Copper(II) complexes with β-diketones and N-donor heterocyclic ligands: Crystal structure, spectral properties, and cytotoxic activity

Almeida, Janaina do Couto; Paixão, Drielly A.; Marzano, Ivana Marques; Ellena, Javier; Pivatto, Marcos; Lopes, Norberto P.; Ferreira, Ana Maria D.C.; Pereira-Maia, Elene C.; Guilardi, Silvana; Guerra, Wendell

doi:10.1016/j.poly.2014.12.026

Cited by 54 publications

(40 citation statements)

References 39 publications

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“…For example, the complex IV exhibits a d _ d band centered at 625 nm (ε = 13 M − 1 cm − 1 ). These observations are consistent with a distortion from the octahedron geometry due to the Jahn-Teller effect [19]. In the solid state, all complexes exhibit the same d _ d band centered at ≈ 608 nm, indicating that the geometry of the complexes in solution differs from that in solid state [19,20].…”

Section: Resultssupporting

confidence: 76%

“…These values are considerably longer than the Cu1eO distance in the basal plane. This elongation can be explained by the Jahn-Teller effect [19]. The Cu1eN phen (1.994(2) and 1.976(2)Å), Cu1eN2 (2.025(2) Å) and Cu1eO1 (1.970(2) Å) bond distances are normal and are comparable to those found for the related copper(II) complexes [31,[38][39][40][41].…”

Section: Crystal Structuresupporting

confidence: 69%

“…In other studies, our research group has also shown that copper(II) complexes containing β-diketones and 2,2′-bipyridine or 1,10-phenanthroline are promising antitumoral agents [19,20]. For example, the compound [Cu(L)(phen)NO 3 ], in which L = 1-(4-chlorophenyl)-4,4,4trifluoro-1,3-butanedione, inhibits the growth of K562 cells with an IC 50 value equal to 2.1 μM [19].…”

Section: Introductionmentioning

confidence: 88%

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Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies

Paixão

Marzano

Jaimes

et al. 2017

Journal of Inorganic Biochemistry

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Five new copper(II) complexes of the type [Cu(NO)(NN)(ClO)], in which NO=4-fluorophenoxyacetic acid hydrazide (4-FH) or 4-nitrobenzoic hydrazide (4-NH) and NN=1,10-phenanthroline (phen), 4-4'-dimethoxy-2-2'-bipyridine (dmb) or 2,2-bipyridine (bipy) were synthesized and characterized using various spectroscopic methods. The X-ray structural analysis of one representative compound indicates that the geometry around the copper ion is distorted octahedron, in which the ion is coordinated to hydrazide via the terminal nitrogen and the carbonyl oxygen, and to heterocyclic bases via their two nitrogen atoms. Two perchlorate anions occupy the apical positions, completing the coordination sphere. The cytotoxic activity of compounds was investigated in three tumor cell lines (K562, MDA-MB-231 and MCF-7). Concerning K562 cell line, the complexes with 1,10-phenanthroline exhibit high cytotoxic activity and are more active than carboplatin, free ligands and [Cu(phen)]. Considering the cytotoxicity results, further investigations for the compounds [Cu(4-FH)(phen)(ClO)] I and [Cu(4-NH)(phen)(ClO)]∙HO III were performed. Flow cytometric analysis revealed that these complexes induce apoptotic cell death in MDA-MB-231 cell line and bind to DNA with K values of 4.38×10 and 2.62×10, respectively. These compounds were also evaluated against wild type Mycobacterium tuberculosis (ATCC 27294) and exhibited antimycobacterial activity, displayed MIC values lower than those of the corresponding free ligands.

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Section: Resultssupporting

confidence: 76%

Section: Crystal Structuresupporting

confidence: 69%

Section: Introductionmentioning

confidence: 88%

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Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies

Paixão

Marzano

Jaimes

et al. 2017

Journal of Inorganic Biochemistry

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“…Tomassini et al reported a series of β-ketoenol derivatives as e ective inhibitors drug of in uenza viral replication in both in vitro cell culture replication assays and in vivo mouse challenge model, without exhibiting any cytotoxicity [2][3][4]. Furthermore, complexes with β-ketoenols have received more attention in the area of medicinal chemistry [5], exhibiting anticancer activity against several tumoral cells strains [6], and cytotoxic activity in a chronic myelogenous leukemia cell line [7]. Herein, we report the preparation of a new pyridine incorporating a β-ketoenol moiety: (Z)-3-hydroxy-3-(4-methoxyphenyl)-1-(pyridin-2-yl) prop-2-en-1-one in moderate yield.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (Z)-3-hydroxy-3-(4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one, C₁₅H₁₃NO₃

Radi

Tighadouini

Eddike

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1525410The asymmetric unit of the title crystal structure is shown in the gure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialTo a suspension of sodium (0.4 g; 17.40 mmol) in anhydrous toluene, was added ethyl 2-picolinate (2 g; 13.28 mmol) in toluene. Then 1-(4-methoxphenyl) ethanone (1.99 g;

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“…Extensive literature is available on the application of β-diketonate complexes in catalysis and as precursors for MOCVD (Bose et al, 2016;Poncelet et al, 2005;Lassahn et al, 2005;Nable et al, 2003.). Studies revealed that β-diketones were used in the design of many luminescence compounds (Ahumada et al, 2018) and the metal complexes were used to inhibit the growth of K562 cell (Almeida et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Physicochemical Studies and Biological Properties of Mixed-Ligand Nickel(II) Complexes Containing β-Diketones With N-donor Ligands

Omoregie¹

2018

IJC

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Some mixed ligand nickel(II) complexes of thenoyltrifluoroacetone (tta-H) with 2,2ꞌ-bipyridine (bipy), 1,10-phenanthroline (phen) and tetramethylethylenediamine (tmen) [Ni(tta)(N-N)(NO3)]; N-N= bipy, phen, or tmen] have been synthesized and characterized by molar conductance measurements, elemental analysis, mass spectrometry, spectral measurements and antimicrobial activities. Attempt to prepare the mixed ligand nickel(II) complexes containing acetylacetone (acacH), benzoylacetone (bzacH), dibenzoylmethane (dbm-H) and thenoyltrifluoroacetone (tta-H) with ethylenediamine associated with NO3 counter ion led to the formation of [Ni(β-diketone)2en]. The β-diketones enolized acting as bidentate ligand, coordinating to the metal with carbonyl and enolic oxygen, ethylenediamine (en) coordinates to the metal using N, N chromophores. The nickel complexes of the type [Ni(tta)(N-N)NO3)] are five-coordinate square pyramidal in geometry while those of the type [Ni(β-diketone)2en] are six-coordinate octahedral geometry. The conductivity measurement in nitromethane revealed that the [Ni(tta)(N-N)NO3)] complexes are non-electrolyte. The complexes were screened for their in-vitro antimicrobial activity against six microorganisms. A comparison of the complexes with gentamicin showed that most of the complexes are resistant to tested organisms except [Ni(tta)2(en)].H2O, [Ni(bzac)2(en)] and [Ni(bta)2(en)] which compared favourably well in Staphylococcus aureus.

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Copper(II) complexes with β-diketones and N-donor heterocyclic ligands: Crystal structure, spectral properties, and cytotoxic activity

Cited by 54 publications

References 39 publications

Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies

Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies

Crystal structure of (Z)-3-hydroxy-3-(4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one, C₁₅H₁₃NO₃

Synthesis, Physicochemical Studies and Biological Properties of Mixed-Ligand Nickel(II) Complexes Containing β-Diketones With N-donor Ligands

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Copper(II) complexes with β-diketones and N-donor heterocyclic ligands: Crystal structure, spectral properties, and cytotoxic activity

Cited by 54 publications

References 39 publications

Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies

Novel copper(II) complexes with hydrazides and heterocyclic bases: Synthesis, structure and biological studies

Crystal structure of (Z)-3-hydroxy-3-(4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one, C15H13NO3

Synthesis, Physicochemical Studies and Biological Properties of Mixed-Ligand Nickel(II) Complexes Containing β-Diketones With N-donor Ligands

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Crystal structure of (Z)-3-hydroxy-3-(4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one, C₁₅H₁₃NO₃