TY  - JOUR
AU  - Mészáros, János P.
AU  - Geisler, Heiko
AU  - Poljarević, Jelena
AU  - Roller, Alexander
AU  - Legina, Maria S.
AU  - Hejl, Michaela
AU  - Jakupec, Michael A.
AU  - Keppler, Bernhard K.
AU  - Kandioller, Wolfgang
AU  - Enyedy, Éva A.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3804
AB  - Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. Comparative studies revealed the influence of the respective metal center (Ru, Os, Rh), leaving group (Cl, Br, I) and arene (p-cymene, toluene, pentamethylcyclopentadienyl), as well as the naphthoquinone ligand on the structural properties and solution speciation. Additionally, cytotoxicity was tested in SW480, CH1/PA-1 and A549 human cancer cell lines showing a broad range of IC50 values.
PB  - Elsevier
T2  - Journal of Organometallic Chemistry
T1  - Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations
VL  - 907
DO  - 10.1016/j.jorganchem.2019.121070
ER  - 

@article{
author = "Mészáros, János P. and Geisler, Heiko and Poljarević, Jelena and Roller, Alexander and Legina, Maria S. and Hejl, Michaela and Jakupec, Michael A. and Keppler, Bernhard K. and Kandioller, Wolfgang and Enyedy, Éva A.",
year = "2020",
abstract = "Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. Comparative studies revealed the influence of the respective metal center (Ru, Os, Rh), leaving group (Cl, Br, I) and arene (p-cymene, toluene, pentamethylcyclopentadienyl), as well as the naphthoquinone ligand on the structural properties and solution speciation. Additionally, cytotoxicity was tested in SW480, CH1/PA-1 and A549 human cancer cell lines showing a broad range of IC50 values.",
publisher = "Elsevier",
journal = "Journal of Organometallic Chemistry",
title = "Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations",
volume = "907",
doi = "10.1016/j.jorganchem.2019.121070"
}

Mészáros, J. P., Geisler, H., Poljarević, J., Roller, A., Legina, M. S., Hejl, M., Jakupec, M. A., Keppler, B. K., Kandioller, W.,& Enyedy, É. A.. (2020). Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations. in Journal of Organometallic Chemistry
Elsevier., 907.
https://doi.org/10.1016/j.jorganchem.2019.121070

Mészáros JP, Geisler H, Poljarević J, Roller A, Legina MS, Hejl M, Jakupec MA, Keppler BK, Kandioller W, Enyedy ÉA. Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations. in Journal of Organometallic Chemistry. 2020;907.
doi:10.1016/j.jorganchem.2019.121070 .

Mészáros, János P., Geisler, Heiko, Poljarević, Jelena, Roller, Alexander, Legina, Maria S., Hejl, Michaela, Jakupec, Michael A., Keppler, Bernhard K., Kandioller, Wolfgang, Enyedy, Éva A., "Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations" in Journal of Organometallic Chemistry, 907 (2020),
https://doi.org/10.1016/j.jorganchem.2019.121070 . .

TY  - DATA
AU  - Mészáros, János P.
AU  - Geisler, Heiko
AU  - Poljarević, Jelena
AU  - Roller, Alexander
AU  - Legina, Maria S.
AU  - Hejl, Michaela
AU  - Jakupec, Michael A.
AU  - Keppler, Bernhard K.
AU  - Kandioller, Wolfgang
AU  - Enyedy, Éva A.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3805
PB  - Elsevier
T2  - Journal of Organometallic Chemistry
T1  - Supplementary data for article: Mészáros, J. P.; Geisler, H.; Poljarević, J. M.; Roller, A.; Legina, M. S.; Hejl, M.; Jakupec, M. A.; Keppler, B. K.; Kandioller, W.; Enyedy, É. A. Naphthoquinones of Natural Origin: Aqueous Chemistry and Coordination to Half-Sandwich Organometallic Cations. Journal of Organometallic Chemistry 2020, 907. https://doi.org/10.1016/j.jorganchem.2019.121070
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3805
ER  - 

@misc{
author = "Mészáros, János P. and Geisler, Heiko and Poljarević, Jelena and Roller, Alexander and Legina, Maria S. and Hejl, Michaela and Jakupec, Michael A. and Keppler, Bernhard K. and Kandioller, Wolfgang and Enyedy, Éva A.",
year = "2020",
publisher = "Elsevier",
journal = "Journal of Organometallic Chemistry",
title = "Supplementary data for article: Mészáros, J. P.; Geisler, H.; Poljarević, J. M.; Roller, A.; Legina, M. S.; Hejl, M.; Jakupec, M. A.; Keppler, B. K.; Kandioller, W.; Enyedy, É. A. Naphthoquinones of Natural Origin: Aqueous Chemistry and Coordination to Half-Sandwich Organometallic Cations. Journal of Organometallic Chemistry 2020, 907. https://doi.org/10.1016/j.jorganchem.2019.121070",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3805"
}

Mészáros, J. P., Geisler, H., Poljarević, J., Roller, A., Legina, M. S., Hejl, M., Jakupec, M. A., Keppler, B. K., Kandioller, W.,& Enyedy, É. A.. (2020). Supplementary data for article: Mészáros, J. P.; Geisler, H.; Poljarević, J. M.; Roller, A.; Legina, M. S.; Hejl, M.; Jakupec, M. A.; Keppler, B. K.; Kandioller, W.; Enyedy, É. A. Naphthoquinones of Natural Origin: Aqueous Chemistry and Coordination to Half-Sandwich Organometallic Cations. Journal of Organometallic Chemistry 2020, 907. https://doi.org/10.1016/j.jorganchem.2019.121070. in Journal of Organometallic Chemistry
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_3805

Mészáros JP, Geisler H, Poljarević J, Roller A, Legina MS, Hejl M, Jakupec MA, Keppler BK, Kandioller W, Enyedy ÉA. Supplementary data for article: Mészáros, J. P.; Geisler, H.; Poljarević, J. M.; Roller, A.; Legina, M. S.; Hejl, M.; Jakupec, M. A.; Keppler, B. K.; Kandioller, W.; Enyedy, É. A. Naphthoquinones of Natural Origin: Aqueous Chemistry and Coordination to Half-Sandwich Organometallic Cations. Journal of Organometallic Chemistry 2020, 907. https://doi.org/10.1016/j.jorganchem.2019.121070. in Journal of Organometallic Chemistry. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_3805 .

Mészáros, János P., Geisler, Heiko, Poljarević, Jelena, Roller, Alexander, Legina, Maria S., Hejl, Michaela, Jakupec, Michael A., Keppler, Bernhard K., Kandioller, Wolfgang, Enyedy, Éva A., "Supplementary data for article: Mészáros, J. P.; Geisler, H.; Poljarević, J. M.; Roller, A.; Legina, M. S.; Hejl, M.; Jakupec, M. A.; Keppler, B. K.; Kandioller, W.; Enyedy, É. A. Naphthoquinones of Natural Origin: Aqueous Chemistry and Coordination to Half-Sandwich Organometallic Cations. Journal of Organometallic Chemistry 2020, 907. https://doi.org/10.1016/j.jorganchem.2019.121070" in Journal of Organometallic Chemistry (2020),
https://hdl.handle.net/21.15107/rcub_cherry_3805 .

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 . .