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Dicopper(II) and dizinc(II) complexes with nonsymmetric dinucleating ligands based on indolo[3,2-c]quinolines: synthesis, structure, cytotoxicity, and intracellular distribution.

ABSTRACT: Dicopper(II) and dizinc(II) complexes [Cu2((MeOOC)L(COO))(CH3COO)2] (1) and [Zn2((MeOOC)L(COO))(CH3COO)2] (2) were synthesized by reaction of Cu(CH3COO)2·H2O and Zn(CH3COO)2·2H2O with a new nonsymmetric dinucleating ligand (EtOOC)HL(COOEt) prepared by condensation of 6-hydrazinyl-11H-indolo[3,2-c]quinoline with diethyl-2,2'-((3-formyl-2-hydroxy-5-methylbenzyl)azanediyl)diacetate. The design and synthesis of this elaborate ligand was performed with the aim of increasing the aqueous solubility of indolo[3,2-c]quinolines, known as biologically active compounds, and investigating the antiproliferative activity in human cancer cell lines and the cellular distribution by exploring the intrinsic fluorescence of the indoloquinoline scaffold. The compounds have been comprehensively characterized by elemental analysis, spectroscopic methods (IR, UV-vis, (1)H and (13)C NMR spectroscopy), ESI mass spectrometry, magnetic susceptibility measurements, and UV-vis complex formation studies (for 1) as well as by X-ray crystallography (1 and 2). The antiproliferative activity of (EtOOC)HL(COOEt), 1, and 2 was determined by the MTT assay in three human cancer cell lines, namely, A549 (nonsmall cell lung carcinoma), CH1 (ovarian carcinoma), and SW480 (colon adenocarcinoma), yielding IC50 values in the micromolar concentration range and showing dependence on the cell line. The effect of metal coordination on cytotoxicity of (EtOOC)HL(COOEt) is also discussed. The subcellular distribution of (EtOOC)HL(COOEt) and 2 was investigated by fluorescence microscopy, revealing similar localization for both compounds in cytoplasmic structures.

SUBMITTER: Primik MF

PROVIDER: S-EPMC3763518 | biostudies-other | 2013 Sep

REPOSITORIES: biostudies-other

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Dicopper(II) and dizinc(II) complexes with nonsymmetric dinucleating ligands based on indolo[3,2-c]quinolines: synthesis, structure, cytotoxicity, and intracellular distribution.

Primik Michael F MF Göschl Simone S Meier Samuel M SM Eberherr Nadine N Jakupec Michael A MA Enyedy Éva A É Novitchi Ghenadie G Arion Vladimir B VB

Inorganic chemistry 20130816 17

Dicopper(II) and dizinc(II) complexes [Cu2((MeOOC)L(COO))(CH3COO)2] (1) and [Zn2((MeOOC)L(COO))(CH3COO)2] (2) were synthesized by reaction of Cu(CH3COO)2·H2O and Zn(CH3COO)2·2H2O with a new nonsymmetric dinucleating ligand (EtOOC)HL(COOEt) prepared by condensation of 6-hydrazinyl-11H-indolo[3,2-c]quinoline with diethyl-2,2'-((3-formyl-2-hydroxy-5-methylbenzyl)azanediyl)diacetate. The design and synthesis of this elaborate ligand was performed with the aim of increasing the aqueous solubility of ...[more]

PMID: 23952332

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Project description:A new family of dicopper(I) complexes [CuI2RL](X)2 (R=H, 1X, R=tBu, 2X and R=NO2, 3X, X=CF3SO3, ClO4, SbF6, or BArF, BArF=[B{3,5-(CF3)2C6H3}4]-), where RL is a Schiff-base ligand containing two tridentate binding sites linked by a xylyl spacer, has been prepared and characterized, and its reaction with O2 has been studied. The complexes were designed with the aim of reproducing structural aspects of the active site of type 3 dicopper proteins; they contain two three-coordinate copper sites and a rather flexible podand ligand backbone. The solid-state structures of 1ClO4, 2CF3SO3, 2ClO4, and 3BArF.CH3CN have been established by single-crystal X-ray diffraction analysis. 1ClO4 adopts a polymeric structure in the solid state while 2CF3SO3, 2ClO4, and 3BArF.CH3CN are monomeric. The complexes have been studied in solution by means of 1H and 19F NMR spectroscopy, which put forward the presence of dynamic processes. 1-3BArF and 1-3CF3SO3 in acetone react rapidly with O2 to generate metaestable [CuIII2(mu-O)2(RL)]2+ 1-3(O2) and [CuIII2(mu-O)2(CF3SO3)(RL)]+ 1-3(O2)(CF3SO3) species, respectively, that have been characterized by UV-vis spectroscopy and resonance Raman analysis. Instead, reaction of 1-3BArF with O2 in CH2Cl2 results in intermolecular O2 binding. DFT methods have been used to study the chemical identities and structural parameters of the O2 adducts, and the relative stability of the CuIII2(mu-O)2 form with respect to the CuII2(mu-eta2:eta2-O2) isomer. The reaction of 1X, X = CF3SO3 and BArF, with O2 in acetone has been studied by stopped-flow UV-vis exhibiting an unexpected very fast reaction rate (k=3.82(4)x10(3) M-1 s-1, DeltaH=4.9+/-0.5 kJ.mol-1, DeltaS=-148+/-5 J.K-1.mol-1), nearly 3 orders of magnitude faster than in the parent [CuI2(m-XYLMeAN)]2+. Thermal decomposition of 1-3(O2) does not result in aromatic hydroxylation. The mechanism and kinetics of O2 binding to 1X (X=CF3SO3 and BArF) are discussed and compared with those associated with selected examples of reported models of O2-processing copper proteins. A synergistic role of the copper ions in O2 binding and activation is clearly established from this analysis.

Dataset Information

Dicopper(II) and dizinc(II) complexes with nonsymmetric dinucleating ligands based on indolo[3,2-c]quinolines: synthesis, structure, cytotoxicity, and intracellular distribution.

Publications

Dicopper(II) and dizinc(II) complexes with nonsymmetric dinucleating ligands based on indolo[3,2-c]quinolines: synthesis, structure, cytotoxicity, and intracellular distribution.

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