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
  • The oxidation of rabbit liver metallothionein-II by 5,5'-dithiobis(2-nitrobenzoic acid) and glutathione disulfide.

    abstract::Because metallothionein (MT) may undergo thiol-disulfide or other redox reactions under certain cellular conditions, the partially and completely oxidized products of the reactions of Cd7-MT-II with the electrophile 5,5'-dithiobis(2-nitrobenzoic acid), ESSE, and oxidized glutathione, GSSG, were characterized. Reaction...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(93)80028-8

    authors: Savas MM,Shaw CF 3rd,Petering DH

    更新日期:1993-12-01 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

  • Synthesis and characterization of new chromium(III), vanadium(IV), and titanium(III) complexes with biologically active isonicotinic acid hydrazide.

    abstract::New complexes of the type [Cr(INH)2Cl2]Cl.2H2O, VO(INH)2Cl2 and TiO(INH)2Cl, where INH = isonicotinic acid hydrazide, have been prepared. The complexes were characterized by infrared and UV-vis spectroscopy, proton nuclear magnetic resonance (NMR) and elemental analyses, molar conductivity and x-ray powder diffraction...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(89)80030-3

    authors: Pin Y,Zhang XP

    更新日期:1989-09-01 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

  • Kinetics and mechanism of reactions of the drug tiopronin with platinum(IV) complexes.

    abstract::Tiopronin, a synthetic thiol-containing drug being used in treatments of cystinuria and certain types of rare arthritis, is also a hepatoprotective and a detoxifying agent. Many analytical methods have been developed based on its redox chemistry with metal ions/complexes, but the kinetic and mechanistic aspects are po...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2013.04.003

    authors: Huo S,Shi H,Liu D,Shen S,Zhang J,Song C,Shi T

    更新日期:2013-08-01 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

  • Release of iron from transferrin by phosphonocarboxylate and diphosphonate chelating agents.

    abstract::The rates at which phosphonocarboxylate and diphosphonate ligands remove iron from the serum iron transport protein transferrin at 25 degrees C and pH 7.4 have been evaluated. These ligands show a combination of saturation and first-order kinetics with respect to the free ligand concentrations. The ability of the liga...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2004.08.008

    authors: Harris WR,Brook CE,Spilling CD,Elleppan S,Peng W,Xin M,Wyk JV

    更新日期:2004-11-01 00:00:00

  • DNA-binding and in vitro cytotoxic activity of platinum(II) complexes of curcumin and caffeine.

    abstract::Three Pt(II) complexes containing the natural ligands curcumin and caffeine, namely [Pt(curc)(PPh3)2]Cl (1), [PtCl(curc)(DMSO)] (2) (curc = deprotonated curcumin) and trans-[Pt(caffeine)Cl2(DMSO)] (3), were synthesized and fully characterized. The data obtained suggest that, for both 1 and 2, the anion of curcumin is ...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2019.110749

    authors: Censi V,Caballero AB,Pérez-Hernández M,Soto-Cerrato V,Korrodi-Gregório L,Pérez-Tomás R,Dell'Anna MM,Mastrorilli P,Gamez P

    更新日期:2019-09-01 00:00:00

  • Ligand replacement study at the His120 site of purple CuA azurin.

    abstract::The CuA center is a dinuclear Cu2S2(Cys) electron transfer center found in cytochrome c oxidase and nitrous oxide reductase. In a previous investigation of the equatorial histidine ligands' effect on the reduction potential, electron transfer and spectroscopic properties of the CuA center, His120 in the engineered CuA...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(99)00214-7

    authors: Berry SM,Wang X,Lu Y

    更新日期:2000-01-15 00:00:00

  • Enantioselective DNA condensation induced by heptameric lanthanum helical supramolecular enantiomers.

    abstract::DNA condensation induced by a pair of heptameric La(III) helical enantiomers M-[La7(S-L)6(CO3)(NO3)6(OCH3)(CH3OH)7]·2CH3OH·5H2O and P-[La7(R-L)6(CO3)(NO3)6(OCH3)(CH3OH)5(H2O)2]·2CH3OH·4H2O (M-La and P-La, L=2-(2-hydroxybenzylamino)-3-carbamoylpropanoic acid) has been investigated by UV/vis spectroscopy, fluorescence s...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2014.05.001

    authors: Bao FF,Xu XX,Zhou W,Pang CY,Li Z,Gu ZG

    更新日期:2014-09-01 00:00:00

  • Kinetic studies of the reaction of heme-thiolate enzyme chloroperoxidase with peroxynitrite.

    abstract::The kinetics of the reaction of chloroperoxidase with peroxynitrite was studied under neutral and acidic pH by stopped-flow spectrophotometry. Chloroperoxidase catalyzed peroxynitrite decay with the rate constant, k(c,) increasing with decreasing pH. The values of k(c) obtained at pH 5.1, 6.1 and 7.1 were equal to: (1...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2006.09.007

    authors: Gebicka L,Didik J

    更新日期:2007-01-01 00:00:00

  • Analysis of metal-containing granules in the barnacle Tetraclita squamosa.

    abstract::Metal-containing granules were isolated from specimens of the barnacle Tetraclita squamosa collected from a metal contaminated site in Hong Kong. The chemical composition, crystallographic and morphological properties of the deposits were analysed by X-ray powder diffraction, electron microscopy, energy dispersive ana...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2004.03.004

    authors: Masala O,O'Brien P,Rainbow PS

    更新日期:2004-06-01 00:00:00

  • Relationship between the antiproliferative properties of Cu(II) complexes with the Schiff base derived from pyridine-2-carboxaldehyde and 5,6-diamino-1,3-dimethyluracil and the redox status mediated by antioxidant defense systems on glioma tumoral cells.

    abstract::A set of new copper(II) complexes containing the Schiff base ligand derived from pyridine-2-carboxaldehyde and 5,6-diamino-1,3-dimethyluracil (6-amino-1,3-dimethyl-5-[(pyridin-2-ylmethylidene)-amino]-pyrimidine-2,4(1H,3H)-dione) with several anions (Cl-, Br-, I-, ClO4-, NO3-) and, two of them with 1,10-phenanthroline,...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2020.111053

    authors: Illán-Cabeza NA,Jiménez-Pulido SB,Hueso-Ureña F,Ramírez-Expósito MJ,Martínez-Martos JM,Moreno-Carretero MN

    更新日期:2020-06-01 00:00:00

  • Effective cleavage of phosphodiester promoted by the zinc(II) and copper(II) inclusion complexes of β-cyclodextrin.

    abstract::To construct the model of metallohydrolase, two inclusion complexes [MLCl2(β-CD)] (1, M=Zn(II); 2, M=Cu(II); L=N,N'-bis(2-pyridylmethyl)amantadine; β-CD=β-cyclodextrin) were synthesized by mixing β-CDs with the pre-synthesized complexes G1, [ZnLCl2] and G2, [CuLCl2]. Structures of G1, G2, 1 and 2 were characterized by...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2016.07.011

    authors: Zhou YH,Chen LQ,Tao J,Shen JL,Gong DY,Yun RR,Cheng Y

    更新日期:2016-10-01 00:00:00

  • Substrate recognition sites in 14alpha-sterol demethylase from comparative analysis of amino acid sequences and X-ray structure of Mycobacterium tuberculosis CYP51.

    abstract::The crystal structure of 14alpha-sterol demethylase from Mycobacterium tuberculosis (MTCYP51) [Proc. Natl. Acad. Sci. USA 98 (2001) 3068-3073] provides a template for analysis of eukaryotic orthologs which constitute the CYP51 family of cytochrome P450 proteins. Putative substrate recognition sites (SRSs) were identif...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(01)00388-9

    authors: Podust LM,Stojan J,Poulos TL,Waterman MR

    更新日期:2001-12-15 00:00:00

  • Cu2+ and Ni2+ interactions with N-terminal fragments of Hpn and Hpn-like proteins from Helicobacter pylori: unusual impact of poly-Gln sequence on the complex stability.

    abstract::The N-terminal protected and unprotected peptides MAHHEEQHG-NH(2), Ac-MAHHEEQHG-NH(2) from Hpn (Helicobacter histidine-rich protein) and MAHHEQQQQQQA-NH(2), Ac-MAHHEQQQQQQA-NH(2) from Hpn-like protein, respectively, were synthesized and their interactions with Cu(2+) and Ni(2+) ions were studied by potentiometric, UV-...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2010.11.004

    authors: Witkowska D,Bielinska S,Kamysz W,Kozlowski H

    更新日期:2011-02-01 00:00:00

  • Biological evaluation of water soluble arene Ru(II) enantiomers with amino-oxime ligands.

    abstract::New water soluble, enantiopure arene ruthenium compound SRuSN-(1R,4S)-[(η6-p-cymene)Ru{ĸNH(Bn),ĸNOH}Cl]Cl (Bn = benzyl, 1a') has been synthesized. The novel compound along with that previously described RRuRN-(1S,4R)-[(η6-p-cymene)Ru{ĸNH(Bn),ĸNOH}Cl]Cl (1a) was evaluated by polarimetry, ultra-violet and circular dichr...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2018.02.018

    authors: de la Cueva-Alique I,Sierra S,Muñoz-Moreno L,Pérez-Redondo A,Bajo AM,Marzo I,Gude L,Cuenca T,Royo E

    更新日期:2018-06-01 00:00:00

  • Human pro-islet amyloid polypeptide (ProIAPP(1-48)) forms amyloid fibrils and amyloid spherulites in vitro.

    abstract::Deposition of beta sheets of islet amyloid polypeptide (IAPP) in pancreatic tissue is implicated in the aetiology of type 2 diabetes mellitus (T2DM). IAPP is cleaved from its precursor protein, pro-islet amyloid polypeptide (ProIAPP) and incomplete cleavage results in ProIAPP(1-48), which is found co-deposited with IA...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2010.05.012

    authors: Exley C,House E,Patel T,Wu L,Fraser PE

    更新日期:2010-10-01 00:00:00

  • In vitro and in vivo antitumor activity of a novel carbonyl ruthenium compound, the ct-[RuCl(CO)(dppb)(bipy)]PF-6[dppb=1,4-bis(diphenylphosphine)butane and bipy=2,2'-bipyridine].

    abstract::This study performed in vitro and in vivo biological assays of the ruthenium (II) compound ct-[RuCl(CO)(dppb)(bipy)]PF6 (where, dppb=1,4-bis(diphenylphosphine)butane and bipy=2,2'-bipyridine). The cytotoxic activity of this compound was evaluated against different tumor cell lines (HeLa, human cervical adenocarcinoma;...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2016.08.010

    authors: Carnizello AP,Barbosa MI,Martins M,Ferreira NH,Oliveira PF,Magalhães GM,Batista AA,Tavares DC

    更新日期:2016-11-01 00:00:00

  • Cleavage of an RNA analog by Zn(II) macrocyclic catalysts appended with a methyl or an acridine group.

    abstract::Two macrocycles (1 and 2) are prepared that incorporate pendent groups in macrocycle 3 (3=1-oxa-4,7,10-triazacyclododecane) with the goal of studying the effect of these pendent groups on metal ion complexation, solution chemistry and catalysis. Zn(1) contains a macrocyclic ligand with a pendent acridine group and Zn(...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2007.03.002

    authors: Rossiter CS,Mathews RA,Morrow JR

    更新日期:2007-06-01 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

  • Synthesis, characterization and DNA-binding of novel chiral complexes delta- and lambda-[Ru(bpy)2L]2+ (L = o-mopip and p-mopip).

    abstract::Novel chiral Ru(II) complexes [Ru(bpy)2L]2+ (bpy = 2,2-bipyridine; L: o-mopip = 2-(2-methoxylphenyl)imidazo[4,5-f][1,10]phenanthroline, p-mopip = 2-(4-methoxylphenyl)imidazo[4,5-f][1,10]phenanthroline) containing -OCH3 at different positions on the phenyl ring have been synthesized and characterized. The DNA-binding a...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2005.12.005

    authors: Shi S,Liu J,Li J,Zheng KC,Huang XM,Tan CP,Chen LM,Ji LN

    更新日期:2006-03-01 00:00:00

  • Cis- and trans-conformations for peroxynitrite anions.

    abstract::The biochemically important anion, peroxynitrite, is commonly thought to have a cis-conformation which is stable. This is thought to have a cyclic structure, which blocks the formation of the trans-conformation. Furthermore, it is often suggested that the latter structure isomerises to the far more stable nitrate ion....

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/s0162-0134(00)00057-x

    authors: Symons MC

    更新日期:2000-03-01 00:00:00

  • The metal complexes of N-confused porphyrin as heme model compounds.

    abstract::Recently, metal complexes of the isomers and analogs of porphyrin have become important model compounds for heme enzymes and proteins. While the chemistry of metalloporphyrins as heme models still attracts attention, the isomers and analogs of porphyrins provide insight into the biological choice of porphine as the ma...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.jinorgbio.2006.01.016

    authors: Harvey JD,Ziegler CJ

    更新日期:2006-04-01 00:00:00

  • Systematic differences in electrochemical reduction of the structurally characterized anti-cancer platinum(IV) complexes [Pt{((p-HC6F4)NCH2)2}-(pyridine)2Cl2], [Pt{((p-HC6F4)NCH2)2}(pyridine)2(OH)2], and [Pt{((p-HC6F4)NCH2)2}(pyridine)2(OH)Cl].

    abstract::The putative platinum(IV) anticancer drugs, [Pt{((R)NCH(2))(2)}(py)(2)XY] (X,Y=Cl, R=p-HC(6)F(4) (1a), C(6)F(5) (1b); X,Y=OH, R=p-HC(6)F(4) (2); X=Cl, Y=OH, R=p-HC(6)F(4) (3), py = pyridine) have been prepared by oxidation of the Pt(II) anticancer drugs [Pt{((R)NCH(2))(2)}(py)(2)] (R=p-HC(6)F(4) (4a) or C(6)F(5) (4b))...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2012.07.016

    authors: Guo SX,Mason DN,Turland SA,Lawrenz ET,Kelly LC,Fallon GD,Gatehouse BM,Bond AM,Deacon GB,Battle AR,Hambley TW,Rainone S,Webster LK,Cullinane C

    更新日期:2012-10-01 00:00:00

  • Synthesis, characterization and crystal structure of novel mononuclear peroxotungsten(VI) complexes. Insulinomimetic activity of W(VI) and Nb(V) peroxo complexes.

    abstract::Two new mononuclear peroxo complexes of tungsten of the formula (gu)(2)[WO(2)(O(2))(2)] (1) and (gu)[WO(O(2))(2)(quin-2-c)] (2a) (where gu(+)=guanidinium ion, CN(3)H(6)(+) and quin-2-c=quinoline-2-carboxylate ion) have been synthesized and characterized by elemental analysis, infrared, Raman, UV-visible and (1)H NMR s...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2009.03.001

    authors: Maniatakou A,Karaliota S,Mavri M,Raptopoulou C,Terzis A,Karaliota A

    更新日期:2009-05-01 00:00:00

  • 1H NMR and UV-Vis spectroscopic characterization of sulfonamide complexes of nickel(II)-carbonic anhydrase. Resonance assignments based on NOE effects.

    abstract::The binding of acetazolamide, p-fluorobenzensulfonamide, p-toluenesulfonamide, and sulfanilamide to nickel(II)-substituted carbonic anhydrase II has been studied by 1H NMR and electronic absorption spectroscopies. These inhibitors bind to the metal ion forming 1:1 complexes and their affinity constants were determined...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/0162-0134(92)84012-c

    authors: Moratal JM,Martinez-Ferrer MJ,Jiménez HR,Donaire A,Castells J,Salgado J

    更新日期:1992-03-01 00:00:00

  • Effects of cadmium on Na+ transport in the isolated skin of the toad Pleurodema thaul.

    abstract::Cadmium ions applied to either (outer or inner) surface of the isolated toad skin dose-dependently increased the short-circuit current (SCC), the potential difference (V) and the active sodium conductance (G(Na)) in the concentration range 0.07-0.50mM. Maximal stimulatory effect was over 30% with an EC(50) of about 0....

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章

    doi:10.1016/j.jinorgbio.2005.09.003

    authors: Suwalsky M,Norris B,Cárdenas H

    更新日期:2005-12-01 00:00:00

  • Does P450-type catalysis proceed through a peroxo-iron intermediate? A review of studies with microperoxidase.

    abstract::Recent stopped-flow kinetics demonstrated the existence of an intermediate before the occurrence of the final product of the reaction of both iron-containing microperoxidase-8 (Fe(III)MP-8) and manganese-containing microperoxidase-8 (Mn(III)MP-8) with H(2)O(2). The intermediate was assigned to be (hydro)peroxo-iron. W...

    journal_title:Journal of inorganic biochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0162-0134(02)00393-8

    authors: Veeger C

    更新日期:2002-07-25 00:00:00

  • 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