Papers by Sanja Grgurić-sipka
Hemijska industrija, 2015
Phenothiazines are a large group of heterocyclic, aromatic molecules with nitrogen and sulphur be... more Phenothiazines are a large group of heterocyclic, aromatic molecules with nitrogen and sulphur between two benzene rings. Their derivatives, N-alkylphenothiazines have substituent on heterocyclic nitrogen atom which gives them different properties. Also, a series of these molecules have substitution on carbon atom at place 2 of phenothiazine benzene ring. Alkylphenothiazines contain aminoalkyl substituent and their alkyl, acyl and sulphonil derivatives, as well as monocyclic and bicyclic heterocycles attached at thiazine nitrogen atom or directly linked to benzene ring. The N-alkylphenothiazines have been known as antipsychotic drugs, but they also possess antibacterial, antifungal, anticancer activity, and ability to react with macromolecules and to coordinate to the metals. Metal complexes with N-alkylphenothiazines are biological active compounds with different antimicrobial activities and cytotoxic effect against tumor cell lines. The large field of application of N-alkylphenothiazines is very attractive in terms of synthesis of new related derivatives, metal complexes, studying their properties and applications. This article presents a review of the literature and a contemporary view at N-alkylphenothiazines-their synthesis and application, as well as their metal complexes which have promising biological effects.
Inorganic Chemistry Communications, 2003
The synthesis and characterization of a new ligand and the first complex with semicarbazide based... more The synthesis and characterization of a new ligand and the first complex with semicarbazide based ligand coordinated to platinum(IV) ion are reported. The new ligand, pyridoxal semicarbazone (H 2 PxSC), and complex [Pt(HPxSC)Cl 3 ] are characterized by elemental analysis, molar conductivity, infrared, electronic and 1 H NMR spectroscopy. The novel complex of platinum(IV) ion contains monoanionic, tridentate ONO ligand, and three chlorine ions.
European Journal of Medicinal Chemistry, 2010
Ruthenium(II)-arene complexes of general formulae [(eta(6)-p-cymene)Ru(L(1-3))Cl(2)], where L(1-3... more Ruthenium(II)-arene complexes of general formulae [(eta(6)-p-cymene)Ru(L(1-3))Cl(2)], where L(1-3) is 3-acetylpyridine (1), 4-acetylpyridine (2) and 2-amino-5-chloropyridine (3), correspondingly, [(eta(6)-p-cymene)Ru(HL(4,5))Cl(2)], where HL(4) and HL(5) are respectively isonicotinic acid (4) and nicotinic acid (5) and [(eta(6)-p-cymene)Ru(HL(6-9))Cl], where H(2)L(6-9) represent 2,3-pyridinedicarboxylic acid (6), 2,4-pyridinedicarboxylic acid (7), 2,5-pyridinedicarboxylic acid (8) and 2,6-pyridinedicarboxylic acid (9), were prepared by the reaction of [(eta(6)-p-cymene)(2)RuCl(2)](2) (10) with the corresponding ligand in 1:2 molar ratio in isopropanol. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. According to these data the molecules adopt the usual "three-leg piano-stool" geometry which is common for this type of complexes. The structures of 1 and 7 were determined by X-ray crystallography. The complexes revealed low antiproliferative activity in six investigated tumor cell lines (HeLa, B16, FemX, MDA-MB-361, MDA-MB-453 and LS-174). The reaction of 6 with 9-methyladenine was studied by (1)H NMR, (1)H, (1)H COSY and (1)H, (1)H NOESY spectroscopy.
European Journal of Medicinal Chemistry, 2009
Novel complexes of platinum(II) with 3- (1) or 4-acetylpyridine (2) have been synthesized and cha... more Novel complexes of platinum(II) with 3- (1) or 4-acetylpyridine (2) have been synthesized and characterized by elemental analyses, IR, (1)H and (13)C NMR spectroscopy. Single crystal X-ray diffraction revealed the trans geometry of complex 2. DFT calculations confirm formation of trans isomers for both complexes. The complexes have been tested for their cytotoxicity against HeLa (human cervical cancer), U2OS (human osteosarcoma), U2OScisR (human osteosarcoma cisplatin resistant), B16 (murine melanoma), MDA-453, MDA-361, and MCF-7 (human breast cancer), LS-174 (human colon cancer) and FemX (human melanoma) cell lines. The most promising compound trans-dichloridobis(4-acetylpyridine)platinum(II) (2) overcomes cisplatin resistance of U2OScisR cells after 48h of drug exposure.
Journal of Inorganic Biochemistry, 2004
A novel class of ruthenium (III) complexes of formulas K[Ru(sar)2Cl2].12H2O and K2[Ru(dmgly)Cl4].... more A novel class of ruthenium (III) complexes of formulas K[Ru(sar)2Cl2].12H2O and K2[Ru(dmgly)Cl4].2H2O, containing bidentate chelates N-methylglycine (sarcosine, sar) or N,N-dimethylglycine (dmgly) and additional chloro ligands were synthesized. The complexes have been obtained by direct reaction of ruthenium(III) chloride with corresponding bidentate ligand followed by addition of base (KOH). These new complexes were characterized by elemental analysis, IR and electronic absorption spectroscopy. As astrocytomas, the most common of all brain tumors, are still very difficult to treat, we examined the influence of newly synthesized ruthenium-based complexes, as well as the earlier synthesized analogue platinum(IV) complexes [Pt(dmgly)2Cl2], [Pt(sar)2Br2] and [Pt(dmgly)2Br2], on rat astrocytoma C6 cells in vitro. Among these complexes only K2[Ru(dmgly)Cl4].2H2O and [Pt(dmgly)2Br2] markedly inhibited the viability of non-confluent C6 cells. Furthermore, only complex K2[Ru(dmgly)Cl4].2H2O was able to reduce viability in confluent C6 cultures. Importantly, this complex was not toxic to primary rat astrocytes or macrophages. Having in mind that appropriate chemotherapy should be effective against tumor cells without harming normal tissues, complex K2[Ru(dmgly)Cl4].2H2O could be a promising agent for developing therapeutics against astrocytomas.
Journal of Coordination Chemistry, 1998
... IZVOD SINTEZA I KARAKTERIZACIJA FACIJALNOG I MERIDIJALNOG IZOMERA uns-cis-(ETILENDIAMIN-N,N&#... more ... IZVOD SINTEZA I KARAKTERIZACIJA FACIJALNOG I MERIDIJALNOG IZOMERA uns-cis-(ETILENDIAMIN-N,N'-DI-3-PROPIONATO)(S-ARGININ)KOBALT(III)-HLORIDA DIHIDRATAVESNA M. \INOVI] i TIBOR J. SABO Hemijski ... 4. JI Legg and DW Cooke, BE Douglas, Inorg. ...
Materials Science Forum, 2005
Pt/Ru-doped ZnO nanophase particles were synthesized using ultrasonic spray pyrolysis. Particles ... more Pt/Ru-doped ZnO nanophase particles were synthesized using ultrasonic spray pyrolysis. Particles were obtained through decomposition of zinc nitrate and newly developed Pt(IV) and Ru(III) complexes. The particle morphology, phase composition and chemical structure were revealed in accordance to various analysis methods (XRD, DSC, SEM/EDS, TEM) and discussed in terms of precursor chemistry and process parameters. The shape of DSC curves, indicating two exothermic effects above 600 0 C in both ZnO:Ru and ZnO:Pt, gave an indication of irreversible structural changes and high reactivity of as-prepared powders. The hexagonal wurtzite-type ZnO phase was revealed in both powdered samples. Small content of an intermediate Zn 5 (NO 3 ) 2 (OH) 8 ·2H 2 O and cubic Zn 2 PtO 4 phase were detected in the Pt-doped ZnO particles. Structural refinements, performed by Koalariet-XFit, suggest the composite internal particle structure composed of primary particles sized less than 100 nm. The estimated values for the unit cell parameters and Zn-O bond lengths imply noble metal ions incorporation into ZnO matrix interstitially, probably in octahedral interstitial environment. It has been shown that different particle growing morphologies (either spheroidally or pyramidally shaped) were influenced by the precursor chemistry, processing parameters and the presence of noble metal ions. Among the many parameters, attaining of the particle shape uniformity and homogeneous distribution of the noble metal cations in as-prepared particles are regarded as the most important factors for dominating microstructure evolution.
Journal of the Serbian Chemical Society
Three octahedral cobalt(III) complexes of the general formula uns-cis-SCo(eddp)(R-en)CClÿ2H2O, wh... more Three octahedral cobalt(III) complexes of the general formula uns-cis-SCo(eddp)(R-en)CClÿ2H2O, where eddp = the tetradentate ONNO-type ligand ethylenediamine-N,N'-di-3-propionate and R-en = a bidentate NN-type ligand, either N-methyl, N-ethyl or N-isopropylethylenediamine. The complexes were prepared by the reaction of sodium uns-cis-(ethylenediamine-N,N'-di-3-propionato)(carbonato)cobaltate(III)dihydrate with the corresponding diamine. They were isolated chromatographically and characterized by elemental analysis, infrared and electronic absorption spectroscopy.
Journal of Coordination Chemistry, 2001
... VESNA M. DINOVIC~, SANJA R. GRGURI?, xu XING-YOU^ and TIBOR J. SABOai* "Faculty of Chemi... more ... VESNA M. DINOVIC~, SANJA R. GRGURI?, xu XING-YOU^ and TIBOR J. SABOai* "Faculty of Chemistry. University of Belgrade, PO Box 158, 11001 Belgrade, Yugoslavia; bDept. ... Chem. SOC. Jpn. 35, 75 (1962). [3] J. 1. Legg and DW Cooke, Znorg. Chem. 4, 1576 (1965). ...
Journal of inorganic biochemistry
In our previous study, ruthenium(II)-p-cymene complexes of general formula [(η(6)-p-cymene)Ru(L)C... more In our previous study, ruthenium(II)-p-cymene complexes of general formula [(η(6)-p-cymene)Ru(L)Cl2], L: 3-acetylpyridine (1), 2-amino-5-chloropyridine (2); and [(η(6)-p-cymene)Ru(HL)Cl], HL: 2,3-pyridinedicarboxylic acid (3), 2,4-pyridinedicarboxylic acid (4), revealed low antiproliferative activity, except complex [(η(6)-p-cymene)RuCl(picolinic acid)]·H(2)O (5) which exhibited IC(50) around 80 μM. In this study we further investigated in vitro potential of antimetastatic action of ruthenium complexes on HeLa and two endothelial cell lines. Comparison of structure and activity of five complexes indicated heterogenic mode of activity, with regard to the potential of antimetastatic and antiproliferative effect. Replacement of substituted pyridine ligand with picolinic acid (complex 5) around Ru(II) center contributed to complex cytotoxicity and ruthenium DNA binding affinity. Analysis of ruthenium(II) accumulation in DNA and protein fractions of HeLa cells, using ICP-OES revealed sig...
Journal of Coordination Chemistry, 1998
... IZVOD SINTEZA I KARAKTERIZACIJA FACIJALNOG I MERIDIJALNOG IZOMERA uns-cis-(ETILENDIAMIN-N,N&#... more ... IZVOD SINTEZA I KARAKTERIZACIJA FACIJALNOG I MERIDIJALNOG IZOMERA uns-cis-(ETILENDIAMIN-N,N'-DI-3-PROPIONATO)(S-ARGININ)KOBALT(III)-HLORIDA DIHIDRATAVESNA M. \INOVI] i TIBOR J. SABO Hemijski ... 4. JI Legg and DW Cooke, BE Douglas, Inorg. ...
BioMetals, 2015
The reactions of four representative metallodrugs with the model protein HEWL were investigated w... more The reactions of four representative metallodrugs with the model protein HEWL were investigated within a non-aqueous environment-i.e. in pure DMSOthrough UV-Vis absorption spectroscopy and ESI MS analysis. Notably, formation of a variety of metallodrugprotein adducts was clearly documented. This is the first example for this kind of protein metalation reactions carried out within a pure organic solvent. It is shown that the applied solution conditions greatly affect the nature of the formed adducts, this being well accounted for by the fact that the overall protein conformation is greatly perturbed within pure DMSO; in addition, the activation profiles of the studied metallodrugs are also highly dependent on the nature of the solvent. The implications of these results are discussed.
European Journal of Cancer, 2014
Journal of Coordination Chemistry, 2002
The synthesis of the binuclear complex [(tren)Cu(4,4'-bipy)Cu(tren)] (ClO4)4 wher... more The synthesis of the binuclear complex [(tren)Cu(4,4'-bipy)Cu(tren)] (ClO4)4 where tren = tris(2-aminoethyl) amine and 4,4'-bipy = 4,4'-bipyridine, is described. Single-crystal X-ray diffraction study of the homobinuclear complex shows that two copper(II) ions are bridged by 4,4'-bipyridine and each copper(II) ion is trigonal-bipyramidally coordinated, with tren occupying four sites [Cu-N = 2.030(2), 2.047(2), 2.078(2), and 2.119(2) Å respectively] and a bridging
Thermochimica Acta, 2003
The thermal properties of some mixed complexes of cobalt(III) containing tetradentate ethylenedia... more The thermal properties of some mixed complexes of cobalt(III) containing tetradentate ethylenediamine-N,N -di-3-propionate (eddp) ligand and several amino acids were investigated by thermogravimetry (TG) and differential scanning calorimetry (DSC). The thermal stability derived from decomposition temperatures was discussed in terms of amino acid present. It was shown that the processes of thermal decomposition of these complexes are multi-step degradation processes. Some of these can be separated into individual steps.
Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2002
The review summarizes the results of recent studies on edda-type metal complexes. It focuses on w... more The review summarizes the results of recent studies on edda-type metal complexes. It focuses on work published during the period 1984–2001. The metals include are Co, Cr, Cu, Ni, Zn, Mn, Sn, Fe, V, Rh, Pt, Ru, whereas edda-type represents ethylenediamine-N,N′-diacetate, ethylenediamine-N,N-di-acetate, N,N′-dimethylethylenediamine-N,N′-diacetate, N,N′-diethylethylenediamine-N,N′-diacetate, 1,2-cyclo-hexanediamine-N,N′-diacetate, N,N′-dimethyl-1,2-cyclohexanediamine-N,N′-diacetate, ethylenediamine-N,N′-di-3-propionate, N,N′-dimethylethylenediamine-N,N′-di-3-propionate, ethylenediamine-N,N′-di-S-α-propionate, N,N′-dimethyl-ethylenediamine-N,N′-di-α-propionate, 1,3-propanediamine-N,N′-diacetate (trimethylenediamine-N,N′-diacetate), 1,3-propanediamine-N,N′-di-3-propionate (trimethylenediamine-N,N′-di-3-propionate), N,N′-dimethylethylenediamine-N,N′-di-α-butyrate, N,N′-diethylethylenediamine-N,N′-di-α-butyrate, 1-diethylenetriamineacetate (8-amino-3,6-diazao-ctanoate), ethylenepropylenetriamineacetate (9-amino-3,6-diazaoc-
Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1999
ABSTRACT A series of octahedral sym-cis and unsym-cis cobalt(III) complexes involving tetradentat... more ABSTRACT A series of octahedral sym-cis and unsym-cis cobalt(III) complexes involving tetradentate ethylenediamine-N, N′-di-3-propionatc ion (eddp) and symmetrical diamines, [ethylenediamine (en), N.N′-dimethylethylenediamine (dmen) and N.N′-diethylethylenediamine (deen)] were prepared by reaction of sodium unsym-cis(.v-(ethylenediamine-N.N′-di-3-propionato)(carbonato)cobaltate(III) dihydrate with the corresponding diamine. The stereochemistry of the complexes prepared was investigated through ion-exchange chromatography, electronic absorption, infrared and H NMR spectroscopy.
Central European Journal of Chemistry, 2010
This paper presents the synthesis of complex compounds of type [M(L1)2], where M(II)= Cu (1), Co ... more This paper presents the synthesis of complex compounds of type [M(L1)2], where M(II)= Cu (1), Co (2), Zn (3), L1=2-aminothiazole-4-acetate and [Mn(L1)2(H2O)] (4) using ethyl 2-(2-aminothiazole-4-yl) acetate (L), and characterization by elemental analysis, magnetic susceptibilities, IR, 1H-NMR, UV-Vis spectroscopy and for [Mn(L1)2(H2O)] also by X-ray diffraction. In vitro cytotoxicity studies were performed on human cervix adenocarcinoma, HeLa cells. The antitumor
Polyhedron, 2011
The reactions of ruthenium(II)-arene complex [Ru II (g 6 -p-cym)(pydc)Cl] (where p-cym = p-isopro... more The reactions of ruthenium(II)-arene complex [Ru II (g 6 -p-cym)(pydc)Cl] (where p-cym = p-isopropyl toluene, pydc = 2,3-pyridinedicarboxylato) with biologically nitrogen-donor nucleophiles, such as guanosine-5 0 -monophosphate (5 0 -GMP), guanosine (Guo) and L-histidine (L-His) were studied by UV-Vis spectrophotometry and 1 H NMR spectroscopy. The reactions were studied at pH 2.5 and at 7.2. All reactions were followed under pseudo-first order conditions with large excess of the nucleophiles. The selected nucleophiles have a high affinity for Ru(II)-arene complex. The reactivity of the used ligands follow the same order at both pH values: Guo > 5 0 -GMP > L-His, while the reactions at pH 7.2 are always faster. The negative entropies of activation (DS -) support an associative mode of activation. However, the rate constants obtained by 1 H NMR at 295 K in D 2 O follow the same order of the ligand reactivity. The hydrolysis of the [Ru II (g 6 -p-cym)(pydc)Cl] complex was very fast and completed by the time the first spectrum was measured. Addition of excess of NaCl to equilibrium solutions reversed the hydrolysis.
Journal of the Serbian Chemical Society, 2011
A ruthenium(II)-arene complex with picolinic acid, [(η 6 -p-cymene)RuCl(pico)]·H 2 O, was prepare... more A ruthenium(II)-arene complex with picolinic acid, [(η 6 -p-cymene)RuCl(pico)]·H 2 O, was prepared by the reaction of [(η 6 -p-cymene)RuCl 2 ] 2 with picolinic acid in a 1:2 molar ratio in 2-propanol. The compound was characterized by elemental analysis, and IR and NMR spectroscopy. X-ray diffraction analysis showed that the molecule adopts a "three-leg piano-stool" geometry, which is common for this type of complexes. The cytotoxic activity of the complex was tested in two human cancer cell lines HeLa (cervix) and FemX (melanoma) by MTT assay. The IC 50 values were at 82.0 and 36.2 µmol dm -3 for HeLa and FemX cells, respectively.
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Papers by Sanja Grgurić-sipka