Phenolic Moieties Research Articles

Infrared spectral features of the charge carriers in nickel salen polymeric complexes

A series of the polymeric complexes (PCs) of nickel(II) with N2O2 Schiff base ligands have been studied by in situ Fourier Transform Infrared (FTIR) spectroelectrochemistry. The molecular structure of the metal-salen complexes as starting materials for the polymer synthesis was modulated by various substituents in the phenolate moieties and diimine bridge. Two groups of the infrared-active vibration (IRAV) bands are obtained in the spectra depending on the oxidation level of the polymers. The assignment of the main IRAV bands was carried out and the electrochemically generated charge carriers were determined. Analysis of the spectroscopic features observed in the mid and near IR region provides information on the charge distribution within the polymer film.

Docking study of ferulic acid derivates on FGFR1, ADME prediction, and QSPR analysis

Background: FGFR-1 is an angiogenic receptor that plays a huge role in the cancer growth pathway. Angiogenesis inhibitory drugs released have significant side effects. Therefore, research into discovering anti-angiogenic agents to achieve good health and well-being is still necessary. Objective: To design the novel anti-angiogenic candidates from ferulic acid (FA) by docking study on FGFR1, to predict the ADME profile, and to find out the structural relationship of their pharmacokinetic properties as QSPR analysis. Method: Autodock Tools performed a docking study. ADME prediction was conducted using SwissADME. The MLR approach determined the QSPR model. Result: The docking results showed that FA-8 and FA-18 had the lowest free energy binding, inhibition constant, and GI absorption. The QSPR analysis obtained the equation model: Log HIA = 0,018 Log P2 + 0,069 Log P + 0,020 CMR + 0,001 Etotal + 1,771 with n = 24, correlation coefficient (r)= 0.621, p-value= 0.046 and F-value= 2.975. Conclusion: Modifying FA on the phenolic moiety replaced by an ester increased the activity and ADME profile. The predicted bioavailability was supported by high Log P, molar refractivity (CMR), and electronic factor (Etotal). It is recommended that lipophilicity be increased to achieve better pharmacokinetic properties.

Photochemical Transformation of Monochloramine Induced by Triplet State Dissolved Organic Matter

The photoexcited dissolved organic matter (DOM) could produce reactive intermediates, affecting chemical oxidant transformation in UV based advanced oxidation processes (AOPs). This study confirmed the critical role of triplet state DOM (3DOM*), generated from DOM photoexcitation, in the transformation of monochloramine (NH2Cl), a commonly used chemical oxidant and disinfectant in water treatment. NH2Cl (42.25 μM, as Cl2) was decayed by 17.4–73.4 % within 60 min, primarily due to 3DOM* , in DOM (2–30 mgC L−1) solutions irradiated by 365 nm, where NH2Cl has no absorption. The second-order quenching rate constants of triplet state model photosensitizers by NH2Cl were determined to be 0.95(± 0.04)–4.49(± 0.04)× 108 M−1 s−1 by using laser flash photolysis. As a reductant, 3DOM* reacted with NH2Cl through one-transfer mechanism, leading to amino radical (NH2•) generation, which then transferred to ammonia (NH4+, pKa 9.25) through H-abstraction by the phenolic moieties in DOM. Additionally, the intermediate product of 3DOM* oxidized by NH2Cl or those triplet state quinones can hydrolyze to form phenolic moieties, elevating NH4+ yield to higher than 99% upon 365 nm irradiation. These findings suggest that the widespread DOM can be applied to convert NH2Cl via 3DOM* with minimal toxic risks.

In-situ acetylation followed by liquid-liquid extraction and gas chromatography – mass spectrometry for the determination of bromophenols in urine

A novel and simple method combining in-situ acetylation, liquid-liquid extraction and gas chromatography-mass spectrometry (GC-MS) has been developed for the quantification of 10 bromophenols in urine, used as biomarkers of exposure to polybrominated diphenyl ethers. The analytical process involves an enzymatic hydrolysis of the bromophenol glucuronide fraction followed by an aqueous derivatization of the phenol group with acetic anhydride. A subsequent liquid-liquid extraction of the sample with hexane allows the injection of the organic layer, using a programmed temperature vaporizer, into a gas chromatograph coupled to a single quadrupole mass spectrometer. Quantification is performed by the standard addition method. Limits of detection are in the pg mL−1 range. Trueness, assessed in terms of percentages of recovery, varies between 100 % and 118 % in synthetic urine and between 79 % and 117 % in human urine. Precision, assessed at two different levels, 0.25 ng mL−1 and 2.5 ng mL−1, shows values of relative standard deviation below 14 % both in intra- and inter-day studies for both matrices. The method has been applied to the analysis of seven urine samples, measuring concentrations higher than the LOQ in three of them. These levels are in agreement with others found in literature, but they have been obtained by applying a much simpler and faster protocol. In addition, the replacement of silylating reagents by acetic anhydride, to derivatize the phenol moiety, provides a greener alternative to other GC-MS procedures published up to date.

Bifunctional ratiometric fluorescent membrane containing pyrene-based probe for visual monitoring and efficient removal of Al3+

A bifunctional fluorescent pyrene-based probe, PYR, was designed by incorporating pyridine and phenolic hydroxyl moieties into pyrene fluorophore, which exhibited ratiometric fluorescent response toward Al3+. PYR underwent unique monomer-excimer conversion in ratiometric manner through the formation of a 2:1 coordination complex and accomplished with fluorescent color variation from green to blue. PYR displayed excellent selectivity, high sensitivity (LOD = 0.33 μM), rapid response (<45 s), and good cytocompatibility to Al3+. Notably, a fluorescent cellulose membrane decorated with PYR was successfully developed and applied for accurately quantify of Al3+ in diverse actual samples, and high-efficiency removal (∼96%) of Al3+ from water systems, with sustainable recycling performance up to 10 times. Bifunctional membranes also played an important role in reducing the LOD of Al3+ to 16 nM through the preconcentration process. Therefore, this study is crucial to the development of environmentally sustainable strategy for monitoring and removing pollution.

Hordatines, dimerised hydroxycinnamoylagmatine conjugates of barley (Hordeum vulgare L.): an appraisal of the biosynthesis, chemistry, identification and bioactivities

AbstractHydroxycinnamoylamides are specialised metabolites widely distributed in the plant kingdom. These are phenolic moieties covalently linked to mono- or polyamines through amide bonds. Their oxidative coupling (dimerisation) leads to neolignanamides, a group of compounds showing high chemical, structural and functional diversity. Typical to barley, dehydro dimers of hydroxycinnamoylagmatines, hordatines are primarily found in germinated seeds and at the seedling stage. The first step in the biosynthesis of hordatines is catalysed by acyl-coenzyme A-dependent N-hydroxycinnamoyltransferases, and lead to the formation of hydroxycinnamoylagmatines (HCAgms). The oxidative homo- or hetero-dimerisation of the latter results in different hordatines (A, B, C or D). Hordatines can also undergo various types of conjugation and form hydroxylated, methylated or glycosylated derivatives. Although the research on the bioactivities of the hordatines is still nascent, the in planta antifungal properties have long been recognised. While hordatines are naturally and uniquely synthesised in barley plants, these molecules or lead compounds derived therefrom, also exhibit medicinal and pharmaceutical uses important for human health, stimulating research into the utilisation of biotechnology in alternative production hosts and to enhance agricultural yields and value-added production. This review summarises the older and recent knowledge about hordatines and derivatives and may serve as a springboard for future research on this intriguing class of secondary plant metabolites.

Difluoroboron Complexes Based on Benzimidazole-Phenolates as Blue Emitters.

Novel four-coordinated boron complexes (1-5) were synthesized via a reaction between BF3·CH3OH and benzimidazole-phenolate ligands (L1-L5), which are N,O-donors. These complexes exhibit intense blue emission in the solution and solid states accompanied by notable fluorescence quantum yields (ΦF). The study of the structure-property relation, through theoretical and experimental approaches, revealed a distinctive trend where compounds incorporating electron-donating substituents (methyl and ethoxy groups) in the phenolate moiety manifest shifts in emission wavelengths across the blue spectrum, concomitant with an increase in ΦF. Furthermore, the incorporation of an aromatic ring into the benzimidazole moiety considerably intensifies the rate of radiative relaxation from excited states. Notably, in the solid phase, either as a crystalline powder or loaded into polymer films, these modified complexes maintain or even surpass ΦF values observed in molecular solutions, ranging from 0.18 to 0.57, depending on the substitution. This characteristic makes these compounds attractive for applications in optoelectronics. All of the compounds were characterized using 1H, 13C, 11B, and 19F NMR, elemental analysis, and the molecular structures were corroborated through single-crystal X-ray diffraction analysis. Computational calculations via time-dependent density functional theory further elucidate the tunability of optical bandgaps through group substitution on ligands, aligning well with experimental observations.

1,2,3-Triazole Hybrids Containing Isatins and Phenolic Moieties: Regioselective Synthesis and Molecular Docking Studies.

The synthesis of hybrid molecules is one of the current strategies of drug discovery for the development of new lead compounds. The 1,2,3-triazole moiety represents an important building block in Medicinal Chemistry, extensively present in recent years. In this paper, we presented the design and the synthesis of new 1,2,3-triazole hybrids, containing both an isatine and a phenolic core. Firstly, the non-commercial azide and the alkyne synthons were prepared by different isatines and phenolic acids, respectively. Then, the highly regioselective synthesis of 1,4-disubstituted triazoles was obtained in excellent yields by a click chemistry approach, catalyzed by Cu(I). Finally, a molecular docking study was performed on the hybrid library, finding four different therapeutic targets. Among them, the most promising results were obtained on 5-lipoxygenase, an enzyme involved in the inflammatory processes.

Antioxidant Activity and DFT Calculations of Metal Complexes Derived from a Schiff Base Ligand: Synthesis, Characterization, and Biological Evaluation

AbstractMetal complexes derived from Schiff bases are known to have a wide range of applications, spanning the areas of material and medicinal sciences. Herein, a Schiff base ligand, (Z)‐2‐(((4‐chlorophenyl)imino)methyl)naphthalen‐1‐ol HL, was synthesized via a condensation reaction between 2‐hydroxy‐1‐naphthaldehyde and 4‐chloroaniline using methanol as a solvent in the presence of a catalytic amount of formic acid. The obtained ligand was further reacted with Mn(II), Ni(II), and Cu(II) using their acetate salts in a 1 : 2 stoichiometric ratio of metal to ligand to afford complexes C1–C3, respectively. Physicochemical and analytical techniques consisting of FTIR, UV‐Vis, elemental (CHN and metal content), TGA, HRMS, 1H, and 13 C NMR spectroscopy were deployed to establish the formation of the compounds. Results show that the ligand coordinated with the metal ions through the oxygen and nitrogen atoms of the phenolate and azomethine moieties, respectively, forming ON‐type complexes. Furthermore, the free ligand and its complexes were evaluated for their antioxidant activity compared to the standard (ascorbic acid) using an in vitro DPPH radical scavenging assay. From this investigation, C1 demonstrated higher radical scavenging activity than the free ligand, the complexes, and the standard (ascorbic acid). But the ligand has better scavenging activity than C2 and C3 at higher concentrations. DFT was also used to examine the electronic properties of the compounds, and the data obtained corroborated well with the experimental study.

Replacing syngas by formic acid and acetic anhydride with advantages: tandem carbonylation of renewable terpenes and propenylbenzenes

The introduction of aldehyde and acetate functionalities in renewable terpenes and propenylbezenes provides useful feedstocks for fine chemicals, especially in the flavor and fragrance segment. Herein we report the rhodium catalyzed hydroformylation and the tandem hydroformylation/hydrogenation/O-acylation of biomass based propenylbenzenes and terpenes with a mixture of formic acid (FA) and acetic anhydride (Ac2O) as a cheaper and less dangerous alternative for flammable and toxic syngas (carbon monoxide and hydrogen mixture) used in the conventional hydroformylation. In addition, we were able to perform the consecutive aldehyde hydrogenation, followed by O-acetylation, formally adding a methyl acetate molecule in a C-C double bond in a tandem process, which was not feasible with the conventional hydroformylation. For propenylbenzenes containing a phenol moiety, the parallel acetoxylation of this group also took place. The protocol allowed to obtain aldehydes and mono- or diacetate esters, which are potentially valuable as fragrance components.

Ferrocene functionalized oligomeric siloxane building blocks as potential linkers for biological active molecules

Despite the fact, that biologically active molecules (e.g., antioxidants, antibiotics and antiviral reagents) were investigated intensively in the last decades, new linker molecules and building blocks, which can enhance the activity and change the polarity of compounds is still a growing field in pharmaceutic research. The application of a ferrocene moiety in combination with a siloxane linker attached to a biological active molecule is realized in the present study for the first time. A method is introduced that uses mono- (FcLi) and dilithioferrocene (FcLi2) to perform anionic ring opening reactions of hexamethylcyclotrisiloxane (D3). The formation of lithium silanolate species αDnLi (α = Fc, D3 = (SiMe2O)3) was observed, followed by the termination of the ring opening reactions with chlorosilanes Cl–ω to obtain siloxane oligomers of type αDnω. Approaches were investigated to enable ω = SiMe2H and ω = SiMe2Cl functionality. It was shown, that oligomeric siloxanes were able to undergo further hydrosilylation reactions with the introduction of a phenol moiety.

The Pseudo Symmetric Crystal Structure of 1,4-Diazabicyclo[2·2·2]octane-1,4-diium bis(5-hydroxy-2,4-dinitrophenolate)

Reaction of 4,6-dinitroresorcinol (1) and the nitrogen base 1,4-diazabicyclo[2·2·2]octane (2) affords the 1:2 salt and proton-transfer compound 1,4-diazabicyclo[2·2·2]octane-1,4-diium bis(5-hydroxy-2,4-dinitrophenolate) (3). Compound 3 crystallizes in the triclinic crystal system (space group P-1) with a = 8.3242(5) Å, b = 11.9915(7) Å, c = 12.4595(7) Å, α = 116.282(2)°, β = 100.576(3)°, γ = 101.051(2)°, 1042.30(11) Å3 and Z = 2. The dication 2-H22+\\documentclass[12pt]{minimal} \\usepackage{amsmath} \\usepackage{wasysym} \\usepackage{amsfonts} \\usepackage{amssymb} \\usepackage{amsbsy} \\usepackage{mathrsfs} \\usepackage{upgreek} \\setlength{\\oddsidemargin}{-69pt} \\begin{document}$${\ ext{H}}_{2}^{2+}$$\\end{document} forms charge assisted donating bifurcated N+−H⋅⋅⋅O− hydrogen bonds to the phenolate moieties of two monoanions of 1. The latter exhibit an intramolecular O−H⋅⋅⋅O hydrogen bond between the hydroxy group and the nitro group in ortho position. The crystal structure of 3 features pseudo B-centering of the lattice, which relates the two crystallographically distinct monoanions of 1 by a pseudo translation. The possible B-centring is broken by the ethylene groups of 2-H22+, which are related in neighbouring molecules by centres of symmetry.Graphical The 1:2 proton-transfer compound 1,4-diazabicyclo[2.2.2]octane-1,4-diium bis(5-hydroxy-2,4-dinitrophenolate) features pseudo B-centering of the lattice.

Sterically hindered phenolic derivatives: effect on the production of Pseudomonas aeruginosa virulence factors, high-throughput virtual screening and ADME properties prediction.

Inhibition of quorum sensing is considered to be an effective strategy of control and treatment of a wide range of acute and persistent infections. Pseudomonas aeruginosa is an opportunistic bacterium with a high adaptation potential that contributes to healthcare-associated infections. In the present study, the effects of the synthesized hybrid structures bearing sterically hindered phenolic and heterocyclic moieties in a single scaffold on the production of virulence factors by P. aeruginosa were determined. It has been shown that the obtained compounds significantly reduce both pyocyanin and alginate production and stimulate the biosynthesis of siderophores in vitro, which may be attributed to their iron-chelating properties. The results of docking-based inverse high-throughput virtual screening indicate that transcription regulator LasR and Cu-transporter OPRC could be potential molecular targets for these compounds. Investigation of the impact small molecules exert on the molecular mechanisms of the production of bacterial virulence factors may pave the way for the design and development of novel antibacterial agents.

Synthesis of β-O-4 linked model oligolignol with a selectively deuterium-labelled methoxy group at the phenolic terminal unit

Abstract A lignin model oligomer with only β-O-4 linkages and a selectively deuterium-labelled methoxy group at the phenolic terminal units was synthesised to clarify the behaviour of the phenolic end of oligolignols. First, t-butoxycarbonylmethyl vanillin was synthesised and oligomerised by nucleophilic addition, a known method. The terminal of the oligomers was then subjected to nucleophilic addition to [3-OCD3]benzyl vanillin to achieve selective labelling of the terminal units. A deuterium-labelled lignin model oligomer (D-LM) was obtained through debenzylation and subsequent reduction. The results of thioacidolysis after methylation revealed that the degree of polymerisation was about five, and the deuterium-labelled phenylpropane unit was located only at the phenolic terminal moiety.

Robust polyurethane networks with flame-retardant, antioxidative, self-healing and reprocessing capabilities from biobased naringenin and vanillin

Biobased reprocessable polyurethane (PU) networks have drawn significant attention due to limited petroleum resources and aggravating environmental issues. However, the preparation of biobased PU networks with simultaneous efficient flame-retardant, antioxidative, self-healing and reprocessing performance is a great challenge due to the complicated structural design required. A novel strategy to fabricate multifunctional PU networks containing dynamic phenol–carbamate bonds from biobased naringenin and vanillin has been developed. First, a vanillin-based diol containing organic phosphorus moieties (VD) was prepared. Then modified diol and naringenin were combined to produce a self-healable, recyclable, antioxidative and flame-retarded PU (NVP-x)s where x represents the molar ratio of n[-OH(VD)] / n{[-OH(naringenin)] + [-OH(VD)] + [-OH(PTMG)]} possesses excellent flame-retardant, antioxidative, self-healing and reprocessing performance due to the presence of dynamic phenol–carbamate bonds, organophosphorus and phenolic moieties. An effective approach to the manufacture of multifunctional PUs with a potential application in the field of self-healing and flame-retardant coating, wound dressing membranes and fire-control engineering materials has been demonstrated.

Altering glycopeptide antibiotic biosynthesis through mutasynthesis allows incorporation of fluorinated phenylglycine residues.

Glycopeptide antibiotics (GPAs) are peptide natural products used as last resort treatments for antibiotic resistant bacterial infections. They are produced by the sequential activities of a linear nonribosomal peptide synthetase (NRPS), which assembles the heptapeptide core of GPAs, and cytochrome P450 (Oxy) enzymes, which perform a cascade of cyclisation reactions. The GPAs contain proteinogenic and nonproteinogenic amino acids, including phenylglycine residues such as 4-hydroxyphenylglycine (Hpg). The ability to incorporate non-proteinogenic amino acids in such peptides is a distinctive feature of the modular architecture of NRPSs, with each module selecting and incorporating a desired amino acid. Here, we have exploited this ability to produce and characterise GPA derivatives containing fluorinated phenylglycine (F-Phg) residues through a combination of mutasynthesis, biochemical, structural and bioactivity assays. Our data indicate that the incorporation of F-Phg residues is limited by poor acceptance by the NRPS machinery, and that the phenol moiety normally present on Hpg residues is essential to ensure both acceptance by the NRPS and the sequential cyclisation activity of Oxy enzymes. The principles learnt here may prove useful for the future production of GPA derivatives with more favourable properties through mixed feeding mutasynthesis approaches.

Chemical fixation of atmospheric CO2 in tricopper(II)-carbonato complexes with tetradentate N-donor ligands: reactive intermediates, probable mechanisms, and catalytic and magneto-structural studies.

In the present era, the fixation of atmospheric CO2 is of significant importance and plays a crucial role in maintaining the balance of carbon and energy flow within ecosystems. Generally, CO2 fixation is carried out by autotrophic organisms; however, the scientific community has paid substantial attention to execute this process in laboratory. In this report, we synthesized two carbonato-bridged trinuclear copper(II) complexes, [Cu3(L1)3(μ3-CO3)](ClO4)3 (1) and [Cu3(L2)3(μ3-CO3)](ClO4)3 (2) via atmospheric fixation of CO2 starting with Cu(ClO4)2·6H2O and easily accessible pyridine/pyrazine-based N4 donor Schiff base ligands L1 and L2, respectively. Under very similar reaction conditions, the ligand framework embedded with the phenolate moiety (HL3) fails to do so because of the reduction of the Lewis acidity of the metal center, inhibiting the formation of a reactive hydroxide bound copper(II) species, which is required for the fixation of atmospheric CO2. X-ray crystal structures display that carbonate-oxygen atoms bridge three copper(II) centers in μ3syn-anti disposition in 1 and 2, whereas [Cu(HL3)(ClO4)] (3) is a mononuclear complex. Interestingly, we also isolated an important intermediate of atmospheric CO2 fixation and structurally characterized it as an anti-anti μ2 carbonato-bridged dinuclear copper(II) complex, [Cu2(L2)2(μ2-CO3)](ClO4)2·MeOH (2-I), providing an in-depth understanding of CO2 fixation in these systems. Variable temperature magnetic susceptibility measurement suggests ferromagnetic interactions between the metal centers in both 1 and 2, and the results have been further supported by DFT calculations. The catalytic efficiency of our synthesized complexes 1-3 was checked by means of catechol oxidase and phenoxazinone synthase-like activities. While complexes 1 and 2 showed oxidase-like activity for aerobic oxidation of o-aminophenol and 3,5-di-tert-butylcatechol, complex 3 was found to be feebly active. ESI mass spectrometry revealed that the oxidation reaction proceeds through the formation of complex-substrate intermediations and was further substantiated by DFT calculations. Moreover, active catalysts 1 and 2 were effectively utilized for the base-free oxidation of benzylic alcohols in the presence of air as a green and sustainable oxidant and catalytic amount of TEMPO in acetonitrile. Various substituted benzylic alcohols smoothly converted to their corresponding aldehydes under very mild conditions and ambient temperature. The present catalytic protocol showcases its environmental sustainability by producing minimal waste.

Water oxidation utilizing a ruthenium complex featuring a phenolic moiety inspired by the oxygen-evolving centre (OEC) of photosystem II

A ruthenium complex bearing a phenolic moiety inspired by the OEC of photosystem II exhibits a high catalytic activity for electrochemical water oxidation, clearly indicating the promoting influence of the phenolic moiety on the catalytic activity.

Synthesis of the first 4-oxobutane-1,1,2,2-tetracarbonitriles containing a phenol fragment and their transformation into cyano-substituted pyrrol-2-ones showing three-position molecular switching.

The first example of the synthesis of 4-oxobutane-1,1,2,2-tetracarbonitriles (OTCs) containing a phenolic moiety has been described. The synthesis is based on the reaction between tetracyanoethylene and 4-hydroxyphenyl-substituted ketones under mild conditions. Due to the presence of a phenolic hydroxyl group, these compounds are more functionalized derivatives of the well-known OTC substrates used for diversity-oriented synthesis (DOS). The preserved synthetic potential of the OTCs for the preparation of phenol-containing derivatives with enhanced capabilities for tuning optical properties has been shown using the targeted synthesis of 2-(2-oxo-1,2-dihydro-3H-pyrrol-3-ylidene)malononitriles. Based on the obtained pyrroles and a model amine (pyrrolidine) a previously unknown type of thermosensitive three-position molecular switch is described. Reversible color changes of the dye are shown in both solution and on filter paper. The results reveal a new research branch of the OTC-based DOS strategy to access functionalized phenol-containing derivatives.

Structurally diverse zinc(II) complexes containing tripodal tetradentate phenoxido-amines with promising antiproliferative effects.

Structurally diverse zinc(II) complexes with tripodal tetradentate phenolic-amines of variable substituents in the phenol and amine moieties were synthesized and thoroughly characterized. The two dinuclear [Zn2(L1)2](ClO4)2·MeOH (1), [Zn2(L2)2](ClO4)2 (2), and four mononuclear [Zn(L3)(H2O)]·MeOH (3), [Zn(L4)] (4), [Zn(L5)] (5) and [Zn(L6)] (6) complexes revealed distorted octahedral, trigonal-bipyramidal or tetrahedral geometries. The free HL1 and H2L3-6 ligands, and complexes 1-6 were evaluated for in vitro cytotoxicity against human cancer cell lines (A2780, A2780R, PC-3 and 22Rv1) and normal healthy MRC-5 cells. Overall results revealed high-to-moderate cytotoxicity (with the best IC50 values for complex 6 ranging from 2.4 to 4.5 μM), which is however, significantly higher than that of the reference drug cisplatin. The moderately active complexes 1-4 showed considerable selectivity on A2780 cells (IC50 ≈ 16.3-19.5 μM) over MRC-5 ones (with IC50 >50 μM for 1, 2 and 4, and with IC50 >25 μM for 3). The complexes 1, 2, and 6 and the ligand H2L6 were chosen for subsequent deeper biological evaluations. Their time-resolved cellular uptake and other cellular effects in A2780 cells were studied, such as cell cycle profile, intracellular ROS production, induction of apoptosis and activation of caspases 3/7. Complexes 1 and 2 caused significant G0/G1 cell cycle arrest in A2780 cells and antioxidant effects at normal conditions. They showed only limited effects on cellular processes connected with cytotoxicity, i.e. induction of apoptosis, depletion of mitochondrial membrane potential, and autophagy. These findings can be at least partly attributed to the low ability of the complexes to enter the A2780 cells and the depression of metabolic activity of the target cancer cells.