Browsing by Author "Graur, Vasilii"

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COORDINATION COMPOUND AS INHIBITOR OF SUPEROXID RADICAL
(2019) Garbuz, Olga; Pantea, Valeria; Usataia, Irina; Graur, Vasilii; Țapcov, Victor; Sardari, Veronica; Tagadiuc, Olga; Gudumac, Valentin; Gulea, Aurelian
A fost obținut un nou compus coordinativ biologic activ, nitratul de cupru [2 - ({2 [(ethylsulfanyl) (prop-2-en-1-yl) carbononoimidooyl] -hydrazinylidene} methyl) phenolate], care face parte din clasa isotiosemicarbazidelor metalelor de tranziție.S-a stabilit că acesta exercită proprietăți anti radicalice performante la acțiunea moleculei organice cu radicalul superoxidic. Datorită acestei poroprietăți compusul obținut poate avea o potențială aplicare in medicină in calitate de inhibitor al radicalilor superoxidici in corpul uman, care poate duce la prevenirea deteriorării tesutului cellular, aterosclerozii si carcinogenezei.Compusul coordinativ sintetizat extinde arsenalul inhibitorilor de radicali superoxidici cu activitate biologică importanta.
COORDINATION COMPOUND, DERIVATIVE OF ISOTHIOSEMICARBAZIDE OF TRANSITION METALS AS AN INHIBITOR OF SUPEROXIDE RADICALS
(2021) Pantea, Valeriana; Graur, Vasilii; Andronache, Lilia; Gulea, Aurelian; Tsapkov, Victor; Sardari, Veronica; Gamaniuc, Marina; Gudumac, Valentin
A new biologically active coordination compound, which belongs to the class of transition metal isotiosemicarbazides - bis (m2-acetate-o) -bis {[N-prop-2-en-1-yl-N'- (pyridin- 2-ylmethylidene) carbamo-hydrazonothioate] copper} dihydrate was obtained. It has established that this compound exhibits strong anti-radical properties to the action of the organic molecule with the superoxide radical. Due to this property, the obtained compound can have a wide application in medicine as an inhibitor of superoxide radicals in the human body, thus preventing damage to cells and tissues, atherosclerosis and carcinogenesis. The synthesized coordination compound expands the arsenal of superoxide radical inhibitors with high biological activity.
COORDINATION COMPOUNDS OF COPPER(II) WITH SUBSTITUTED 3-{[(2-HYDROXYPHENYL)METHYLIDENE]AMINO}PROPANE-1,2-DIOLS
(2013) Gulea, Aurelian; Ciumacov, Iurie; Graur, Vasilii; Țapcov, Victor
3-{[(2-Hydroxyphenyl)methylidene]amino}propane-1,2-diol, its 5-chloro-,5-bromo-, 5-nitro-, 3-methoxy derivatives, and 3-{[(2-hydroxynaphthyl- 1)methylidene]amino}propane-1,2-diol react with hydrates of copper(II) chloride, bromide and nitrate in ethanol to form coordination compounds Cu(L)X·nH2O. Template condensation reaction between 3-aminopropane-1,2-diol and 2,3-, 2,4- or 2,5-dihydroxybenzaldehyde in the presence of copper(II) nitrate trihydrate results in similar compounds Cu(L)NO3·nH2O. Structure of some of the condensation products was identified by X-ray analysis. Thermolysis of the substances obtained occurs through the dehydration step (70-90 C) and complete thermal decomposition (290-560 C).
COPPER (II) ACETATE COORDINATION COMPOUND WITH 2-FORMYLPYRIDINE 4-ALLYLTHIOSEMICARBAZONE MANIFESTS INHIBITORY ACTIVITY AGAINST SUPEROXIDE RADICALS
(Marina Sokolova Publishings, 2021) Pantea, Valeriana; Graur, Vasilii; Andronache, Lilia; Gulea, Aurelian; Tsapkov, Victor; Sardari, Veronica; Gamaniuc, Mariana; Gudumac, Valentin
A new biologically active coordination compound, which belongs to the class of transition metal isotiosemicarbazides - bis (2-acetate-o) -bis {[N-prop-2-en-1-yl-N'- (pyridin- 2-ylmethylidene) carbamo-hydrazonothioate] copper} dihydrate was obtained. It has established that this compound exhibits strong anti-radical properties to the action of the organic molecule with the superoxide radical. Due to this property, the obtained compound can have a wide application in medicine as an inhibitor of superoxide radicals in the human body, thus preventing damage to cells and tissues, atherosclerosis and carcinogenesis. The synthesized coordination compound expands the arsenal of superoxide radical inhibitors with high biological activity.
COPPER(II) COORDINATION COMPOUNDS WITH 2-ACETYLPYRIDINE N4-(BICYCLO[2.2.1]HEPTAN-2-YL)THIOSEMICARBAZONE AS POTENTIAL ANTIBACTERIAL AGENTS
(CEP USM, 2023) Graur, Vasilii; Graur, Ianina; Gulea, Aurelian; Teleucă, Iulia; Lozan-Tîrșu, Carolina; Bălan, Greta
The paper presents the synthesis of the new 2-acetylpyridine N4-(bicyclo[2.2.1]hept-2-yl)thiosemicarbazone (HL) and its three copper(II) coordination compounds: [Cu(L)X] (X = NO3- (I), Cl- (II), CHCl2COO- (III)). The obtained compounds were studied by NMR and FTIR spectroscopies, elemental analysis, and molar electric conductibility. The antibacterial activity towards Gram-positive (Staphylococcus aureus, Bacillus cereus) and Gram-negative (Escherichia coli, Acinetobacter baumannii) standard strains was studied for the HL and complexes I-III. The coordination of the HL to the copper(II) atom leads to the increase of activity against almost all microorganisms. Complex I is the most active one towards Gram-positive microorganisms, while complex III is the most active one towards Gram-negative microorganisms. They in many cases surpass the activity of Furacillinum and are practically on the same level as Tetracycline towards Gram-positive microorganisms.
COPPER(II) COORDINATION COMPOUNDS WITH THIOSEMICARBAZIDE DERIVATIVES AS INHIBITORS OF SUPEROXIDE RADICALS
(Marina Sokolova Publishings, 2022) Gulea, Aurelian; Tsapkov, Victor; Graur, Vasilii; Pantea, Valeriana; Andronache, Lilia; Shvets, I.; Matusovsky, V.; Lisii, D.; Botnaru, M.; Gudumac, Valentin
New biologically active coordination compounds of copper(II) based on substituted 3-(phenyl)-1-(pyridin-2-yl)prop-2-en- 1-one 4-allylthiosemicarbazones have been obtained. It was found that these compounds exhibit strong antiradical properties when interacting with a superoxide radical. Due to this property, the obtained compounds can find wide application in medicine as inhibitors of superoxide radicals in the human body, thus preventing damage of cells and tissues, multifactorial diseases, including carcinogenesis. The synthesized coordination compounds expand the arsenal of superoxide radical inhibitors with high biological activity. Their possible significance for the development of new treatment strategies for diseases associated with the overproduction of superoxide radicals discussed.
CRYSTAL STRUCTURE OF NITRATE TRIS (4-ALLYLTHIOSEMICARBAZIDE)- CHROMIUM(III) HYDRATE
(2016) Ciumacov, Iurie; Petrenko, Peter A.; Graur, Vasilii; Țapcov, Victor; Gulea, Aurelian
The crystal structure of nitrate tris(4-allylthiosemicarbazide)chromium(III) hydrate [CrL3](NO3)3(H2O)1.05 (I), where L is 4-allylthiosemicarbazide, is determined. The asymmetric unit of the cell of the crystal structure of I contains a complex of a chromium ion with three bidentate coordinated molecules L. The outer coordination sphere of the central atom contains a disordered water molecule and three nitrate ions. The coordination polyhedron of the chromium atom in complex I is an octahedron. In the crystal, the complexes of the compound under study are joined with each other by the outer-sphere nitrato groups into a three-dimensional branched net of hydrogen bonds.
CRYSTAL STRUCTURE OF THE ACETIC ACID SOLVATE OF N-(PROP-2-EN-1-YL)-2-(PYRID-2- YLMETHYLIDENE)HYDRAZINECARBOSELENOAMIDE
(2018) Ciumacov, Iurie; Petrenko, Peter A.; Graur, Vasilii; Țapcov, Victor; Gulea, Aurelian
The crystal structure of the acetic acid solvate of N-(prop-2-en-1-yl)-2-(pyrid-2- ylmethylidene)hydrazinecarboselenoamide (I) is determined. The asymmetric unit of the unit cell in its crystal structure contains a molecule of I and an acetic acid molecule. The molecule of I is non-planar; the angle between the mean square planes of hydrazinecarboselenoamide A(Sе1N1N2N3С1C2) and prop-2-en-1-yl (С5С6C7) moieties is 82.3°. In the crystal, the acetic acid molecules link the molecules of I in endless chains along the [010] direction.
CRYSTAL STRUCTURES OF [N′-(2- OXIDOBENZYLIDENE)-N-(PROP-2-EN-1-YL)- CARBAMOHYDRAZONOTHIOATO(2-)](1,10- PHENANTHROLINE)COPPER AND [N′-(2- OXIDOBENZYLIDENE)-N-(PROP-2-EN-1-YL)- CARBAMOHYDRAZONOTHIOATO(2-)](2,2′- BIPYRIDINE)COPPER HEMIHYDRATES
(2022) Ciumacov, Iurie; Graur, Vasilii; Ulchina, Ianina; Smaglii, Vadim; Gulea, Aurelian; Garbuz, Olga; Țapcov, Victor
The crystal structures and biological properties of [N′-(2-oxidobenzylidene)-N-(prop-2-en-1-yl)-carbamohydrazonothioato(2-)](1,10-phenanthroline)copper hemihydrate [Cu(1,10-Phen)(L)]·0.5H2O (I) and [N′-(2-oxidobenzylidene)-N-(prop-2-en-1-yl)-carbamohydrazonothioato(2-)](2,2′-bipyridine)copper hemihydrate [Cu(2,2′-BPy)(L)]·0.5H2O (II), where Н2L is 2-(2-hydroxybenzylidene)-N-(prop-2-en-1-yl)hydrazinecarbothioamide, are determined. The asymmetric unit of the unit cell in the crystal structures of I and II contains a copper complex with bidentate amine and a ligand coordinated by the azomethine nitrogen atom, the deprotonated phenolic oxygen atom, and the sulfur atom in the thiol form. The coordination polyhedron of the copper atom in compounds I and II is a distorted tetragonal pyramid. Obtained coordination compounds I and II exhibit antimicrobial and antifungal activities and have minimum inhibitory concentration and bactericidal concentration values in a range of 1.5-500 µg/mL. The study of the antioxidant activity shows that compounds I and II are less active than uncoordinated thiosemicarbazone H2L, but more active than trolox used in medical practice.
CU(II) COMPLEXES WITH 4-ALLYLTHIOSEMICARBAZONE AS POSSIBLE ANTIOXIDANT AGENTS
(CEP USM, 2022-09-29) Ulchina, Ianina; Graur, Vasilii; Țapcov, Victor; Celac, Marina; Garbuz, Olga; Gulea, Aurelian
CU(II) COMPLEXES WITH 4-ALLYLTHIOSEMICARBAZONE AS POSSIBLE ANTIOXIDANT AGENTS
(2022) Ulchina, Ianina; Celac, Marina; Graur, Vasilii; Tsapkov, Victor; Garbuz, Olga; Gulea, Aurelian
Oxidation is an essential part of aerobic metabolism in living organisms. In this process, free radicals are constantly generated. It is widely known that free radicals play a dual role in vivo as both beneficial and adverse compounds. In order to maintain the balance of the activity of the free radicals in living cells, the organism has evolved antioxidant defense systems, protecting against free radical damage. However, when our endogenous defense system has incomplete efficiency, or a rise in free radicals under special conditions like smoking, chemical air pollutants, radiation, and inflammation, the imbalance between free radicals and antioxidants results in oxidative stress, which is now believed to be one of the important factors in the occurrence of certain human diseases including atherosclerosis, rheumatoid arthritis, cancer, and neurodegenerative diseases. So, the search of possible antioxidants agents is of interest, because they protect the body against damage by harmful free radicals. For this purpose two copper(II) coordination compounds of 1-(morpholin-4-yl) propane-1,2-dione 4- allylthiosemicarbazone (HL) with 1,10-phenantroline (1,10-Phen) and 2,2’-bipyridyl (2,2’- Bpy) were synthesized. On the first stage of the experiment the ethanolic solution of Cu(NO3)2⸱3H2O reacts with 4-allylthiosemicarbazone HL and on the second stage the ethanolic solution of the prepared precursor Cu(L)NO3 reacts with bidentate amines forming crystalline coordination compounds. The composition of these compounds was determined using elemental analysis for copper: Cu(1,10-Phen)(L)NO3, Cu(2,2’-Bpy)(L)NO3. The molar conductivity values of the synthesized coordination compounds are in the range 82-98 Ω- 1∙cm2∙mol-1 that indicates that these complexes are 1:1 electrolytes. A standard ABTS•+ method has been used to determine the antioxidant properties of synthesized compounds and trolox was used as a reference. The pro-ligand HL is less active than trolox, its coordination to copper(II) atom decreases antioxidant activity. The introduction of bidentate amines into the internal sphere of precursor increases the activity of complexes, that become 4 times more active than pro-ligand HL, 6 times more active than precursor, and also more active than
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.
INTRODUCING N-HETEROAROMATIC BASES INTO COPPER(II) THIOSEMICARBAZON COMPLEXES: A WAY TO CHANGE THEIR BIOLOGICAL ACTIVITY
(2022) Ulchina, Ianina; Graur, Vasilii; Țapcov, Victor; Ciumacov, Iurie; Garbuz, Olga; Burduniuc, Olga; Ceban, Emil; Gulea, Aurelian
Three new copper(II) complexes, [Cu(1,10-Phen)(L)] (1), [Cu(2,2’- Bpy)(L)] (2) and [Cu(3,4-Lut)(L)] (3), where H2L=2-[(2,4- dihydroxyphenyl)methylidene]-N-(prop-2-en-1-yl)hydrazine-1- carbothioamide, 1,10-Phen=1,10-phenanthroline, 2,2’-Bpy= 2,2’-bipyridine, 3,4-Lut=3,4-lutidine, have been synthesized and characterized by elemental analysis, FTIR spectroscopy and single crystal X-ray crystallography (1, 2). All compounds are mononuclear. The introduction of a monodentate N-heteroaromatic base (3,4-dimethylpyridine) has led to a significant increase of antimicrobial activity against Gram-negative Escherichia coli and antifungal activity against Candida albicans compared to the pro-ligand and the precursor complex [Cu- (L)H2O]. The introduction of bidentate N-heteroaromatic bases did not lead to such increase of antimicrobial and antifungal activities. Moreover, complex 3 surpasses the inhibitory activity of tetracycline toward Enterobacter cloacae and the inhibitory activity of fluconazole toward Candida parapsilosis and Cryptococcus neoformans. The study of antioxidant activity against cation radicals ABTS* + showed that complexes 1–3 are more active than Trolox, but only introduction of the monodentate Nheteroaromatic base (3,4-dimethylpyridine) led to the increase of antioxidant properties compared to the precursor complex.
MICROMOLECULAR INHIBITORS OF SUPEROXIDE RADICALS
(2021) Andronache, Lilia; Pantea, Valeriana; Gulea, Aurelian; Șveț, Inna; Graur, Vasilii; Matcovschi, Valerii; Gamaniuc, Marina; Gudumac, Valentin
Background: Currently, there is a growing interest in new copper (Cu2+) heterocyclic coordination compounds (CC), isothiosemicarbazide derivates, which demonstrated multiple beneficial properties, but their effect on reactions with free radicals such as the superoxide radical has not been investigated. Material and methods: The action of new micromolecular complexes of copper (Cu2+) chloride and bromide with methyl n- (prop-2-en-1-yl) -2- (pyridin2-ylmethylidene) hydrazine carbimidothioate on capturing activity of the superoxide radical was determined by the spectrophotometric method in vitro experiments. Results: It was established that the micromolecular complexes of copper (II) chloride and bromide with methyl n-(prop-2-en-1-yl)-2-(pyridin-2ylmethylidene) hydrazine carbimidothioate have been found to possess strong superoxide radical inhibitor properties when interacting with a superoxide radical. In addition to this, the IC50 of the studied compounds depends on the nature of the acid-ligand in the internal sphere of the complex and increases in the following sequence: Cl-–Br-. Conclusions: The established property of mentioned compounds is new, because their use as micromolecular inhibitors of superoxide radicals has not been described so far. The synthesized CC expand the arsenal of superoxide radical inhibitors with high biological activity. Their possible significance for the development of new treatment strategies for diseases associated with the overproduction of superoxide radicals is discussed.
NICKEL(II) COMPLEXES WITH PENTANE-2,4-DIONE BIS(4-ALLYLTHIOSEMICARBAZONE)
(2020) Gulea, Aurelian; Graur, Vasilii; Ciumacov, Iurie; Petrenko, Peter; Garbuz, Olga; Țapcov, Victor; Gudumac, Valentin
Reaction of pentane-2,4-dione with N-(prop-2-en-1-yl)hydrazinecarbothioamide at a 1: 2 molar ratio in ethanol resulted in the formation of a pyrazole derivative. The latter reacted with nickel perchlorate at a 1: 1 molar ratio to form the nickel complex with pentane-2,4-dione bis(4-allylthiosemicarbazone). The same type of nickel complex was obtained as a result of N-(prop-2-en-1-yl)hydrazinecarbothioamide reaction with pentane-2,4-dione and nickel nitrate at a 2: 1: 1 molar ratio. Antimicrobial, antifungal, antioxidant, and anticancer activities of the obtained compounds were studied.
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.
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
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.
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.
NOVEL COPPER(II) COMPLEXES WITH N4,S-DIALLYLISOTHIOSEMICARBAZONES AS POTENTIAL ANTIBACTERIAL/ANTICANCER DRUGS
(2023) Graur, Vasilii; Usataia, Irina; Graur, Ianina; Garbuz, Olga; Bouroș, Paulina; Cravțov, Victor; Lozan-Tîrșu, Carolina; Balan, Greta; Fala, Valeriu; Gulea, Aurelian
The six new copper(II) coordination compounds [Cu(HL1)Cl2] (1), [Cu(HL1)Br2] (2), [Cu(H2O)(L1)(CH3COO)]·1.75H2O (3), [Cu(HL2)Cl2] (4), [Cu(HL2)Br2] (5), [Cu(H2O)(L2)(CH3COO)] (6) were synthesized with 2-formyl- and 2-acetylpyridine N4,S-diallylisothiosemicarbazones (HL1 and HL2). The new isothiosemicarbazones were characterized by NMR, FTIR spectroscopy, and X-ray crystallography ([H2L2]I). All copper(II) coordination compounds were characterized by elemental analysis, FTIR spectroscopy, and molar conductivity of their 1mM methanol solutions. Furthermore, the crystal structure of complex 3 was determined using single-crystal X-ray diffraction analysis. The studied complexes manifest antibacterial and antifungal activities, that in many cases are close to the activity of medical drugs used in this area, and in some cases even exceed them. The complexes 4 and 5 showed the highest indexes of selectivity (280 and 154) and high antiproliferative activity against BxPC-3 cell lines that surpass the activity of Doxorubicin. The complexes 1–3 also manifest antioxidant activities against cation radicals ABTS•+ that are close to that of trolox, the antioxidant agent used in medicine.