Heteroleptic NiII complexes: Synthesis, structural characterization, computational studies and amoebicidal activity evaluation

Hernández‐Ayala, Luis Felipe; Toledano-Magaña, Yanis; Ortiz‐Frade, Luis; Flores‐Álamo, Marcos; Galindo‐Murillo, Rodrigo; Reina, Miguel; García‐Ramos, Juan Carlos; Ruíz-Azuara, Lena

doi:10.1016/j.jinorgbio.2020.111043

Cited by 3 publications

(6 citation statements)

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“…[28] DFT calculations have proven to be a useful tool to reproduce the experimental redox potentials [32,67,68] and to calculate indexes to analyze the reactivity and biological activity of the complexes. [30,32,69,70] To study the redox behavior, a computational protocol was performed to calculate reactivity indexes and Ru II j Ru III redox potential (E 0 calc ), the results are reported in the Table S4 and the correlations with experimental Ru II j Ru III redox potentials (E 0 exp ) are presented in the Figure 2. Correlations show an excellent agreement (R 2 > 0.95) between E 0 exp with ionization energy (IE), HOMO-LUMO band gap (ΔΕ HÀ L ), electron affinity (EA), electrophilicity (ω), electronegativity (χ) and E 0 calc .…”

Section: Compound (Pfmentioning

confidence: 99%

“…Regarding to this, octanol-water partition coefficient and molar volume can be used to depict the biological activity. [30,32,77,78] Therefore, log K O/W and V M indexes were computationally calculated to study their relevance in the antiproliferative effect of the ruthenium containing selenium complexes synthetized here.…”

Section: Cell Growth Inhibitionmentioning

confidence: 99%

“…The activity equation has the same form that previously reported for Ru-pdto amebicide agents. [32] According to our group experience in metallodrugs, [30][31][32] the studied compounds might act by increasing oxidative stress through radical oxygen species (ROS) generation as one possible amebicide pathway. As previously studied for Ru-pdto and other Ru II systems, ROS could be one possible action mechanism, among other.…”

Section: Cell Growth Inhibitionmentioning

confidence: 99%

“…[26,27] In general, pdto complexes are used as conductive polymers, SODmimics and antiparasitic agents. [28][29][30][31] Recently, it has been proved that Ru II -pdto complexes have showed high amoebicidal efficiency against E. histolytica amoeba strains. Some of these compounds are several times more active than metronidazole, usually employed as clinical drug.…”

Section: Introductionmentioning

confidence: 99%

“…[50][51][52] In addition, they are very electronegative and poorly steric groups that can modulate the redox potential and volume of the compounds. It is well known that those properties can strongly influence the cytotoxicity of the compounds, particularly in some parasitic and malignant cells strains [30][31][32]53] In this report, synthesis and characterization of novel ruthenium (II) containing seleno-ligand complexes with general formulae: [Ru( BP3Se Complexes were fully characterized by elemental analyses, conductivity and several spectroscopic techniques: FT-IR, FAB + -MS and 1 H-NMR, 13 C-NMR, 31 P-NMR, and 77 Se-NMR. Moreover, cyclic voltammetry measurements were made to explore the redox behavior and to obtain the redox potentials (E 0 ) values.…”

Section: Introductionmentioning

confidence: 99%

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Mixed Ru^IIComplexes Containing Diseleno‐Ligand and α,β‐Diketones Donors with Anticancer Activity. Synthesis, Characterization, Electrochemical and DFT Studies

et al. 2021

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This work presents the synthesis, characterization, electrochemical studies, DFT calculations and in vitro evaluation of antiproliferative activity in HeLa cells of four novel direct bonded ruthenium-selenium compounds. The complexes are [Ru(BP3Se 2 )Cl(PPh 3 )]Cl (1) and mixed [Ru(BP3Se 2 )(OÀ O)(PPh 3 )]Cl (2 a, 2 b, 2 c) systems with diseleno-ligand BP3Se 2 : 1,9-bis(2pyridyl)-3,7-diselenanonane as a primary donor and OÀ O: α,βdiketones as a secondary donors. In 1, BP3Se 2 is linked in tetradentate N 2 Se 2 form while in mixed complexes, present a tridentate NSe 2 linkage. Diketone nature and electroactive groups has a fundamental role in the modulation of the electronic, steric and lipophilic properties as well as in its cytotoxic activity. Among the tested compounds, 2 c has the best cytotoxic performance (IC 50 = 2.8 μmol/L) even higher than metallodrug cisplatin. In this regard, cytotoxic activity is strongly determined by experimental redox potential (E 0 ) and calculated molar volume (V M ) of the compounds.

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Section: Compound (Pfmentioning

confidence: 99%

Section: Cell Growth Inhibitionmentioning

confidence: 99%

Section: Cell Growth Inhibitionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Mixed Ru^IIComplexes Containing Diseleno‐Ligand and α,β‐Diketones Donors with Anticancer Activity. Synthesis, Characterization, Electrochemical and DFT Studies

et al. 2021

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The Amoebicidal Activity of Diferrocenyl Derivatives: A Significant Dependence on the Electronic Environment

et al. 2023

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Amoebiasis is the second leading cause of death worldwide associated with parasitic disease and is becoming a critical health problem in low-income countries, urging new treatment alternatives. One of the most promising strategies is enhancing the redox imbalance within these susceptible parasites related to their limited antioxidant defense system. Metal-based drugs represent a perfect option due to their extraordinary capacity to stabilize different oxidation states and adopt diverse geometries, allowing their interaction with several molecular targets. This work describes the amoebicidal activity of five 2-(Z-2,3-diferrocenylvinyl)-4X-4,5-dihydrooxazole derivatives (X = H (3a), Me (3b), iPr (3c), Ph (3d), and benzyl (3e)) on Entamoeba histolytica trophozoites and the physicochemical, experimental, and theoretical properties that can be used to describe the antiproliferative activity. The growth inhibition capacity of these organometallic compounds is strongly related to a fine balance between the compounds’ redox potential and hydrophilic character. The antiproliferative activity of diferrocenyl derivatives studied herein could be described either with the redox potential, the energy of electronic transitions, logP, or the calculated HOMO–LUMO values. Compound 3d presents the highest antiproliferative activity of the series with an IC50 of 23 µM. However, the results of this work provide a pipeline to improve the amoebicidal activity of these compounds through the directed modification of their electronic environment.

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New Protein-Coated Silver Nanoparticles: Characterization, Antitumor and Amoebicidal Activity, Antiproliferative Selectivity, Genotoxicity, and Biocompatibility Evaluation

et al. 2021

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Nanomaterials quickly evolve to produce safe and effective biomedical alternatives, mainly silver nanoparticles (AgNPs). The AgNPs’ antibacterial, antiviral, and antitumor properties convert them into a recurrent scaffold to produce new treatment options. This work reported the full characterization of a highly biocompatible protein-coated AgNPs formulation and their selective antitumor and amoebicidal activity. The protein-coated AgNPs formulation exhibits a half-inhibitory concentration (IC50) = 19.7 µM (2.3 µg/mL) that is almost 10 times more potent than carboplatin (first-line chemotherapeutic agent) to inhibit the proliferation of the highly aggressive human adenocarcinoma HCT-15. The main death pathway elicited by AgNPs on HCT-15 is apoptosis, which is probably stimulated by reactive oxygen species (ROS) overproduction on mitochondria. A concentration of 111 µM (600 µg/mL) of metallic silver contained in AgNPs produces neither cytotoxic nor genotoxic damage on human peripheral blood lymphocytes. Thus, the AgNPs formulation evaluated in this work improves both the antiproliferative potency on HCT-15 cultures and cytotoxic selectivity ten times more than carboplatin. A similar mechanism is suggested for the antiproliferative activity observed on HM1-IMSS trophozoites (IC50 = 69.2 µM; 7.4 µg/mL). There is no change in cell viability on mice primary cultures of brain, liver, spleen, and kidney exposed to an AgNPs concentration range from 5.5 µM to 5.5 mM (0.6 to 600 µg/mL). The lethal dose was determined following the OECD guideline 420 for Acute Oral Toxicity Assay, obtaining an LD50 = 2618 mg of Ag/Kg body weight. All mice survived the observational period; the histopathology and biochemical analysis show no differences compared with the negative control group. In summary, all results from toxicological evaluation suggest a Category 5 (practically nontoxic) of the Globally Harmonized System of Classification and Labelling of Chemicals for that protein-coated AgNPs after oral administration for a short period and urge the completion of its preclinical toxicological profile. These findings open new opportunities in the development of selective, safe, and effective AgNPs formulations for the treatment of cancer and parasitic diseases with a significant reduction of side effects.

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Heteroleptic NiII complexes: Synthesis, structural characterization, computational studies and amoebicidal activity evaluation

Cited by 3 publications

References 55 publications

Mixed Ru^IIComplexes Containing Diseleno‐Ligand and α,β‐Diketones Donors with Anticancer Activity. Synthesis, Characterization, Electrochemical and DFT Studies

Mixed Ru^IIComplexes Containing Diseleno‐Ligand and α,β‐Diketones Donors with Anticancer Activity. Synthesis, Characterization, Electrochemical and DFT Studies

The Amoebicidal Activity of Diferrocenyl Derivatives: A Significant Dependence on the Electronic Environment

New Protein-Coated Silver Nanoparticles: Characterization, Antitumor and Amoebicidal Activity, Antiproliferative Selectivity, Genotoxicity, and Biocompatibility Evaluation

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Heteroleptic NiII complexes: Synthesis, structural characterization, computational studies and amoebicidal activity evaluation

Cited by 3 publications

References 55 publications

Mixed RuIIComplexes Containing Diseleno‐Ligand and α,β‐Diketones Donors with Anticancer Activity. Synthesis, Characterization, Electrochemical and DFT Studies

Mixed RuIIComplexes Containing Diseleno‐Ligand and α,β‐Diketones Donors with Anticancer Activity. Synthesis, Characterization, Electrochemical and DFT Studies

The Amoebicidal Activity of Diferrocenyl Derivatives: A Significant Dependence on the Electronic Environment

New Protein-Coated Silver Nanoparticles: Characterization, Antitumor and Amoebicidal Activity, Antiproliferative Selectivity, Genotoxicity, and Biocompatibility Evaluation

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Product

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Mixed Ru^IIComplexes Containing Diseleno‐Ligand and α,β‐Diketones Donors with Anticancer Activity. Synthesis, Characterization, Electrochemical and DFT Studies

Mixed Ru^IIComplexes Containing Diseleno‐Ligand and α,β‐Diketones Donors with Anticancer Activity. Synthesis, Characterization, Electrochemical and DFT Studies