Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity"

In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.The supporting information for: Stevanović, Nevena, Zlatar, Matija, Novaković, Irena, Pevec, Andrej, Radanović, Dušanka, Matić, Ivana Z., Đorđić Crnogorac, Marija, Stanojković, Tatjana, Vujčić, Miroslava, Gruden, Maja, Sladić, Dušan, Anđelković, Katarina, Turel, Iztok, Čobeljić, Božidar, "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity" in Dalton Transactions, 51, no. 1 (2022):185-196, [https://doi.org/10.1039/D1DT03169D]Published article: [https://cer.ihtm.bg.ac.rs/handle/123456789/4901]Related crystallographic data (CCDC 2110386): [https://cer.ihtm.bg.ac.rs/handle/123456789/4903]Related crystallographic data (CCDC 2110387): [https://cer.ihtm.bg.ac.rs/handle/123456789/4904]Related crystallographic data (CCDC 2110388): [https://cer.ihtm.bg.ac.rs/handle/123456789/4905

Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity"

In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.The supporting information for: Stevanović, Nevena, Zlatar, Matija, Novaković, Irena, Pevec, Andrej, Radanović, Dušanka, Matić, Ivana Z., Đorđić Crnogorac, Marija, Stanojković, Tatjana, Vujčić, Miroslava, Gruden, Maja, Sladić, Dušan, Anđelković, Katarina, Turel, Iztok, Čobeljić, Božidar, "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity" in Dalton Transactions, 51, no. 1 (2022):185-196, [https://doi.org/10.1039/D1DT03169D]Published article: [https://cherry.chem.bg.ac.rs/handle/123456789/4857]Related crystallographic data (CCDC 2110386): [https://cherry.chem.bg.ac.rs/handle/123456789/4859]Related crystallographic data (CCDC 2110387): [https://cherry.chem.bg.ac.rs/handle/123456789/4860]Related crystallographic data (CCDC 2110388): [https://cherry.chem.bg.ac.rs/handle/123456789/4861

Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity

In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.Related crystallographic data (CCDC 2110386): []Related crystallographic data (CCDC 2110387): []Related crystallographic data (CCDC 2110388): [

Anthropometric parameters and aesthetics in the making of fixed prosthodontic restaurations: Part 2

Introduction: The role of aesthetic dentistry in the field of fixed dental prosthetics is to redesign the smile, which means not only the treatment on the teeth, but also the treatment of the surrounding soft tissues. Successful therapy can be achieved by establishing the harmony between the static (teeth, gingiva) and dynamic factors (lips, cheeks, mimic muscles) at rest and when performing various functions of the orofacial system. The aim: of the study was to analyze the parameters of the oral soft tissues (gingival health, gingival height, gingival zeniths, lip line and symmetry and balance of the dentition) that affect the aesthetics of fixed prosthodontic restorations. Literature data and clinical experience were used. Conclusion: Adherence to the described parameters is of great importance in the development of aesthetic and functional fixed prosthetic restoration

Supplementary data for the article: Stevanović, N.; Mazzeo, P. P.; Bacchi, A.; Matić, I. Z.; Đorđić Crnogorac, M.; Stanojković, T.; Vujčić, M.; Novaković, I.; Radanović, D.; Šumar-Ristović, M.; Sladić, D.; Čobeljić, B.; Anđelković, K. Synthesis, Characterization, Antimicrobial and Cytotoxic Activity and DNA-Binding Properties of d-Metal Complexes with Hydrazones of Girard’s T and P Reagents. J Biol Inorg Chem 2021. https://doi.org/10.1007/s00775-021-01893-5.

In this work synthesis, characterization and crystal structures of 1, Zn(II) complex ([ZnL1(NCS)2]), with (E)-1-(2-oxo-2-(2-(quinolin-2-ylmethylene)hydrazinyl)ethyl)pyridin-1-ium chloride (HL1Cl) and 2, Bi(III) complex ([BiHL2Cl4] × 1/2CH3OH), with (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL2Cl), have been reported. Zn(II) complex possesses a distorted trigonal bipyramidal geometry while surroundings around Bi(III) ion are extended pentagonal bipyramidal. Antimicrobial activity, brine shrimp assay and DPPH radical scavenging activity of both complexes, including previously synthesized complexes with HL2Cl ligand (Zn(II) and Ni(II)) and complexes with (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL3Cl) (Zn(II), Cu(II), Cd(II), Co(II), Fe(III), Ni(II)), were evaluated. For the most active complexes, cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and normal cell line HaCaT, as well as generation of reactive oxygen species (ROS), was tested.Supplementary material for: [https://doi.org/10.1007/s00775-021-01893-5]Related to published version: [https://cherry.chem.bg.ac.rs/handle/123456789/4673

Distribution and diversity of brown frogs (Rana spp., Anura, Amphibia) in Serbia

In this study, we present updated distribution data for all three brown frog species (Rana spp.) inhabiting Serbia. The data provided consists of newly collected field records and compiled data previously published in literature or via Internet. Of the three species found in Serbia, Rana dalmatina is the most widespread, present in all three altitudinal regions and all biogeographical regions. Rana graeca is confined to Mountain-valley altitudinal region in permanent fastflowing rivers or streams and it reaches its northern range boundaries in Serbia. Rana temporaria is the rarest of the three, with fragmented range restricted to the high mountains or few isolated lowland populations, and in the north-eastern Serbia, it is vicariant with R. graeca in canyons and gorges of montane rivers. The presence of Rana arvalis in Serbia is mentioned in literature but was not confirmed during the subsequent field surveys, so we consider it only as a potential species for the Serbian batrachofauna. The brown frog faunal composition of Serbia is identical to that of Albania, Bosnia and Herzegovina, Bulgaria, Greece, Macedonia and Montenegro, while it is somewhat different from that of Hungary and Romania and the most different from Croatia and Slovenia. Serbian brown frogs belong to European (R. temporaria) and South-European (R. dalmatina, R. graeca) chorotypes. All species of brown frogs present or potentially present in Serbia and their habitats are identified as great conservation priorities

Pro12Ala gene polymorphism in the peroxisome proliferator-activated receptor gamma as a risk factor for the onset of type 2 diabetes mellitus in the Serbian population

The peroxisome proliferator-activated receptor gamma (PPARγ) is a gene candidate for the onset of type 2 diabetes mellitus (T2DM). We investigated the association of the PPARγ Pro12Ala gene with the onset of T2DM for the first time in the Serbian population. The study population consisted of 197 controls and 163 T2DM patients. The 12Ala allele tended to be more frequent in the group of T2DM patients (0.11) compared to the control subjects (0.09). The results from this study indicate that the PPARγ2 12Ala allele presents a non-significant risk factor for T2DM development in the Serbian population

The digital database of aquatic and semiaquatic vegetation in Serbia

Despite the absence of a centralized national phytocoenological database of Serbia, over 16,000 relevés of all vegetation types have been gathered and stored in the database “Phytocoenosis of Serbia” as a result of the Project “Habitats of Serbia”. However, as the data on aquatic and semiaquatic vegetation comprise only 5% of the collected relevés, the aim of this paper is to expand on this, complete the database and present the data on these vegetation types in Serbia. The work included the expansion of the existing database with the addition of relevant sources, their digitalization, using Flora and Turboveg programs, and their subsequent georeferencing, using OziExplorer and DIVAGIS softwares. Consequently, the phytocoenological database on aquatic and semiaquatic vegetation in Serbia now stores 1,720 relevés from 243 phytocoenological tables, collected and published by 24 authors during the period of 70 years (1940-2010), with the majority of the relevés collected over the last decade (56.40%). Phragmito-Magno-Caricetea Klika in Klika et Novák 1941 (Syn: Phragmitetea communis R. Tx. et Prsg. 1942), Potametea Klika in Klika et Novák 1941 (Syn: Potametea R. Tx. et Preising 1942) and Lemnetea de Bolós et Masclans 1955 (Syn: Lemnetea minoris W. Koch et R. Tx. 1955) have proven to be the most represented classes, while Scirpo-Phragmitetum W. Koch 1926 (nomen ambiguum) and Salvinio natantis-Spirodeletum polyrrhizae Slavnić 1956 are associations with the highest number of relevés in the database. Accordingly, the most common species (>500 relevés) are Ceratophyllum demersum L. subsp. demersum, Lemna minor L. and Spirodela polyrhiza (L.) Schleiden

Copper(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines: Anticancer, antioxidant, antigenotoxic effects and interaction with DNA and albumins

In this article, cytotoxicity, the mechanisms of cytotoxic activity, genotoxicity, and interaction with DNA and proteins, of two Cu(II) complexes with a salicylaldehyde derivative (4-(diethylamino)salicylaldehyde) and α-diimine (2,2′-bipyridine (bipy) and 1,10-phenanthroline (phen)) are reported. Both Cu(II) complexes performed cytotoxic effects against all tested malignant cell lines. Complexes exerted highest cytotoxicity against HeLa and A375 malignant cell lines. The cytotoxic activity of Cu(II) complex with phen as a α-diimine co-ligand was significantly higher in comparison with cytotoxic activity of Cu(II) complex with bipy. Pretreatment with specific inhibitors of caspase-3, caspase-8 or caspase-9, in order to clear up the mode of cell death triggered by two Cu(II) complexes in HeLa cells, indicated the ability of these complexes to induce apoptosis through activation of target caspases. Cu(II)-phen complex exhibited significant antioxidant activity compared with Cu(II)-bipy complex, and showed a better effect on reducing intracellular ROS levels in HeLa cells. Tested complexes did not display genotoxic potential in human peripheral blood leucocytes, but exhibited an antigenotoxic effect in post-treatment, after H2O2 exposure. The study of the in vitro biological properties regarding their affinity towards CT (calf-thymus) DNA and serum albumins showed that the compounds can intercalate to CT DNA, and bind reversibly and tightly to the albumins. Molecular docking studies of the ability of compounds to bind to biomacromolecules are consistent with in vitro studies

Cu(ii) complexes with a salicylaldehyde derivative and a-diimines as co-ligands: synthesis, characterization, biological activity. Experimental and theoretical approach

Copper(II) complexes with an α-diimine show a wide variety of biological activities, such as antibacterial, antifungal, antioxidant and anticancer. In this work, we synthesized and structurally characterized two novel Cu(II) complexes with methyl 3-formyl-4-hydroxybenzoate (HL) and α-diimines: 2,2′-bipyridine (bipy) and 1,10-phenanthroline (phen). Crystal structure analysis shows that the formulas of the compounds are [Cu(bipy)(L)(BF4)] (1) and [Cu(phen)(L)(H2O)](BF4)·H2O (2), with BF4− as a ligand in complex 1, which is rarely coordinated to metals. Both complexes have a square pyramidal geometry, while DFT calculations showed that the most stable structures of complexes 1 and 2 in a water/DMSO mixture are square-planar derivatives [Cu(bipy)(L)]+ and [Cu(phen)(L)]+. The antibacterial activity of compounds was evaluated in vitro on four Gram-negative and four Gram-positive bacterial strains. Complex 2 showed greater antibacterial activity towards all bacterial strains comparable to the control compound Amikacin. Complex 2 exerted a strong cytotoxic effect against the tested cancer cell lines (IC50 values ranging from 0.32 to 0.44 μM). Both complexes caused apoptotic cell death in HeLa cells and a noticeable in vitro antiangiogenic effect. In the concentration range of 5 to 100 μM, the complexes showed the absence of a genotoxic effect and displayed a protective effect against oxidative DNA damage induced by H2O2 in human peripheral blood cells. The interaction between the compounds and calf–thymus DNA was evaluated by diverse techniques suggesting a tight binding, which was also confirmed by molecular docking. In addition, it was found that the complexes bind tightly and reversibly to bovine and human serum albumin