Br-, ClO(-)4, NO(-)3, SCN-, and SO(2-)4 was prepared. Their structures and properties were characterized by elemental analysis, IR, UV-Vis and ESR spectroscopy, molar conductivity, and magnetic moment measur...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(96)00122-5

    authors: Ramadan AM

    更新日期:1997-02-15 00:00:00

  • The reaction between ferrous polyaminocarboxylate complexes and hydrogen peroxide: an investigation of the reaction intermediates by stopped flow spectrophotometry.

    abstract::The reactions of Fe(II)EDTA, Fe(II)DTPA, and Fe(II)HEDTA with hydrogen peroxide near neutral pH have been investigated. All these reactions have been assumed to proceed through an active intermediate, I1, (Formula: see text) where pac is one of the three polyaminocarboxylates mentioned above. I1, whether .OH radical o...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(87)80027-2

    authors: Rush JD,Koppenol WH

    更新日期:1987-03-01 00:00:00

  • Antioxidant effect of inorganic ions on UVC and UVB induced lipid peroxidation.

    abstract::Phosphate buffer suspensions of unilamellar liposomes of phosphatidylcholine were irradiated with UVC (254 nm) and UVB (300 nm) light. The irradiation provoked lipid peroxidation and liposome lysis with release of entrapped glucose-6-phosphate. At the same intensity of absorbed light, the photochemical effect at 254 n...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(94)00048-f

    authors: Costanzo LL,De Guidi G,Giuffrida S,Sortino S,Condorelli G

    更新日期:1995-07-01 00:00:00

  • Copper(II) complexes of tridentate pyridylmethylethylenediamines: role of ligand steric hindrance on DNA binding and cleavage.

    abstract::Copper(II) complexes of three linear unsymmetrical tridentate ligands viz. N-methyl-N'-(pyrid-2-ylmethyl)ethylenediamine (L1), N,N-dimethyl-N'-(pyrid-2-ylmethyl)ethylenediamine (L2) and N,N-dimethyl-N'-((6-methyl)pyrid-2-ylmethyl)ethylenediamine (L3) have been isolated and characterized by elemental analysis, electron...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2005.05.014

    authors: Raja A,Rajendiran V,Uma Maheswari P,Balamurugan R,Kilner CA,Halcrow MA,Palaniandavar M

    更新日期:2005-08-01 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

  • Electrochemical generation of a high-valent state of cytochrome P450.

    abstract::Cyclic voltammetry performed at rapid scan rates on cytochrome P450 from Pseudomonas putida (P450CAM) in didodecyldimethylammonium bromide (DDAB) films on graphite electrodes revealed a couple (E) at 830mV (vs Ag/AgCl). E was not significantly observed at scan rates less than 30V/s at room temperature, suggesting that...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2006.01.011

    authors: Udit AK,Hill MG,Gray HB

    更新日期:2006-04-01 00:00:00

  • Intercalation of tetracationic metalloporphyrins and related compounds into DNA.

    abstract::Electron paramagnetic resonance (e.p.r.) studies of thin DNA-chelate films indicate that both the water soluble planar macrocyclic chelates, cobalt (II) tetra (2,3-N-methylpyridinium) porphyrazine (cobalt (II) TMTPPA), and vanadyl (II) 5,10,15,20-tetra-(4-methylpyridinium) porphyrin (Vo (II) TMTPyP) can bind to calf t...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(88)85021-9

    authors: Dougherty G

    更新日期:1988-10-01 00:00:00

  • Copper(II) and nickel(II) ternary complexes of L-dopa and related compounds.

    abstract::The stability constants of the mixed ligand complexes of L-dopa, L-tyrosine, L-phenylalanine, and dopamine with copper(II) and nickel(II) ions and with 2,2'-bipyridyl and 1,10-phenanthroline were determined pH-metrically at 25 degrees C and an ionic strength of 0.2 mol/dm3 (KCl). Spectral studies were made to establis...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(85)80024-6

    authors: Kiss T,Gergely A

    更新日期:1985-12-01 00:00:00

  • Probing the effect of N-alkylation on the molecular recognition abilities of the major groove N7-binding site of purine ligands.

    abstract::The study of the metal binding pattern of N-methyladenines (1-, 3-, 7- or 9-Meade) towards CuII-iminodiacetate-like chelates is addressed on the basis of XRD crystal structures of sixteen novel ternary compounds. Except for three compounds, all others feature an square-based Cu(II) coordination, type 4 + 1, and the ef...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110801

    authors: García-Rubiño ME,Barceló-Oliver M,Castiñeiras A,Domínguez-Martín A

    更新日期:2019-11-01 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

  • Accommodation of CO in the di-heme active site of cytochrome bd terminal oxidase from Escherichia coli.

    abstract::Catalytic mechanisms of reduction of O(2) to 2H(2)O by respiratory terminal oxidases have been extensively investigated. Tri-heme (b(558), b(595), d) cytochrome bd oxidases presumably utilize a dihemic site composed of high-spin hemes d and b(595). We performed a CO photolysis/recombination study of the purified fully...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2012.09.016

    authors: Borisov VB,Verkhovsky MI

    更新日期:2013-01-01 00:00:00

  • Synthesis, characterization, DNA binding, topoisomerase I inhibition and antiproliferation activities of three new functionalized terpyridine platinum(II) complexes.

    abstract::Three new platinum(II) complexes with pendent morpholine were synthesized, namely complex 1 ([Pt(L)Cl]CF3SO3), complex 2 ([Pt(L)(NH3)](CF3SO3)2) and complex 3 ([Pt(L)(PPh3)](CF3SO3)2), where L = 4'-[4-(4-morpholinobutyloxy)phenyl]-2,2':6',2″-terpyridine and PPh3 = triphenylphosphine. The detailed molecular structures ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2018.12.003

    authors: Chai K,Kuang W,Lan Z,Zhang L,Jiang Y,Han T,Niu J,Wang J,Duan X

    更新日期:2019-03-01 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

  • Kinetics of Pseudomonas aeruginosa cytochrome c551 and cytochrome oxidase oxidation by Co(phen)3(3+) and Mn(CyDTA)(H2O)-.

    abstract::The reaction between reduced Pseudomonas cytochrome c551 and cytochrome oxidase with two inorganic metal complexes, Co(phen)3(3+) and Mn(CyDTA)(H2O)-, has been followed by stopped-flow spectrophotometry. The electron transfer to cytochrome c551 by both reactants is a simple process, characterized by the following seco...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(87)80060-0

    authors: Tordi MG,Silvestrini MC,Adzamli K,Brunori M

    更新日期:1987-07-01 00:00:00

  • Synthesis and characterization of novel platinum(IV) complexes with non-functionalized acetylated carbohydrates.

    abstract::[PtMe3(Me2CO)3]BF4 (1) reacts in acetone with 1,2,3,4-tetraacetyl-beta-D-glucopyranose (C2), pentaacetyl-alpha-D-glucopyranose (C3), pentaacetyl-beta-D-mannopyranose (C4) and pentaacetyl-beta-D-galactopyranose (C5) to give trimethyl(carbohydrate)platinum tetrafluoroborate complexes [PtMe3L]BF4 (2-5) (2, L=C2; 3, L=C3;...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(00)00088-x

    authors: Junicke H,Kluge R,Steinborn D

    更新日期:2000-07-15 00:00:00

  • A dinuclear zinc(II) complex of a new unsymmetric ligand with an N(5)O(2) donor set: a structural and functional model for the active site of zinc phosphoesterases.

    abstract::The dinuclear complex [Zn(2)(DPCPMP)(pivalate)](ClO4), where DPCPMP is the new unsymmetrical ligand [2-(N-(3-((bis((pyridin-2-yl)methyl)amino)methyl)-2-hydroxy-5-methylbenzyl)-N-((pyridin-2-yl)methyl)amino)acetic acid], has been synthesized and characterized. The complex is a functional model for zinc phosphoesterases...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2013.08.001

    authors: Das B,Daver H,Pyrkosz-Bulska M,Persch E,Barman SK,Mukherjee R,Gumienna-Kontecka E,Jarenmark M,Himo F,Nordlander E

    更新日期:2014-03-01 00:00:00

  • Platinum(II) and palladium(II) complexes with (N,N') and (C,N,N')- ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities.

    abstract::The study of the reactivity of three 1-(2-dimethylaminoethyl)-1H-pyrazole derivatives of general formula [1-(CH(2))(2)NMe(2)}-3,5-R(2)-pzol] {where pzol represents pyrazole and R=H (1a), Me (1b) or Ph (1c)} with [MCl(2)(DMSO)(2)] (M=Pt or Pd) under different experimental conditions allowed us to isolate and characteri...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2011.09.021

    authors: Quirante J,Ruiz D,Gonzalez A,López C,Cascante M,Cortés R,Messeguer R,Calvis C,Baldomà L,Pascual A,Guérardel Y,Pradines B,Font-Bardía M,Calvet T,Biot C

    更新日期:2011-12-01 00:00:00

  • The use of root growth and modelling data to investigate amelioration of aluminium toxicity by silicon in Picea abies seedlings.

    abstract::Three-week-old Picea abies seedlings were grown for 7 days in 100 microM aluminium (Al), combined with 1000 or 2000 microM silicon (Si). Solution pH was adjusted to 4.00, 4.25, 4.50, 4.75, or 5.00. In the absence of Si, solution pH had no effect on the decrease in root growth caused by 100 microM Al. Silicon did not a...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(03)00181-8

    authors: Ryder M,Gérard F,Evans DE,Hodson MJ

    更新日期:2003-09-15 00:00:00

  • Micropattern immobilization of polysaccharide.

    abstract::Two types of polysaccharides, sulfated hyaluronic acid and heparin, were pattern-immobilized on a poly(ethylene terephthalate) and polystyrene film, respectively, in a specific pattern by photolithography. Sulfated hyaluronic acid was prepared from hylaronic acid by the treatment of sulfur trioxide/pyridine complex. H...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(99)00159-2

    authors: Ito Y

    更新日期:2000-04-01 00:00:00

  • Stimulation of cyclic AMP production in chick renal tissue by cadmium and manganese.

    abstract::The effects of cadmium on production of cyclic AMP by partially purified chick renal plasma membrane preparations and binding of 125I-parathyrin to the membranes have been investigated. At certain concentrations Cd2+ ions (and Mn2+ ions) markedly stimulated the production of cyclic AMP by the tissue. It was found that...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(85)85005-4

    authors: Cook DB,Dewar JH,Ershadi SS

    更新日期:1985-07-01 00:00:00

  • Changes in poly[d(T-G).d(C-A)] chirality due to Hg(II)-binding: circular dichroism (CD) studies.

    abstract::The conformation of poly[d(T-G).d(C-A)] in aqueous solution (0.1 M NaClO4, 5 mM cacodylic acid buffer, pH 6.9) was studied by circular dichroism (CD) spectroscopy in the ultraviolet. The conformation of the polynucleotide, as reflected by its chiroptical signature, changes in a highly cooperative fashion in the presen...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(91)84066-i

    authors: Gruenwedel DW,Cruikshank MK

    更新日期:1991-07-01 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

  • Siderophore-mediated iron acquisition in the staphylococci.

    abstract::Iron is frequently a growth-limiting nutrient due to its propensity to interact with oxygen to form insoluble precipitates and, therefore, biological systems have evolved specialized uptake mechanisms to obtain this essential nutrient. Many pathogenic bacteria are capable of obtaining stringently sequestered iron from...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.jinorgbio.2009.09.011

    authors: Beasley FC,Heinrichs DE

    更新日期:2010-03-01 00:00:00