TY  - JOUR
AU  - Mészáros, János P.
AU  - Poljarević, Jelena
AU  - Szatmári, István
AU  - Csuvik, Oszkár
AU  - Fülöp, Ferenc
AU  - Szoboszlai, Norbert
AU  - Spengler, Gabriella
AU  - Enyedy, Éva A.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4050
AB  - Herein the design and synthesis of a new 8-hydroxyquinoline derivative, (S)-5-chloro-7-((proline-1-yl)methyl)8-hydroxyquinoline (HQCl-Pro), with good water solubility and multidrug resistance reversal activity are reported. In this work the proton dissociation processes of HQCl-Pro and its complex formation with [Rh(η5-C5Me5)(H2O)3]2+, [Ru(η6-p-cymene)(H2O)3]2+and [Ru(η6-toluene)(H2O)3]2+were investigated by the combined use of pH-potentiometry, UV-visible spectrometry and1H NMR spectroscopy. Our results revealed the prominent solution stability of the complexes in all cases. The lipophilicity of the complexes increased with the chloride ion concentration, and the complexes showed moderate log Dvalues (−0.8 to +0.4) at pH 7.4 at all tested Cl−concentrations. The formation of mixed hydroxido complexes from the aqua complexes was characterized by relatively high pKavalues (8.45-9.62 in chloride-free medium). Complexation processes are much slower with the Ru(η6-arene) triaqua cations than with [Rh(η5-C5Me5)(H2O)3]2+. Both the pKavalues and H2O/Cl−exchange constants of the Ru-complexes are lower by 0.5-1.0 orders of magnitude than those of the Rh analogue. Arene loss (p-cymene and toluene) and oxidation were found in the case of Ru-complexes when an excess of HQCl-Pro and aromatic (N,N) bidentate ligands was added. The cytotoxicity and antiproliferative effect of HQCl-Pro and its complexes were assayedin vitro. In contrast to the structurally familiar 8-hydroxyquinoline, HQCl-Pro and its Rh(η5-C5Me5) complex were somewhat more effective against drug resistant Colo 320 adenocarcinoma human cells compared to the drug sensitive Colo 205 cells. The Ru- and Rh-complexes showed a similar metal uptake level after 4 h, while a longer incubation time resulted in higher cellular Rh concentration.
PB  - Royal Society of Chemistry
T2  - Dalton Transactions
T1  - An 8-hydroxyquinoline–proline hybrid with multidrug resistance reversal activity and the solution chemistry of its half-sandwich organometallic Ru and Rh complexes
VL  - 49
IS  - 23
SP  - 7977
EP  - 7992
DO  - 10.1039/d0dt01256d
ER  - 

@article{
author = "Mészáros, János P. and Poljarević, Jelena and Szatmári, István and Csuvik, Oszkár and Fülöp, Ferenc and Szoboszlai, Norbert and Spengler, Gabriella and Enyedy, Éva A.",
year = "2020",
abstract = "Herein the design and synthesis of a new 8-hydroxyquinoline derivative, (S)-5-chloro-7-((proline-1-yl)methyl)8-hydroxyquinoline (HQCl-Pro), with good water solubility and multidrug resistance reversal activity are reported. In this work the proton dissociation processes of HQCl-Pro and its complex formation with [Rh(η5-C5Me5)(H2O)3]2+, [Ru(η6-p-cymene)(H2O)3]2+and [Ru(η6-toluene)(H2O)3]2+were investigated by the combined use of pH-potentiometry, UV-visible spectrometry and1H NMR spectroscopy. Our results revealed the prominent solution stability of the complexes in all cases. The lipophilicity of the complexes increased with the chloride ion concentration, and the complexes showed moderate log Dvalues (−0.8 to +0.4) at pH 7.4 at all tested Cl−concentrations. The formation of mixed hydroxido complexes from the aqua complexes was characterized by relatively high pKavalues (8.45-9.62 in chloride-free medium). Complexation processes are much slower with the Ru(η6-arene) triaqua cations than with [Rh(η5-C5Me5)(H2O)3]2+. Both the pKavalues and H2O/Cl−exchange constants of the Ru-complexes are lower by 0.5-1.0 orders of magnitude than those of the Rh analogue. Arene loss (p-cymene and toluene) and oxidation were found in the case of Ru-complexes when an excess of HQCl-Pro and aromatic (N,N) bidentate ligands was added. The cytotoxicity and antiproliferative effect of HQCl-Pro and its complexes were assayedin vitro. In contrast to the structurally familiar 8-hydroxyquinoline, HQCl-Pro and its Rh(η5-C5Me5) complex were somewhat more effective against drug resistant Colo 320 adenocarcinoma human cells compared to the drug sensitive Colo 205 cells. The Ru- and Rh-complexes showed a similar metal uptake level after 4 h, while a longer incubation time resulted in higher cellular Rh concentration.",
publisher = "Royal Society of Chemistry",
journal = "Dalton Transactions",
title = "An 8-hydroxyquinoline–proline hybrid with multidrug resistance reversal activity and the solution chemistry of its half-sandwich organometallic Ru and Rh complexes",
volume = "49",
number = "23",
pages = "7977-7992",
doi = "10.1039/d0dt01256d"
}

Mészáros, J. P., Poljarević, J., Szatmári, I., Csuvik, O., Fülöp, F., Szoboszlai, N., Spengler, G.,& Enyedy, É. A.. (2020). An 8-hydroxyquinoline–proline hybrid with multidrug resistance reversal activity and the solution chemistry of its half-sandwich organometallic Ru and Rh complexes. in Dalton Transactions
Royal Society of Chemistry., 49(23), 7977-7992.
https://doi.org/10.1039/d0dt01256d

Mészáros JP, Poljarević J, Szatmári I, Csuvik O, Fülöp F, Szoboszlai N, Spengler G, Enyedy ÉA. An 8-hydroxyquinoline–proline hybrid with multidrug resistance reversal activity and the solution chemistry of its half-sandwich organometallic Ru and Rh complexes. in Dalton Transactions. 2020;49(23):7977-7992.
doi:10.1039/d0dt01256d .

Mészáros, János P., Poljarević, Jelena, Szatmári, István, Csuvik, Oszkár, Fülöp, Ferenc, Szoboszlai, Norbert, Spengler, Gabriella, Enyedy, Éva A., "An 8-hydroxyquinoline–proline hybrid with multidrug resistance reversal activity and the solution chemistry of its half-sandwich organometallic Ru and Rh complexes" in Dalton Transactions, 49, no. 23 (2020):7977-7992,
https://doi.org/10.1039/d0dt01256d . .

TY  - DATA
AU  - Meszaros, Janos P.
AU  - Poljarević, Jelena
AU  - Gal, Tamas G.
AU  - May, Nora V.
AU  - Spengler, Gabriella
AU  - Enyedy, Eva A.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2875
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Supplementary data for the article: Meszaros, J. P.; Poljarević, J.; Gal, T. G.; May, N. V.; Spengler, G.; Enyedy, E. A. Comparative Solution and Structural Studies of Half-Sandwich Rhodium and Ruthenium Complexes Bearing Curcumin and Acetylacetone. Journal of Inorganic Biochemistry 2019, 195, 91–100. https://doi.org/10.1016/j.jinorgbio.2019.02.015
UR  - https://hdl.handle.net/21.15107/rcub_cherry_2875
ER  - 

@misc{
author = "Meszaros, Janos P. and Poljarević, Jelena and Gal, Tamas G. and May, Nora V. and Spengler, Gabriella and Enyedy, Eva A.",
year = "2019",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Supplementary data for the article: Meszaros, J. P.; Poljarević, J.; Gal, T. G.; May, N. V.; Spengler, G.; Enyedy, E. A. Comparative Solution and Structural Studies of Half-Sandwich Rhodium and Ruthenium Complexes Bearing Curcumin and Acetylacetone. Journal of Inorganic Biochemistry 2019, 195, 91–100. https://doi.org/10.1016/j.jinorgbio.2019.02.015",
url = "https://hdl.handle.net/21.15107/rcub_cherry_2875"
}

Meszaros, J. P., Poljarević, J., Gal, T. G., May, N. V., Spengler, G.,& Enyedy, E. A.. (2019). Supplementary data for the article: Meszaros, J. P.; Poljarević, J.; Gal, T. G.; May, N. V.; Spengler, G.; Enyedy, E. A. Comparative Solution and Structural Studies of Half-Sandwich Rhodium and Ruthenium Complexes Bearing Curcumin and Acetylacetone. Journal of Inorganic Biochemistry 2019, 195, 91–100. https://doi.org/10.1016/j.jinorgbio.2019.02.015. in Journal of Inorganic Biochemistry
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_2875

Meszaros JP, Poljarević J, Gal TG, May NV, Spengler G, Enyedy EA. Supplementary data for the article: Meszaros, J. P.; Poljarević, J.; Gal, T. G.; May, N. V.; Spengler, G.; Enyedy, E. A. Comparative Solution and Structural Studies of Half-Sandwich Rhodium and Ruthenium Complexes Bearing Curcumin and Acetylacetone. Journal of Inorganic Biochemistry 2019, 195, 91–100. https://doi.org/10.1016/j.jinorgbio.2019.02.015. in Journal of Inorganic Biochemistry. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_2875 .

Meszaros, Janos P., Poljarević, Jelena, Gal, Tamas G., May, Nora V., Spengler, Gabriella, Enyedy, Eva A., "Supplementary data for the article: Meszaros, J. P.; Poljarević, J.; Gal, T. G.; May, N. V.; Spengler, G.; Enyedy, E. A. Comparative Solution and Structural Studies of Half-Sandwich Rhodium and Ruthenium Complexes Bearing Curcumin and Acetylacetone. Journal of Inorganic Biochemistry 2019, 195, 91–100. https://doi.org/10.1016/j.jinorgbio.2019.02.015" in Journal of Inorganic Biochemistry (2019),
https://hdl.handle.net/21.15107/rcub_cherry_2875 .

TY  - JOUR
AU  - Meszaros, Janos P.
AU  - Poljarević, Jelena
AU  - Gal, Tamas G.
AU  - May, Nora V.
AU  - Spengler, Gabriella
AU  - Enyedy, Eva A.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2873
AB  - Half-sandwich organometallic complexes of curcumin are extensively investigated as anticancer compounds.
Speciation studies were performed to explore the solution stability of curcumin complexes formed with [Rh(η5- C5Me5)(H2O)3]2+. Acetylacetone (Hacac), as the simplest β-diketone ligand bearing (O,O) donor set, was involved for comparison and its Ru(η6‑p‑cymene), Ru(η6‑toluene) complexes were also studied. 1H NMR, UV–visible and pH-potentiometric titrations revealed a clear trend of stability constants of the acac complexes: Ru(η6‑p‑cymene) > Ru(η6‑toluene) > Rh(η5-C5Me5). Despite this order, the highest extent of complex formation is seen for the Rh(η5-C5Me5) complexes at pH 7.4. Formation constant of [Rh(η5-C5Me5)(H2curcumin) (H2O)]+ reveals similar solution stability to that of the acac complex. Additionally, structures of two complexes were determined by X-ray crystallography. The in vitro cytotoxicity of curcumin was not improved by the complexation with these organometallic cations.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone
VL  - 195
SP  - 91
EP  - 100
DO  - 10.1016/j.jinorgbio.2019.02.015
ER  - 

@article{
author = "Meszaros, Janos P. and Poljarević, Jelena and Gal, Tamas G. and May, Nora V. and Spengler, Gabriella and Enyedy, Eva A.",
year = "2019",
abstract = "Half-sandwich organometallic complexes of curcumin are extensively investigated as anticancer compounds.
Speciation studies were performed to explore the solution stability of curcumin complexes formed with [Rh(η5- C5Me5)(H2O)3]2+. Acetylacetone (Hacac), as the simplest β-diketone ligand bearing (O,O) donor set, was involved for comparison and its Ru(η6‑p‑cymene), Ru(η6‑toluene) complexes were also studied. 1H NMR, UV–visible and pH-potentiometric titrations revealed a clear trend of stability constants of the acac complexes: Ru(η6‑p‑cymene) > Ru(η6‑toluene) > Rh(η5-C5Me5). Despite this order, the highest extent of complex formation is seen for the Rh(η5-C5Me5) complexes at pH 7.4. Formation constant of [Rh(η5-C5Me5)(H2curcumin) (H2O)]+ reveals similar solution stability to that of the acac complex. Additionally, structures of two complexes were determined by X-ray crystallography. The in vitro cytotoxicity of curcumin was not improved by the complexation with these organometallic cations.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone",
volume = "195",
pages = "91-100",
doi = "10.1016/j.jinorgbio.2019.02.015"
}

Meszaros, J. P., Poljarević, J., Gal, T. G., May, N. V., Spengler, G.,& Enyedy, E. A.. (2019). Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone. in Journal of Inorganic Biochemistry
Elsevier., 195, 91-100.
https://doi.org/10.1016/j.jinorgbio.2019.02.015

Meszaros JP, Poljarević J, Gal TG, May NV, Spengler G, Enyedy EA. Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone. in Journal of Inorganic Biochemistry. 2019;195:91-100.
doi:10.1016/j.jinorgbio.2019.02.015 .

Meszaros, Janos P., Poljarević, Jelena, Gal, Tamas G., May, Nora V., Spengler, Gabriella, Enyedy, Eva A., "Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone" in Journal of Inorganic Biochemistry, 195 (2019):91-100,
https://doi.org/10.1016/j.jinorgbio.2019.02.015 . .

TY  - JOUR
AU  - Meszaros, Janos P.
AU  - Poljarević, Jelena
AU  - Gal, Tamas G.
AU  - May, Nora V.
AU  - Spengler, Gabriella
AU  - Enyedy, Eva A.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2891
AB  - Half-sandwich organometallic complexes of curcumin are extensively investigated as anticancer compounds.Speciation studies were performed to explore the solution stability of curcumin complexes formed with [Rh(η5- C5Me5)(H2O)3]2+. Acetylacetone (Hacac), as the simplest β-diketone ligand bearing (O,O) donor set, was involved for comparison and its Ru(η6‑p‑cymene), Ru(η6‑toluene) complexes were also studied. 1H NMR, UV–visible and pH-potentiometric titrations revealed a clear trend of stability constants of the acac complexes: Ru(η6‑p‑cymene) > Ru(η6‑toluene) > Rh(η5-C5Me5). Despite this order, the highest extent of complex formation is seen for the Rh(η5-C5Me5) complexes at pH 7.4. Formation constant of [Rh(η5-C5Me5)(H2curcumin) (H2O)]+ reveals similar solution stability to that of the acac complex. Additionally, structures of two complexes were determined by X-ray crystallography. The in vitro cytotoxicity of curcumin was not improved by the complexation with these organometallic cations.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone
VL  - 195
SP  - 91
EP  - 100
DO  - 10.1016/j.jinorgbio.2019.02.015
ER  - 

@article{
author = "Meszaros, Janos P. and Poljarević, Jelena and Gal, Tamas G. and May, Nora V. and Spengler, Gabriella and Enyedy, Eva A.",
year = "2019",
abstract = "Half-sandwich organometallic complexes of curcumin are extensively investigated as anticancer compounds.Speciation studies were performed to explore the solution stability of curcumin complexes formed with [Rh(η5- C5Me5)(H2O)3]2+. Acetylacetone (Hacac), as the simplest β-diketone ligand bearing (O,O) donor set, was involved for comparison and its Ru(η6‑p‑cymene), Ru(η6‑toluene) complexes were also studied. 1H NMR, UV–visible and pH-potentiometric titrations revealed a clear trend of stability constants of the acac complexes: Ru(η6‑p‑cymene) > Ru(η6‑toluene) > Rh(η5-C5Me5). Despite this order, the highest extent of complex formation is seen for the Rh(η5-C5Me5) complexes at pH 7.4. Formation constant of [Rh(η5-C5Me5)(H2curcumin) (H2O)]+ reveals similar solution stability to that of the acac complex. Additionally, structures of two complexes were determined by X-ray crystallography. The in vitro cytotoxicity of curcumin was not improved by the complexation with these organometallic cations.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone",
volume = "195",
pages = "91-100",
doi = "10.1016/j.jinorgbio.2019.02.015"
}

Meszaros, J. P., Poljarević, J., Gal, T. G., May, N. V., Spengler, G.,& Enyedy, E. A.. (2019). Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone. in Journal of Inorganic Biochemistry
Elsevier., 195, 91-100.
https://doi.org/10.1016/j.jinorgbio.2019.02.015

Meszaros JP, Poljarević J, Gal TG, May NV, Spengler G, Enyedy EA. Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone. in Journal of Inorganic Biochemistry. 2019;195:91-100.
doi:10.1016/j.jinorgbio.2019.02.015 .

Meszaros, Janos P., Poljarević, Jelena, Gal, Tamas G., May, Nora V., Spengler, Gabriella, Enyedy, Eva A., "Comparative solution and structural studies of half-sandwich rhodium and ruthenium complexes bearing curcumin and acetylacetone" in Journal of Inorganic Biochemistry, 195 (2019):91-100,
https://doi.org/10.1016/j.jinorgbio.2019.02.015 . .

TY  - DATA
AU  - Poljarević, Jelena
AU  - Gal, Tamas G.
AU  - May, Nora V.
AU  - Spengler, Gabriella
AU  - Domotor, Orsolya
AU  - Savić, Aleksandar
AU  - Grgurić-Šipka, Sanja
AU  - Enyedy, Eva A.
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3123
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Supplementary data for the article: Poljarević, J. M.; Tamás Gál, G.; May, N. V.; Spengler, G.; Dömötör, O.; Savić, A. R.; Grgurić-Šipka, S.; Enyedy, É. A. Comparative Solution Equilibrium and Structural Studies of Half-Sandwich Ruthenium(II)(η 6 -Toluene) Complexes of Picolinate Derivatives. J. Inorg. Biochem. 2018, 181, 74–85. https://doi.org/10.1016/j.jinorgbio.2017.12.017
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3123
ER  - 

@misc{
author = "Poljarević, Jelena and Gal, Tamas G. and May, Nora V. and Spengler, Gabriella and Domotor, Orsolya and Savić, Aleksandar and Grgurić-Šipka, Sanja and Enyedy, Eva A.",
year = "2018",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Supplementary data for the article: Poljarević, J. M.; Tamás Gál, G.; May, N. V.; Spengler, G.; Dömötör, O.; Savić, A. R.; Grgurić-Šipka, S.; Enyedy, É. A. Comparative Solution Equilibrium and Structural Studies of Half-Sandwich Ruthenium(II)(η 6 -Toluene) Complexes of Picolinate Derivatives. J. Inorg. Biochem. 2018, 181, 74–85. https://doi.org/10.1016/j.jinorgbio.2017.12.017",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3123"
}

Poljarević, J., Gal, T. G., May, N. V., Spengler, G., Domotor, O., Savić, A., Grgurić-Šipka, S.,& Enyedy, E. A.. (2018). Supplementary data for the article: Poljarević, J. M.; Tamás Gál, G.; May, N. V.; Spengler, G.; Dömötör, O.; Savić, A. R.; Grgurić-Šipka, S.; Enyedy, É. A. Comparative Solution Equilibrium and Structural Studies of Half-Sandwich Ruthenium(II)(η 6 -Toluene) Complexes of Picolinate Derivatives. J. Inorg. Biochem. 2018, 181, 74–85. https://doi.org/10.1016/j.jinorgbio.2017.12.017. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York..
https://hdl.handle.net/21.15107/rcub_cherry_3123

Poljarević J, Gal TG, May NV, Spengler G, Domotor O, Savić A, Grgurić-Šipka S, Enyedy EA. Supplementary data for the article: Poljarević, J. M.; Tamás Gál, G.; May, N. V.; Spengler, G.; Dömötör, O.; Savić, A. R.; Grgurić-Šipka, S.; Enyedy, É. A. Comparative Solution Equilibrium and Structural Studies of Half-Sandwich Ruthenium(II)(η 6 -Toluene) Complexes of Picolinate Derivatives. J. Inorg. Biochem. 2018, 181, 74–85. https://doi.org/10.1016/j.jinorgbio.2017.12.017. in Journal of Inorganic Biochemistry. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3123 .

Poljarević, Jelena, Gal, Tamas G., May, Nora V., Spengler, Gabriella, Domotor, Orsolya, Savić, Aleksandar, Grgurić-Šipka, Sanja, Enyedy, Eva A., "Supplementary data for the article: Poljarević, J. M.; Tamás Gál, G.; May, N. V.; Spengler, G.; Dömötör, O.; Savić, A. R.; Grgurić-Šipka, S.; Enyedy, É. A. Comparative Solution Equilibrium and Structural Studies of Half-Sandwich Ruthenium(II)(η 6 -Toluene) Complexes of Picolinate Derivatives. J. Inorg. Biochem. 2018, 181, 74–85. https://doi.org/10.1016/j.jinorgbio.2017.12.017" in Journal of Inorganic Biochemistry (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3123 .

TY  - JOUR
AU  - Poljarević, Jelena
AU  - Gal, Tamas G.
AU  - May, Nora V.
AU  - Spengler, Gabriella
AU  - Domotor, Orsolya
AU  - Savić, Aleksandar
AU  - Grgurić-Šipka, Sanja
AU  - Enyedy, Eva A.
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2119
AB  - Five Ru(II)(eta(6)-toluene) complexes formed with 2-picolinic acid and its various derivatives have been synthesized and characterized. X-ray structures of four complexes are also reported. Complex formation processes of [Ru(II) (eta(6)-toluene)(H2O)(3)](2+) organometallic cation with the metal-free ligands were studied in aqueous solution in the presence of chloride ions by the combined use of H-1 NMR spectroscopy, UV-visible spectrophotometry and pH-potentiometry. Solution stability, chloride ion affinity and lipophilicity of the complexes were characterized together with in vitro cytotoxic and antiproliferative activity in cancer cell lines being sensitive and resistant to classic chemotherapy and in normal cells as well. Formation of mono complexes such as [Ru(eta(6)-toluene)(L) (Z)](+/0) (L: completely deprotonated ligand; Z = H2O/Cl-) with high stability and [Ru(eta(6)-toluene)(L)(OH)] was found in solution. The plc values (8.3-8.7) reflect the formation of low amount of mixed hydroxido species at pH 7.4 at 0.2 M KCl ionic strength. The complexes are fairly hydrophilic and show moderate chloride ion affinity and fast chloride-water exchange processes. The studied complexes exhibit no cytotoxic activity in human cancer cells (IC50  gt  100 mu M), only complexes formed with 2-picolinic acid (1) and its 3-methyl derivative (2) represented a moderate antiproliferative effect (IC50 = 84.8 (1), 79.2 mu M (2)) on a multidrug resistant colon adenocarcinoma cell line revealing considerable multidrug resistant selectivity. Complexes 1 and 2 bind to human serum albumin covalently and relatively slowly with moderate strength at multiple binding sites without ligand cleavage.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives
VL  - 181
SP  - 74
EP  - 85
DO  - 10.1016/j.jinorgbio.2017.12.017
ER  - 

@article{
author = "Poljarević, Jelena and Gal, Tamas G. and May, Nora V. and Spengler, Gabriella and Domotor, Orsolya and Savić, Aleksandar and Grgurić-Šipka, Sanja and Enyedy, Eva A.",
year = "2018",
abstract = "Five Ru(II)(eta(6)-toluene) complexes formed with 2-picolinic acid and its various derivatives have been synthesized and characterized. X-ray structures of four complexes are also reported. Complex formation processes of [Ru(II) (eta(6)-toluene)(H2O)(3)](2+) organometallic cation with the metal-free ligands were studied in aqueous solution in the presence of chloride ions by the combined use of H-1 NMR spectroscopy, UV-visible spectrophotometry and pH-potentiometry. Solution stability, chloride ion affinity and lipophilicity of the complexes were characterized together with in vitro cytotoxic and antiproliferative activity in cancer cell lines being sensitive and resistant to classic chemotherapy and in normal cells as well. Formation of mono complexes such as [Ru(eta(6)-toluene)(L) (Z)](+/0) (L: completely deprotonated ligand; Z = H2O/Cl-) with high stability and [Ru(eta(6)-toluene)(L)(OH)] was found in solution. The plc values (8.3-8.7) reflect the formation of low amount of mixed hydroxido species at pH 7.4 at 0.2 M KCl ionic strength. The complexes are fairly hydrophilic and show moderate chloride ion affinity and fast chloride-water exchange processes. The studied complexes exhibit no cytotoxic activity in human cancer cells (IC50  gt  100 mu M), only complexes formed with 2-picolinic acid (1) and its 3-methyl derivative (2) represented a moderate antiproliferative effect (IC50 = 84.8 (1), 79.2 mu M (2)) on a multidrug resistant colon adenocarcinoma cell line revealing considerable multidrug resistant selectivity. Complexes 1 and 2 bind to human serum albumin covalently and relatively slowly with moderate strength at multiple binding sites without ligand cleavage.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives",
volume = "181",
pages = "74-85",
doi = "10.1016/j.jinorgbio.2017.12.017"
}

Poljarević, J., Gal, T. G., May, N. V., Spengler, G., Domotor, O., Savić, A., Grgurić-Šipka, S.,& Enyedy, E. A.. (2018). Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 181, 74-85.
https://doi.org/10.1016/j.jinorgbio.2017.12.017

Poljarević J, Gal TG, May NV, Spengler G, Domotor O, Savić A, Grgurić-Šipka S, Enyedy EA. Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives. in Journal of Inorganic Biochemistry. 2018;181:74-85.
doi:10.1016/j.jinorgbio.2017.12.017 .

Poljarević, Jelena, Gal, Tamas G., May, Nora V., Spengler, Gabriella, Domotor, Orsolya, Savić, Aleksandar, Grgurić-Šipka, Sanja, Enyedy, Eva A., "Comparative solution equilibrium and structural studies of half-sandwich ruthenium(II)(eta(6)-toluene) complexes of picolinate derivatives" in Journal of Inorganic Biochemistry, 181 (2018):74-85,
https://doi.org/10.1016/j.jinorgbio.2017.12.017 . .