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Öğe Addition of tetraethylthiuram disulfide to antimony(III) iodide; synthesis, characterization and biological activity(Elsevier Science Sa, 2016) Urgut, O. S.; Öztürk, İbrahim İsmet; Banti, Christina N.; Kourkoumelis, Nikolaos; Manoli, Maria; Tasiopoulos, Anastasios J.; Hadjikakou, Sotiris K.Three new antimony(III) iodide complexes with the N,N-diethylcarbamodithioic acid of formulae {[(SbI(Et2DTC)(2))(I-2)](n)} (1), {[(Sb(Et2DTC)(2))(4) (SbI6) (I-3)](n)} (2) and {[SbI(Et2DTC)(2)](2)} (3), (Et2DTCH: N,N-diethylcarbamodithioic acid, C5H11NS2) were synthesized from the reaction of antimony(III) iodide with tetraethylthiuram disulfide in 1: 1 stoichiometry. The complexes 1-3 were characterized by melting point, elemental analysis, FT-IR spectroscopy, Raman spectroscopy, H-1, C-13 NMR spectroscopy and Thermal Gravimetry-Differential Thermal Analysis (TG-DTA). Moreover, crystal structures of complexes 1-3 were determinated with single crystal X-ray diffraction analysis. Complexes 1-3 derived from ligand reduction with concomitant degradation of the tetraethylthiuram disulfide to dithiocarbamates. Complexes 1 and 2 are polymer but complex 3 is dimmer. Complex 1 consists of two residues, [SbI (Et2DTC)(2)] and [I-2], while 2 consists of three residues, four cationic [Sb(Et(2)dtc)(2)](+), one [SbI6](3-) and one [I-3](-) counter anion. Complexes 1-3 were evaluated for their in vitro cytotoxic activity against human breast adenocarcinoma (MCF-7) and human cervix adenocarcinoma (HeLa) cells. Structure Activity Relationship (SAR) studies reveal that the high activity of the complexes is positively correlated with the low H-all atoms intermolecular contacts. (C) 2016 Elsevier B.V. All rights reserved.Öğe Antimony(III) halide compounds of thioureas: Structures and biological activity(Pergamon-Elsevier Science Ltd, 2014) Han, A.; Öztürk, İbrahim İsmet; Banti, Christina N.; Kourkoumelis, Nikolaos; Manoli, Maria; Tasiopoulos, Anastasios J.; Hadjikakou, Sotiris K.Antimony(III) halide compounds (SbX3, X = Cl and Br) of thioureas; tetramethylthiourea (TMTU), N,N'-diethylthiourea (DETU) and 1,3-diisopropy1-2-thiourea (DIPTU) of formulae {[SbCl3(TMTU)](n)} (1), {[SbBr3(TMTU)](n)} (2), {[mer-SbCl3(DIPTU)(3))] [fac-SbCl3(DIPTU)(3)] C6H6} (3) and {[SbBr2(DETU)(2)](+)center dot Br-}(n) (4) were synthesized. The complexes were characterized by their melting point, elemental analysis, FT-IR spectroscopy, FT-Raman spectroscopy, H-1 and C-13 NMR spectroscopy and Thermal Gravimetry-Differential Thermal Analysis (TG-DTA). The crystal and molecular structures of complexes 2-4 were determined with single crystal X-ray diffraction analysis. Compounds 1 and 2 are polymers with pseudo-trigonal bipyramidal (Psi-TBP) geometry in each monomeric unit. Compound 3 is a monomer with octahedral (Oh) geometry around Sb(III). Two different coordination modes of the ligands around antimony ions are observed in 3 forming two units. One with meridional orientation and the other with facial one. This complex is the first example of polymeric antimony(III) where two sequential antimony atoms have two different coordination modes. Two sulfur atoms and two bromines form a pseudotrigonal bipyramidal cationic [SbBr2(L)(2)](+) part with a bromide as counter anion in complex 4. Complexes 1-4 and their ligands were evaluated for their in vitro cytotoxic activity against human breast adenocarcinoma (MCF-7) and human cervical adenocarcinoma (HeLa) cells. Principal components analysis (PCA) was performed to discriminate the significant physicochemical molecular descriptors while regression analysis successfully relates the experimental inhibitory concentrations, (IC50) to the independent variables indexed by PCA. (C) 2014 Elsevier Ltd. All rights reserved.Öğe Bismuth(III) bromide-thioamide complexes: synthesis, characterization and cytotoxic properties(Walter De Gruyter Gmbh, 2018) Çakmak, Mehmet; Öztürk, İbrahim İsmet; Banti, Christina N.; Manoli, Maria; Moushi, E.; Tasiopoulos, Anastasios J.; Hadjikakou, Sotiris K.New bismuth(III) bromine compounds of the heterocyclic thioamides were prepared and structurally characterized. The reaction of heterocyclic thioamides with bismuth(III) bromide resulted in the formation of the {[BiBr2(mu(2)-Br)(MMI)(2)](2)center dot CH3COCH3 center dot H2O} (1), {[BiBr2(MBZIM)(4)]center dot Br center dot 2H(2)O} (2), {[BiBr2(mu(2)-Br)(tHPMT)(2)](2)center dot CH3CN} (3), {[BiBr2(mu(2)-Br)(PYT)(2)](2)center dot CH3CN} (4) and {[BiBr2(mu(2)-Br)(MBZT)(2)](2) 2CH(3)OH} (5) complexes (MMI: 2-mercapto-1-methylimidazole, MBZIM: 2-mercaptobenzimidazole, tHPMT: 2-mercapto-3,4,5,6-tetrahydro-pyrimidine, PYT: 2-mercaptopyridine and MBZT: 2-mercaptobenzothiazole). The complexes 1-5 were characterized by melting point (m.p.), elemental analysis (c.a.), molar conductivity, Fourier-transform infrared (FT-IR), Fourier-transform Raman (FT-Raman), nuclear magnetic resonance (H-1 and (CNMR)-C-13) spectroscopy, UV-Vis spectroscopy and thermogravimetric-differential thermal analysis (TG-DTA). The molecular structures of 1-5 were determined by single-crystal X-ray diffraction. Complex 2 is a first ionic monomuclear octahedral bismuth(III) bromide, while the complexes 1,3-5 are the first examples of dinuclear bismuth(III) bromide derivatives. Complexes 1-5 were evaluated in terms of their in vitro cytotoxic activity against human adenocarcinoma breast (MCF-7) and cervix (HeLa) cells. The toxicity on normal human fetal lung fibroblast cells (MRC-5) was also evaluated. Moreover, the complexes 1-5 and free heterocyclic thioamide ligands were studied upon the catalytic peroxidation of the linoleic acid by the enzyme lipoxygenase (LOX).Öğe Bismuth(III) halide complexes of aromatic thiosemicarbazones: Synthesis, structural characterization and biological evaluation(Elsevier Ltd, 2021) Öztürk, İbrahim İsmet; Banti, Christina N.; Hadjikakou, Sotiris K.; Panagiotou, Nikos; Tasiopoulos, Anastasios J.Four new bismuth(III) thiosemicarbazone complexes, {BiCl3(?1-S-Hacptsc)3} (1), {[BiBr3(?1-S-Hacptsc)3]·CH3OH} (2), {[BiI2(µ2-I](?1-S-Hacptsc)]2} (3) and {[BiCl2(µ2-Cl)(?1-S-Hbztsc)2]2} (4), were prepared with the ligands acetophenone thiosemicarbazone (Hacptsc) and benzaldehyde thiosemicarbazone (Hbztsc). The complexes were characterized by a series of spectroscopic techniques. The crystal structures of 1–4 were also determined by X-ray diffraction. To the best of our knowledge, complexes 1–4 are the first examples of bismuth(III) halide aromatic thiosemicarbazones. Hirshfeld surface analysis studies show that H…H and X…H/H…X interactions of complexes 1–4 play an important role in the formation of supramolecular aggregation. Complexes 1–4 have been tested for their in vitro cytotoxic activity against human breast adenocarcinoma (MCF-7) cells. The toxicity of 1–4 has been evaluated on normal human fetal lung fibroblast cells (MRC-5). Complexes 1–4 appeared to show low cytotoxic activity and low toxicity. The antibacterial activity of 1–4 and their ligands was evaluated against the Gram negative species Pseudomonas aeruginosa (P. aeruginosa) and Escherichia coli (E. coli) and Gram positive ones Staphylococcus epidermidis (S. epidermidis) and Staphylococcus aureus (S. aureus) by the Inhibition Zone (IZ) method. The influence of 1–4 on the catalytic peroxidation of linoleic acid by the enzyme lipoxygenase (LOX) has been determined experimentally. The IC50 values reveal that the synthesized bismuth(III) aromatic thiosemicarbazone complexes have good potential to inhibit lipoxygenase, with values better than the free aromatic thiosemicarbazone ligands and cisplatin. © 2021 Elsevier LtdÖğe Group VA Aromatic Thiosemicarbazone Complexes: Synthesis, Characterization, Biological Activity, and Topological Studies(Mdpi, 2024) Ozturk, Ibrahim I.; Sumer, Emine I.; Dutkiewicz, Grzegorz; Banti, Christina N.; Hadjikakou, Sotiris K.; Grzeskiewicz, Anita M.; Kubicki, MaciejThe antiproliferative and antibacterial activities of thiosemicarbazones increase markedly with the presence of metal ions. One of the factors determining the activity of metal thiosemicarbazone complexes is the coordination structure. In this study, the biological effects of new antimony (III) and bismuth (III) thiosemicarbazone complexes with different binding modes and geometrical structures were demonstrated. Three new complexes, with the formulae {[SbCl3(mu 2-S-Hacptsc)(eta 1-S-Hacptsc)], 2/3H2O,1/3CH2Cl2}, {[SbCl3(kappa 2-S,N-Hacpmtsc)(eta 1-S-Hacpmtsc)2CH2Cl2]}, and{[BiCl3(eta 1-S-Hbzmtsc)3]C2H5OH}, where Hacptsc: acetophenone thiosemicarbazone, Hacpmtsc: acetophenone-N-methyl thiosemicarbazone, Hbzmtsc: benzaldehyde-N-methyl thiosemicarbazone) were elucidated by different methods and deeply analyzed in accordance with their structure by X-ray structure analysis and Atoms-In-Molecules topological analysis. This analysis provided a deeper understanding of the coordination spheres of the Sb/Bi complexes. For instance, the first reported two binding modes of the same ligand are observed in a single crystal structure of antimony (III) halide complexes. Additionally, in one of the complexes, a solid-to-solid phase transition was detected and analyzed in detail. Those complexes, very unique in terms of their geometry, have also been tested for their in vitro cytotoxic activity against human adenocarcinoma cervical cancer (HeLa) cells, whereas antimony (III) complex 1is the most active complex of this study. Further, the antibacterial activity of the complexes has been screened against two Gram-negative (Pseudomonas aeruginosa and Escherichia coli) and two Gram-positive (Staphylococcus epidermidis and Staphylococcus aureus) pathogenic bacteria. From the results, it is found that all the complexes exhibited significant activity against the Gram-negative pathogenic bacteria.Öğe Heteroleptic six-coordinate bismuth(iii) complexes with 2-acetylthiophene thiosemicarbazones: synthesis, characterization, and biological properties(Royal Soc Chemistry, 2023) Ozturk, Ibrahim I.; Turk, Kadriye; Grzeskiewicz, Anita M.; Kubicki, Maciej; Banti, Christina N.; Hadjikakou, Sotiris K.The present study aimed to prepare and then evaluate the antiproliferative and antibacterial activities of bismuth(III) thiosemicarbazone complexes. Five bismuth(III) halide complexes of general formulae [BiX3(HL)(3)] (X: Cl; 1 and 2) and [BiX2(mu(2)-X)(HL)(2)](2) (X: Br and I; 3,4 and 5), where HL is a thiosemicarbazone bearing an acetylthiophene moiety, have been synthesized and fully characterized, including their X-ray crystal structures. In all cases, the thiosemicarbazone ligand coordinated in a monodentate mode via the sulfur atom. Complexes 1 and 2 are mononuclear bismuth(III) complexes with octahedral (Oh) geometry around the metal ion formed by three sulfur and three chlorine atoms. However, the coordination mode of the ligands varied around the bismuth centers. Complex 1 contains one molecule with only a meridional orientation in its asymmetric unit, while complex 2 contains two molecules in its asymmetric unit, one with meridional orientation and the other with facial one. Two bismuth(III) atoms in dinuclear complexes (3, 4 and 5) were coordinated with each other by two halogen bridges. The bismuth(III) complexes 1-5 and their free ligands have been tested for their in vitro cytotoxic activity against human adenocarcinoma cervical cancer (HeLa) cells. The complexes showed promising results as antiproliferative agents for the HeLa cell line, with IC50 values ranging from 4.5 +/- 0.4 to 24.3 +/- 1.7 mu M. All these complexes were also tested against a series of bacteria, and they proved to be ineffective against Gram-positive bacteria (S. epidermidis and S. aureus) and moderately active against Gram-negative bacteria (P. aeruginosa and E. coli).Öğe Monomeric octahedral bismuth(III) benzaldehyde-N-1-alkyl thiosemicarbazones: Synthesis, characterization and biological properties(Pergamon-Elsevier Science Ltd, 2022) Aygün, Özlem; Grzeskiewicz, Anita M.; Banti, Christina N.; Hadjikakou, Sotiris K.; Kubicki, Maciej; Öztürk, İbrahim İsmetDue to their chemical and biological properties, the interest in thiosemicarbazones and their metal complexes is increasing day by day. In this study, the effect of the substituents at the N-1 atoms of the thiosemicarbazones and the effect of halogen atoms on the type and biological properties of bismuth(III) complexes is investigated. The reactions of bismuth(III) halide with a series of benzaldehyde-N-1-alkyl-thiosemicarbazones in 1:3 M ratio yield bismuth(III) halide complexes: {BiBr3(eta(1)-S-Hbztsc)3} (1), {BiCl3(eta(1)-S-Hbzmtsc)(3)} (2), {BiBr3(eta(1)-S-Hbzmtsc)(3)} (3), {[BiCl3(eta(1)-S-Hbzetsc)(3)].CH3OH} (4) and {BiBr3(eta(1)-S-Hbzetsc)(3)} (5). Complexes 1-5 were characterized by a number of different spectroscopic methods. The crystal structures of complexes 1-5 and the free ligand benzaldehyde-N-methyl-thiosemicarbazone were determined by X-ray diffraction. Complexes 1-5 were tested for their in vitro cytotoxic activity against human breast adenocarcinoma (MCF-7) cell line. Complexes 1-5 showed low cytotoxic activity. The antibacterial activities of 1-5 and their free ligands against four strains bacteria of Staphylococcus epidermidis, Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli have been examined. The results indicated that bismuth(III) complexes 1-5 are most active against E. coli and, among them, complex 4 exhibits the highest activity. Lipoxygenase (LOX) inhibitory activity of the bismuth(III) halide complexes 1-5 and the free ligands has been detected experimentally. The IC50 values indicate that bismuth(III) halide complexes 1-5 have a higher enzyme inhibition potential than free ligands and cisplatin.Öğe New antimony(III) halide complexes with dithiocarbamate ligands derived from thiuram degradation: the effect of the molecule's close contacts on in vitro cytotoxic activity(Elsevier, 2016) Urgut, O. S.; Öztürk, İbrahim İsmet; Banti, Christina N.; Kourkoumelis, Nikolaos; Manoli, Maria; Tasiopoulos, Anastasios J.; Hadjikakou, Sotiris K.Antimony(III) halide complexes of the formulae {[SbBr(Me2DTC)(2)](n)} (1), {[SbI(Me2DTC)(2)](n)} (2) and {[(Me2DTC)(2)Sb(mu(2)-I)Sb(Me2DTC)(2)](+)center dot I-3(-)} (3) (Me2DTC = dimethyldithiocarbomate) were synthesized from SbX3, (X = Br or I) and tetramethylthiuram monosulfide (Me(4)tms) or tetramethylthiuram disulfide (Me(4)tds). The complexes were characterized by melting point (m.p.), elemental analysis (e.a.), Fourier-transform InfraRed (FT-IR), Fourier-transform Raman (FT-Raman), Nuclear Magnetic Resonance (H-1,C-13-NMR) spectroscopy and Thermogravimetric-Differential Thermal Analysis (TG-DTA). Crystal structures of complexes 1-3 were determined with single crystal X-ray diffraction analysis. Complexes 1 and 2 are polymers with distorted square pyramidal (SP) geometry in each monomeric unit, whereas complex 3 is ionic, containing an iodonium linkage SbI+-Sb and an I-3(-) counter anion; to the best of our knowledge, this is the first ionic antimony(III) iodide complex. The in vitro cytotoxic activity of 1-3 against human adenocarcinoma cells: breast (MCF-7) and cervix (HeLa) cells and non-cancerous cells: MRC-5 (normal human fetal lung fibroblast cells) was evaluated with trypan blue (TB) and sulforhodamine B (SRB) assays. Among antimony(III) compounds with sulfur containing ligand, those of dithiocarbamates exhibit significant cytotoxic activity. Hirshfeld surface volumes were analyzed to clarify the nature of the intermolecular interactions by the 2D fingerprint plot. Molecules with lower H-all atoms intermolecular interactions exhibit the higher activity against MCF-7 cells. The in vivo genotoxicity of 1-3 was evaluated by the mean of Allium cepa test. Alterations in the mitotic index values due to the chromosomal aberrations were observed in the case of complexes 2 and 3. Since, no such alteration is caused by 1, it makes this compound candidate for further study as potential drug. (C) 2015 Elsevier B.V. All rights reserved.Öğe Novel bismuth compounds: synthesis, characterization and biological activity against human adenocarcinoma cells(Royal Soc Chemistry, 2016) Arda, M.; Öztürk, İbrahim İsmet; Banti, Christina N.; Kourkoumelis, Nikolaos; Manoli, Maria; Tasiopoulos, Anastasios J.; Hadjikakou, Sotiris K.Five new bismuth(III) halide compounds (BiX3, X = Br or I) of formulae {[BiBr(Me2DTC)(2)](n)} (1), {[BiBr2(Et2DTC)](n)} (2), {[BiI2(Me2DTC)](n)} (3), {[BiI(Et2DTC)(2)](n)} (4) and {[BiI(mu(2)-I)(Et2DTC)(2)](2)}(n) (5) (Me2DTCH = dimethyldithiocarbamate, C3H7NS2 and Et2DTCH = diethyldithiocarbamate, C5H11NS2) were synthesized from the reactions between bismuth(III) bromide (BiBr3) or bismuth(III) iodide (BiI3) with tetramethylthiuram monosulfide (Me(4)tms), tetramethylthiuram disulfide (Me(4)tds) or tetraethylthiuram disulfide (Et(4)tds). The complexes were characterized by melting point, elemental analysis, FT-IR spectroscopy, Raman spectroscopy, H-1, C-13 NMR spectroscopy and Thermal Gravimetry-Differential Thermal Analysis (TG-DTA). Moreover, the crystal structures of 1-5 were determined with single crystal X-ray diffraction analysis. The ligands of compounds 1-5 were derived from reduction with concomitant degradation to dithiocarbamates. Complexes 1-4 are polymers, whereas complex 5 is a dimer, built up from monomeric units with square pyramidal (SP) geometry (1, 4 and 5) and pentagonal bipyramidal geometry (2 and 3) around the bismuth center. Complexes 1-5 were evaluated for their in vitro cytotoxic activity against human adenocarcinoma breast (MCF-7) and cervix (HeLa) cells. The toxicity on normal human fetal lung fibroblast cells (MRC-5) is also evaluated. Since estrogen receptors (ERs) are located in MCF-7, in contrast to HeLa cells, the estrogenic effect of 1-5 on MCF-7 cells was studied by means of a methylene blue assay. Hirshfeld surface volumes were analyzed to clarify the nature of the intermolecular interactions. Molecules with lower H-all atoms inter-molecular interactions tend to exhibit higher activity against both MCF-7 and HeLa cells. Structure-activity relationship (SAR) studies were performed for these complexes using 2D topological based disparity analysis. This finding underlines the significance of the halogen atoms in the coordination sphere of the metal ion.Öğe QSAR studies on antimony(III) halide complexes with N-substituted thiourea derivatives(Pergamon-Elsevier Science Ltd, 2017) Öztürk, İbrahim İsmet; Yarar, S.; Banti, Christina N.; Kourkoumelis, Nikolaos; Chrysouli, M. P.; Manoli, Maria; Hadjikakou, Sotiris K.The synthesis, characterization and biological studies of three novel antimony(III) complexes (SbX3, X = Cl and Br) with N-substituted thioureas; N,N-dimethylthiourea (DMTU) and N,N-diethylthiourea (DETU) of formulae [fac-SbCl3(DMTU)(3)] (1), Imer-SbBr3(DMTU)(3)] (2) and b,c,d-ClSbCl3(DETU)(2)] (3) are reported. The compounds were characterized by melting point (m.p.), elemental analysis (e.a.), molar conductivity, FT-IR, FT-Raman, H-1, C-13 NMR, UV-Vis spectroscopic techniques and Thermogravimetric-Differential Thermal Analysis (TG-DTA). The crystal structures of complexes were also determined by X-ray diffraction. Complexes 1 and 2 are monomers with octahedral (Oh) geometry around the metal ion, which is formed by three sulfur and three halide atoms. However the coordination mode of the ligands varied around the metal centers. Thus, 1 possesses the facial isomeric form, while 2 the meridional form. In case of 3 two sulfur atoms from thiourea ligands and three chlorides form a trigonal pyramidal geometry b,c, d-C1-[SbCI3(DETU)(2)] which finally turns to be a polymeric one through-C1 bonds and Oh geometry around each Sb ion. A chloride counter anion neutralizes the whole complex. Complexes 1-3 were evaluated for their in vitro cytotoxic activity against human breast (MCF-7) and cervix (HeLa) adenocarcinoma cells. The toxicity of the complexes was studied against human fetal lung fibroblast cells (MRC5). The apoptotic type of the cells death was confirmed by cell cycle arrest. The influence of 1-3 upon the catalytic peroxidation of linoleic acid to hyperoxolinoleic acid by the enzyme lipoxygenase (LOX) was kinetically studied. QSAR study reveals a linear correlation between experimental and calculated IC50 values. The model predict the activity of Sb complexes successfully, if log(IC50) > 0. (C) 2016 Elsevier Ltd. All rights reserved.Öğe Recent advances on antimony(III/V) compounds with potential activity against tumor cells(Elsevier Science Inc, 2015) Hadjikakou, Sotiris K.; Öztürk, İbrahim İsmet; Banti, Christina N.; Kourkoumelis, Nikolaos; Hadjiliadis, N.Antimony one of the heavier pnictogens, has been in medical use against microbes and parasites as well. Antimony-based drugs have been prescribed against leishmaniasis since the parasitic transmission of the tropical disease was understood in the beginning of the 20th century. The activity of arsenic against visceral leishmaniasis led to the synthesis of an array of arsenic-containing parasitic agents, among them the less toxic pentavalent antimonials: Stibosan, Neostibosan, and Ureastibamine. Other antimony drugs followed: sodium stibogluconate (Pentostam) and melglumine antimoniate (Glucantim or Glucantime); both continue to be in use today despite their toxic side effects and increasing loss in potency due to the growing resistance of the parasite against antimony. Antimony compounds and their therapeutic potentials are under consideration from many research groups, while a number of early reviews recording advances of antimony biomedical applications are also available. However, there are only few reports on the screening for antitumor potential of antimony compounds. This review focuses upon results obtained on the anti-proliferative activity of antimony compounds in the past years. This survey shows that antimony(III/V) complexes containing various types of ligands such as thiones, thiosemicarbazones, dithiocarbamates, carboxylic acids, or ketones, nitrogen donor ligands, exhibit selectivity against a variety of cancer cells. The role of the ligand type of the complex is elucidated within this review. The complexes and their biological activity are already reported elsewhere. However quantitative structure-activity relationship (QSAR) modeling studies have been carried out and they are reported for the first time here. (C) 2015 Elsevier Inc. All rights reserved.Öğe Structural architectures and biological properties of main group bismuth(III) iodide complexes with heterocyclic thioamides(Elsevier S.A., 2019) Öztürk, İbrahim İsmet; Banti, Christina N.; Hadjikakou, Sotiris K.; Panagiotou, Nikos; Tasiopoulos, Anastasios J.A series of mononuclear, dinuclear and polynuclear bismuth(III) iodide complexes (1–5) bearing heterocyclic thioamide ligands, 2-mercapto-3,4,5,6-tetrahydro-pyrimidine (tHPMT), 2-mercapto-benzimidazole (MBZIM), 2-mercapto-1-methylimidazole (MMI), 2-mercaptobenzothiazole (MBZT) and 2-mercaptopyridine (PYT), have been synthesized and characterized by melting point, elemental analysis, FT-IR spectroscopy, Raman spectroscopy, 1H, 13C NMR spectroscopy, UV–Vis spectroscopy and Thermal Gravimetry-Differential Thermal Analysis (TG-DTA). Moreover, the crystal structures of 1–5 have been also determined with single crystal X-ray diffraction analysis. The use of the above mentioned heterocyclic thioamide ligands have allowed synthesis of the first examples of bismuth(III) iodide thioamide complexes. {[BiI3(tHPMT)3]} (1) is the first structural example of a neutral mononuclear bismuth(III) iodide complex with octahedral geometry around the bismuth(III) ion with meridional conformation. {[BiI2(µ2-I)(MBZIM)2]2} (2) is the first example of a dinuclear bismuth(III) iodide complex with octahedral geometry around the bismuth(III) ion with trans-S/cis-I arrangement. {[BiI(µ2-I)2(MMI)]n} (3) and {[BiI(µ2-I)2(MBZT)]n·CH3OH} (4) are the first examples of the polynuclear bismuth(III) iodide complexes with octahedral geometry around the bismuth(III) ions. The ligand molecules are coordinated via the thione sulfur atoms in both complexes but in complex 3, ligand molecules are trans to each other in polymeric chain while, in complex 4, ligand molecules are cis to each other in polymeric chain. {[BiI(µ2-S,N-PYT)2]n} (5) is the first example of a polynuclear bismuth(III) iodide complex with pentagonal bipyramidal geometry around the bismuth(III) ions. The seven coordinate bismuth(III) atom has a N2S4I-donor set consisting of one iodine atom and two chelating and bridging ?2-S,N (?2-S:?1-N) pyridine-2-thionate anions. Complexes 1–5 were evaluated for their in vitro cytotoxic activity against human adenocarcinoma cervix (HeLa) and breast (MCF-7) cancer cells. The toxicity of the complexes was studied against human fetal lung fibroblast cells (MRC-5). The influence of 1–5, upon the catalytic peroxidation of the linoleic acid by the enzyme lipoxygenase (LOX), was evaluated experimentally. © 2019 Elsevier B.V.Öğe Structural characterization and biological evaluation of antimony(III) and bismuth(III) complexes with imidazolidine-2-thione(Elsevier B.V., 2021) Uçar, Okan; Grze?kiewicz, Anita M.; Banti, Christina N.; Hadjikakou, Sotiris K.; Öztürk, İbrahim İsmetThere is an emerging interest in the synthesis of antimony(III) and bismuth(III) complexes with sulfur containing ligands, this has been attributed to their wide structural diversity and their interesting application as biological agents. In the present work, four new antimony(III) and bismuth(III) complexes {[SbCl(IMT)3(?-Cl)SbCl3(?-Cl)]n} (1), {[SbBr2(IMT)2(?-Br)]n} (2), {[BiBr2(IMT)2(?-Br)]n} (3), and {mer-[BiI3(IMT)3]} (4) with imidazolidine-2-thione (IMT) have been prepared and characterized structurally, spectroscopically, and thermogravimetrically. The crystal structures of 1-4 have been determined by single-crystal X-ray diffraction. Complex 1 is the first structural example of polymeric antimony(III) chloride thioamide complex containing two different metallic centers. Complexes 2 and 3 are isostructural and the central atoms are six-coordinate in a distorted octahedral geometry with the zigzag chains formed by corner-sharing octahedra. Complex 4 is an example of neutral mononuclear bismuth(III) iodide complex with octahedral geometry. Complexes 1-4 have been evaluated for in vitro cytotoxic activity against human breast adenocarcinoma (MCF-7) cells. Complexes 1-4 appeared to show low cytotoxic activity against MCF-7 cells. The toxicity of 1-4 has been evaluated on normal human fetal lung fibroblast cells (MRC-5). The toxicity of antimony compounds 1-2 was greater than that of bismuth compounds 3-4. The influence of 1-4, on the catalytic peroxidation of the linoleic acid by the enzyme lipoxygenase (LOX) has been determined experimentally. © 2021Öğe Synthesis, characterization and biological activity of antimony(III) or bismuth(III) chloride complexes with dithiocarbamate ligands derived from thiuram degradation(Pergamon-Elsevier Science Ltd, 2014) Öztürk, İbrahim İsmet; Banti, Christina N.; Kourkoumelis, Nikolaos; Manos, Manolis; Tasiopoulos, Anastasios J.; Owczarzak, A. M.; Hadjikakou, Sotiris K.Antimony(III) or bismuth(III) complexes of formulae {[SbCI(Me2DTC)(2)](n)} (I), {[BiCl(Me2DTC)(2)](n)} (2) and {[Bi(Et2DTC)(3)](2)} (3) (Me2DTCH = dimethyldithiocarbamate, C3H7NS2 and Et2DTCH = diethyldithiocarbamate, C-5-H11NS2) were isolated from the reactions between SbCl3 or BiCl3 with tetramethylthiuram monosulfide (Me(4)tms), tetramethylthiuram disulfide (Me(4)tds) or tetraethylthiuram disulfide (Et(4)tds). In the case of 1 two polymorphs were isolated depending on the synthetic procedure followed. Crystal growth from the reaction of antimony(III)-chloride with Me(4)tms in methanol produced la polymorph, while those derived from Me(4)tds in acetonitrile/dichloromethane produced lb form. The complexes 1-3 were characterized by m.p., e.a., FT-IR, FT-Raman, H-1, C-13 NMR spectroscopy and Thermal Gravimetry-Differential Thermal Analysis (TGA-DTA). Moreover, single crystal X-ray diffraction analysis was carried out for 1a, 2b, 2 and 3. X-ray powder diffraction data confirm the existence of one polymorph in the bulk of each sample of 1a and 1b. H-1 NMR spectra in the DMSO-d(6) solutions of 1a and 1b suggest the retention of the structural variations. Complexes 1 and 2 are polymers with distorted square pyramidal (SPY) geometry in each monomeric unit. The known structure of 3 was re-determined to be used for the theoretical and structure activity relationship studies (SAR). Complexes 1-3 were evaluated for their in vitro cytotoxic activity against human breast adenocarcinoma (MCF-7) and human cervix adenocarcinoma (HeLa) cells. Complex 3 is more active against HeLa cells whereas 1a, 1b and 2 against MCF-7. Compound la shows slightly higher activity than lb. Principal components analysis (PCA) was performed to discriminate the significant physicochemical molecular descriptors while regression analysis successfully related the experimental inhibitory concentration, (IC50) to the independent variables indexed by PCA. The calculated IC50 values are satisfactorily compared with the measured inhibitory activity of the complexes. (C) 2013 Elsevier Ltd. All rights reserved.Öğe Synthesis, characterization and biological evaluation of novel antimony(III) iodide complexes with tetramethylthiourea and N-ethylthiourea(Elsevier S.A., 2019) Öztürk, İbrahim İsmet; Yarar, S.; Gürgan, Muazzez; Ceyhan, Deniz; Banti, Christina N.; Hadjikakou, Sotiris K.; Tasiopoulos, Anastasios J.Novel trivalent antimony(III) complexes with tetramethylthiourea (TMTU) and N-ethylthiourea (NETU) were synthesized by the reaction of antimony(III) iodide (SbI3). Antimony(III) iodide complexes of formulae {[SbI2(µ2-I)(TMTU)2]2} (1) and {[(NETU)SbI2(µ2-I)2(µ2-S-NETU)SbI2(NETU)]} (2) were characterized by spectroscopic techniques (FT-IR, FT-Raman, 1H and 13C NMR), TG-DTA analysis and X-ray diffraction (XRD) analysis. Single-crystal X-ray diffraction studies showed that the complexes existed as doubly bridged (1) and triply bridged (2) dimers. Crystal structure of the ligand N-ethylthiourea was also determined with single crystal X-ray diffraction analysis. Complexes 1 and 2 were evaluated for their in vitro cytotoxic activity against human adenocarcinoma cells HeLa (cervix). The toxicity of 1 and 2 was evaluated on normal human fetal lung fibroblast cells (MRC-5). Both complexes showed selectivity against the cancerous, than normal cells. The influence of 1 and 2, on the catalytic peroxidation of the linoleic acid by the enzyme lipoxygenase (LOX) was determined experimentally and theoretically. The complexes 1 and 2 exhibited higher activity than free ligands against LOX. The in vitro antibacterial activities of free ligands and their antimony(III) iodide complexes 1 and 2 were tested against two Gram-negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) and two Gram-positive (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212) bacteria. The complexes 1 and 2 were much more effective in terms of antimicrobial activity compared to the free ligands. © 2019 Elsevier B.V.Öğe Synthesis, characterization and biological studies of new antimony(III) halide complexes with omega-thiocaprolactam(Elsevier Science Inc, 2012) Öztürk, İbrahim İsmet; Banti, Christina N.; Manos, Manos J.; Tasiopoulos, Anastasios J.; Kourkoumelis, Nikolaos; Charalabopoulos, Konstantinos; Hadjikakou, Sotiris K.Three new antimony(III) halide complexes (SbX3, X = Cl, Br and I) with the heterocyclic thione omega-thiocaprolactam (1-azacycloheptane-2-thione, (Hthcl)) of formulae {[SbCl2(mu(2)-Cl)(Hthcl)(2)](n)} (1), {[(SbBr2(mu(2)-Br)(Hthcl)(2))(2)]} (2) and {[(Sbl(2)(mu(2)-I)(Hthcl)(2))(2)]} (3) were synthesized from the reaction of antimony(III) halides with w-thiocaprolactam in 1:2 stoichiometry. The complexes were characterized by elemental analysis, FT-IR spectroscopy, H-1, C-13 NMR spectroscopy and Thermal Gravimetry-Differential Thermal Analysis (TG-DTA). Crystal structures of the ligand w-thiocaprolactam and its complexes 1-3 were determined with single crystal X-ray diffraction analysis. Complexes 1-3 and w-thiocaprolactam were evaluated for their in vitro cytotoxic activity against leiomyosarcoma (LMS) and human breast adenocarcinoma (MCF-7) tumor cell lines. Antimony complexes 1-3 exhibit strong antiproliferative activity against both cell lines tested. The higher such activity was found for 3 with IC50 values of 0.12 +/- 0.04 mu M (LMS) and 0.76 +/- 0.16 mu M (MCF-7) which are 60 and 10 times respectively, stronger than that of cisplatin. The influence of these complexes 1-3 and w-thiocaprolactam upon the catalytic peroxidation of linoleic acid to hyperoxolinoleic acid by the enzyme lipoxygenase (LOX) was kinetically and theoretically studied. The results were shown negligible inhibitory activity of 1-3 against LOX. (C) 2012 Elsevier Inc. All rights reserved.Öğe Synthesis, characterization and cytotoxic properties of bismuth(III) chloride complexes with heterocyclic thioamides(Elsevier Science Sa, 2018) Yarar, S.; Öztürk, İbrahim İsmet; Banti, Christina N.; Panagiotou, Nikos; Papatriantafyllopoulou, C.; Manoli, Maria; Hadjikakou, Sotiris K.Bismuth(III) complexes of the formulae [BiCl3(MBZT)(2)] center dot H2O} (1), {[BiCl2(mu(2)-Cl)(MMI)(2)](2)center dot(CH3)(2)CO} (2), {[BiCl3(mu(2)-S-PYT)(PYT)](2)} (3) {([BiCl2(MBZIM)(4)](+))center dot 2(Cl-) center dot(H3O+)center dot 2H(2)O} (4) and [BiCl3(tHPMT)(3)] (5) (where MBZT: 2-mercaptobenzothiazole, MMI: 2-mercapto-1-methylimidazole, PYT: 2-mercaptopyridine, MBZIM: 2-mercaptobenzimidazole, tHPMT: 2-mercapto-3,4,5,6-tetrahydro-pyrimidine) are reported. The compounds were characterized by spectroscopic techniques including FT-IR, FT-Raman, UV-Vis, H-1-, C-13-NMR spectroscopies, TG-DTA, e. a, molar conductivity and by single-crystal X-ray diffraction analysis. While 1, 4 and 5 are mononuclear compounds, 2 and 3 are dinuclear complexes in which the two Bi3+ ions are bridged through Cl- and SR groups respectively. Interestingly, 3 is the first example of dinuclear Bi3+ complex containing two Bi-(mu-SR)-Bi bridges between the two metal centers formed by covalent bonds. Compounds 1-5 were evaluated for their in vitro cytotoxic activity against human adenocarcinoma cervix (HeLa) and breast (MCF-7) cells. The toxicity of 1-5 was evaluated on normal human fetal lung fibroblast cells (MRC-5). The influence of 1-5, on the catalytic peroxidation of the linoleic acid by the enzyme lipoxygenase (LOX) was determined experimentally. (C) 2017 Elsevier B.V. All rights reserved.Öğe Synthesis, Characterization, and Biological Investigation of Antimony(III) Halide Complexes With Different Coordination Architectures Constructed From Thiophene Thiosemicarbazones(Wiley, 2025) Ucar, Okan; Ozturk, Ibrahim I.; Grzeskiewicz, Anita M.; Kubicki, Maciej; Banti, Christina N.; Hadjikakou, Sotiris K.In this study, we report the synthesis, characterization, and biological investigation of antimony(III) halide complexes with various coordination architectures constructed from thiophene thiosemicarbazones. Antimony(III) thiophene-2-carbaldehyde thiosemicarbazone complexes (1, 2, 4, and 5) exhibit a square pyramidal geometry, with ligands coordinated to the central antimony atom in two distinct binding modes. In contrast, antimony(III) 2-acetylthiophene thiosemicarbazone complexes (3, 6, and 7) adopt a seesaw geometry. These complexes (1-7) represent the first reported examples of antimony(III) halide thiosemicarbazone compounds. The unique coordination environments observed in these complexes are of significant importance within the realm of antimony chemistry. These synthesized complexes exhibit different coordination geometries as well as potential biological activities. The antiproliferative activity against the human breast adenocarcinoma (MCF-7) cell line and antimicrobial activity against Gram-positive and Gram-negative bacteria were assessed. Antimony(III) thiophene-2-carbaldehyde thiosemicarbazone complexes (1, 2, 4, and 5) showed significant antiproliferative activity with IC50 values ranging from 8.5 to 19.1 mu M, while antimony(III) 2-acetylthiophene thiosemicarbazone complexes (3, 6, and 7) had higher IC50 values. Additionally, the antimony complexes demonstrated selective antimicrobial activity against Gram-negative bacteria.Öğe Synthesis, characterization, and biological properties of mono-, di- and poly-nuclear bismuth(III) halide complexes containing thiophene-2-carbaldehyde thiosemicarbazones(Elsevier Science Inc, 2022) Türk, Kadriye; Grzeskiewicz, Anita M.; Banti, Christina N.; Hadjikakou, Sotiris K.; Kubicki, Maciej; Öztürk, İbrahim İsmetIn order to investigate the coordination chemistry and pharmacological applications of bismuth compounds, a series of new bismuth(III) halide thiosemicarbazone complexes were synthesized. The reactions of thiophene-2-carbaldehyde-N-substituted thiosemicarbazones with bismuth(III) halides resulted in the formation of the {[[BiCl2(eta 1-S-Httsc)4]+.Cl-][BiCl2(mu 2-Cl)(eta 1-S-Httsc)2]2} (1), {[BiCl3(eta 1-S-Htmtsc)3].CH3OH} (2), {[BiCl3(eta 1-S-Htetsc)3].CH3OH} (3), {[BiBr2(mu 2-Br)(eta 1-S-Httsc)2]2.CH3OH} (4), {[BiBr2(mu 2-Br)(eta 1-S-Htmtsc)2]n} (5), and {[BiI2(mu 2-I)(eta 1-S-Httsc)2]2} (6) complexes (Httsc: thiophene-2-carbaldehyde thiosemicarbazone, Htmtsc: thio-phene-2-carbaldehyde-N-methyl thiosemicarbazone, Htetsc: thiophene-2-carbaldehyde-N-ethyl thio-semicarbazone). The complexes were characterized by a number of different spectroscopic techniques and the crystal structures of all bismuth(III) complexes (1-6) were determined by using single crystal X-ray diffraction study. In addition, the thermal stability of the complexes was compared using Thermogravimetric-differential thermal analysis. Crystal structures of the two free ligands, thiophene-2-carbaldehyde-N-methyl-thio-semicarbazone and thiophene-2-carbaldehyde-N-ethyl-thiosemicarbazone, were also determined by using single crystal X-ray diffraction analysis. The Hirshfeld surface of the bismuth(III) complexes and free ligands were additionally analyzed to verify the intermolecular interactions. Biological studies showed that all six bismuth(III) thiosemicarbazone complexes (1-6) exhibited biological activities against selected bacteria and the human breast adenocarcinoma (MCF-7) cell line.Öğe Synthesis, structural characterization and cytostatic properties of N,N-dicyclohexyldithiooxamide complexes of antimony(III) halides (SbX3, X: Br or I)(Pergamon-Elsevier Science Ltd, 2014) Öztürk, İbrahim İsmet; Ürgüt, O.; Banti, Christina N.; Kourkoumelis, Nikolaos; Owczarzak, A. M.; Kubicki, M.; Hadjikakou, Sotiris K.The novel antimony(III) halide complexes with the bi-dentate substituted dithiooxamide ligand, N,N-dicyclohexyldithiooxamide (HDTOA) of formulae {[SbBr3(HDTOA)(1.5)]}(n) (I) and ([SbI3(HDTOA)(1.5)]center dot C6H6}(n) (2), were prepared by reacting antimony(III) bromide or antimony(III) iodide with HDTOA in 1:1 molar ratio. The compounds were characterized by their m.p., FT-IR spectroscopy, Raman spectroscopy, H-1, C-13 NMR spectroscopy, Thermal Gravi metric - Differential Thermal Analysis (TG-DTA) and single crystal X-ray diffraction analysis. Both complexes are polymeric consisting by [SbX3(HDTOA)(1.5)] building blocks. The octahedral geometric demand of the metal center is covered by three halides and three sulfur atoms from three different HDTOA ligands with facial conformation in both complexes. Each ligand bridged two metal centers of two units, through sulfur donor atoms, acting as bi-dentate bridging ligand. Complexes 1 and 2 were also tested for in vitro cytotoxic activity against human breast adenocarcinoma (MCF-7) and human cervical adenocarcinoma (HeLa) cells. Principal components analysis (PCA) was performed to discriminate the significant physicochemical molecular descriptors while regression analysis successfully related the experimental inhibitory concentrations, (IC50) to the independent variables indexed by PCA. The calculated IC50 values are satisfactorily compared with the measured inhibitory activity of the complexes. (C) 2013 Elsevier Ltd. All rights reserved.
