Synthesis, characterization and biological studies on NiII and CuII complexes of two novel α,β-unsaturated 1,3-diketones related to curcuminoids

Thomas, Deepthi; Venugopalan, P.

doi:10.1016/j.ica.2016.05.045

Cited by 15 publications

(6 citation statements)

References 73 publications

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“…12 Due to the presence of the distinctive keto group, which serves as a building block for numerous physiologically active heterocyclic compounds, dimedones form an important class of chemicals. 13 Several cases where enzymes are triggered via metal serve as examples of the significant roles that mixedligand complexes perform in biological systems. 14 Copper (II) complexes have concerned an excessive deal of interest among the different coordination compounds owing to their steadiness in an aerobic atmosphere, and intriguing elastic shape.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, in vitro biological activity, and DFT calculations of Cu(II) complex

Amri,

Alaghaz,

Bedowr

et al. 2024

Applied Organom Chemis

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Using a diazonium combination of aniline and 1,3‐diphenylpropane‐1,3‐dione, the Japp‐Klingemann reaction yielded the 1,3‐diphenyl‐2‐(2‐phenylhydrazono)propane‐1,3‐dione ligand (HL). The copper (II) complex has been made using copper (II) acetate salt. The geometry of HL and its Cu (II) chelate were described through CHN analyses, FTIR, UV–Visible, XRD, TGA, and magnetic susceptibility tests. According to the spectral data, the ligand exhibits monobasic bidentate behavior by connecting through the N atom of hydrazone moiety (=N − NH−) by deprotonating beside the oxygen atom of the carbonyl (C=O) group forming octahedral geometry. Density functional theory (DFT) calculations were done by molecular studio software to examine the optimal geometry of HL and its complexity. MCF‐7 and HepG‐2 cell lines demonstrated anticancer action in response to the HL and its copper (II) complex. Additionally, inhibition zone diameter was used to assess the in vitro antibacterial action of HL and particular complex toward Gram +ve bacteria Staphylococcus aureus and Gram‐ve bacteria Escherichia coli (E. coli). Both viscosity and absorption spectra of Calf‐thymus DNA binding experimentations were used to examine the compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, in vitro biological activity, and DFT calculations of Cu(II) complex

Amri,

Alaghaz,

Bedowr

et al. 2024

Applied Organom Chemis

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“…Among non-platinum based compounds, in 1995, Hanauske and coworkers introduced budotitane as the first titanium(IV) drug for cancer treatment [10]. Other cytotoxic β-dicarbonyls exploit the presence of Ru II [11], Co II [12], Cu II [13,14], Ni II [15,16] and oxovanadium(IV) [17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and DNA-Binding Affinity of a New Zinc(II) Bis(5-methoxy-indol-3-yl)propane-1,3-dione Complex

et al. 2021

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The novel zinc(II) µ-oxo-bridged-dimeric complex [Zn2(µ-O)2(BMIP)2] (BMIP = 1,3-bis(5-methoxy-1-methyl-1H-indol-3-yl)propane-1,3-dione), 1, was synthetized and fully characterized. The spectral data indicate a zincoxane molecular structure, with the BMIP ligand coordinating in its neutral form via its oxygen atoms. Structural changes in 1 in dimethylsulfoxide (DMSO) were evidenced by means of spectroscopic techniques including infrared absorption and nuclear magnetic resonance, showing DMSO entrance in the coordination sphere of the metal ion. The resulting complex [Zn2(µ-O)2(BMIP)2(DMSO)], 2, readily reacts in the presence of N-methyl-imidazole (NMI), a liquid-phase nucleoside mimic, to form [Zn2(µ-O)2(BMIP)2(NMI)], 3, through DMSO displacement. The three complexes show high thermal stability, demonstrating that 1 has high affinity for hard nucleophiles. Finally, with the aim of probing the suitability of this system as model scaffold for new potential anticancer metallodrugs, the interactions of 1 with calf thymus DNA were investigated in vitro in pseudo-physiological environment through UV-Vis absorption and fluorescence emission spectroscopy, as well as time-resolved fluorescence studies. The latter analyses revealed that [Zn2(µ-O)2(BMIP)2(DMSO)] binds to DNA with high affinity upon DMSO displacement, opening new perspectives for the development of optimized drug substances.

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“…Isso é decorrente de dois fatores: devido à existente de uma ligação intramolecular de hidrogênio; e ressonância da carbonila na forma enol, o que corrobora para a diminuição da frequência de estiramento(SILVERSTEIN, 2005). frequências um pouco menores que as regiões citadas(DEEPTHI;VENUGOPALAN, 2016;COUTO ALMEIDA ET AL.,2014). Ampliação dos espectros no IV do complexo [RuCl(BTA)(ƞ 6 -p-cimeno)] (azul) e complexo precursor [RuCl2(ƞ 6 -p-cimeno)]2 (preto) referente ao estiramentoRu-Cl.…”

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Síntese, caracterização e estudo das estruturas eletrônicas de complexos à base de rutênio(II) contendo β-dicetonas: avaliação da atividade leishmanicida

Macêdo¹

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This work describes the synthesis, characterization, theoretical study of electronic structures and in vitro leishmanicidal activity of eight new ruthenium(II) complexes obtained from the cis-[RuCl2(dppm)2] and [RuCl2(ƞ 6-p-cymene)]2 precursors, where dppm=1,1-bis(diphenylphosphine)methane. The synthesized complexes were defined as cis-[Ru(O-O)(dppm)2]PF6 and [RuCl(O-O)(ƞ 6-p-cymene)], where O-O corresponds to the chelating β-diketones ligand: 1,3-butanedione-1-phenyl-4,4,4-trifluoro (BTA), 2thenoyltrifluoroacetone (TTA), 1,3-butanedione-1-(4-bromophenyl)-4,4,4-trifluoro (TFBr) and 1,3-butanedione-1-(4-fluorophenyl)-4,4,4-trifluoro (TFF), respectively. The empirical formulas, as well as the bidentate coordination (OO) modes of the inserted ligands and the geometries of the synthesized complexes were suggested by the techniques of elemental analysis (CHN), infrared spectroscopy (ATR-FTIR), 1 H (proton), 31 P{ 1 H} (phosphorus) and 19 F{ 1 H} (fluorine) nuclear magnetic resonance (NMR). The electron transitions observed in the UV-Vis spectra were confirmed by the theoretical calculations and for the crystals obtained from the [RuCl (ƞ 6-p-cymene)] complex, the technique for single-crystal X-ray diffraction confirmed the proposed structure. In vitro viability assays against the Leishmania (L.) amazonensis species, all the complexes were found to be active, with complexes derived from the cis-[RuCl2(dppm)2] precursor. The IC50 values obtained were between 24.7 μM and 3.9 μM, being comparable to values referring to the second choice compounds currently used in the treatment against leishmaniasis, which makes the complexes synthesized promising leishmanicidal agents.

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Synthesis, characterization and biological studies on NiII and CuII complexes of two novel α,β-unsaturated 1,3-diketones related to curcuminoids

Cited by 15 publications

References 73 publications

Synthesis, structural characterization, in vitro biological activity, and DFT calculations of Cu(II) complex

Synthesis, structural characterization, in vitro biological activity, and DFT calculations of Cu(II) complex

Synthesis, Characterization and DNA-Binding Affinity of a New Zinc(II) Bis(5-methoxy-indol-3-yl)propane-1,3-dione Complex

Síntese, caracterização e estudo das estruturas eletrônicas de complexos à base de rutênio(II) contendo β-dicetonas: avaliação da atividade leishmanicida

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