50 results on '"Jeferson G. Da Silva"'
Search Results
2. ROS-Mediated Cytotoxic Effect of Copper(II) Hydrazone Complexes against Human Glioma Cells
- Author
-
Angel A. Recio Despaigne, Jeferson G. Da Silva, Pryscila R. da Costa, Raquel G. dos Santos, and Heloisa Beraldo
- Subjects
pyridine-derived hydrazones ,copper(II) complexes ,cytotoxicity ,glioma cells ,ROS generation ,Organic chemistry ,QD241-441 - Abstract
2-Acetylpyridine acetylhydrazone (H2AcMe), 2-benzoylpyridine acetylhydrazone (H2BzMe) and complexes [Cu(H2AcMe)Cl2] (1) and [Cu(H2BzMe)Cl2] (2) were assayed for their cytotoxicity against wild type p53 U87 and mutant p53 T98 glioma cells, and against MRC-5 fibroblast cells. Compounds 1 and 2 proved to be more active than the corresponding hydrazones against U87, but not against T98 cells. Compound 1 induced higher levels of ROS than H2AcMe in both glioma cell lines. H2AcMe and 1 induced lower levels of ROS in MRC5 than in U87 cells. Compound 2 induced lower levels of ROS in MRC5 than in T98 cells. The cytotoxic effect of 1 in U87 cells could be related to its ability to provoke the release of ROS, suggesting that the cytotoxicity of 1 might be somehow p53 dependent.
- Published
- 2014
- Full Text
- View/download PDF
3. Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi
- Author
-
Jacqueline A. Takahashi, Isolda C. Mendes, Camila F. Vilela, Nayane F. Silva, Jeferson G. Da Silva, Angel A. Recio Despaigne, Débora C. Reis, and Heloisa Beraldo
- Subjects
imidazole ,hydrazones ,thiosemicarbazones ,antifungal activity ,Organic chemistry ,QD241-441 - Abstract
New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehyde-para-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-para-nitrobenzoyl hydrazone (4(5)ImpNO2Ph), 4-(imidazole-1-yl)acetophenone-para-chloro-benzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitro-benzoylhydrazone (4ImAcpNO2Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO2Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.
- Published
- 2013
- Full Text
- View/download PDF
4. Rheological and Colloidal Characterization of Xanthan Biosynthesized from Glucose
- Author
-
Kátia M. de O. Almeida, Alan R. de Oliveira, Juliano R. Pereira, Jeferson G. da Silva, Humberto M. Húngaro, Mirian P. Rodarte, Priscila L. Sequetto, and Ângelo M. L. Denadai
- Subjects
General Chemistry - Published
- 2021
5. Epoxy/ferrite nanocomposites as microwave absorber materials: effect of multilayered structure
- Author
-
Bluma G. Soares, Jeferson G. Da Silva, Ana Pacheli Heitmann, Ângelo M. L. Denadai, Tamara Indrusiak, and Iaci M. Pereira
- Subjects
010302 applied physics ,Nanocomposite ,Materials science ,Reflection loss ,Composite number ,Dielectric ,Epoxy ,Condensed Matter Physics ,01 natural sciences ,Atomic and Molecular Physics, and Optics ,Electronic, Optical and Magnetic Materials ,Transmission electron microscopy ,visual_art ,0103 physical sciences ,Monolayer ,visual_art.visual_art_medium ,Ferrite (magnet) ,Electrical and Electronic Engineering ,Composite material - Abstract
In the present work, different ferrite-type nanoparticles (Ni0.5Zn0.5Fe2O4, NiFe2O4 and Fe3O4) were incorporated into an epoxy resin to obtain composites loaded with 20 and 40 wt% of filler. The morphology of these monolayered composites was investigated by small-angle X-ray scattering (SAXS) and transmission electron microscopy (TEM), which allow identifying a fractal structure of the ferrite-based filler with rough surface. The electromagnetic properties of the monolayer composites with 1 mm thickness were evaluated by the transmission line method in X-band (8.2–12.4 GHz), whose better response in terms of reflection loss was obtained for the composite filled with Ni0.5Zn0.5Fe2O4. Epoxy-based composites containing 20 and 40 wt% of Ni0.5Zn0.5Fe2O4 in the form of plaques were arranged in two types of three-layered structures: (i) stacked monolayers and (ii) low dielectric spacer sandwiches between monolayers (air, honeycomb and foam), whose structure sequence was built based on the reflectivity simulation. The best system, designed by mathematical simulation and experimental results, consisted of ER/NiZn(40)–honeycomb–ER/NiZn(20) arrangement, which presented RL of around − 40 dB at a frequency of 8.75 GHz. Broadband with > 90% attenuation (minimum of − 10 dB) with band width of around 1.2 GHz and minimum RL ≈ 20 dB (Eabs ≈ 99%) was achieved for both three-layered structures contain in PU foam or honeycomb as low dielectric spacer. The ferrite-based multilayer structures with only 6 mm of thickness constitute promising absorbing materials for applications in both civil and military fields.
- Published
- 2020
6. Mechanisms of interaction of Cetylpyridinium chloride with Staphylococcus aureus in the presence of β-cyclodextrin
- Author
-
Alan R. de Oliveira, Jeferson G. Da Silva, Larissa M. D. Andrade, Guilherme F. da Silva, Gabriella Freitas Ferreira, Thiago M. de Miranda, and Ângelo M. L. Denadai
- Subjects
chemistry.chemical_classification ,Cyclodextrin ,010405 organic chemistry ,technology, industry, and agriculture ,Isothermal titration calorimetry ,macromolecular substances ,General Chemistry ,010402 general chemistry ,Condensed Matter Physics ,medicine.disease_cause ,Antimicrobial ,Cetylpyridinium chloride ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Dynamic light scattering ,Pulmonary surfactant ,Staphylococcus aureus ,Zeta potential ,medicine ,Food Science ,Nuclear chemistry - Abstract
Cetylpyridinium chloride (CPC) is a cationic surfactant, which has a biocidal activity against a broad spectrum of bacteria, including Staphylococcus aureus. This microorganism, although frequently found in the normal human microbiota, can become a pathogen that causes a wide variety of infections. Thus, the present work aims to investigate the effect of the β-cyclodextrin (βCD) on CPC antimicrobial activity against S. aureus, especially in the mechanism of interaction with S. aureus membrane. For these purposes, in vitro antimicrobial susceptibility of CPC and CPC/βCD compounds against S. aureus were determined by calculating the lower concentration capable of reducing cell viability by 50 and 100 percent, and the kinetics of bacterial death were evaluated by kill curves for the two systems. After that, the colloidal mechanisms of interaction of the CPC and CPC/βCD against S. aureus were investigated by Dynamic Light Scattering (DLS) and Zeta Potential (ZP) titrations. Finally, the thermodynamic parameters of drug-cell interaction were determined by Isothermal Titration Calorimetry (ITC), in order to obtain deeper understanding of the mechanism of drug interactions. The results of DLS, ZP and ITC showed that in presence of βCD occurs a different mechanism of interaction with S. aureus membrane, explaining therefore the higher antimicrobial activity of CPC/βCD system.
- Published
- 2020
7. Nanostructured Insecticide Composition through the Incorporation of Natural Abamectin in β-Cyclodextrin: Activity against Aedes aegypti Larvae
- Author
-
Cibele Velloso Rodrigues, Keyller Bastos Borges, Antônio Frederico de Freitas Gomides, Gustavo Ferreira Martins, Ana Maria dos Santos Moreira, Ângelo M. L. Denadai, Vanessa C. E. Bittencourt, Alexandre A Ferreira, Jeferson G. Da Silva, and Erúzia A. E Ferreira
- Subjects
chemistry.chemical_classification ,Cyclodextrin ,Supramolecular chemistry ,Isothermal titration calorimetry ,General Chemistry ,abamectin ,Inclusion compound ,hydrophobic nanoprecipitates ,chemistry.chemical_compound ,Aedes aegypti ,chemistry ,Dynamic light scattering ,β-cyclodextrin ,Zeta potential ,Abamectin ,Benzofuran ,Nuclear chemistry - Abstract
This study searched for a new pre-formulation based on the natural compound from the class of the avermectins, named abamectin (ABA), in order to improve its action against Aedes aegypti larvae by complexation with β-cyclodextrin (βCD). Concerning the low aqueous solubility of ABA, even in the presence of βCD, it was also invoked the strategy of working with hydrophobic nanoprecipitates (HNPs). For these purposes, molecular and supramolecular characterizations of 1:1 ABA/βCD complex and evaluation of its toxicity against A. aegypti larvae were performed. In the physical-chemistry characterizations, changes in the infrared spectra and thermal profiles in relation to precursors confirmed the occurrence of interactions between ABA and βCD in solid state. Nuclear magnetic resonance (NMR) data suggest the inclusion of ABA in βCD via benzofuran ring. Isothermal titration calorimetry (ITC) experiments allowed to verify the formation of complex with a 1:1 stoichiometry, which was entropy driven. The dynamic light scattering and zeta potential data from inclusion compounds demonstrated changes in the size of the ABA/βCD HNP if compared with the ABA HNP. Finally, the results for biological assays demonstrate that the strategy to prepare the inclusion compound led to an increase in the larvicidal activity in relation to free ABA.
- Published
- 2021
8. Inclusion vs. micellization in the cethylpyridine chloride / β-cyclodextrin system: A structural and thermodynamic approach
- Author
-
Ivana Silva Lula, Ângelo M. L. Denadai, Clebio S. Nascimento, Jeferson G. Da Silva, Alan R. de Oliveira, Thiago M. de Miranda, and Juliano R. Pereira
- Subjects
chemistry.chemical_classification ,Cyclodextrin ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Enthalpy ,Supramolecular chemistry ,Isothermal titration calorimetry ,010402 general chemistry ,01 natural sciences ,Micelle ,Binding constant ,0104 chemical sciences ,Analytical Chemistry ,Inorganic Chemistry ,Critical micelle concentration ,Physical chemistry ,Titration ,Spectroscopy - Abstract
In the present work we have performed a structural and thermodynamic characterization of supramolecular structures formed by interaction between cethylpyridine chloride (CPC) surfactant and β-cyclodextrin (βCD), using several physical-chemistry methods. Initially, qualitative CPC/βCD interactions in solid state were confirmed by FTIR and TGA/DTA. 2D NMR ROESY experiment showed strong correlations between hydrogens of βCD cavity with aromatic and aliphatic hydrogens of CPC, suggesting the existence of different complexes in solution. This information was corroborated by structures assessed by computational approach and stoichiometric coefficient obtained by ITC (N = 1.45). ITC experiments (at constant concentration of CPC) also showed that host-guest complexation occur with very high binding constant (Kb = 38,300.0), and driven by enthalpy and entropy. However, as CPC is an amphiphilic molecule, it is able to form micelles at critical micellar concentration close to 1 mM. In presence of βCD, it was observed that micellization was delayed, so that the cmc values increased according to the empiric equation: cmc = 1.02 + 0.5[βCD]. Moreover, thermodynamic data obtained by combination of conductometric and isothermal calorimetry titrations showed that the presence of increasing concentrations of βCD causes an increase of free energy of micellization, specially by gradual reduction of entropy of micellization, due to the difficult of micelles encapsulate the inclusion compounds. The overall study was rationalized in terms of competition between micellization vs. host-guest complexation.
- Published
- 2019
9. Structural studies and antileishmanial activity of 2-acetylpyridine and 2-benzoylpyridine nitroimidazole-derived hydrazones
- Author
-
Magna Suzana Alexandre-Moreira, Renata Diniz, Jeferson G. Da Silva, Isabella P. Ferreira, Heloisa Beraldo, Mariana da Silva Santos, Ana Carolina Santana Vieira, Ana P. A. Oliveira, and Angel A. Recio Despaigne
- Subjects
chemistry.chemical_classification ,Nitroimidazole ,medicine.drug_class ,Stereochemistry ,Hydrazone ,Crystal structure ,Prodrug ,010402 general chemistry ,010403 inorganic & nuclear chemistry ,Condensed Matter Physics ,01 natural sciences ,0104 chemical sciences ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,Materials Chemistry ,Antiprotozoal ,medicine ,Imidazole ,Physical and Theoretical Chemistry ,2-Acetylpyridine - Abstract
Three imidazole hydrazone compounds, namely 2-(4-nitro-1H-imidazol-1-yl)-N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide, C12H12N6O3, (1), 2-(2-nitro-1H-imidazol-1-yl)-N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide, C12H12N6O3, (2), and 2-(2-nitro-1H-imidazol-1-yl)-N′-[(phenyl)(pyridin-2-yl)methylidene]acetohydrazide, C17H14N6O3, (3), were obtained and fully characterized, including their crystal structure determinations. While all the compounds proved not to be cytotoxic to J774.A1 macrophage cells, (1) and (3) exhibited activity against Leishmania chagasi, whereas (2) was revealed to be inactive. Since both (1) and (3) exhibited antileishmanial effects, while (2) was devoid of activity, the presence of the acetyl or benzoyl groups was possibly not a determining factor in the observed antiprotozoal activity. In contrast, since (1) and (3) are 4-nitroimidazole derivatives and (2) is a 2-nitroimidazole-derived compound, the presence of the 4-nitro group probably favours antileishmanial activity over the 2-nitro group. The results suggested that further investigations on compounds (1) and (3) as bioreducible antileishmanial prodrug candidates are called for.
- Published
- 2019
10. Luminescence and positron spectroscopies studies of tris(2,2,6,6-tetramethyl-3,5-heptanedionate) europium(III) and terbium(III) complexes containing 2-pyrrolidone as coligand
- Author
-
Renata Diniz, Tatiana A. Ribeiro-Santos, Dario Windmöller, W.F. Magalhães, Alex S. Borges, Jeferson G. Da Silva, Maria Helena Araujo, and F. Fulgêncio
- Subjects
Materials science ,Ligand ,Biophysics ,chemistry.chemical_element ,Terbium ,02 engineering and technology ,General Chemistry ,Crystal structure ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Condensed Matter Physics ,01 natural sciences ,Biochemistry ,Atomic and Molecular Physics, and Optics ,0104 chemical sciences ,Positronium ,chemistry ,Excited state ,Physical chemistry ,Molecule ,0210 nano-technology ,Europium ,Luminescence - Abstract
In this work is reported the synthesis, characterization, luminescent properties and positronium formation yields of europium(III) and terbium(III) complexes of stoichiometric formula Ln(dpm)3(2-pyr), where: Ln = Eu and Tb, dpm = 2,2,6,6-tetramethyl-3,5-heptanedionato (dipivaloylmethanate) ion, a β-diketonate ligand, and 2-pyr = 2-pyrrodilidone, a γ-lactam. The crystal structures were determined by single-crystal X-ray diffraction. The complexes crystallize in the space group Pī with one complex in the asymmetric unit. The Eu(III) and Tb(III) ions are seven-coordinated by six O atoms of three β-diketonate ligands, and one O atom of γ-lactam molecule. We present and discuss experimental intensity parameters of 4f-4f transitions in the Eu(III) complexes under UV excitation. The photoluminescent properties of the complexes depend on the energy positions of the ligand-to-metal charge transfer (LMCT) states. The temperature dependence of the Eu(III) 5D0 relaxation rate of the Eu(III) complexes are presented. Positronium formation in Ln(dpm)3 and Ln(dpm)3(2-pyr) (Ln = Eu and Tb) complexes were investigated. A correlation between the parameters of luminescence and positron annihilation spectroscopies has been observed. The results, which strongly evidence the participation of molecular excited states in the positronium formation, were then discussed in terms of the recently proposed Ps formation mechanism, named cybotactic correlated system kinetic mechanism (CCSKM).
- Published
- 2019
11. Multifunctionality of βCD/Ofloxacin and HPβCD/Ofloxacin Complexes: Improvement of the Antimicrobial Activity and Apoptosis Induction on Lung Adenocarcinoma A549 Cells
- Author
-
Alessandra P. Carli, Cleonice Aparecida Souza, Paloma E. Carvalho, Sandra B.R. Castro, Oswaldo Cardoso, Gabriella Freitas Ferreira, Bolivar R. Amaro, Ângelo M. L. Denadai, Caio César de Souza Alves, Fabiana S. Machado, and Jeferson G. Da Silva
- Subjects
MTT ,Thermogravimetric analysis ,Chemistry ,complexation ,flow cytometry ,toxicity ,Biological activity ,Isothermal titration calorimetry ,General Chemistry ,Antimicrobial ,Minimum inhibitory concentration ,medicine ,Ofloxacin ,MIC ,Fourier transform infrared spectroscopy ,Cytotoxicity ,Nuclear chemistry ,medicine.drug - Abstract
The ofloxacin (OFLOX) is a second-generation synthetic antibiotic that can be classified as a multifunctional drug, but is a poorly soluble drug, which influences its efficiency. The inclusion complexes of OFLOX with β-cyclodextrin (βCD) or hydroxypropyl-β-cyclodextrin (HPβCD) can improve the chemical characteristics of the drug; however, studies showing the biological activity of these inclusion complexes are still scarce. The present work aimed to investigate the multifunctionality of the OFLOX and their inclusion complexes. Thus, the 1:1 βCD/OFLOX or HPβCD/OFLOX were prepared and analyzed by Fourier transform infrared spectroscopy (FTIR), thermogravimetric and differential thermal analysis (TGA and DTA), 1H nuclear magnetic resonance (NMR) and isothermal titration calorimetry (ITC). The antitumor and antibacterial effects were assessed. The results confirm the formation of the inclusion complexes, which had lower minimum inhibitory concentration (MIC) values, higher cytotoxicity and promoted the apoptosis. The present study showed, for the first time, the promising effects of the inclusion complexes as antitumor, improving the biological activities of the uncomplexed ofloxacin.
- Published
- 2020
12. Indium(III) complexes with 2-acetylpyridine-derived thiosemicarbazones exhibit cytotoxic activity against human leukemia and solid tumor cell lines
- Author
-
Gabriele de Matos Cardoso Perdigão, Alexandre A. Oliveira, Jeferson G. Da Silva, Elaine M. Souza-Fagundes, and Heloisa Beraldo
- Subjects
inorganic chemicals ,010405 organic chemistry ,Stereochemistry ,organic chemicals ,food and beverages ,010402 general chemistry ,medicine.disease ,01 natural sciences ,Jurkat cells ,0104 chemical sciences ,Inorganic Chemistry ,chemistry.chemical_compound ,Leukemia ,chemistry ,Cell culture ,Materials Chemistry ,Vero cell ,medicine ,Cytotoxic T cell ,Physical and Theoretical Chemistry ,Cytotoxicity ,2-Acetylpyridine ,Semicarbazone - Abstract
Complexes [In(2Ac4Ph)2]NO3·H2O (1), [In(2Ac4mClPh)2]NO3·1.5H2O (2), [In(2Ac4pClPh)2]NO3·2H2O (3) and [In(2Ac4pIPh)2]NO3·H2O (4) were obtained with N(4)-phenyl-2-acetylpyridine thiosemicarbazone (H2Ac4Ph), and its N(4)-meta-chlorophenyl-(H2Ac4mClPh), N(4)-para-chlorophenyl-(H2Ac4pClPh) and N(4)-para-iodophenyl-(H2Ac4pIPh) derivatives. The crystal structures of [In(2Ac4Ph)2]NO3·MeOH (1a), [In(2Ac4mClPh)2]NO3·EtOH·H2O (2a) and [In(2Ac4pClPh)2]·NO3 (3a) were determined. The cytotoxic effects of the thiosemicarbazone ligands and of complexes (1–4) were evaluated against HL-60, Jurkat and THP-1 leukemia cells and against MCF-7, MDA-MB-231 and HCT-116 solid tumor cells, as well as against mammalian healthy Vero cells. Upon coordination to indium(III) cytotoxicity increased in several cases. In addition, complex (1) was active in sub-micromolar doses against all tested cell lineages, with selectivity indexes (SI = IC50 Vero/IC50 tumor cell) ranging from 3 (against THP-1 cells) to 144 (against HCT-116 cells).
- Published
- 2017
13. Investigation on the physicochemical properties of trans -4-stilbenecarboxaldehyde-derived hydrazones and their copper(II) complexes
- Author
-
Sonia R.W. Louro, Jeferson G. Da Silva, Matheus Campos Quintão, Lenka V. Tamayo, Heloisa Beraldo, and Hélio A. Duarte
- Subjects
Lattice energy ,Denticity ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Infrared spectroscopy ,chemistry.chemical_element ,010402 general chemistry ,01 natural sciences ,Copper ,Spectral line ,0104 chemical sciences ,law.invention ,Inorganic Chemistry ,NMR spectra database ,Crystallography ,law ,Materials Chemistry ,Chelation ,Physical and Theoretical Chemistry ,Electron paramagnetic resonance - Abstract
[Cu(HL)2Cl2] complexes (1–6) were prepared with trans-4-stilbenecarboxaldehyde-para-tolyl-hydrazone HStpT (HL1), trans-4-stilbenecarboxaldehyde-para-chloro-phenylhydrazone HStpClPh (HL2), trans-4-stilbenecarboxaldehyde-para-hydroxy-phenylhydrazone HStpOHPh (HL3), trans-4-stilbenecarboxaldehyde-para-nitro-phenylhydrazone HStpNO2Ph (HL4), trans-4-stilbenecarboxaldehyde-acetylhydrazone HStAc (HL5), and trans-4-stilbenecarboxaldehyde-benzoylhydrazone HStBz (HL6). Infrared spectra suggested that the hydrazones act as bidentate ligands which bind to the copper(II) center through the Nimine-O chelating system. EPR spectra of complexes (1–6) were recorded at room temperature for powder samples and at 77 K for DMSO solution. The EPR parameters were compatible with the presence of copper(II). Since the spectroscopic data for complexes (1–6) did not allow the unambiguous determination of the exact geometry of the complexes in the solid state or in solution, theoretical studies were carried out considering five possible isomers, in order to get information on the predominant species. However, although one of the isomers revealed to be the most thermodynamically favorable, free energy differences were not larger than 3 kcal·mol−1. Hence, differences in lattice energy or packing forces could influence the geometry adopted in the solid. The thermodynamic analysis of the five isomers indicated that all of them are in equilibrium in solution. EPR studies suggested that complexes (1–6) interact with bovine (BSA) and human (HSA) serum albumin, with displacement of the hydrazone ligands and coordination of copper(II) to site 1, together with formation of hydrazone-cysteine mixed-ligand copper(II) complexes at site 2 of the albumins.
- Published
- 2017
14. Effect of composition on rheological behavior of iron oxides produced by hydrothermal method
- Author
-
Éwerton Machado Veloso, Ângelo M. L. Denadai, Alan R. de Oliveira, Jeferson G. Da Silva, Renata Diniz, Afshin Abrishamkar, Juliano R. Pereira, and Fernando C. de Oliveira
- Subjects
Aqueous solution ,Materials science ,Shear thinning ,Process Chemistry and Technology ,Mineralogy ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,Hydrothermal circulation ,Isothermal process ,0104 chemical sciences ,Surfaces, Coatings and Films ,Electronic, Optical and Magnetic Materials ,Shear rate ,Metal ,Viscosity ,Rheology ,Chemical engineering ,visual_art ,Materials Chemistry ,Ceramics and Composites ,visual_art.visual_art_medium ,0210 nano-technology - Abstract
The aim of the present work was to investigate the rheological properties of different iron oxides (Fe 3 O 4 , NiFe 2 O 4 , ZnFe 2 O 4 and Ni 0.5 Zn 0.5 Fe 2 O 4 ) aqueous suspensions. The oxides were produced through mixing the respective metallic sulfates within a closed isothermal reactor at 100 °C and at pH ≈12, in an oxidant environment (provided by H 2 O 2 0.63% w/v). The reactor was coupled with an adequate real-time data (RTD) acquisition system enabling measurement of temperature, pH and pressure. Obtained RTD data showed that once the isothermal conditions are reached, the pressure slowly decreases over time, which is a result of O 2 consumption through oxidation of Fe 2+ to Fe 3+ . To characterize the suspensions as a function of temperature and shear rate, the steady rheology was used. The results revealed that the effect of temperature on viscosity of all suspensions was insignificant while steady rheology showed pseudoplastic behavior for all ferrites. The magnitude of viscosity and pseudoplasticity turned out to be in agreement with the hydrodynamic diameters of particles complying with the order: NiFe 2 O 4 >Fe 3 O 4 >Ni 0.5 Zn 0.5 Fe 2 O 4 >ZnFe 2 O 4 . Finally, the rheological behavior of suspensions was attributed to the concentration of OH groups on the surface of particles and this hypothesis was effectively supported by DRX, FTIR and TGA/DTA measurements.
- Published
- 2017
15. Neutron activation of In(<scp>iii</scp>) complexes with thiosemicarbazones leads to the production of potential radiopharmaceuticals for the treatment of breast cancer
- Author
-
Raquel Gouvêa dos Santos, Lucas L. Franco, Elaine M. Souza-Fagundes, Alexandre A. Oliveira, Jeferson G. Da Silva, Gabriele de Matos Cardoso Perdigão, and Heloisa Beraldo
- Subjects
0301 basic medicine ,Chemistry ,Stereochemistry ,General Chemistry ,medicine.disease ,Catalysis ,03 medical and health sciences ,chemistry.chemical_compound ,030104 developmental biology ,0302 clinical medicine ,Breast cancer ,medicine.anatomical_structure ,030220 oncology & carcinogenesis ,Materials Chemistry ,medicine ,Cytotoxic T cell ,Selectivity ,Cytotoxicity ,Fibroblast ,Semicarbazone ,Intracellular ,Neutron activation - Abstract
In(III) complexes [In(2Ac4oClPh)2]NO3 (1) and [In(2Ac4pFPh)2]NO3·1.5H2O (2) were obtained with N(4)-ortho-chlorophenyl-2-acetylpyridine thiosemicarbazone (H2Ac4oClPh) and N(4)-para-fluorophenyl-2-acetylpyridine thiosemicarbazone (H2Ac4pFPh). Neutron activation of complexes (1) and (2), and of previously prepared [In(2Ac4oClPh)Cl2(MeOH)] (3) and [In(2Ac4pFPh)Cl2(MeOH)] (4) resulted in the formation of 114mIn/115mIn analogues (*1–*4). The cytotoxic activities of the compounds under study were investigated on MCF-7 breast cancer cells as well as against non-malignant MRC-5 fibroblast cells. Upon coordination to In(III) the cytotoxicity against MCF-7 cells significantly increased in complexes (1–4), suggesting that complexation was a good strategy to improve the cytotoxic effect. While both non-radioactive and radioactive In(III) salts were inactive against MCF-7 cells, the radioactive complexes (*1–*4) proved to be 102 to 104 times more potent than the non-radioactive analogues (1–4). For the non-radioactive In(III) complexes (1–4) the selectivity indexes (SI), defined as IC50 MRC-5/IC50 MCF-7, were SI = 0.07–0.36, while high values of SI were found for the radioactive In(III) analogues (*1–*4), SI = 46–4716, indicating that irradiation represented an interesting strategy for increasing the selectivity. Since cytotoxicity was evaluated following 48 h of treatment and 72 h after neutron activation, the observed cytotoxic effects were attributed mainly to 114mIn, the contribution of the 115mIn (t1/2 = 4.5 h) isomer being considered irrelevant. Complexes (*1–*4) induced higher levels of intracellular ROS in MCF-7 cells in comparison to the parent compounds. The results suggest that 114mIn complexes with thiosemicarbazones might show potential for application as radiopharmaceuticals for the treatment of breast cancer.
- Published
- 2017
16. Hydrophobic nanoprecipitates formed by benzoylphenylureas and β-cyclodextrin inclusion compounds: synthesis, characterization and toxicity against aedes aegypti larvae
- Author
-
Regina Gendzzelevski Kelmann, Ana Maria dos Santos Moreira, Ivana Silva Lula, Leonardo Meneghin Mendonça, Jeferson G. Da Silva, Vanessa C. E. Bittencourt, Ângelo M. L. Denadai, Antônio Frederico de Freitas Gomides, and Cibele Velloso-Rodrigues
- Subjects
0301 basic medicine ,Titration curve ,Inclusion compounds ,Endothermic process ,Article ,Benzoylphenylureas ,03 medical and health sciences ,Hydrophobic nanoprecipitate ,0302 clinical medicine ,Larvicidal activity ,Computational chemistry ,lcsh:Social sciences (General) ,lcsh:Science (General) ,chemistry.chemical_classification ,Cyclodextrins ,Multidisciplinary ,Aqueous solution ,Cyclodextrin ,Chemistry ,Chemical shift ,Intermolecular force ,030104 developmental biology ,Physical chemistry ,Proton NMR ,Thermodynamics ,Titration ,lcsh:H1-99 ,Controlled release system ,030217 neurology & neurosurgery ,lcsh:Q1-390 - Abstract
The aim of this work was to synthesize and characterize the inclusion compounds formed by the complexation of β-cyclodextrin (βCD) with insecticides from the class of benzoylphenylureas (BPUs), named novaluron (NOV) and diflubenzuron (DIF), beyond evaluate their larvicidal activity against Aedes aegypti larvae. Solid state characterization by FTIR showed changes in the main peaks of BPUs and βCD, suggesting the formation of inclusion compounds in solid phase. DTA and TGA thermal analysis showed changes in temperatures of BPUs decomposition as result of molecular interactions. 1H NMR experiments allowed to observe the occurrence of interactions in solution through changes in chemical shifts of BPUs aromatic hydrogens. However, the presence of H–H intermolecular correlations in 2D ROESY was found only for the DIF/βCD complex, suggesting different topology for each complex. Such hypothesis was corroborated by thermodynamic analysis using ITC, which showed different profile of titration curves, beyond endothermic and exothermic interactions for NOV/βCD and DIF/βCD complexes, respectively. DLS titrations of BPUs or BPUs/βCD DMSO solutions in aqueous solution demonstrated that the spontaneously formed hydrophobic nanoprecipitates (HNPs) have different profile of sizes depending on the BPU/βCD system, corroborating also with the hypothesis about the existence of different topologies for each complex. Finally, the HNPs of inclusion compounds showed to be more efficient than free BPUs, allowing proposing a new insecticide formulation.
- Published
- 2019
17. Luminescence and positron spectroscopies studies of Eu3+ complexes containing tris(2,2,6,6-tetramethyl-3,5-heptanedionate) and 2-pyrrolidone as ligands
- Author
-
W.F. Magalhães, F. Fulgêncio, Alex S. Borges, Jeferson G. Da Silva, Tatiana Ribeiro, Maria Helena Araujo, Renata Diniz, and Dario Windmöller
- Subjects
Materials science ,Positron ,Excited state ,Intramolecular force ,Annihilation radiation ,Physical chemistry ,Luminescence ,Spectroscopy ,Positronium ,Doppler broadening - Abstract
This work is reports the luminescent properties and positronium formation yields of the Eu(dpm)3 and Eu(dpm)3(2-pyr) complexes, where dpm = 2,2,6,6-tetramethyl-3,5-heptanedionato (dipivaloylmethanate) ion and 2-pyr = 2-pyrrodilidone. We present and discuss experimental intensity parameters of 4f-4f transitions in the Eu3+ complexes under UV excitation. Positron annihilation lifetime spectroscopy (PALS) and Doppler broadening of annihilation radiation lineshape (DBARL) measurements were also performed. It was observed that the photoluminescent properties and Ps formation yields of the complexes are related to intramolecular processes, such as a ligand-to-metal charge transfer (LMCT). The results, which strongly evidence the participation of molecular excited states in the positronium formation, were then discussed in terms of the recently proposed Ps formation mechanism, named cybotactic correlated system kinetic mechanism (CCSKM).This work is reports the luminescent properties and positronium formation yields of the Eu(dpm)3 and Eu(dpm)3(2-pyr) complexes, where dpm = 2,2,6,6-tetramethyl-3,5-heptanedionato (dipivaloylmethanate) ion and 2-pyr = 2-pyrrodilidone. We present and discuss experimental intensity parameters of 4f-4f transitions in the Eu3+ complexes under UV excitation. Positron annihilation lifetime spectroscopy (PALS) and Doppler broadening of annihilation radiation lineshape (DBARL) measurements were also performed. It was observed that the photoluminescent properties and Ps formation yields of the complexes are related to intramolecular processes, such as a ligand-to-metal charge transfer (LMCT). The results, which strongly evidence the participation of molecular excited states in the positronium formation, were then discussed in terms of the recently proposed Ps formation mechanism, named cybotactic correlated system kinetic mechanism (CCSKM).
- Published
- 2019
18. Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
- Author
-
Jonas Pereira Ramos, Pedro H.D.M. Prazeres, Lucas Bonfim Marques, Elaine M. Souza-Fagundes, Elisa D.L. Piló, Heloisa Beraldo, Isabella P. Ferreira, Willian R. Rocha, Angel A. Recio-Despaigne, Jacqueline A. Takahashi, and Jeferson G. Da Silva
- Subjects
Cell Survival ,Pyridines ,Stereochemistry ,Clinical Biochemistry ,Pharmaceutical Science ,Clonogenic survival ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Jurkat cells ,Colony-Forming Units Assay ,Inhibitory Concentration 50 ,Structure-Activity Relationship ,chemistry.chemical_compound ,Anti-Infective Agents ,Coordination Complexes ,Benzoylpyridinephenyl hydrazones ,Cell Line, Tumor ,Neoplasms ,Chlorocebus aethiops ,Drug Discovery ,medicine ,Animals ,Humans ,Cytotoxic T cell ,Cytotoxicity ,Vero Cells ,Molecular Biology ,Bacteria ,Cytotoxic activity ,010405 organic chemistry ,Organic Chemistry ,Hydrazones ,Bismuth(III) complexes ,Acetylpyridinephenyl hydrazones ,medicine.disease ,Antimicrobial ,0104 chemical sciences ,Leukemia ,chemistry ,Vero cell ,Molecular Medicine ,Antibacterial activity ,2-Acetylpyridine ,Bismuth - Abstract
Complexes [Bi(2AcPh)Cl2]·0.5H2O (1), [Bi(2AcpClPh)Cl2] (2), [Bi(2AcpNO2Ph)Cl2] (3), [Bi(2AcpOHPh)Cl2]·2H2O (4), [Bi(H2BzPh)Cl3]·2H2O (5), [Bi(H2BzpClPh)Cl3] (6), [Bi(2BzpNO2Ph)Cl2]·2H2O (7) and [Bi(H2BzpOHPh)Cl3]·2H2O (8) were obtained with 2-acetylpyridine phenylhydrazone (H2AcPh), its -para-chloro-phenyl- (H2AcpClPh), -para-nitro-phenyl (H2AcpNO2Ph) and -para-hydroxy-phenyl (H2AcpOHPh) derivatives, as well as with the 2-benzoylpyridine phenylhydrazone analogues (H2BzPh, H2BzpClPh, H2BzpNO2Ph, H2BzpOHPh). Upon coordination to bismuth(III) antibacterial activity against Gram-positive and Gram-negative bacterial strains significantly improved except for complex (4). The cytotoxic effects of the compounds under study were evaluated on HL-60, Jurkat and THP-1 leukemia, and on MCF-7 and HCT-116 solid tumor cells, as well as on non-malignant Vero cells. In general, 2-acetylpyridine-derived hydrazones proved to be more potent and more selective as cytotoxic agents than the corresponding 2-benzoylpyridine-derived counterparts. Exposure of HCT-116 cells to H2AcpClPh, H2AcpNO2Ph and complex (3) led to 99% decrease of the clonogenic survival. The IC50 values of these compounds were three-fold smaller when cells were cultured in soft-agar (3D) than when cells were cultured in monolayer (2D), suggesting that they constitute interesting scaffolds, which should be considered in further studies aiming to develop new drug candidates for the treatment of colon cancer.
- Published
- 2016
19. Modulation of size and viscosity of Ni/Zn ferrites: Effect of doping with βCD and chemical treatment with HNO3 and NaOH
- Author
-
Jeferson G. Da Silva, Jéssyca M.L. Corrêa, Afshin Abrishamkar, Juliano R. Pereira, Fernando C. de Oliveira, and Ângelo M. L. Denadai
- Subjects
Thixotropy ,Shear thinning ,Chemistry ,Organic Chemistry ,Mineralogy ,Analytical Chemistry ,Inorganic Chemistry ,Shear rate ,Chemical engineering ,Rheology ,Newtonian fluid ,Ferrite (magnet) ,Particle size ,Reduced viscosity ,Spectroscopy - Abstract
In this work, we have studied the rheological properties of nickel–zinc and nickel–zinc-β-cyclodextrin (Fe–Ni/Zn and Fe–Ni/Zn/βCD) ferrite suspensions as a function of temperature, solids content, shear rate and NaOH/HNO 3 concentration. The goal was to investigate the conditions where the particle size and viscosity are both lower. In both suspensions, temperature had insignificant impact on viscosity, suggesting no destructive effect on the particles. The Fe–Ni/Zn/βCD suspension exhibited lower viscosity, Newtonian profile and lower dependence of viscosity upon the solids content in comparison with Fe–Ni/Zn, which was pseudoplastic and thixotropic. These differences were ascribed to the lower particle size caused by incorporation of βCD. Considering both ferrites, HNO 3 was more efficient in reducing the particles size and viscosity than NaOH, which affected only the Fe–Ni/Zn. This behavior was rationalized in terms of chemical equilibrium of FeOOH at the surface of particles, which was supported by structural characterization as well as elementary analysis.
- Published
- 2015
20. Physical-chemical characterization of commercial honeys from Minas Gerais, Brazil
- Author
-
Wesley William Gonçalves Nascimento, André Narvaes da Rocha Campos, Juliano R. Pereira, Geraldo F. David, Ângelo M. L. Denadai, Vanessa Riani Olmi Silva, Maurício Henriques Louzada Silva, Jeferson G. Da Silva, and Fabíola Cristina de Oliveira
- Subjects
Honey Bees ,Production area ,Geography ,business.industry ,Physical chemical ,business ,Biochemistry ,Food Science ,Biotechnology - Abstract
Honey is a natural product produced by honey bees whose composition depends on factors such as climate, soil and floral source. It is one of the foods naturally produced, with a characteristic taste and considerable nutritional value. Due to the worldwide demand for large-scale production and seasonality, adulteration has become increasingly frequent. Minas Gerais is the fourth largest Brazilian state producer of honey. Considering that there are few studies on the characterization of honeys in this state and none related to its mesoregions, the objective of this study was to evaluate the physical-chemical, electrical and rheological characteristics of 48 honeys collected in 6 mesoregions of Minas Gerais, corresponding to 75% of its production area. The present study focused on characterization, investigation of the possibility of adulteration and the influence of blossom and regions on the physical-chemical, rheological and electrical properties. Statistical characterization using principal component analysis and clustering were also used. The results suggested that the samples were compatible with the identity and quality standards recommended by Brazilian legislation. Furthermore, the results from rheological analysis and impedance spectroscopy showed that there was a profile specific for each type of blossom. The use of statistical methods on physical-chemical results was a useful tool to characterize different types of honey based on the variables of each group in relation to the similarity between the samples.
- Published
- 2020
21. Hydrophobic Nanoprecipitates of β-Cyclodextrin/Avermectins Inclusion Compounds Reveal Insecticide Activity against Aedes aegypti Larvae and Low Toxicity against Fibroblasts
- Author
-
Clebio S. Nascimento, Ângelo M. L. Denadai, Ana Maria dos Santos Moreira, Vanessa C. E. Bittencourt, Gustavo Ferreira Martins, Warley de Souza Borges, Maria Elena de Lima, Keyller Bastos Borges, Jeferson G. Da Silva, Miriam T. P. Lopes, and Fábio L. S. Costa
- Subjects
Male ,Insecticides ,Magnetic Resonance Spectroscopy ,Cell Survival ,Beta-Cyclodextrins ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,chemistry.chemical_compound ,Aedes ,Animals ,Solubility ,chemistry.chemical_classification ,Aqueous solution ,Ivermectin ,Cyclodextrin ,Dimethyl sulfoxide ,beta-Cyclodextrins ,Isothermal titration calorimetry ,General Chemistry ,Nuclear magnetic resonance spectroscopy ,Fibroblasts ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,Nanostructures ,chemistry ,Larva ,Titration ,Female ,0210 nano-technology ,General Agricultural and Biological Sciences ,Hydrophobic and Hydrophilic Interactions ,Nuclear chemistry - Abstract
In the present work, hydrophobic nanoprecipitates (HNPs) of inclusion complexes formed between β-cyclodextrin (βCD) and the avermectins (AVMs) named eprinomectin (EPRI) and ivermectin (IVER) were synthesized and characterized, and their larvicidal activity against Aedes aegypti and human safety against fibroblasts were evaluated. Initially, thermogravimetric analysis/differential thermal analysis data revealed that inclusion increased the thermal stability of AVMs in the presence of βCD. Nuclear magnetic resonance experiments and density functional theory calculations pointed out the inclusion of the benzofuran ring of the two AVMs in the βCD cavity. Isothermal titration calorimetry experiments allowed identification of different binding constants for EPRI/βCD ( Kb = 1060) and βCD/IVER ( Kb = 1700) systems, despite the structural similarity. Dynamic light scattering titrations of AVMs' dimethyl sulfoxide solution in βCD aqueous solution demonstrated that the formed HNPs have lower sizes in the presence of βCD. Finally, the inclusion of EPRI in βCD increased its larval toxicity and reduced its human cytotoxicity, while for IVER/βCD no beneficial effect was observed upon inclusion. These results were rationalized in terms of structural differences between the two molecules. Finally, the EPRI/βCD complex has great potential as an insecticide against A. aegypti larvae with high human safety.
- Published
- 2018
22. Effect of coordination to antimony(III) on the antifungal activity of 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones
- Author
-
Jaqueline A. Takahashi, Isabella P. Ferreira, Jeferson G. Da Silva, Angel A. Recio-Despaigne, Heloisa Beraldo, and Elisa D.L. Piló
- Subjects
Antifungal ,biology ,Candida glabrata ,medicine.drug_class ,Stereochemistry ,Candida lusitaniae ,chemistry.chemical_element ,biology.organism_classification ,Inorganic Chemistry ,chemistry.chemical_compound ,Nystatin ,chemistry ,Antimony ,Miconazole Nitrate ,Materials Chemistry ,medicine ,Physical and Theoretical Chemistry ,2-Acetylpyridine ,Candida dubliniensis ,medicine.drug - Abstract
Antimony(III) [Sb(L)Cl2] complexes were obtained with 2-acetylpyridine-phenylhydrazone (H2AcPh), 2-acetylpyridine-para-chloro-phenylhydrazone (H2AcpClPh), 2-acetylpyridine-para-nitro-phenylhydrazone (H2AcpNO2Ph) and 2-acetylpyridine-para-hydroxy-phenylhydrazone (H2AcpOHPh) along with the 2-benzoylpyridine-phenylhydrazone analogs H2BzPh, H2BzpClPh, H2BzpNO2Ph, H2BzpOHPh (HL). [Sb(2BzpClPh)Cl2], complex (6), (IC50 = 4.91 ± 1.20 μmol L−1) was as active as nystatin (IC50 = 4.44 ± 0.76 μmol L−1) and twofold more active than H2BzpClPh (IC50 = 10.05 ± 0.67 μmol L−1) against Candida dubliniensis. While H2BzpClPh proved to be inactive against Candida glabrata, 6 (IC50 = 10.11 ± 0.64 μmol L−1) was more active than miconazole nitrate (IC50 = 19.50 ± 4.53 μmol L−1). Similarly, H2BzpNO2Ph revealed to be inactive against Candida lusitaniae whereas complex [Sb(2BzpNO2Ph)Cl2] (7) (IC50 = 8.54 ± 2.21 μmol L−1) proved to be as active as nystatin (IC50 = 5.31 ± 0.84 μmol L−1).
- Published
- 2015
23. COMPORTAMENTO TÉRMICO-REOLÓGICO DE XAROPES COMPOSTOS POR MEL E EXTRATOS NATURAIS
- Author
-
A.M.L. Denadai, Marco T. R. Alves, Rodrigo Luiz Fabri, Pâmela S. Silva, Lorrayne O. Nascimento, Clarisse L. de Assis, Leonardo Meneghin Mendonça, Juliano R. Pereira, and Jeferson G. Da Silva
- Subjects
Animal Science and Zoology - Abstract
O presente trabalho teve como objetivo avaliar o comportamento termico/reologico de tres diferentes composicoes fitoterapicas a base de mel e extratos naturais (denominadas amostras I, II e III), comercializadas na regiao de Governador Valadares – MG. Os espectros de infravermelho dos xaropes apresentaram grandes similaridades entre se a amostras puras de mel, sugerindo qualitativamente composicao quimica semelhante. Do ponto de vista fisico-quimico, as amostras I e II apresentaram comportamentos bem similares, com valores aproximados de massa seca, pH, brix, indice de refracao e tendencia de ionizacao. As amostras I e II apresentaram comportamento quase newtoniano para um ciclo ascendente-descendente de cisalhamento. A amostra III, de maior massa seca, foi a que apresentou maiores valores de viscosidade aparente alem de pseudoplasticidade e histerese reologica, os quais foram atribuidos a presenca de estrutura tridimensional do liquido. Quando diluidas em agua, apesar da brusca queda da viscosidade, as tres amostras assumiram comportamento dilatante, devido a espontânea formacao de nanoestruturas ionicas deformaveis, cujo tamanho se reduz com o aumento de temperatura.
- Published
- 2017
24. ROS-Mediated Cytotoxic Effect of Copper(II) Hydrazone Complexes against Human Glioma Cells
- Author
-
Heloisa Beraldo, Pryscila R. da Costa, Raquel Gouvêa dos Santos, Angel A. Recio Despaigne, and Jeferson G. Da Silva
- Subjects
Mutant ,Pharmaceutical Science ,chemistry.chemical_element ,Hydrazone ,Article ,Cell Line ,Analytical Chemistry ,lcsh:QD241-441 ,lcsh:Organic chemistry ,Cell Line, Tumor ,copper(II) complexes ,Glioma ,Drug Discovery ,medicine ,Humans ,Cytotoxic T cell ,Physical and Theoretical Chemistry ,Cytotoxicity ,Fibroblast ,neoplasms ,chemistry.chemical_classification ,Chemistry ,Organic Chemistry ,Hydrazones ,Wild type ,Fibroblasts ,medicine.disease ,Molecular biology ,Copper ,nervous system diseases ,medicine.anatomical_structure ,Biochemistry ,glioma cells ,Chemistry (miscellaneous) ,cytotoxicity ,ROS generation ,Molecular Medicine ,Tumor Suppressor Protein p53 ,Reactive Oxygen Species ,pyridine-derived hydrazones - Abstract
2-Acetylpyridine acetylhydrazone (H2AcMe), 2-benzoylpyridine acetylhydrazone (H2BzMe) and complexes [Cu(H2AcMe)Cl2] (1) and [Cu(H2BzMe)Cl2] (2) were assayed for their cytotoxicity against wild type p53 U87 and mutant p53 T98 glioma cells, and against MRC-5 fibroblast cells. Compounds 1 and 2 proved to be more active than the corresponding hydrazones against U87, but not against T98 cells. Compound 1 induced higher levels of ROS than H2AcMe in both glioma cell lines. H2AcMe and 1 induced lower levels of ROS in MRC5 than in U87 cells. Compound 2 induced lower levels of ROS in MRC5 than in T98 cells. The cytotoxic effect of 1 in U87 cells could be related to its ability to provoke the release of ROS, suggesting that the cytotoxicity of 1 might be somehow p53 dependent.
- Published
- 2014
25. 8-Hydroxyquinoline Schiff-base compounds as antioxidants and modulators of copper-mediated Aβ peptide aggregation
- Author
-
Rafael P. Vieira, Tim Storr, Heloisa Beraldo, Luiza M.F. Gomes, Michael R. Jones, Elaine M. Souza-Fagundes, Christine Dyrager, Michael C. P. Wang, and Jeferson G. Da Silva
- Subjects
Cell Survival ,Stereochemistry ,Trolox equivalent antioxidant capacity ,Peptide ,Crystallography, X-Ray ,Biochemistry ,Oligomer ,Inorganic Chemistry ,Jurkat Cells ,Protein Aggregates ,chemistry.chemical_compound ,Western blot ,Coordination Complexes ,medicine ,Humans ,Semicarbazone ,Schiff Bases ,Semicarbazones ,chemistry.chemical_classification ,Amyloid beta-Peptides ,Schiff base ,medicine.diagnostic_test ,Ligand ,Free Radical Scavengers ,Oxyquinoline ,chemistry ,PBT2 ,Copper - Abstract
One of the hallmarks of Alzheimer's disease (AD) in the brain are amyloid-β (Aβ) plaques, and metal ions such as copper(II) and zinc(II) have been shown to play a role in the aggregation and toxicity of the Aβ peptide, the major constituent of these extracellular aggregates. Metal binding agents can promote the disaggregation of Aβ plaques, and have shown promise as AD therapeutics. Herein, we describe the syntheses and characterization of an acetohydrazone (8-H 2 QH), a thiosemicarbazone (8-H 2 QT), and a semicarbazone (8-H 2 QS) derived from 8-hydroxyquinoline. The three compounds are shown to be neutral at pH 7.4, and are potent antioxidants as measured by a Trolox Equivalent Antioxidant Capacity (TEAC) assay. The ligands form complexes with Cu II , 8-H 2 QT in a 1:1 metal:ligand ratio, and 8-H 2 QH and 8-H 2 QS in a 1:2 metal:ligand ratio. A preliminary aggregation inhibition assay using the Aβ 1–40 peptide showed that 8-H 2 QS and 8-H 2 QH inhibit peptide aggregation in the presence of Cu II . Native gel electrophoresis/Western blot and TEM images were obtained to give a more detailed picture of the extent and pathways of Aβ aggregation using the more neurotoxic Aβ 1 −42 in the presence and absence of Cu II , 8-H 2 QH, 8-H 2 QS and the drug candidate PBT2. An increase in the formation of oligomeric species is evident in the presence of Cu II . However, in the presence of ligands and Cu II , the results match those for the peptide alone, suggesting that the ligands function by sequestering Cu II and limiting oligomer formation in this assay.
- Published
- 2014
26. Molecular and supramolecular characterization of Ni(II)/losartan hydrophobic nanoprecipitate
- Author
-
Jeferson G. Da Silva, Afshin Abrishamkar, Ângelo M. L. Denadai, Antonio S. Mangrich, Amanda A. de França, Lorrayne O. Nascimento, Pedro P. Goulart, and Jéssyca M.L. Corrêa
- Subjects
chemistry.chemical_classification ,Organic Chemistry ,Inorganic chemistry ,Supramolecular chemistry ,Nanoparticle ,Analytical Chemistry ,Coordination complex ,Inorganic Chemistry ,Metal ,chemistry ,Rheology ,visual_art ,visual_art.visual_art_medium ,Zeta potential ,Physical chemistry ,Titration ,Solubility ,Spectroscopy - Abstract
In this work, a contribution to understanding of the formation of metal(II)/losartan hydrophobic nanoprecipitate is reported. A Ni(II)/Los system was prepared and characterized in solid state and in solution. Solubility studies confirmed the formation of hydrophobic precipitate. Obtained spectroscopic data suggest a sort of coordination between tetrazolic ring as well as OH, and a D 4h geometry around the nickel cation. Thermodynamic studies demonstrated that complexation is a stepwise process, with equal enthalpic and entropic contributions for free energy of complexation. DLS and zeta potential titrations indicate the formation of stable nanoparticles of size and charge dependent on the molar ratio. Finally, rheological studies demonstrate a Bingham plastic behavior for Ni(II)/Los suspension.
- Published
- 2014
27. Cytotoxic and antimicrobial effects of indium(iii) complexes with 2-acetylpyridine-derived thiosemicarbazones
- Author
-
Alexandre A. Oliveira, Gabriele de Matos Cardoso Perdigão, Willian R. Rocha, Jeferson G. Da Silva, Jacqueline A. Takahashi, Luana E. Rodrigues, Elaine M. Souza-Fagundes, and Heloisa Beraldo
- Subjects
Models, Molecular ,Thiosemicarbazones ,Antifungal Agents ,Stereochemistry ,Molecular Conformation ,Antineoplastic Agents ,010402 general chemistry ,Candida parapsilosis ,Ligands ,01 natural sciences ,Indium ,Inorganic Chemistry ,chemistry.chemical_compound ,Inhibitory Concentration 50 ,Structure-Activity Relationship ,Cell Line, Tumor ,Organometallic Compounds ,Animals ,Humans ,Candida albicans ,Semicarbazone ,Candida ,Aqueous solution ,biology ,010405 organic chemistry ,Chemistry ,Ligand ,Candida lusitaniae ,DNA ,biology.organism_classification ,0104 chemical sciences ,Cattle ,2-Acetylpyridine ,Candida dubliniensis - Abstract
Complexes [In(2Ac4oClPh)Cl2(MeOH)] (1), [In(2Ac4pFPh)Cl2(MeOH)] (2), [In(2Ac4pClPh)Cl2(MeOH)] (3) and [In(2Ac4pIPh)Cl2(MeOH)] (4) were obtained with N(4)-ortho-chlorophenyl-2-acetylpyridine thiosemicarbazone (H2Ac4oClPh), N(4)-para-fluorophenyl-2-acetylpyridine thiosemicarbazone (H2Ac4pFPh), N(4)-para-chlorophenyl-2-acetylpyridine thiosemicarbazone (H2Ac4pClPh) and N(4)-para-iodophenyl-2-acetylpyridine thiosemicarbazone (H2Ac4pIPh). Theoretical studies suggested that the coordinated methanol molecule can be easily replaced by DMSO used in the preparation of stock solutions, with the formation of [In(L)Cl2(DMSO)] (HL = thiosemicarbazonate ligand), and that the replacement of DMSO by water is unfavorable. However, for all complexes the displacement of one or two chloride ligands by water in aqueous solution is extremely favorable. The cytotoxic activity of the compounds was evaluated against HL-60, Jurkat and THP-1 leukemia and against MDA-MB-231 and HCT-116 solid tumor cell lines, as well as against Vero non-malignant cells. The cytotoxicity and selectivity indexes (SI) increased in several cases for the indium(III) complexes in comparison with the free thiosemicarbazones. The antimicrobial activity of the compounds was investigated against Candida albicans, Candida dubliniensis, Candida lusitaniae and Candida parapsilosis. In many cases complexation resulted in a substantial increase of the antifungal activity. Complexes (1–4) were revealed to be very active against C. lusitaniae and C. dubliniensis. Structure–activity relationship (SAR) studies were carried out to identify the physico-chemical properties that might be involved in the antifungal action, as well as in the cytotoxic effect of the compounds against HL-60 cells. In both cases, correlations between the bioactivity and physico-chemical properties did not appreciably change when the chloride ligands in [In(L)Cl2(DMSO)] were replaced by water molecules, suggesting [In(L)Cl(H2O)(DMSO)]+ or [In(L)(H2O)2(DMSO)]2+ to be the species that interact with the biological media.
- Published
- 2016
28. Investigation on the bioactivities of clioquinol and its bismuth(III) and platinum(II,IV) complexes
- Author
-
Enrique J. Baran, Karina S.O. Ferraz, Elaine M. Souza-Fagundes, Heloisa Beraldo, Débora C. Reis, and Jeferson G. Da Silva
- Subjects
Cisplatin ,biology ,Stereochemistry ,Chemistry ,Clioquinol ,chemistry.chemical_element ,biology.organism_classification ,Jurkat cells ,Inorganic Chemistry ,Cell culture ,Materials Chemistry ,medicine ,Cytotoxic T cell ,Physical and Theoretical Chemistry ,Cytotoxicity ,Candida albicans ,Platinum ,medicine.drug - Abstract
Complexes [Bi(HCQ)2(H2O)Cl3] (1), [Pt(CQ)2]·2KCl (2) and [Pt(CQ)2Cl2]·KCl (3) were obtained with 5-chloro-7-iodo-8-hydroxyquinoline, “clioquinol”, HCQ. Upon coordination to bismuth(III) the antimicrobial activity improved. Complex (1) was 70-fold more active than fluconazole against Candida albicans. HCQ proved to be cytotoxic to HL-60 and Jurkat human leukemia cells. Although coordination to bismuth(III) did not result in significant modification of HCQ’s cytotoxic effect, on coordination to platinum(II, IV) cytotoxicity improved against both cell lines. Complexes (2) and (3) were more active than HCQ against HL-60 cells. Complex (2) also revealed to be the most cytotoxic compound against Jurkat cells, being fivefold more active than cisplatin. Although HCQ and 1 did not show a pro-apoptotic effect, 2 and 3 presented moderate pro-apoptotic activity.
- Published
- 2013
29. Chalcone-derived thiosemicarbazones and their zinc(II) and gallium(III) complexes: spectral studies and antimicrobial activity
- Author
-
Jeferson G. Da Silva, Camila C.H. Perdigao, Heloisa Beraldo, and Nivaldo L. Speziali
- Subjects
Chalcone ,biology ,Pseudomonas aeruginosa ,Stereochemistry ,chemistry.chemical_element ,Zinc ,medicine.disease_cause ,Antimicrobial ,biology.organism_classification ,chemistry.chemical_compound ,chemistry ,Staphylococcus aureus ,Materials Chemistry ,medicine ,Physical and Theoretical Chemistry ,Gallium ,Candida albicans ,Semicarbazone ,Nuclear chemistry - Abstract
Chalcone-derived 3-phenyl-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCTPh) (1), 3-(4-chlorophenyl)-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4ClPh) (2), 3-(4-bromophenyl)-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4BrPh) (3), and 3-(4-nitrophenyl-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4NO2Ph) (4) were obtained as well as their gallium(III) and zinc(II) complexes [Ga(PyCTPh)2]NO3 (Ga1), [Ga(PyCT4ClPh)2]NO3 (Ga2), [Ga(PyCT4BrPh)2]NO3 (Ga3), [Ga(PyCT4NO2Ph)2]NO3 (Ga4), [Zn(PyCTPh)2] (Zn1), [Zn(PyCT4ClPh)2] (Zn2), [Zn(PyCT4BrPh)2] (Zn3), and [Zn(PyCT4NO2Ph)2] (Zn4). The chalcones, thiosemicarbazones, and zinc(II) complexes were not active against Pseudomonas aeruginosa. The thiosemicarbazones proved to be more active than the parent chalcones against Staphylococcus aureus and Candida albicans. Coordination to zinc(II) resulted in activity improvement of most thiosemicarbazones against S. aureus. Coordination to gallium(III) significantly improved the antimicrobia...
- Published
- 2013
30. Phthalazine-triones: Calix[4]arene-assisted synthesis using green solvents and their anticancer activities against human cancer cells
- Author
-
Daniel L. da Silva, Jeferson G. Da Silva, Sergio Antonio Fernandes, Ângelo de Fátima, Cleiton Moreira da Silva, Yuri F. Rego, Ana Lúcia Tasca Gois Ruiz, and João E. de Carvalho
- Subjects
Green chemistry ,Chemistry(all) ,General Chemical Engineering ,Antiproliferative activity ,Sulfonic acid ,010402 general chemistry ,01 natural sciences ,Catalysis ,lcsh:Chemistry ,chemistry.chemical_compound ,Dimedone ,Organic chemistry ,Ethyl lactate ,p-Sulfonic acid calix[4]arene ,chemistry.chemical_classification ,010405 organic chemistry ,General Chemistry ,Combinatorial chemistry ,0104 chemical sciences ,Solvent ,lcsh:QD1-999 ,chemistry ,Cancer cell ,Chemical Engineering(all) ,Microwave assisted synthesis ,Phthalazine - Abstract
Fourteen phthalazine-triones bearing different substituents at C-4 position were synthesized through multicomponent reactions (MCR) by using phthalhydrazide, dimedone and diferent aldehydes as starting materials, p-sulfonic acid calix[4]arene as catalyst and ethyl lactate as solvent under microwave irradiation. Compounds 7–16 were obtained in excellent to moderate yields (94–51%) in only 10 min of reaction using this methodology. The antiproliferative activity against cancer cells was disclosed, for the first time, for synthesized compounds. The capacity of all compounds to inhibit cancer cells growth was dependent on the histological origin of cells. Compound 20 was active against more than one strain. Keywords: Catalysis, Green chemistry, Microwave assisted synthesis, Antiproliferative activity, p-Sulfonic acid calix[4]arene
- Published
- 2016
- Full Text
- View/download PDF
31. Metal complexes of 3-(4-bromophenyl)-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone: cytotoxic activity and investigation on the mode of action of the gold(III) complex
- Author
-
Jonas Pereira Ramos, Silvia Castelli, Luciana B.P. Sâmia, Alessandro Desideri, Venn Vutey, Elaine M. Souza-Fagundes, Jeferson G. Da Silva, Heloisa Beraldo, and Gabrieli L. Parrilha
- Subjects
Pyridines ,Thioredoxin reductase ,Cytotoxic activities ,Type I ,Drug Screening Assays ,01 natural sciences ,Thiosemicarbazone ,chemistry.chemical_compound ,Chalcone ,Coordination Complexes ,Topoisomerase IB ,Cytotoxic T cell ,Enzyme Inhibitors ,Tumor ,biology ,Molecular Structure ,Metals and Alloys ,DNA Topoisomerases, Type I ,Monocytic leukemia ,Drug ,General Agricultural and Biological Sciences ,Thiosemicarbazones ,Thioredoxin-Disulfide Reductase ,Stereochemistry ,Cell Survival ,Antineoplastic Agents ,010402 general chemistry ,General Biochemistry, Genetics and Molecular Biology ,Cell Line ,Biomaterials ,Dose-Response Relationship ,Structure-Activity Relationship ,Metal complexes ,Cell Line, Tumor ,Structure–activity relationship ,Humans ,Cell Proliferation ,Dose-Response Relationship, Drug ,Drug Screening Assays, Antitumor ,Settore BIO/10 ,Semicarbazone ,010405 organic chemistry ,Topoisomerase ,Active site ,Antitumor ,0104 chemical sciences ,chemistry ,biology.protein ,DNA Topoisomerases - Abstract
Complexes [Au(PyCT4BrPh)Cl]Cl (1), [Pt(PyCT4BrPh)Cl]0.5KCl (2), and [Pd(PyCT4BrPh)Cl]KCl (3) were obtained with 3-(4-bromophenyl)-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4BrPh). Although complexes (2) and (3) did not exhibit potent cytotoxic activity, HPyCT4BrPh and its gold(III) complex (1) proved to be highly cytotoxic against HL-60 (human promyelocytic leukemia) and THP-1 (human monocytic leukemia) cells, and against MDA-MB 231 and MCF-7 (human breast adenocarcinoma) solid tumor cells. Except for HL-60 cells, upon coordination to gold(III) a 2- to 3-fold increase in the cytotoxic effect was observed. An investigation on the possible biological targets of the gold(III) complex was carried out. Complex (1) but not the free thiosemicarbazone inhibits the enzymatic activity of thioredoxin reductase (TrxR). The affinity of 1 for TrxR suggests metal binding to a selenol residue in the active site of the enzyme. While HPyCT4BrPh was inactive, 1 was able to inhibit topoisomerase IB (Topo IB) activity. Hence, inhibition of TrxR and Topo IB could contribute to the mechanism of cytotoxic action of complex (1).
- Published
- 2016
32. Coordination of Thiosemicarbazones and Bis(thiosemicarbazones) to Bismuth(III) as a Strategy for the Design of Metal‐Based Antibacterial Agents
- Author
-
Lúcia T. Paradizzi, Heloisa Beraldo, Mariany de Fátima A. Carvalho, Sarah A. Siqueira, Josane A. Lessa, Débora C. Reis, Jeferson G. Da Silva, and Nayane F. Silva
- Subjects
Models, Molecular ,Thiosemicarbazones ,Staphylococcus aureus ,Magnetic Resonance Spectroscopy ,Stereochemistry ,chemistry.chemical_element ,Bioengineering ,Microbial Sensitivity Tests ,Crystallography, X-Ray ,medicine.disease_cause ,Biochemistry ,Medicinal chemistry ,Enterococcus faecalis ,Bismuth ,Metal ,chemistry.chemical_compound ,Coordination Complexes ,Staphylococcus epidermidis ,medicine ,Molecular Biology ,Semicarbazone ,Bacteria ,Molecular Structure ,biology ,Pseudomonas aeruginosa ,General Chemistry ,General Medicine ,biology.organism_classification ,Anti-Bacterial Agents ,chemistry ,visual_art ,visual_art.visual_art_medium ,Molecular Medicine ,Antibacterial activity ,Enterococcus - Abstract
Complexes [Bi(2Fo4Ph)Cl(2)] (1), [Bi(2Ac4Ph)Cl(2)] (2), [Bi(2Bz4Ph)Cl(2)] (3), [Bi(H(2)Gy3DH)Cl(3)] (4), [Bi(H(2)Gy4Et)(OH)(2)Cl] (5), and [Bi(H(2)Gy4Ph)Cl(3)] (6) were prepared with pyridine-2-carbaldehyde 4-phenylthiosemicarbazone (H2Fo4Ph), 1-(pyridin-2-yl)ethanone 4-phenylthiosemicarbazone (H2Ac4Ph), phenyl(pyridin-2-yl)methanone 4-phenylthiosemicarbazone (H2Bz4Ph), as well as with glyoxaldehyde bis(thiosemicarbazone) (H(2)Gy4DH) and its 4-Et (H(2)Gy4Et) and 4-Ph (H(2)Gy4Ph) derivatives. The complexes exhibited antibacterial activities against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, and Pseudomonas aeruginosa. Coordination to Bi(III) proved to be an effective strategy to increase the antibacterial activity of the thiosemicarbazones and bis(thiosemicarbazones).
- Published
- 2012
33. Investigation on the pharmacological profile of 2,6-diacetylpyridine bis(benzoylhydrazone) derivatives and their antimony(III) and bismuth(III) complexes
- Author
-
Luana F. de Miranda, Karina S.O. Ferraz, Elaine M. Souza-Fagundes, Jeferson G. Da Silva, Heloisa Beraldo, Isolda C. Mendes, Nayane F. Silva, and Carla F.D. Romeiro
- Subjects
Antimony ,Pyridines ,Stereochemistry ,HL60 ,chemistry.chemical_element ,Antineoplastic Agents ,Microbial Sensitivity Tests ,Crystal structure ,Medicinal chemistry ,Breast tumor ,Bismuth ,chemistry.chemical_compound ,Anti-Infective Agents ,Cell Line, Tumor ,Candida albicans ,Drug Discovery ,Organometallic Compounds ,Animals ,Humans ,Cytotoxicity ,Pharmacology ,Bacteria ,Organic Chemistry ,General Medicine ,Antimicrobial ,Peripheral blood ,chemistry - Abstract
Complexes [Sb(HAcPh)Cl(2)] (1), [Sb(HAcpClPh)Cl(2)] (2), [Sb(HAcpNO(2)Ph)Cl(2)] (3) and [Bi(HAcPh)Cl(2)] (4), [Bi(HAcpClPh)Cl(2)] (5), [Bi(HAcpNO(2)Ph)Cl(2)] (6) were obtained with 2,6-diacetylpyridine bis(benzoylhydrazone) (H(2)AcPh), 2,6-diacetylpyridine bis(para-chlorobenzoylhydrazone) (H(2)AcpClPh), and 2,6-diacetylpyridine bis(para-nitrobenzoylhydrazone) (H(2)AcpNO(2)Ph). The bis(benzoylhydrazones) were inactive as antimicrobial agents against gram-positive and gram-negative bacteria and against Candida albicans but upon coordination to antimony(III) and bismuth(III) antimicrobial activity was demonstrated. The studied compounds were tested for their cytotoxic activities against Jurkat and HL60 (leukemia), MCF-7 (breast tumor), HCT-116 (colorectal carcinoma) and peripheral blood mononuclear (PBMC) cells. All bis(benzoylhydrazones) proved to be poorly cytotoxic. Upon coordination of the bis(benzoylhydrazones) to antimony(III) and bismuth(III) cytotoxicity significantly improved. Complex (5) presented high therapeutic indexes (TI = 11-508) against all cell lineages.
- Published
- 2012
34. N4-Phenyl-substituted 2-acetylpyridine thiosemicarbazones: Cytotoxicity against human tumor cells, structure–activity relationship studies and investigation on the mechanism of action
- Author
-
Heloisa Beraldo, Josane A. Lessa, Marcella A. Soares, Billy W. Day, Andreas Vogt, Adriano D. Andricopulo, Hikmat N. Daghestani, Lívia B. Salum, Raquel Gouvêa dos Santos, Jorge L. Pesquero, Jeferson G. Da Silva, Isolda C. Mendes, and Willian R. Rocha
- Subjects
Programmed cell death ,Stereochemistry ,Cytotoxicity ,Clinical Biochemistry ,Pharmaceutical Science ,Biochemistry ,chemistry.chemical_compound ,Breast cancer ,Tubulin ,Drug Discovery ,medicine ,Cytotoxic T cell ,Structure–activity relationship ,Molecular Biology ,Semicarbazone ,Medicine(all) ,biology ,Organic Chemistry ,Mechanism of action ,chemistry ,Cell culture ,2-Acetylpyridine thiosemicarbazones ,NEOPLASIAS ,biology.protein ,Molecular Medicine ,medicine.symptom ,Glioblastoma - Abstract
N(4)-Phenyl 2-acetylpyridine thiosemicarbazone (H2Ac4Ph; N-(phenyl)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide) and its N(4)-ortho-, -meta- and -para-fluorophenyl (H2Ac4oFPh, H2Ac4mFPh, H2Ac4pFPh), N(4)-ortho-, -meta- and -para-chlorophenyl (H2Ac4oClPh, H2Ac4mClPh, H2Ac4pClPh), N(4)-ortho-, -meta- and -para-iodophenyl (H2Ac4oIPh, H2Ac4mIPh, H2Ac4pIPh) and N(4)-ortho-, -meta- and -para-nitrophenyl (H2Ac4oNO(2)Ph, H2Ac4mNO(2)Ph, H2Ac4pNO(2)Ph) derivatives were assayed for their cytotoxicity against human malignant breast (MCF-7) and glioma (T98G and U87) cells. The compounds were highly cytotoxic against the three cell lineages (IC(50): MCF-7, 52-0.16 nM; T98G, 140-1.0 nM; U87, 160-1.4 nM). All tested thiosemicarbazones were more cytotoxic than etoposide and did not present any haemolytic activity at up to 10(-5)M. The compounds were able to induce programmed cell death. H2Ac4pClPh partially inhibited tubulin assembly at high concentrations and induced cellular microtubule disorganization.
- Published
- 2012
35. Structural studies on acetophenone- and benzophenone-derived thiosemicarbazones and their zinc(II) complexes
- Author
-
Heloisa Beraldo, Jeferson G. Da Silva, Nayane F. Silva, Isolda C. Mendes, Nivaldo L. Speziali, and Karina S.O. Ferraz
- Subjects
Organic Chemistry ,chemistry.chemical_element ,Zinc ,Crystal structure ,Medicinal chemistry ,Analytical Chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,Benzophenone ,Acetone ,Organic chemistry ,Semicarbazone ,Spectroscopy ,Acetophenone - Abstract
In the present work N(3)-meta-chlorophenyl-(HAc3mCl, 1) and N(3)-meta-fluorphenyl-(HAc3mF, 2) acetophenone thiosemicarbazone, and N(3)-meta-chlorophenyl-(HBz3mCl, 3) and N(3)-meta-fluorphenyl-(HBz3mF, 4) benzophenone thiosemicarbazone were obtained, as well as their zinc(II) complexes [Zn(Ac3mCl)2] (5), [Zn(Ac3mF)2] (6), [Zn(Bz3mCl)2] (7) and [Zn(Bz3mF)2] (8). Upon re-crystallization in DMSO:acetone conversion of 8 into [Zn(Bz3mF)2]·(DMSO) (8a) occurred. The crystal structures of 2, 5 and 8a were determined.
- Published
- 2012
36. Pyridine-derived thiosemicarbazones and their tin(IV) complexes with antifungal activity against Candida spp
- Author
-
Nivaldo L. Speziali, Roberta P. Dias, Ludmila Ferreira Gouveia, Alan Kiill Gasparoto, Heloisa Beraldo, Jeferson G. Da Silva, Daniel Assis Santos, Gabrieli L. Parrilha, and Willian R. Rocha
- Subjects
Models, Molecular ,Thiosemicarbazones ,Antifungal Agents ,Pyridines ,Stereochemistry ,Microbial Sensitivity Tests ,Crystallography, X-Ray ,Candida parapsilosis ,Structure-Activity Relationship ,chemistry.chemical_compound ,Minimum inhibitory concentration ,Candida krusei ,Drug Discovery ,Organometallic Compounds ,medicine ,Candida albicans ,Semicarbazone ,Candida ,Pharmacology ,Molecular Structure ,biology ,Candida glabrata ,Organic Chemistry ,Stereoisomerism ,General Medicine ,biology.organism_classification ,Corpus albicans ,chemistry ,Tin ,Fluconazole ,medicine.drug - Abstract
[(n-Bu)Sn(2Ac4oClPh)Cl2] (1), [(n-Bu)Sn(2Ac4oFPh)Cl2] (2), [(n-Bu)Sn(2Ac4oNO2Ph)Cl2] (3), [(n-Bu)Sn(2Bz4oClPh)Cl2] (4), [(n-Bu)Sn(2Bz4oFPh)Cl2] (5) and [(n-Bu)Sn(2Bz4oNO2Ph)Cl2] (6) were obtained by reacting [(n-Bu)SnCl3] with 2-acetylpyridine-N4-orthochlorophenyl thiosemicarbazone (H2Ac4oClPh), 2-acetylpyridine-N4-orthofluorphenyl thiosemicarbazone (H2Ac4oFPh), 2-acetylpyridine-N4-orthonitrophenyl thiosemicarbazone (H2Ac4oNO2Ph), and with the corresponding 2-benzoylpyridine-derived thiosemicarbazones (H2Bz4oClPh, H2ABz4oFPh and H2Bz4oNO2Ph). The antifungal activity of the studied compounds was evaluated against several Candida species. Upon coordination of H2Bz4oNO2Ph to tin in complex (6) the antifungal activity increased three times against Candida albicans and Candida krusei and six times against Candida glabrata and Candida parapsilosis. The minimum inhibitory concentration (MIC) values of H2Ac4oNO2Ph and its complex (3) against C. albicans, C. parapsilosis and C. glabrata are similar to that of fluconazole. All studied compounds were more active than fluconazole against C. krusei.
- Published
- 2011
37. Increasing the antibacterial activity of gallium(III) against Pseudomonas aeruginosa upon coordination to pyridine-derived thiosemicarbazones
- Author
-
Solange M. S. V. Wardell, James L. Wardell, Jeferson G. Da Silva, Lucas S. Azzolini, and Heloisa Beraldo
- Subjects
Gallium nitrate ,Stereochemistry ,Ligand ,chemistry.chemical_element ,Crystal structure ,Medicinal chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,Pyridine ,Materials Chemistry ,medicine ,Chelation ,Physical and Theoretical Chemistry ,Gallium ,Antibacterial activity ,Semicarbazone ,medicine.drug - Abstract
Reaction of N(4)-phenyl-2-formylpyridine thiosemicarbazone (H2Fo4Ph), N(4)-phenyl-2-acetylpyridine thiosemicarbazone (H2Ac4Ph) and N(4)-phenyl-2-benzoylpyridine thiosemicarbazone (H2Bz4Ph) with gallium nitrate gave [Ga(H2Fo4Ph)2](NO3)3 (1), [Ga(2Ac4Ph)2]NO3 (2) and [Ga(2Bz4Ph)2]NO3 (3). In all complexes coordination of the thiosemicarbazone via the Npy–N–S chelating system occurs. In 1 the thiosemicarbazone acts as a neutral ligand while in 2 and 3 the ligand is anionic. Upon slow diffusion of 2 in DMSO [Ga(2Ac4Ph)2]NO3·DMSO (2a) was formed. The crystal structure of 2a was determined. Upon coordination the antibacterial activity of both gallium and thiosemicarbazones against Pseudomonas aeruginosa significantly increases.
- Published
- 2009
38. Zinc(II) complexes of 2-pyridine-derived N (4)- p -tolyl thiosemicarbazones: study of in vitro antibacterial activity
- Author
-
Heloisa Beraldo, Jeferson G. Da Silva, Solange M. S. V. Wardell, and James L. Wardell
- Subjects
chemistry.chemical_compound ,chemistry ,Stereochemistry ,Pyridine ,Materials Chemistry ,chemistry.chemical_element ,Zinc ,Physical and Theoretical Chemistry ,Antibacterial activity ,Semicarbazone ,Medicinal chemistry ,In vitro - Abstract
Reaction of N(4)-p-tolyl-2-formylpyridine thiosemicarbazone (H2Fo4pT), N(4)-p-tolyl-2-acetylpyridine thiosemicarbazone (H2Ac4pT), and N(4)-p-tolyl-2-benzoylpyridine thiosemicarbazone (H2Bz4pT) with ZnCl2 gave [Zn(H2Fo4pT)Cl2] (1), [Zn(H2Ac4pT)Cl2] (2), and [Zn(H2Bz4pT)Cl2] (3). In the first two complexes a tridentate Npy–N–S thiosemicarbazone binds to the zinc while in the latter N–S coordination occurs. Upon coordination the antibacterial activity against Salmonella typhimurium increases in 1 and 3.
- Published
- 2009
39. Copper(II) and zinc(II) complexes with 2-benzoylpyridine-methyl hydrazone
- Author
-
Eduardo E. Castellano, Ana Cerúlia M. do Carmo, Heloisa Beraldo, Jeferson G. Da Silva, Angel A. Recio Despaigne, and Oscar E. Piro
- Subjects
chemistry.chemical_classification ,Coordination sphere ,ESPECTROSCOPIA (ESTUDO) ,Stereochemistry ,Ligand ,Organic Chemistry ,Hydrazone ,chemistry.chemical_element ,Zinc ,Crystal structure ,Copper ,Analytical Chemistry ,Inorganic Chemistry ,Deprotonation ,chemistry ,Polymer chemistry ,Chelation ,Spectroscopy - Abstract
2-Benzoylpyridine-methyl hydrazone (HBzMe) has been obtained as well as its copper(II) [Cu(HBzMe)Cl2] (1) and zinc(II) [Zn(HBzMe)Cl2] (2) complexes. Upon re-crystallization in 1 – 9 DMSO:acetone conversion of 1 into dimeric [Cu(BzMe)Cl]2 (1a) occurred. The crystal structures of HBzMe, 1, 1a, and 2 were determined. HBzMe adopts the ZE conformation in the solid. In all complexes the hydrazone adopts the E configuration to attach to the metal through the Npy N2 O chelating system. In 1 and 2 a neutral hydrazone coordinates to the metal center while in 1a deprotonation occurs with coordination of an anionic ligand. 1a presents a dimeric structure, having two copper(II) ions per asymmetric unit. Two chlorides are also present in the copper coordination sphere, which act as bridging ligands and connect the copper centers to each other.
- Published
- 2009
40. Oxovanadium(IV) and (V) complexes of acetylpyridine-derived semicarbazones exhibit insulin-like activity
- Author
-
Ana Mena Barreto Bastos, Heloisa Beraldo, Alzir A. Batista, Pedro I. S. Maia, Elke Niquet, Adaliene Versiani Matos Ferreira, Jeferson G. Da Silva, Victor M. Deflon, and Leida Maria Botion
- Subjects
Stereochemistry ,Glycerol release ,Glucose uptake ,Insulin ,medicine.medical_treatment ,Vanadium ,chemistry.chemical_element ,Crystal structure ,Oxovanadium IV ,Medicinal chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,Materials Chemistry ,medicine ,Physical and Theoretical Chemistry ,Acetonitrile ,Semicarbazone - Abstract
Reaction of 2-acetylpyridine semicarbazone (H2APS), 3-acetylpyridine semicarbazone (H3APS) and 4-acetylpyridine semicarbazone (H4APS) with [VO(acac)2] (acac = acetylacetonate) gave [VO(H2APS)(acac)2] (1), [VO(H3APS)(acac)2] (2) and [VO(4APS)(acac)(H2O)] · 1/2H2O (3). Oxidation of complex 1 in acetonitrile gave [VO2(2APS)] (4). The crystal structures of complexes 1 and 4 have been determined. Complexes 1–3 were able to enhance glucose uptake and to inhibit glycerol release from adipocytes, which indicate their potential to act as insulin-mimics.
- Published
- 2008
41. Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in Vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages
- Author
-
Maria Norma Melo, Filipe Moan Berbet, Frédéric Frézard, Arshad Islam, Cynthia Demicheli, Sydnei Magno da Silva, Bernardo L. Rodrigues, Heloisa Beraldo, and Jeferson G. Da Silva
- Subjects
Antimony ,Staphylococcus aureus ,crystal structure ,organoantimony(V) ,organobismuth(V) ,carboxylate ,cytotoxicity ,antileishmanial ,antibacterial ,Stereochemistry ,Pharmaceutical Science ,Crystal structure ,Ligands ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,Metal ,Mice ,chemistry.chemical_compound ,Deprotonation ,lcsh:Organic chemistry ,Terphenyl Compounds ,Drug Discovery ,Organometallic Compounds ,Animals ,Carboxylate ,Leishmania infantum ,Physical and Theoretical Chemistry ,Antibacterial agent ,Benzoic acid ,Chemistry ,Macrophages ,Organic Chemistry ,Benzoic Acid ,Anti-Bacterial Agents ,Trigonal bipyramidal molecular geometry ,Chemistry (miscellaneous) ,visual_art ,Pseudomonas aeruginosa ,visual_art.visual_art_medium ,Molecular Medicine ,Selectivity - Abstract
Two novel organoantimony(V) and two organobismuth(V) complexes of the type ML2 were synthesized, with L = acetylsalicylic acid (HL1) or 3-acetoxybenzoic acid (HL2) and M = triphenylantimony(V) (M1) or triphenylbismuth(V) (M2). Complexes, [M1(L1)2] (1), [M1(L2)2]∙CHCl3 (2), [M2(L1)2], (3) and [M2(L2)2] (4), were characterized by elemental analysis, IR and NMR. Crystal structures of triphenylantimony(V) dicarboxylate complexes 1 and 2 were determined by single crystal X-ray diffraction. Structural analyses revealed that 1 and 2 adopt five-coordinated extremely distorted trigonal bipyramidal geometries, binding with three phenyl groups in the equatorial position and two deprotonated organic ligands (L) in the axial sites. The metal complexes, their metal salts and ligands were evaluated in vitro for their activities against Leishmania infantum and amazonensis promastigotes and Staphylococcus aureus and Pseudomonas aeruginosa bacteria. Both the metal complexes showed antileishmanial and antibacterial activities but the bismuth complexes were the most active. Intriguingly, complexation of organobismuth(V) salt reduced its activity against Leishmania, but increased it against bacteria. In vitro cytotoxic test of these complexes against murine macrophages showed that antimony(V) complexes were the least toxic. Considering the selectivity indexes, organoantimony(V) complexes emerge as the most promising antileishmanial agents and organobismuth(V) complex 3 as the best antibacterial agent.
- Published
- 2014
- Full Text
- View/download PDF
42. Synthesis, crystal structure and luminescence properties of the Ln(III)-picrate complexes with 1-ethyl-3-methylimidazolium as countercations
- Author
-
Jeferson G. Da Silva, Hermi F. Brito, Maria Helena Araujo, Alex S. Borges, Nivaldo L. Speziali, José Diogo L. Dutra, and José D. Ayala
- Subjects
Lanthanide ,Luminescence ,Picrate ,Inorganic chemistry ,Molar conductivity ,Infrared spectroscopy ,Ionic Liquids ,Crystal structure ,Crystallography, X-Ray ,Lanthanoid Series Elements ,Analytical Chemistry ,LANTANÍDIOS ,chemistry.chemical_compound ,Picrates ,Molecule ,Instrumentation ,Spectroscopy ,Imidazoles ,Tricapped trigonal prismatic molecular geometry ,Models, Theoretical ,Atomic and Molecular Physics, and Optics ,chemistry ,Energy Transfer ,Models, Chemical ,Physical chemistry ,Crystallization - Abstract
New anionic complexes of lanthanide picrates containing 1-ethyl-3-methylimidazolium (EMIm) as countercation have been prepared. The Ln(III) complexes were characterized by complexometric titration, elemental analyses, infrared spectroscopy and molar conductivity. The molecular structures of the (EMIm)2[Ln(Pic)4(H2O)2]Pic complexes, Ln(III)=Sm, Eu, Gd and Tb, and Pic=picrate, were determined by X-ray crystallography. In these structures the picrate anion appears in three forms: as uncoordinated counteranion, as monodentated and bidentate ligand. The coordination polyhedron around the Ln(III) atom can be described as tricapped trigonal prismatic molecular geometry. The theoretical molecular structures of the complexes were also calculated using the Sparkle/PM3 model for Ln(III) complexes, allowing analysis of intramolecular energy transfer processes of the Eu(III) compound. The spectroscopic properties of the 4f(6) intraconfigurational transitions of the Eu(III) complex were then studied experimentally and theoretically. The low value of emission quantum efficiency of (5)D0 emitting level (η) of Eu(III) ion (ca. 10%) is due to the vibrational modes of the water molecule that act as luminescence quenching. In addition, the luminescence decay curves, the experimental intensity parameters (Ωλ), lifetimes (τ), radiative (Arad) and non-radiative (Anrad) decay rates, theoretical quantum yield (q) were also determined and discussed.
- Published
- 2014
43. Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi
- Author
-
Heloisa Beraldo, Camila F Vilela, Jacqueline A. Takahashi, Nayane F. Silva, Débora C. Reis, Angel A. Recio Despaigne, Jeferson G. Da Silva, and Isolda C. Mendes
- Subjects
Crops, Agricultural ,Models, Molecular ,Thiosemicarbazones ,Nystatin ,Antifungal Agents ,Stereochemistry ,Molecular Conformation ,Pharmaceutical Science ,Cladosporium cladosporioides ,Hydrazone ,Microbial Sensitivity Tests ,imidazole ,hydrazones ,thiosemicarbazones ,antifungal activity ,Hydrazide ,Medicinal chemistry ,Article ,Analytical Chemistry ,Benzaldehyde ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,X-Ray Diffraction ,Drug Discovery ,Candida albicans ,Imidazole ,Physical and Theoretical Chemistry ,Semicarbazone ,Plant Diseases ,chemistry.chemical_classification ,biology ,Candida glabrata ,Organic Chemistry ,Hydrazones ,Imidazoles ,Hydrogen Bonding ,biology.organism_classification ,chemistry ,Chemistry (miscellaneous) ,Molecular Medicine ,Cladosporium ,Acetophenone ,Aspergillus flavus - Abstract
New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehyde-para-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-para-nitrobenzoyl hydrazone (4(5)ImpNO2Ph), 4-(imidazole-1-yl)acetophenone-para-chloro-benzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitro-benzoylhydrazone (4ImAcpNO2Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO2Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.
- Published
- 2013
- Full Text
- View/download PDF
44. N(4)-tolyl-2-acetylpyridine thiosemicarbazones and their platinum(II,IV) and gold(III) complexes: cytotoxicity against human glioma cells and studies on the mode of action
- Author
-
Heloisa Beraldo, Jeferson G. Da Silva, Raquel Gouvêa dos Santos, Karina S.O. Ferraz, Bruno Melo Mendes, Bernardo L. Rodrigues, and Flávia Mesquita Costa
- Subjects
Models, Molecular ,Thiosemicarbazones ,Auranofin ,Organoplatinum Compounds ,Stereochemistry ,Thioredoxin reductase ,chemistry.chemical_element ,Antineoplastic Agents ,General Biochemistry, Genetics and Molecular Biology ,Biomaterials ,chemistry.chemical_compound ,Structure-Activity Relationship ,medicine ,Tumor Cells, Cultured ,Humans ,Cytotoxicity ,Mode of action ,Semicarbazone ,Cell Proliferation ,Cisplatin ,Cell Death ,Dose-Response Relationship, Drug ,Molecular Structure ,Chemistry ,Metals and Alloys ,Glioma ,Drug Screening Assays, Antitumor ,General Agricultural and Biological Sciences ,Platinum ,2-Acetylpyridine ,Organogold Compounds ,medicine.drug - Abstract
Complexes [Au(2Ac4oT)Cl][AuCl2] (1), [Au(Hpy2Ac4mT)Cl2]Cl·H2O (2), [Au(Hpy2Ac4pT)Cl2]Cl (3), [Pt(H2Ac4oT)Cl]Cl (4), [Pt(2Ac4mT)Cl]·H2O (5), [Pt(2Ac4pT)Cl] (6) and [Pt(L)Cl2OH], L = 2Ac4mT (7), 2Ac4oT (8), 2Ac4pT (9) were prepared with N(4)-ortho- (H2Ac4oT), N(4)-meta- (H2Ac4mT) and N(4)-para- (H2Ac4pT) tolyl-2-acetylpyridine thiosemicarbazone. The cytotoxic activities of all compounds were assayed against U-87 and T-98 human malignant glioma cell lines. Upon coordination cytotoxicity improved in 2, 5 and 8. In general, the gold(III) complexes were more cytotoxic than those with platinum(II,IV). Several of these compounds proved to be more active than cisplatin and auranofin used as controls. The gold(III) complexes probably act by inhibiting the activity of thioredoxin reductase enzyme whereas the mode of action of the platinum(II,IV) complexes involves binding to DNA. Cells treated with the studied compounds presented morphological changes such as cell shrinkage and blebs formation, which indicate cell death by apoptosis induction.
- Published
- 2012
45. Control of size in losartan/copper(II) coordination complex hydrophobic precipitate
- Author
-
Izabela M.P. Daniel, Heloisa Beraldo, Rubén D. Sinisterra, Ângelo M. L. Denadai, Pedro P.G. Guimarães, Edivaltrys Inayve Pissinati de Rezende, Leonardo Bertolini S. Gomes, Antonio S. Mangrich, and Jeferson G. Da Silva
- Subjects
Light ,Static Electricity ,Supramolecular chemistry ,chemistry.chemical_element ,Bioengineering ,Losartan ,Coordination complex ,Biomaterials ,Dynamic light scattering ,Coordination Complexes ,Zeta potential ,Chemical Precipitation ,Scattering, Radiation ,Solubility ,Particle Size ,chemistry.chemical_classification ,Chromatography ,Calorimetry, Differential Scanning ,technology, industry, and agriculture ,Electron Spin Resonance Spectroscopy ,Titrimetry ,Water ,Isothermal titration calorimetry ,Copper ,Solutions ,Crystallography ,Kinetics ,chemistry ,Nonlinear Dynamics ,Mechanics of Materials ,Thermogravimetry ,Regression Analysis ,Thermodynamics ,Titration ,Hydrophobic and Hydrophilic Interactions - Abstract
Reaction of highly soluble orally active, non-peptide antihypertensive drug losartan with copper(II) leads to the spontaneous formation of a very insoluble 2:1 covalent complex, which self assembles in a hydrophobic supramolecular structure of nanometric dimensions. Thermal analysis showed that Los/Cu(II) complex presents intermediate stability in comparison with its precursors KLos and Cu(OAc)2·H2O. Isothermal titration calorimetry indicated complexation to be a stepwise process, driven by enthalpy and entropy. Zeta potential and DLS measurements showed that it is possible to control the size and charge of nanoprecipitates by adjusting the relative concentration of Los(-) and Cu(II).
- Published
- 2012
46. N⁴-Phenyl-substituted 2-acetylpyridine thiosemicarbazones: cytotoxicity against human tumor cells, structure-activity relationship studies and investigation on the mechanism of action
- Author
-
Marcella A, Soares, Josane A, Lessa, Isolda C, Mendes, Jeferson G, Da Silva, Raquel G, Dos Santos, Lívia B, Salum, Hikmat, Daghestani, Adriano D, Andricopulo, Billy W, Day, Andreas, Vogt, Jorge L, Pesquero, Willian R, Rocha, and Heloisa, Beraldo
- Subjects
Thiosemicarbazones ,Cell Death ,Dose-Response Relationship, Drug ,Molecular Structure ,Antineoplastic Agents ,Apoptosis ,Breast Neoplasms ,Glioma ,Adenocarcinoma ,Crystallography, X-Ray ,Microtubules ,Central Nervous System Neoplasms ,Inhibitory Concentration 50 ,Structure-Activity Relationship ,Tubulin ,Cell Line, Tumor ,Humans ,Female ,Drug Screening Assays, Antitumor ,Tumor Suppressor Protein p53 ,Glioblastoma ,Etoposide - Abstract
N(4)-Phenyl 2-acetylpyridine thiosemicarbazone (H2Ac4Ph; N-(phenyl)-2-(1-(pyridin-2-yl)ethylidene)hydrazinecarbothioamide) and its N(4)-ortho-, -meta- and -para-fluorophenyl (H2Ac4oFPh, H2Ac4mFPh, H2Ac4pFPh), N(4)-ortho-, -meta- and -para-chlorophenyl (H2Ac4oClPh, H2Ac4mClPh, H2Ac4pClPh), N(4)-ortho-, -meta- and -para-iodophenyl (H2Ac4oIPh, H2Ac4mIPh, H2Ac4pIPh) and N(4)-ortho-, -meta- and -para-nitrophenyl (H2Ac4oNO(2)Ph, H2Ac4mNO(2)Ph, H2Ac4pNO(2)Ph) derivatives were assayed for their cytotoxicity against human malignant breast (MCF-7) and glioma (T98G and U87) cells. The compounds were highly cytotoxic against the three cell lineages (IC(50): MCF-7, 52-0.16 nM; T98G, 140-1.0 nM; U87, 160-1.4 nM). All tested thiosemicarbazones were more cytotoxic than etoposide and did not present any haemolytic activity at up to 10(-5)M. The compounds were able to induce programmed cell death. H2Ac4pClPh partially inhibited tubulin assembly at high concentrations and induced cellular microtubule disorganization.
- Published
- 2012
47. Synthesis and characterization of the europium(III) pentakis(picrate) complexes with imidazolium countercations: structural and photoluminescence study
- Author
-
Oscar L. Malta, Jeferson G. Da Silva, Ricardo O. Freire, Maria Helena Araujo, Renaldo T. Moura, José Diogo L. Dutra, Alex S. Borges, and Hermi F. Brito
- Subjects
chemistry.chemical_classification ,Lanthanide ,Models, Molecular ,Denticity ,Molecular Structure ,Picrate ,Inorganic chemistry ,Imidazoles ,chemistry.chemical_element ,Crystal structure ,Crystallography, X-Ray ,EURÓPIO ,Coordination complex ,Inorganic Chemistry ,Crystallography ,chemistry.chemical_compound ,chemistry ,Europium ,Picrates ,Intramolecular force ,Ionic liquid ,Luminescent Measurements ,Organometallic Compounds ,Physical and Theoretical Chemistry - Abstract
Six new lanthanide complexes of stoichiometric formula (C)(2)[Ln(Pic)(5)]--where (C) is a imidazolium cation coming from the ionic liquids 1-butyl-3-methylimidazolium picrate (BMIm-Pic), 1-butyl-3-ethylimidazolium picrate (BEIm-Pic), and 1,3-dibutylimidazolium picrate (BBIm-Pic), and Ln is Eu(III) or Gd(III) ions--have been prepared and characterized. To the best of our knowledge, these are the first cases of Ln(III) pentakis(picrate) complexes. The crystal structures of (BEIm)(2)[Eu(Pic)(5)] and (BBIm)(2)[Eu(Pic)(5)] compounds were determined by single-crystal X-ray diffraction. The [Eu(Pic)(5)](2-) polyhedra have nine oxygen atoms coordinated to the Eu(III) ion, four oxygen atoms from bidentate picrate, and one oxygen atom from monodentate picrate. The structures of the Eu complexes were also calculated using the sparkle model for lanthanide complexes, allowing an analysis of intramolecular energy transfer processes in the coordination compounds. The photoluminescence properties of the Eu(III) complexes were then studied experimentally and theoretically, leading to a rationalization of their emission quantum yields.
- Published
- 2012
48. Gold(I) complexes with thiosemicarbazones: cytotoxicity against human tumor cell lines and inhibition of thioredoxin reductase activity
- Author
-
Luana F. de Miranda, Jeferson G. Da Silva, Isolda C. Mendes, Elaine M. Souza-Fagundes, Carla F.D. Romeiro, Heloisa Beraldo, Nivaldo L. Speziali, Josane A. Lessa, and Juliana C. Guerra
- Subjects
Models, Molecular ,Thiosemicarbazones ,Auranofin ,Thioredoxin-Disulfide Reductase ,Stereochemistry ,Cell Survival ,Thioredoxin reductase ,Molecular Conformation ,Antineoplastic Agents ,DNA Fragmentation ,Crystallography, X-Ray ,Biochemistry ,Peripheral blood mononuclear cell ,Jurkat cells ,Inorganic Chemistry ,Inhibitory Concentration 50 ,Coordination Complexes ,Cell Line, Tumor ,medicine ,Cytotoxic T cell ,Humans ,Cytotoxicity ,Chemistry ,DNA, Superhelical ,Myeloid leukemia ,Cell culture ,Leukocytes, Mononuclear ,Gold ,medicine.drug - Abstract
Complexes [Au(H2Ac4DH)Cl]∙MeOH ( 1 ) [Au(H 2 2Ac4Me)Cl]Cl ( 2 ) [Au(H 2 2Ac4Ph)Cl]Cl∙2H 2 O ( 3 ) and [Au(H 2 2Bz4Ph)Cl]Cl ( 4 ) were obtained with 2-acetylpyridine thiosemicarbazone (H2Ac4DH), its N (4)-methyl (H2Ac4Me) and N (4)-phenyl (H2Ac4Ph) derivatives, as well as with N (4)-phenyl 2-benzoylpyridine thiosemicarbazone (H2Bz4Ph). The compounds were cytotoxic to Jurkat (immortalized line of T lymphocyte), HL-60 (acute myeloid leukemia), MCF-7 (human breast adenocarcinoma) and HCT-116 (colorectal carcinoma) tumor cell lines. Jurkat and HL-60 cells were more sensitive than MCF-7 and HCT-116 cells. Upon coordinating to the gold(I) metal centers in complexes ( 2) and ( 4 ), the cytotoxic activity of the H2Ac4Me and H2Bz4Ph ligands increased against the HL-60 and Jurkat tumor cell lines. 2 was more active than auranofin against both leukemia cells. Most of the studied compounds were less toxic than auranofin to peripheral blood mononuclear cells (PBMC). All compounds induced DNA fragmentation in HL-60 and Jurkat cells indicating their pro-apoptotic potential. Complex ( 2 ) strongly inhibited the activity of thioredoxin reductase (TrxR), which suggests inhibition of TrxR to be part of its mechanism of action.
- Published
- 2011
49. Copper(II) and zinc(II) complexes with 2-formylpyridine-derived hydrazones
- Author
-
Eduardo E. Castellano, F. R. Sives, Jeferson G. Da Silva, Angel A. Recio Despaigne, Oscar E. Piro, Heloisa Beraldo, and Ana Cerúlia M. do Carmo
- Subjects
chemistry.chemical_classification ,Chemistry ,Inorganic chemistry ,chemistry.chemical_element ,Hydrazone ,Crystal structure ,Zinc ,Copper ,Inorganic Chemistry ,chemistry.chemical_compound ,2-Formylpyridine ,Polymer chemistry ,MOLÉCULA (ESTRUTURA) ,Materials Chemistry ,Acetone ,Physical and Theoretical Chemistry - Abstract
In the present work 2-formylpyridine-para-chloro-phenyl hydrazone (H2FopClPh) and 2-formylpyridine-para-nitro-phenyl hydrazone (H2FopNO2Ph) were obtained, as well as their copper(II) and zinc(II) complexes [Cu(H2FopClPh)Cl2] (1), [Cu(2FopNO2Ph)Cl] (2), [Zn(H2FopClPh)Cl2] (3) and [Zn(H2FopNO2Ph)Cl2] (4). Upon re-crystallization in DMSO:acetone conversion of 2 into [Cu(2FopNO2Ph)Cl(DMSO)] (2a) and of 4 into [Zn(2FopNO2Ph)Cl(DMSO)] (4a) occurred. The crystal structures of 1, 2a, 3 and 4a were determined.
- Published
- 2009
50. Structural studies on zinc(II) complexes with 2-benzoylpyridine-derived hydrazones
- Author
-
Angel A. Recio Despaigne, Oscar E. Piro, Ana Cerúlia M. do Carmo, Jeferson G. Da Silva, Heloisa Beraldo, and Eduardo E. Castellano
- Subjects
chemistry.chemical_classification ,ESPECTROSCOPIA (ESTUDO) ,Inorganic chemistry ,chemistry.chemical_element ,Hydrazone ,Zinc ,Crystal structure ,Medicinal chemistry ,Chloride ,Ion ,Inorganic Chemistry ,Metal ,chemistry.chemical_compound ,chemistry ,Octahedron ,visual_art ,Materials Chemistry ,Acetone ,visual_art.visual_art_medium ,medicine ,Physical and Theoretical Chemistry ,medicine.drug - Abstract
2-Benzoylpyridine-phenylhydrazone (H2BzPh), 2-benzoylpyridine- para -chloro-phenylhydrazone (H2BzpClPh), and 2-benzoylpyridine- para -nitro-phenyl (H2BzpNO 2 Ph) hydrazone were obtained and fully characterized, as well as their zinc(II) complexes [Zn(H2BzPh)Cl 2 ] ( 1 ), [Zn(H2BzClPh)Cl 2 ] ( 2 ) and [Zn(H2BzpNO 2 Ph)Cl 2 ] ( 3 ). During the syntheses of complex 1 a second product crystallized, which was characterized as [Zn(2BzPh) 2 ] ( 1a ). Upon re-crystallization in 1:9 DMSO:acetone conversion of 2 into [Zn(H2BzpClPh)Cl 2 ] · H 2 O ( 2a ) and of 3 into [Zn(2BzpNO 2 Ph)Cl(DMSO)] ( 3a ) occurred. The crystal structures of 1a , 2a and 3a were determined. In 1a the two nearly perpendicular H2BzPh ligands give rise to a distorted octahedral environment around the metal. The 5-fold coordination around the metal is completed with two chloride ions in 2a and with one chloride and one oxygen atom from DMSO in 3a .
- Published
- 2009
Catalog
Discovery Service for Jio Institute Digital Library
For full access to our library's resources, please sign in.