Facultatea de Chimie şi Tehnologie Chimică / Faculty of Chemistry and Chemical Technology

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Start date: 2014Subject: search.filters.subject.antimicrobial activity

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    Synthesis, Structure, and Biological Activity of Mixed-Ligand Amine-Containing Copper(II) Coordination Compounds with 2-(2-Hydroxybenzylidene)-N-(prop-2-en-1-yl)hydrazinecarbothioamide [Articol]
    (2021) Gulea, Aurelian; Graur, Vasilii; Ulchina, Ianina; Bouroș, Pavlina; Smaglii, Vadim; Garbuz, Olga; Țapcov, Victor
    Сopper(II) nitrate reacts in ethanol with 2-(2-hydroxybenzylidene)-N-(prop-2-en-1-yl)hydrazinecarbothioamide H2L in an 1 : 1 molar ratio to form the coordination compound Cu(HL)NO3·H2O. The introduction of amines [imidazole (Im), 3,5-dibromopyridine (3,5-Br2Py), and 4-methylpyridine (4-Pic)] into the reaction mixture in a molar ratio 1 : 1 : 2 leads to the formation of CuA(HL)NO3·nH2O [A = Im, 3,5-Br2Py, 4-Pic; n = 0, 3] complexes. The structure of the obtained compounds was determined by X-ray structural analysis. The synthesized complexes exhibit antimicrobial, antifungal, antioxidant, and anticancer activities.
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    Synthesis, Structure, and Biological Activity of Copper(II), Nickel(II), Cobalt(III), and Iron(III) Coordination Compounds with 2-{2-[(Prop-2-en-1-yl)carbamothioyl]hydrazinylidene}propanoic Acid [Articol]
    (2020) Gulea, Aurelian; Graur, Vasilii; Diurici, E.; Ulchina, Ianina; Bouroș, Pavlina; Balan, Greta; Burduniuc, Olga; Țapcov, Victor; Rudic, Valeriu
    2-Oxopropanoic acid reacts in ethanol with N-(prop-2-en-1-yl)hydrazinecarbothioamide in a 1 : 1 mole ratio to form thiosemicarbazone H2L. Coordination compounds Cu(HL)X [X = Cl–, Br–, NO3–], Cu(H2O)(L), Ni(HL)2, Co(HL)2X [X = Cl–, Br–], and Fe(HL)2X [X = NO3–, Br–] are formed in the reactions of H2L with copper(II), nickel(II), cobalt(II), and iron(III) salts. The reactions of Cu(H2O)(L) with imidazole (Im) and 3,4-dimethylpyridine (3,4-Lut) result in mixed-ligand complexes Cu(A)(L) [A = Im, 3,4-Lut]. The structures of two copper complexes were determined by single crystal X-ray diffraction analysis. The synthesized complexes exhibit selective antimicrobial and antifungal activity in the concentration range of 15.62–1000 μg/mL. The introduction of amines into the inner sphere of copper complexes leads to an increase in the antimicrobial activity.
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    Synthesis, Structure and Biological Activity of Coordination Compounds of Copper, Nickel, Cobalt, and Iron with Ethyl N'-(2-Hydroxybenzylidene)-N-prop-2-en-1-ylcarbamohydrazonothioate [Articol]
    (2020) Gulea, Aurelian; Usataia, Irina; Graur, Vasilii; Ciumacov, Iurie; Petrenko, Peter; Balan, Greta; Burduniuc, Olga; Țapcov, Victor; Rudic, Valeriu
    N-(Prop-2-en-1-yl)hydrazonocarbothioamide reacts with iodoethane in methanol with further addition of 2-hydroxybenzaldehyde to form hydroiodide of carbamohydrazonothioate (HL·HI). The coordination compounds were obtained by interaction of HL or HL·HI with copper, nickel, cobalt and iron salts CuLХ·nH2O [X = Cl–, Br–, NO3–; n = 0–1], Ni(L)2·HI·CH3OH, Сo(L)2X [X = I–, NO3–] and Fe(L)2NO3. The structures of three complexes were established by single crystal X-ray analysis. The synthesized complexes exhibit selective antimicrobial and antifungal activity against a series of standard microorganisms and fungi in the concentration range of 30–500 μg/mL. In addition, nickel and iron complexes selectively inhibit the growth and proliferation of cancer cells and do not adversely affect normal cells.
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    Synthesis, Structure, and Biological Activity of Coordination Compounds of Cobalt(II), Nickel(II), and Copper(II) with N-(Methoxyphenyl)-2-[(5-nitrofuryl)methylene]hydrazine Carbothioamides [Articol]
    (2019) Gulea, Aurelian; Mitchevici, N.; Ciumacov, Iurie; Petrenko, Peter; Balan, Greta; Burduniuc, Olga; Țapcov, Victor
    4-(2-Methoxyphenyl)-, 4-(3-methoxyphenyl)-, and 4-(4-memoxyphenyl)-2-[(5-mttofuryl)methylene]-hydrazine carboxamide (HL1–3) react with hydrates of cobalt (nickel, copper) chloride (nitrate, acetate) with the formation of the M(HL1–3)2X2 (M = Co2+, Ni2+, Cu2+; X = Cl−, NO3−) and M(L1–3)2 (M = Ni2+, Cu2+) coordination compounds. Structure of the obtained compounds has been studied by means of X-ray diffraction analysis. Their antimicrobial and antifungal activity towards a series of Staphylococcus aureus, Escherichia coli, and yeast-like fungi standard strains has been investigated.
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    Synthesis, characterization, molecular docking studies and in vitro screening of new metal complexes with Schiff base as antimicrobial and antiproliferative agents [Articol]
    (2019) Paponțu, Elena; Proks, Maria; Șova, Sergiu; Lupașcu, Gina; Ilieș, Diana Carolina; Bărbuceanu, Ștefania Felicia; Socea, Laura Ileana; Badea, Mihaela; Păunescu, Virgil; Istrati, Dorin; Gulea, Aurelian; Drăgănescu, Doina; Dinu Pîrvu, Cristina Elena
    A series of Cu(II), Co(II), Pd(II), Pt(II), Zn(II), Cd(II) and Fe(III) complexes were designed and synthesized using Schiff base 1-phenyl-2,3-dimethyl-4-(N-3-formyl-6-methylchromone)-3-pyrazolin-5-one (HL). The new metal complexes were investigated using various physicochemical techniques including elemental and thermal analyses, molar electric conductivity and magnetic susceptibility measurements, as well as spectroscopic methods. Also, the crystal structures of ligand HL and the Pd(II) complex were determined using single-crystal X-ray diffraction analysis. For all compounds, the antimicrobial activity was studied against a series of standard strains: Staphylococcus aureus, Bacillus cereus, Enterococcus faecalis, Escherichia coli, Acinetobacter baumannii, Candida albicans, Candida krusei and Cryptococcus neoformans. The in vitro antiproliferative activity of the ligand and complexes was evaluated against ten cancer cell lines: MSC, A375, B16 4A5, HT-29, MCF-7, HEp-2, BxPC-3, RD, MDCK and L20B. At 10 μM concentration a significant cytotoxic effect of the Co(II), Pd(II) and Cd(II) complexes was observed against B16 4A5 murine melanoma cells. The Zn(II) complex is active against HEp-2, RD and MDCK cancer cell lines, where IC50 values vary between 1.0 and 77.6 and for BxPC-3 the activity index versus doxorubicin is 3.7 times higher.
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    Synthesis, Structure, and Biological Activity of Copper and Cobalt Coordination Compounds with Substituted 2-(2-Hydroxybenzylidene)-N-(prop-2-en-1-yl) hydrazinecarbothioamides [Articol]
    (2019) Gulea, Aurelian; Graur, Vasilii; Ciumacov, Iurie; Petrenko, Peter A.; Balan, Greta; Burduniuc, Olga; Țapcov, Victor; Rudic, Valeriu
    The reaction of N-(prop-2-en-1-yl)hydrazinecarbothioamide with substituted 2-hydroxybenzaldehydes afforded the corresponding Schiff bases which were used as ligands to obtain copper and cobalt coordination compounds Cu(NL1–6)X · n H2O (X = Cl−, NO3−; n = 0–3), Co(HL2)2NO3, and Co(NL6)2Cl. The structure of the isolated complexes was determined by NMR spectroscopy and X-ray analysis. The complexes were tested for antimicrobial and antifungal activity against S. aureus, E. coli, and yeast-like fungi. Inhibitory effect of the initial thioamides and their complexes against human myeloid leukemia HL-60 cancer cell line was also studied.
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    Synthesis, characterization, crystal structure and antimicrobial activity of copper(II) complexes with the Schiff base derived from 2-hydroxy-4-methoxybenzaldehyde [Articol]
    (2015) Pahonțu, Elena; Ilieș, Diana Carolina; Șova, Sergiu; Paraschivescu, Codruța; Badea, Mihaela; Gulea, Aurelian; Roșu, Tudor
    A novel Schiff base, ethyl 4-[(E)-(2-hydroxy-4-methoxyphenyl)methyleneamino] benzoate (HL), was prepared and structurally characterized on the basis of elemental analyses, 1H NMR, 13C NMR, UV-Vis and IR spectral data. Six new copper(II) complexes, [Cu(L)(NO3)(H2O)2] (1), [Cu(L)2] (2), [Cu(L)(OAc)] (3), [Cu2 (L)2Cl2(H2O)4] (4), [Cu(L)(ClO4)(H2O)] (5) and [Cu2(L2S)(ClO4)(H2O)]ClO4·H2O (6) have been synthesized. The characterization of the newly formed compounds was done by IR, UV-Vis, EPR, FAB mass spectroscopy, elemental and thermal analysis, magnetic susceptibility measurements and molar electric conductivity. The crystal structures of Schiff base and the complex [Cu2(L2S)(ClO4)(H2O)]ClO4·H2O (6) have been determined by single crystal X-ray diffraction studies. Both copper atoms display a distorted octahedral coordination type [O4NS]. This coordination is ensured by three phenol oxygen, two of which being related to the μ-oxo-bridge, the nitrogen atoms of the azomethine group and the sulfur atoms that come from the polydentate ligand. The in vitro antimicrobial activity against Escherichia coli ATCC 25922, Salmonella enteritidis, Staphylococcus aureus ATCC 25923, Enterococcus and Candida albicans strains was studied and compared with that of free ligand. The complexes 1, 2, 5 showed a better antimicrobial activity than the Schiff base against the tested microorganisms
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    Synthesis, characterization, antimicrobial and antiproliferative activity evaluation of Cu(II), Co(II), Zn(II), Ni(II) and Pt(II) complexes with isoniazid-derived compound [Articol]
    (2017) Pahonțu, Elena; Ilieș, Diana Carolina; Șova, Sergiu; Oprean, Camelia; Păunescu, Virgil; Olaru, Octavian Tudorel; Rădulescu, Flavian Ștefan; Gulea, Aurelian; Roșu, Tudor; Drăgănescu, Doina
    Hydrazone complexes of Cu(II), Co(II), Zn(II), Ni(II) and Pt(II) with N-isonicotinoyl-N′-(3-metoxy-2 hydroxybenzaldehyde)-hydrazone (HL) were synthesized and characterized by different physico-chemical techniques including elemental and thermal analysis, magnetic susceptibility measurements, molar electric conductivity, as well as IR (infrared), 1H-NMR and 13C-NMR (hydrogen and carbon nuclear magnetic resonance, UV-Vis (ultraviolet-visible), FAB (fast atom bombardment), EPR (electron paramagnetic resonance), and mass spectroscopies. The crystal structure of ligand was determined by single crystal X-ray diffraction studies. Spectral data showed that hydrazone behaves as an ONO tridentate ligand through the azomethine nitrogen, phenolate and keto oxygen atoms. For the copper(II) complexes, metal-ligand bonding parameters were evaluated from the EPR spectra. These parameters indicate the presence of in-plane π bonding. In addition, the f values of complexes 1-4 indicate small distortion from planarity. The effect of these complexes on proliferation of human breast cancer (MCF-7 and SKBR-3), human melanoma (A375), lung adenocarcinoma cells (NCI-H1573) and their antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Candida albicans strains were studied and compared with those of free ligand. The ligand and complexes 1-3 showed significant antimicrobial activity against the Gram-positive bacteria Staphylococcus aureus and Candida albicans in comparison to the control drugs. The complexes 2-4 could be potential antitumor agents, leading to a significant improvement of the cytotoxic activity when compared with HL.
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    Synthesis and characterization of novel Cu(II), Pd(II) and Pt(II) complexes with 8-ethyl-2-hydroxytricyclo(7.3.1.02,7) tridecan-13-one-thiosemicarbazone:Antimicrobial and in Vitro antiproliferative activity [Articol]
    (2016) Pahonțu, Elena; Paraschivescu, Codruța; Ilieș, Diana Carolina; Poirier, Donald; Oprean, Camelia; Păunescu, Virgil; Gulea, Aurelian; Roșu, Tudor; Bratu, Ovidiu
    New Cu(II), Pd(II) and Pt(II) complexes, (Cu(L)(H2O)2(OAc)) (1), (Cu(HL)(H2O)2(SO4)) (2), (Cu(L)(H2O)2(NO3)) (3), (Cu(L)(H2O)2(ClO4)) (4), (Cu(L)2(H2O)2) (5), (Pd(L)(OAc))H2O (6), and (Pt(L)2) (7) were synthesized from 8-ethyl-2-hydroxytricyclo(7.3.1.02,7)tridecan-13-one thiosemicarbazone (HL). The ligand and its metal complexes were characterized by IR, 1H-NMR, 13C-NMR, UV-Vis, FAB, EPR, mass spectroscopy, elemental and thermal analysis, magnetic susceptibility measurements and molar electric conductivity. The free ligand and the metal complexes have been tested for their antimicrobial activity against E. coli, S. enteritidis, S. aureus, E. faecalis, C. albicans and cytotoxicity against the NCI-H1573 lung adenocarcinoma, SKBR-3 human breast, MCF-7 human breast, A375 human melanoma and HL-60 human promyelocytic leukemia cell lines. Copper complex 2 exhibited the best antiproliferative activities against MCF-7 human breast cancer cells. A significant inhibition of malignant HL-60 cell growth was observed for copper complex 2, palladium complex 6 and platinum complex 7, with IC50 values of 1.6 μM, 6.5 μM and 6.4 μM, respectively.
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    Novel 2-formylpyridine 4-allyl-S-methylisothiosemicarbazone and Zn(II), Cu(II), Ni(II) and Co(III) complexes: Synthesis, characterization, crystal structure, antioxidant, antimicrobial and antiproliferative activity [Articol]
    (2019) Balan, Greta; Usataia, Irina; Graur, Vasilii; Ciumacov, Iurie; Petrenko, Peter; Gudumac, Valentin; Gulea, Aurelian; Pahonțu, Elena; Burduniuc, Olga
    New zinc (II), copper (II), nickel (II) and cobalt (III) complexes, [Zn (HL)2]I2 (1), [Cu (HL)Cl2] (2), [Cu (HL)Br2] (3), [Cu (HL)(H2O)2](ClO4)2 (4), [Ni (HL)2]I2·H2O (5), [Co(L)2]Cl (6), [Co(L)2]NO3 (7), [Co(L)2]I·[Co(L)2](I3) (8) were obtained with 2-formylpyridine 4-allyl-S-methylisothiosemicarbazone (HL). The isothiosemicarbazone ligand was characterized by NMR (1H and 13C), IR spectroscopy and X-ray diffraction. All the complexes were characterized by elemental analysis, IR, UV–Vis, ESI-MS spectroscopy, molar conductivity, magnetic susceptibility measurements. X-ray diffraction analysis on the monocrystal and powder elucidated the structure of the complexes 1, 5, 7 and 8. The ligand and the complexes were tested for their antioxidant and antimicrobial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae and Candida albicans. Also, the antiproliferative properties of these compounds on human leukemia HL-60, human cervical epithelial HeLa, human epithelial pancreatic adenocarcinoma BxPC-3, human muscle rhabdomyosarcoma spindle, large multinucleated RD cells and normal MDCK cells have been investigated. The nickel complex 5 and cobalt complexes 6, 7 showed promising antiproliferative activity and low toxicity.