TY  - JOUR
AU  - Nikolić, Stefan
AU  - Ćirić, Ivanka
AU  - Roller, Alexander
AU  - Lukeš, Vladimir
AU  - Arion, Vladimir B.
AU  - Grgurić-Šipka, Sanja
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2485
AB  - Mono and dinuclear p-cymene-ruthenium(II) complexes [RuCl(L-1)(eta(6)-p-cymene)]Cl, where L-1 is propionic acid hydrazide (1) and [Ru2Cl2(L-2)(eta(6)-p-cymene)2], where H2L2 is N-1,N-2-dipropionylhydrazine (2), were prepared by a reaction of [RuCl2(eta(6)-p-cymene)](2) with the corresponding ligand precursor. Upon the reaction of [RuCl2(eta(6)-p-cymene)](2) with butyric acid hydrazide and pentanoic acid hydrazide in a 1:1 molar ratio in situ formation of tetradentate bridging ligands, N-1,N-2-dibutanoylhydrazine and N1,N2-dipentanoylhydrazine, respectively, occurred and the dinuclear complexes [Ru2Cl2(L-3)(eta(6)-p-cymene)2] (3) and [Ru2Cl2(L-4)(eta(6)-p-cymene)(2)] (4) were isolated. The compounds were characterised by elemental analysis, ESI-mass spectrometry, IR and 1D and 2D NMR spectroscopies. The structures of all complexes were established using single crystal X-ray crystallography. According to these data in both the mono- and dinuclear complexes the ruthenium atoms adopt the usual three-leg piano-stool geometry which is common for this type of complexes. Combining DFT calculations with the characterisation of the final products using X-ray diffraction, a possible reaction mechanism was discussed.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex
VL  - 41
IS  - 14
SP  - 6857
EP  - 6865
DO  - 10.1039/c7nj00965h
ER  - 

@article{
author = "Nikolić, Stefan and Ćirić, Ivanka and Roller, Alexander and Lukeš, Vladimir and Arion, Vladimir B. and Grgurić-Šipka, Sanja",
year = "2017",
abstract = "Mono and dinuclear p-cymene-ruthenium(II) complexes [RuCl(L-1)(eta(6)-p-cymene)]Cl, where L-1 is propionic acid hydrazide (1) and [Ru2Cl2(L-2)(eta(6)-p-cymene)2], where H2L2 is N-1,N-2-dipropionylhydrazine (2), were prepared by a reaction of [RuCl2(eta(6)-p-cymene)](2) with the corresponding ligand precursor. Upon the reaction of [RuCl2(eta(6)-p-cymene)](2) with butyric acid hydrazide and pentanoic acid hydrazide in a 1:1 molar ratio in situ formation of tetradentate bridging ligands, N-1,N-2-dibutanoylhydrazine and N1,N2-dipentanoylhydrazine, respectively, occurred and the dinuclear complexes [Ru2Cl2(L-3)(eta(6)-p-cymene)2] (3) and [Ru2Cl2(L-4)(eta(6)-p-cymene)(2)] (4) were isolated. The compounds were characterised by elemental analysis, ESI-mass spectrometry, IR and 1D and 2D NMR spectroscopies. The structures of all complexes were established using single crystal X-ray crystallography. According to these data in both the mono- and dinuclear complexes the ruthenium atoms adopt the usual three-leg piano-stool geometry which is common for this type of complexes. Combining DFT calculations with the characterisation of the final products using X-ray diffraction, a possible reaction mechanism was discussed.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex",
volume = "41",
number = "14",
pages = "6857-6865",
doi = "10.1039/c7nj00965h"
}

Nikolić, S., Ćirić, I., Roller, A., Lukeš, V., Arion, V. B.,& Grgurić-Šipka, S.. (2017). Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 41(14), 6857-6865.
https://doi.org/10.1039/c7nj00965h

Nikolić S, Ćirić I, Roller A, Lukeš V, Arion VB, Grgurić-Šipka S. Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex. in New Journal of Chemistry. 2017;41(14):6857-6865.
doi:10.1039/c7nj00965h .

Nikolić, Stefan, Ćirić, Ivanka, Roller, Alexander, Lukeš, Vladimir, Arion, Vladimir B., Grgurić-Šipka, Sanja, "Conversion of hydrazides into N,N '-diacylhydrazines in the presence of a ruthenium(II)-arene complex" in New Journal of Chemistry, 41, no. 14 (2017):6857-6865,
https://doi.org/10.1039/c7nj00965h . .

TY  - JOUR
AU  - Pantić, Darko N.
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Roller, Alexander
AU  - Arion, Vladimir B.
AU  - Grgurić-Šipka, Sanja
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2297
AB  - Three new ruthenium(II)-earene halido complexes of general formula [(eta(6-)p-cymene)RuX(L)] (C1-C3) were synthesised by reaction of [(eta(6)-p-cymene)RuX2](2) (X- = Cl-, Br-, I-) with 1H-benzimidazole-2-carboxylic acid (HL) in ethanol. The complexes were characterised by elemental analysis, mass spectrometry, IR, H-1 and C-13 NMR spectroscopy. The 1H-benzimidazole-2-carboxylate was found to act as a bidentate N,-Oechelating ligand. Single-crystal X-ray diffraction analysis confirmed the "piano-stool" geometry of C3. The cytotoxic activity of the ligand precursor and ruthenium complexes was tested in human cancer cell lines: cervical carcinoma (HeLa), breast carcinoma (MDA-MB-231), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5), by MTT assay. The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to that of HL. The latter was devoid of activity in the range of concentrations up to 300 mu M. Complex C3, carrying an iodido leaving ligand, exhibited moderate, but selective cytotoxicity toward HeLa, MDA-MB-231 and K562 cell lines, with IC50 values: 73.7, 60.9 and 53.9 mu M, respectively, being less toxic against MRC-5 cells (IC50 - 175.9 mu M). Complexes C1 and C2 showed moderate to low cytotoxicity in HeLa and K562 cells. (C) 2016 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Sa, Lausanne
T2  - Journal of Organometallic Chemistry
T1  - Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid
VL  - 819
SP  - 61
EP  - 68
DO  - 10.1016/j.jorganchem.2016.06.024
ER  - 

@article{
author = "Pantić, Darko N. and Aranđelović, Sandra and Radulović, Siniša and Roller, Alexander and Arion, Vladimir B. and Grgurić-Šipka, Sanja",
year = "2016",
abstract = "Three new ruthenium(II)-earene halido complexes of general formula [(eta(6-)p-cymene)RuX(L)] (C1-C3) were synthesised by reaction of [(eta(6)-p-cymene)RuX2](2) (X- = Cl-, Br-, I-) with 1H-benzimidazole-2-carboxylic acid (HL) in ethanol. The complexes were characterised by elemental analysis, mass spectrometry, IR, H-1 and C-13 NMR spectroscopy. The 1H-benzimidazole-2-carboxylate was found to act as a bidentate N,-Oechelating ligand. Single-crystal X-ray diffraction analysis confirmed the "piano-stool" geometry of C3. The cytotoxic activity of the ligand precursor and ruthenium complexes was tested in human cancer cell lines: cervical carcinoma (HeLa), breast carcinoma (MDA-MB-231), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5), by MTT assay. The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to that of HL. The latter was devoid of activity in the range of concentrations up to 300 mu M. Complex C3, carrying an iodido leaving ligand, exhibited moderate, but selective cytotoxicity toward HeLa, MDA-MB-231 and K562 cell lines, with IC50 values: 73.7, 60.9 and 53.9 mu M, respectively, being less toxic against MRC-5 cells (IC50 - 175.9 mu M). Complexes C1 and C2 showed moderate to low cytotoxicity in HeLa and K562 cells. (C) 2016 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Journal of Organometallic Chemistry",
title = "Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid",
volume = "819",
pages = "61-68",
doi = "10.1016/j.jorganchem.2016.06.024"
}

Pantić, D. N., Aranđelović, S., Radulović, S., Roller, A., Arion, V. B.,& Grgurić-Šipka, S.. (2016). Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid. in Journal of Organometallic Chemistry
Elsevier Science Sa, Lausanne., 819, 61-68.
https://doi.org/10.1016/j.jorganchem.2016.06.024

Pantić DN, Aranđelović S, Radulović S, Roller A, Arion VB, Grgurić-Šipka S. Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid. in Journal of Organometallic Chemistry. 2016;819:61-68.
doi:10.1016/j.jorganchem.2016.06.024 .

Pantić, Darko N., Aranđelović, Sandra, Radulović, Siniša, Roller, Alexander, Arion, Vladimir B., Grgurić-Šipka, Sanja, "Synthesis, characterisation and cytotoxic activity of organoruthenium(II)-halido complexes with 1H-benzimidazole-2-carboxylic acid" in Journal of Organometallic Chemistry, 819 (2016):61-68,
https://doi.org/10.1016/j.jorganchem.2016.06.024 . .

TY  - JOUR
AU  - Ivanović, Ivanka
AU  - Gligorijević, Nevenka
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Roller, Alexander
AU  - Keppler, Bernhard K.
AU  - Tešić, Živoslav Lj.
AU  - Grgurić-Šipka, Sanja
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1386
AB  - Metal semicarbazone and thiosemicarbazone complexes have attracted much attention due to their diverse biological activities. Because of the ability of ruthenium(II)-arene species to coordinate to different classes of ligands, they are suitable for fine-tuning chemical and pharmaceutical properties. Ruthenium(II) arene-complexes containing different types of ligands: namely caprylic hydrazide (a hydrazide with a long hydrocarbon chain), isonicotinic acid hydrazide (a hydrazide with an aromatic pyridine ring), thiosemicarbazones and semicarbazones (derived from the reaction of 3- and 4-acetylpyridine with either thiosemicarbazide or caprylic hydrazide), were obtained in the reaction of [(eta(6)-p-cymene)RuCl2](2) with the corresponding ligands in a 1:2 or 1:2.2 molar ratio in methanol, ethanol or isopropanol with mild heating. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. The structure of complex 1 was determined by X-ray crystallography. Antiproliferative activity of the investigated complexes, determined for three human cancer cell lines (HeLa, A549 and LS-174) revealed moderate activity without significant influence on the matrix metalloproteinases (MMP-2 and MMP-9) activity.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Polyhedron
T1  - New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity
VL  - 61
SP  - 112
EP  - 118
DO  - 10.1016/j.poly.2013.05.050
ER  - 

@article{
author = "Ivanović, Ivanka and Gligorijević, Nevenka and Aranđelović, Sandra and Radulović, Siniša and Roller, Alexander and Keppler, Bernhard K. and Tešić, Živoslav Lj. and Grgurić-Šipka, Sanja",
year = "2013",
abstract = "Metal semicarbazone and thiosemicarbazone complexes have attracted much attention due to their diverse biological activities. Because of the ability of ruthenium(II)-arene species to coordinate to different classes of ligands, they are suitable for fine-tuning chemical and pharmaceutical properties. Ruthenium(II) arene-complexes containing different types of ligands: namely caprylic hydrazide (a hydrazide with a long hydrocarbon chain), isonicotinic acid hydrazide (a hydrazide with an aromatic pyridine ring), thiosemicarbazones and semicarbazones (derived from the reaction of 3- and 4-acetylpyridine with either thiosemicarbazide or caprylic hydrazide), were obtained in the reaction of [(eta(6)-p-cymene)RuCl2](2) with the corresponding ligands in a 1:2 or 1:2.2 molar ratio in methanol, ethanol or isopropanol with mild heating. The complexes were characterized by elemental analysis, mass spectrometry, IR and NMR spectroscopies. The structure of complex 1 was determined by X-ray crystallography. Antiproliferative activity of the investigated complexes, determined for three human cancer cell lines (HeLa, A549 and LS-174) revealed moderate activity without significant influence on the matrix metalloproteinases (MMP-2 and MMP-9) activity.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Polyhedron",
title = "New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity",
volume = "61",
pages = "112-118",
doi = "10.1016/j.poly.2013.05.050"
}

Ivanović, I., Gligorijević, N., Aranđelović, S., Radulović, S., Roller, A., Keppler, B. K., Tešić, Ž. Lj.,& Grgurić-Šipka, S.. (2013). New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity. in Polyhedron
Pergamon-Elsevier Science Ltd, Oxford., 61, 112-118.
https://doi.org/10.1016/j.poly.2013.05.050

Ivanović I, Gligorijević N, Aranđelović S, Radulović S, Roller A, Keppler BK, Tešić ŽL, Grgurić-Šipka S. New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity. in Polyhedron. 2013;61:112-118.
doi:10.1016/j.poly.2013.05.050 .

Ivanović, Ivanka, Gligorijević, Nevenka, Aranđelović, Sandra, Radulović, Siniša, Roller, Alexander, Keppler, Bernhard K., Tešić, Živoslav Lj., Grgurić-Šipka, Sanja, "New ruthenium(II)-arene complexes bearing hydrazides and the corresponding (thio)semicarbazones of 3-and 4-acetylpyridine: Synthesis, characterization, crystal structure determination and antiproliferative activity" in Polyhedron, 61 (2013):112-118,
https://doi.org/10.1016/j.poly.2013.05.050 . .

TY  - JOUR
AU  - Ivanović, Ivanka
AU  - Grgurić-Šipka, Sanja
AU  - Gligorijević, Nevenka
AU  - Radulović, Siniša
AU  - Roller, Alexander
AU  - Tešić, Živoslav Lj.
AU  - Keppler, Bernhard K.
PY  - 2011
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1149
AB  - A ruthenium(II)-arene complex with picolinic acid, [(eta(6)-p-cymene)RuCl(pico)]center dot H(2)O, was prepared by the reaction of [(eta(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 mu mol dm(-3) for HeLa and FemX cells, respectively.
AB  - Rutenijum(II)-arenski kompleks sa pikolinskom kiselinom [(η6-p-cimen)RuCl(pikolinato)]·H2O sintetisan je u reakciji [(η6-p-cimen)RuCl2]2 kompleksa sa pikolinskom kiselinom u molskom odnosu 1:2 u izopropanolu. Jedinjenje je okarakterisano elementalnom analizom, IC i NMR spektroskopijom. Analiza difrakcijom X-zracima pokazala je da molekul ima tzv. 'three-leg piano-stool' geometriju koja je karakteristična za ovaj tip kompleksa. Citotoksična aktivnost kompleksa je određena na dve humane tumorske ćelijske linije, HeLa (grlića materice) i FemX (melanoma), MTT testom. IC50 vrednosti su bile 82,0 i 36,2 µmol dm-3 za HeLa i FemX ćelije, redom.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - X-Ray structure and cytotoxic activity of a picolinate ruthenium(II)-arene complex
T1  - Rendgenska strukturna analiza i citotoksična aktivnost pikolinato rutenijum(II)-arenskog kompleksa
VL  - 76
IS  - 1
SP  - 53
EP  - 61
DO  - 10.2298/JSC100517017I
ER  - 

@article{
author = "Ivanović, Ivanka and Grgurić-Šipka, Sanja and Gligorijević, Nevenka and Radulović, Siniša and Roller, Alexander and Tešić, Živoslav Lj. and Keppler, Bernhard K.",
year = "2011",
abstract = "A ruthenium(II)-arene complex with picolinic acid, [(eta(6)-p-cymene)RuCl(pico)]center dot H(2)O, was prepared by the reaction of [(eta(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 mu mol dm(-3) for HeLa and FemX cells, respectively., Rutenijum(II)-arenski kompleks sa pikolinskom kiselinom [(η6-p-cimen)RuCl(pikolinato)]·H2O sintetisan je u reakciji [(η6-p-cimen)RuCl2]2 kompleksa sa pikolinskom kiselinom u molskom odnosu 1:2 u izopropanolu. Jedinjenje je okarakterisano elementalnom analizom, IC i NMR spektroskopijom. Analiza difrakcijom X-zracima pokazala je da molekul ima tzv. 'three-leg piano-stool' geometriju koja je karakteristična za ovaj tip kompleksa. Citotoksična aktivnost kompleksa je određena na dve humane tumorske ćelijske linije, HeLa (grlića materice) i FemX (melanoma), MTT testom. IC50 vrednosti su bile 82,0 i 36,2 µmol dm-3 za HeLa i FemX ćelije, redom.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "X-Ray structure and cytotoxic activity of a picolinate ruthenium(II)-arene complex, Rendgenska strukturna analiza i citotoksična aktivnost pikolinato rutenijum(II)-arenskog kompleksa",
volume = "76",
number = "1",
pages = "53-61",
doi = "10.2298/JSC100517017I"
}

Ivanović, I., Grgurić-Šipka, S., Gligorijević, N., Radulović, S., Roller, A., Tešić, Ž. Lj.,& Keppler, B. K.. (2011). X-Ray structure and cytotoxic activity of a picolinate ruthenium(II)-arene complex. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 76(1), 53-61.
https://doi.org/10.2298/JSC100517017I

Ivanović I, Grgurić-Šipka S, Gligorijević N, Radulović S, Roller A, Tešić ŽL, Keppler BK. X-Ray structure and cytotoxic activity of a picolinate ruthenium(II)-arene complex. in Journal of the Serbian Chemical Society. 2011;76(1):53-61.
doi:10.2298/JSC100517017I .

Ivanović, Ivanka, Grgurić-Šipka, Sanja, Gligorijević, Nevenka, Radulović, Siniša, Roller, Alexander, Tešić, Živoslav Lj., Keppler, Bernhard K., "X-Ray structure and cytotoxic activity of a picolinate ruthenium(II)-arene complex" in Journal of the Serbian Chemical Society, 76, no. 1 (2011):53-61,
https://doi.org/10.2298/JSC100517017I . .

TY  - JOUR
AU  - Grgurić-Šipka, Sanja
AU  - Kowol, Christian R.
AU  - Valiahdi, Seied-Mojtaba
AU  - Eichinger, Rene
AU  - Jakupec, Michael A.
AU  - Roller, Alexander
AU  - Shova, Sergiu
AU  - Arion, Vladimir B.
AU  - Keppler, Bernhard K.
PY  - 2007
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/849
AB  - Two ruthenium(II) complexes of 2-acetylpyridine N ',N '-dimethylthiosemicarbazone (HL1) and phenanthrenequinone thiosemicarbazone (HL2), namely [(RuCI)-C-II(L-1)(PPh3)(2)] (1) and [(RuCl)-Cl-II(L-2) (PPh3)(2)] (2), have been synthesised and characterised by IR, UV/Vis and NMR spectroscopy, electrospray mass spectrometry, cyclic voltammetry and X-ray crystallography. In addition, the X-ray crystal structure of [(RuCl2)-Cl-III(L-2)- PPh3]center dot dmso center dot 1.25H(2)O (3 center dot dmso center dot 1.25H(2)O) is reported. The reaction of [(RuCl2)-Cl-II(dmsO)(4)] with HL1 and 1,3,5-triaza-7-phosphaadamantane (PTA) gives the highly water-soluble complex [(RuCl)-Cl-II(L-1)(HPTA)(2)]Cl-2 center dot C2H5OH center dot H2O (4 center dot C2H5OH center dot H2O) (S-25 degrees C - gt = 250 mg/mL), which has been fully characterised. Complex 4 shows strong antiproliferative effects in low micromolar concentrations in the ovarian carcinoma cell line 41M (IC50 = 0.87 mu m) and more moderate activity in the breast cancer cell line SK-BR-3 (IC50 = 39 mu m). The activity of the compound is 6.5- and 5.4-times higher at pH = 6.0 than at pH = 7.4 in the non-small cell lung cancer cell line A549 and the colon carcinoma cell line HT-29 (GI(50) = 24 and 8.0 mu m at pH = 6.0 for A549 and HT-29, respectively). ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Inorganic Chemistry
T1  - Ruthenium(II) complexes of thiosemicarbazones: The first Walter-soluble complex with pH-Dependent antiproliferative activity
IS  - 18
SP  - 2870
EP  - 2878
DO  - 10.1002/ejic.200601196
ER  - 

@article{
author = "Grgurić-Šipka, Sanja and Kowol, Christian R. and Valiahdi, Seied-Mojtaba and Eichinger, Rene and Jakupec, Michael A. and Roller, Alexander and Shova, Sergiu and Arion, Vladimir B. and Keppler, Bernhard K.",
year = "2007",
abstract = "Two ruthenium(II) complexes of 2-acetylpyridine N ',N '-dimethylthiosemicarbazone (HL1) and phenanthrenequinone thiosemicarbazone (HL2), namely [(RuCI)-C-II(L-1)(PPh3)(2)] (1) and [(RuCl)-Cl-II(L-2) (PPh3)(2)] (2), have been synthesised and characterised by IR, UV/Vis and NMR spectroscopy, electrospray mass spectrometry, cyclic voltammetry and X-ray crystallography. In addition, the X-ray crystal structure of [(RuCl2)-Cl-III(L-2)- PPh3]center dot dmso center dot 1.25H(2)O (3 center dot dmso center dot 1.25H(2)O) is reported. The reaction of [(RuCl2)-Cl-II(dmsO)(4)] with HL1 and 1,3,5-triaza-7-phosphaadamantane (PTA) gives the highly water-soluble complex [(RuCl)-Cl-II(L-1)(HPTA)(2)]Cl-2 center dot C2H5OH center dot H2O (4 center dot C2H5OH center dot H2O) (S-25 degrees C - gt = 250 mg/mL), which has been fully characterised. Complex 4 shows strong antiproliferative effects in low micromolar concentrations in the ovarian carcinoma cell line 41M (IC50 = 0.87 mu m) and more moderate activity in the breast cancer cell line SK-BR-3 (IC50 = 39 mu m). The activity of the compound is 6.5- and 5.4-times higher at pH = 6.0 than at pH = 7.4 in the non-small cell lung cancer cell line A549 and the colon carcinoma cell line HT-29 (GI(50) = 24 and 8.0 mu m at pH = 6.0 for A549 and HT-29, respectively). ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Inorganic Chemistry",
title = "Ruthenium(II) complexes of thiosemicarbazones: The first Walter-soluble complex with pH-Dependent antiproliferative activity",
number = "18",
pages = "2870-2878",
doi = "10.1002/ejic.200601196"
}

Grgurić-Šipka, S., Kowol, C. R., Valiahdi, S., Eichinger, R., Jakupec, M. A., Roller, A., Shova, S., Arion, V. B.,& Keppler, B. K.. (2007). Ruthenium(II) complexes of thiosemicarbazones: The first Walter-soluble complex with pH-Dependent antiproliferative activity. in European Journal of Inorganic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(18), 2870-2878.
https://doi.org/10.1002/ejic.200601196

Grgurić-Šipka S, Kowol CR, Valiahdi S, Eichinger R, Jakupec MA, Roller A, Shova S, Arion VB, Keppler BK. Ruthenium(II) complexes of thiosemicarbazones: The first Walter-soluble complex with pH-Dependent antiproliferative activity. in European Journal of Inorganic Chemistry. 2007;(18):2870-2878.
doi:10.1002/ejic.200601196 .

Grgurić-Šipka, Sanja, Kowol, Christian R., Valiahdi, Seied-Mojtaba, Eichinger, Rene, Jakupec, Michael A., Roller, Alexander, Shova, Sergiu, Arion, Vladimir B., Keppler, Bernhard K., "Ruthenium(II) complexes of thiosemicarbazones: The first Walter-soluble complex with pH-Dependent antiproliferative activity" in European Journal of Inorganic Chemistry, no. 18 (2007):2870-2878,
https://doi.org/10.1002/ejic.200601196 . .