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

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Author: search.filters.author.Graur, VasiliiSubject: search.filters.subject.antioxidant activity

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    SYNTHESIS AND BIOLOGICAL ACTIVITY OF N-(4-METHOXYPHENYL)-2-OXOPROPANAMIDE 4-PHENYLTHIOSEMICARBAZONE AND ITS COPPER(II) COMPLEXES
    (CEP USM, 2024) Graur, Ianina; Usataia, Irina; Graur, Vasilii; Tsapkov, Victor; Gulea, Aurelian; Garbuz, Olga; Balan, Greta
    The new N-(4-methoxyphenyl)-2-oxopropanamide 4-phenylthiosemicarbazone (HL) and its 5 copper(II) coordination compounds [Cu(L)X] (X = Cl- (I); Br- (II); NO3- (III); CH3COO- (IV); Cl2CHCOO- (V)) have been synthesized and characterized by elemental analysis, FTIR and NMR spectra. Coordination of 4-phenylthiosemicarbazone HL with the copper(II) atom led to increased antibacterial activity against Staphylococcus aureus and Bacillus cereus. Non-coordinated 4-phenylthiosemicarbazone (HL) showed the highest activity in relation to ABTS•+ cation radicals; its activity is close to that of Trolox, which is used in medicine. The antibacterial and antioxidant activities of the synthesized complexes are influenced by the nature of the acidic residue in their composition.
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    EXPLORING THE ANTIOXIDANT ACTIVITY OF 1-(PIPERIDIN-1-YL) PROPANE-1,2-DIONE 4-PHENYLTHIOSEMICARBAZONE AND 3d METAL COORDINATION COMPOUNDS WITH THIS LIGAND
    (CEP USM, 2024) Graur, Ianina; Maxim, Mihail; Graur, Vasilii; Tsapkov, Victor; Gulea, Aurelian; Garbuz, Olga
    The new 1-(piperidin-1-yl)propane-1,2-dione 4-phenylthiosemicarbazone (HL) and its 7 coordination compounds [Cu(L)X] (X = Br- (I); Cl- (II); NO3 - (III); CH3COO- (IV); Cl2CHCOO- (V)), [Co(L)2]NO3 (VI), [Fe(L)2]NO3 (VII) have been synthesized and characterized by elemental analysis, FTIR, 1H, 13C NMR spectra and molar electric conductibility. For the obtained compounds it was studied the antioxidant activity towards ABTS•+ radical cation. Uncoordinated 4-phenylthiosemicarbazone HL is the most active one with IC50 14.1 μM. Its activity is higher than that of Trolox which is used in medicine as an antioxidant. Among all the synthesized coordination compounds, the iron(III) complex VII showed the greatest activity. The antioxidant activity of metal complexes is influenced by the anion and the nature of the central metal atom.
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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
    (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.
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    SYNTHESIS, CHARACTERIZATION, CRYSTAL STRUCTURE OF NOVEL CU (II), CO (III), FE (III) AND CR (III) COMPLEXES WITH 2‐ HYDROXYBENZALDEHYDE‐4‐ALLYL‐S‐METHYLISOTHIOSEMICARBAZONE: ANTIMICROBIAL, ANTIOXIDANT AND IN VITRO ANTIPROLIFERATIVE ACTIVITY
    (2018) Pahonțu, Elena; Usataia, Irina; Graur, Vasilii; Ciumacov, Iurie; Petrenko, Peter; Gudumac, Valentin; Gulea, Aurelian
    2-Hydroxybenzaldehyde-4-allyl-S-methylisothiosemicarbazone and Cu (II), Co (III), Fe (III) and Cr (III) complexes were synthesized and characterized. The new obtained compounds were investigated by elemental analysis, magnetic susceptibility measurements, molar electric conductivity, IR, 1H NMR, 13C NMR, UV–Vis spectroscopy. In addition, the structure of the ligand and six complexes has been determined by single-crystal X-ray diffraction analysis. The Cu atom in complex 3 is penta-coordinated in a distorted square–pyramidal coordination geometry, while the metals in complexes 5–9 are in a distorted octahedral environment. For all compounds the antimicrobial activity was studied on a series of standard strains, such as Staphylococcus aureus, Escherichia coli, Enterococcus faecalis, Salmonella abony and Candida albicans. The in vitro antiproliferative activity of the ligand and complexes was screened on human leukemia HL-60 cells, human cervical epithelial HeLa cells, human epithelial pancreatic adenocarcinoma BxPC-3 cells, human muscle rhabdomyosarcoma spindle and large multinucleated RD cells. The primary screening on a wider series of cancer cells showed that copper coordination compound 2 manifests high activity towards HeLa, BxPC-3 and RD cancer cells, which is three–six times higher than the activity of doxorubicin. The selectivity index that is the ratio between the IC50 value for the normal MDCK cells and IC50 values for the cancer cells varies in the range 2.44–21.17. This index is 5.5–11 times higher for the copper coordination compound 2 than for the doxorubicin. Cr (III), Fe (III) and Co (III) coordination compounds 6–9 manifest high antioxidant activity towards ABTS•+ that exceeds 47–67 times the activity of Trolox.
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    NOVEL ANTIOXIDANTS BASED ON SELECTED 3D METAL COORDINATION COMPOUNDS WITH 2-HYDROXYBENZALDEHYDE 4,S-DIALLYLISOTHIOSEMICARBAZONE
    (2023) Graur, Vasilii; Mardari, Anastasia; Bouroș, Pavlina; Cravțov, Victor; Usataia, Irina; Ulchina, Ianina; Garbuz, Olga; Gulea, Aurelian
    2-Hydroxybenzaldehyde 4,S-diallylisothiosemicarbazone (HL) was synthesized and characterized by 1H, 13C NMR and FTIR spectroscopies. It exists in solution in two isomeric forms: cis (~25%) and trans (~75%). Six stable complexes were obtained by interaction of HL with copper(II), nickel(II), cobalt(III) and iron(III) salts: [Cu(L)Cl] (1), [Cu(L)NO3] (2), [Cu(3,4-Lut)(L)NO3] (3), [Ni(L)OAc] (4), [Co(L)2]Cl (5), [Fe(L)2]NO3 (6). The synthesized complexes have been studied by elemental analysis, FTIR, molar electrical conductivity and single crystal X-ray diffraction (6). For all compounds the antioxidant activity against cation radicals ABTS•+ was studied. All complexes and free ligand are more active than trolox that is used in medicine practice. Complex 4 (IC50=7.20µM) is the most active one. The introduction of heterocyclic amine did not improve the antioxidant activity. The introduction of S-allyl group into isothiosemicarbazone affected the activity of the synthesized substances, and in some cases the resulting complexes exhibit greater activity than complexes with isothiosemicarbazones with other S-radicals.
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    NOVEL ANTIOXIDANTS BASED ON SELECTED 3D METAL COORDINATION COMPOUNDS WITH 2-HYDROXYBENZALDEHYDE 4,S-DIALLYLISOTHIOSEMICARBAZONE
    (2023) Graur, Vasilii; Mardari, Anastasia; Bourosh, Pavlina; Kravtsov, Victor; Usataia, Irina; Ulchina, Ianina; Garbuz, Olga; Gulea, Aurelian
    2-Hydroxybenzaldehyde 4,S-diallylisothiosemicarbazone (HL) was synthesized and characterized by 1H, 13C NMR and FTIR spectroscopies. It exists in solution in two isomeric forms: cis (~25%) and trans (~75%). Six stable complexes were obtained by interaction of HL with copper(II), nickel(II), cobalt(III) and iron(III) salts: [Cu(L)Cl] (1), [Cu(L)NO3] (2), [Cu(3,4-Lut)(L)NO3] (3), [Ni(L)OAc] (4), [Co(L)2]Cl (5), [Fe(L)2]NO3 (6). The synthesized complexes have been studied by elemental analysis, FTIR, molar electrical conductivity and single crystal X-ray diffraction (6). For all compounds the antioxidant activity against cation radicals ABTS•+ was studied. All complexes and free ligand are more active than trolox that is used in medicine practice. Complex 4 (IC50=7.20µM) is the most active one. The introduction of heterocyclic amine did not improve the antioxidant activity. The introduction of S-allyl group into isothiosemicarbazone affected the activity of the synthesized substances, and in some cases the resulting complexes exhibit greater activity than complexes with isothiosemicarbazones with other S-radicals.
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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
    (John Wiley & Sons Ltd, 2020) Balan, Greta; Burduniuc, Olga; Usataia, Irina; Graur, Vasilii; Chumakov, Yurii; Petrenko, Peter; Gudumac, Valentin; Gulea, Aurelian; Pahontu, Elena
    New zinc (II), copper (II), nickel (II) and cobalt (III) complexes, [Zn (HL) 2 ]I 2 (1), [Cu (HL)Cl 2 ](2), [Cu (HL)Br 2 ](3), [Cu (HL)(H 2 O) 2 ](ClO 4 ) 2 (4), [Ni (HL) 2 ]I 2 H 2 O(5), [Co(L) 2 ]Cl (6), [Co(L) 2 ]NO 3 (7), [Co(L) 2 ]I[Co(L) 2 ](I 3 ) (8) were obtained with 2-formylpyridine 4-allyl-S-methylisothiosemicarbazone (HL). The isothiosemicarbazone ligand was characterized by NMR ( 1 H and 13 C), IR spectroscopy and X-ray diffraction. All the complexes were character- ized by elemental analysis, IR, UV–Vis, ESI-MS spectroscopy, molar conductiv- ity, magnetic susceptibility measurements. X-ray diffraction analysis on the monocrystal and powder elucidated the structure of the complexes 1,5, 7and 8. The ligand and the complexes were tested for their antioxidant and antimi- crobial 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 5and cobalt complexes 6,7showed promising antiproliferative activity and low toxicity
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    SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY OF COPPER(II), NICKEL(II), COBALT(III) AND IRON(III) COORDINATION COMPOUNDS WITH 2-HYDROXY-3-METHOXYBENZALDEHYDE N(4)-ALLYL-S-METHYLISOTHIOSEMICARBAZONE
    (CEP USM, 2018) Usataia, Irina; Graur, Vasilii; Tsapcov, Victor; Gulea, Aurelian
    The paper presents the synthesis of the 2-hydroxy-3-methoxybenzaldehyde N(4)-allyl-S-methylisothiosemicarbazone (HL) and seven coordination compounds of copper, nickel, cobalt and iron with this ligand. The new obtained compounds were studied using IR, 1H and 13C NMR spectroscopy, elemental analysis, molar electric conductibility and magnetic susceptibility. The in vitro antiproliferative activity of the HL and synthesized coordination compounds was screened on HeLa cancer cells and normal MDCK cells. The isothiosemicarbazone HL shows better anticancer activity towards HeLa cancer cells than doxorubicin that is used in medical practice and it also practically does not affect the growth and proliferation of normal cells. Moreover, it manifests high antioxidant activity towards ABTS•+ radical cation that exceeds the activity of trolox.
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    SYNTHESIS AND BIOLOGICAL ACTIVITY OF 2-FORMYLPYRIDINE N(4)-ALLYL-3-SELENO-SEMICARBAZONE AND ITS COPPER COORDINATION COMPOUND
    (2015) Graur, Vasilii; Garbuz, Olga; Zariciuc, Elena; Gudumac, Valentin; Gulea, Aurelian
    The paper presents the synthesis of the 2-formylpyridine N(4)-allyl-3-seleno-semicarbazone that was studied using NMR spectroscopy. This ligand was used for the synthesis of a copper(II) chloride coordination compound. The study of antimicrobial and antifungal activities showed that these substances possess bacteriostatic and bactericidal activities towards a series of gram-positive and gram-negative bacteria and fungi in the range of concentration 0.7-500μg/mL. The activity of the copper(II) coordination compound towards gram-negative microorganisms significantly exceeds the activity of the ligand. The antioxidant activity of the synthesized selenosemicarbazones exceeds the activity of the coordination compound. These substances inhibit proliferation of MeW-164, HL-60 and HeLa tumor cells. 16 references, 1 table, 7 schemes